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Siesta Key Pet Friendly Vacation Rentals

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    Travellers to Siesta Key are booking February dates now. Secure your vacation rental today, and have the perfect trip.
    79 Matching Rentals in Siesta KeyView all 540 rentals
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    Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment1 / 32
    (23)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Sandy Toes Siesta Key Florida   (6798)1 / 37
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sandy Toes Siesta Key Florida  (6796)1 / 40
    (18)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa1 / 28
    (2)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We booked the house for Thanksgiving week for six adults and five kids and the layout was perfect. The heated, screened pool is literally an extension of the house and there...
    Reviewed 11 August 2017
    There are nine of us that travel together every year, and this home and David made Siesta Key our best vacation yet. The location is a block away from beach pavilion. We loaded...
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    About this property
    Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage, Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. This Home Entertains Excellent Because The Pool Area Is...
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    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    4 Bd Waterfront Home w/Pool, Close to Siesta Beach1 / 37
    (7)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Porch
    • Internet Access
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2017
    This beautiful Siesta Key pool home is only a short 3 block walk to the beach. The newly acquired beach cart holds 1,000 lbs of stuff. I could have wheeled a small army with the...
    Reviewed 12 August 2015
    Stayed at this house for two weeks in July. Pictures do not do this house justice. House was much more beautiful. Views of the canal, that can be seen from all along back of...
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    About this property
    Oh what a great feeling you get when you are looking out over the pool to the relaxing waters of the Grand Canal. This home is special with 188 ft. of canal wrapping the back of the home so you get to enjoy the views from three bedrooms, the kitchen, living and two dinning areas. Open all the...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 bedroom/1 bath Contemporary Beach Cottage1 / 10
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Balcony
    • Parking
    • Patio
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2017
    It was like home away from home. Glad we were able to take our dog and cottage was fully equipped with everything necessary for our stay.
    Reviewed 31 May 2016
    The space seems bigger than the pictures lead it on to be which is a plus! We really enjoyed our stay as the master bedroom was very spacious. We visit Siesta Key almost every...
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    About this property
    Half Mile to the Beach This recently remodeled Beach house has both inside and outside living spaces. There is a combination Kitchen/dining/living area with windows on every wall allowing in loads of the wonderful Florida natural light. The kitchen is all white with stainless appliances and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Key West Suite next to Siesta Key Beach1 / 25
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    • Balcony
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 May 2016
    Spacious enough for 3 little ones and 2 adults. My wifeet and I stayed in the makeshift room next to family room. Very clean and well kept. We were spoiled and had the property...
    Reviewed 27 June 2015
    The suite 5610 was on the ground level, perfect for kids. The suite and outside areas were very clean and offered a lot of amenities. The pool was very clean and just the right...
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    About this property
    2 apartments to choose from: Key West Suite A relaxed beach experience. This cozy two bedrooms & den apartment, full 2 baths (1 King bed + 2 Twins + 1 Queen) 1,200 sq/ft. suite on second level with two private balconies and partial Gulf view from the den. This apartment is fully furnished and...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Charming Siesta Key Condo, Walk to Beach, Pool1 / 29
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Balcony
    • Wi-Fi
    • Parking
    • Sauna
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 May 2017
    The location is perfect, the beautiful white beach of Siesta Key is on your doorstep. If you feel energetic it is a brisk 25 minute walk into the village from the condominium or...
    Reviewed 10 July 2016
    Very short walk to the beach! Sue is so friendly! The condo was in excellent condition! We will definitely stay here again!
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    About this property
    Spacious Condo on Siesta Key with 2 Queen Beds is beautifully furnished, all new, and super clean! WALK RIGHT OVER TO THE #1 BEACH IN AMERICA, you do not need a car on this vacation stay. And if you want to see the rest of Siesta Key you can take the free shuttles, and the new Siesta Key Trolley...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You need a vacation and we've got just the place! Not only are we a 5 minute walk to beach, but we're only 2 blocks to the famous Siesta Key Village with all the shops, restaurants and bars. If you don't want to eat out, you have a grocery store right in the village. They have already made...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Steps from the Village and #1 Beach in the USA!1 / 52
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 2017
    What a beautiful modern and superbly located house. Immaculate and well maintained with everything you could possibly need. Our host Randy was excellent and answered our...
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    About this property
    Steps from the islands best restaurants, shops (in the Village area) and a short walk to the #1 beach in the USA! Great home with 2 car and 1 car private garages. Recently renovated including a screened in patio, hot tub and pool. Brand new appliances making this home a great place for monthly...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    PRISTINE SIESTA KEY VILLAGE HOME1 / 28
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2017
    Beautiful accommodation, superbly located and very well equipped. The new swimming pool is the jewel in the crown, and Cydney was a pleasure to deal with. We would hope to go back.
    Reviewed 20 July 2017
    I can't say enough wonderful comments about this house. It's charming, comfortable, gorgeous, adorable, lovely....I could go on and on. My family has enjoyed walking to...
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    About this property
    Hidden behind a contemporary privacy wall, enter into our front yard oasis. The perfect setting for tanning, dining and entertaining alongside the waterfall feature. Extensive renos offering a stunning gourmet kitchen, updated bathrooms, flat screen tv's in bedrooms and the most appealing Lanai...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It will be love at first sight with our tiny Blue Oasis; her cerulean color with bright white trim tells you you have arrived in the tropics, and her welcoming front porch is just big enough for you to engage in the southern pastime of porch sittin’. Cool off inside where the bleached white wood...
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    Location Information
    Siesta Key, Florida 34231
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Siesta Key 3 Bdrm Private House with Heated Pool minutes from village and beach1 / 29
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2017
    I travelled to Florida with my fiancee for work and decided to extend our stay to enjoy a little R & R. We have used AirB&B in the past and we found this gorgeous home to...
    Reviewed 10 April 2017
    This is a beautiful home a short bike ride to Siesta Beach. It comfortably sleeps 8 on beds in 3 large rooms. 2 of the rooms have a glass door that opens up to the pool and...
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    About this property
    Surrounded by lush, tropical garden, our private villa is situated on a quiet cul-de-sac bordered on two sides by Lake Nancy. A birdwatchers and nature lovers delight! Sip your coffee in your PJs on the private, sunny terrace. Enjoy a dip in the large heated pool, or explore the lake in 'Red...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Siesta Key Beachfront 3 Bedroom Home, Sarasota1 / 26
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Cable/satellite TV
    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 November 2017
    We enjoyed our stay at this well maintained tastefully decorated 3 bedroom home a short walk on the beach to the village of Seista Key. It was clean and recently updated...
    Reviewed 14 August 2017
    The location of this house is perfect. It's a quick walk along a path to wide open beach area, never crowded. And the siesta key village is in walking distance. The house slept...
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    About this property
    Description:Walk out the back door to the clean white sand of Siesta Key Beach. This home has private Siesta Key beach frontage on the prime section of beach, there are no homes between you and the beach. Nearly every room has a full view of the beach. The entire back of this house opens with...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine Yourself At (Tiny) Home: Beach life is best! Enter through the bright yellow, life-sized replica of a Siesta Key lifeguard stand, and drop your beach bags on the two stools beneath our surfboard-shaped breakfast bar. Passing through the living room, decorated with just a touch of...
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    Siesta Key, Florida 34231
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Beach Place Siesta Key Cottages - 30 Seconds to the Sand, sleep up to 13 guests1 / 28
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Patio
    • Parking
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 March 2017
    The location was perfect - right across the street from the north end of Siesta Key public beach. The public beach house was accessible for lunch/bathrooms, or walking back to...
    Reviewed 8 March 2017
    What s pleasant surprise 1befroom cottage ;cute and comfortable. Across the street from beautiful siesta key beach. Leslie gave us tips on where to go. And we were glad we...
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    About this property
    One bedroom tropical garden beach cottages located at Siesta Key Beach. Cottages sleeps four. Perfect for large families or groups traveling together. Total of 12 / 13 guests. Prices are per cottage. The Beach Place is Old Florida charm that's becoming hard to find. Private, quiet and relaxing....
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Flip Flop Cottages Siesta Key Florida1 / 42
    (2)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Patio
    • Porch
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 May 2015
    Nice overall for what we needed-good location for beach hoppers like ourselves. Could get to Lido beach and turn around and go to Venice beach with still many beaches between...
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    About this property
    YOUR PRIVATE GETAWAY ON THE KEY ASK ABOUT OUR SUMMER SPECIALS!!!!!!!!! Does not include Weekends or Holidays!!! Looking to relax, Flip Flop Cottages is the place to be for a quaint and private vacation in Siesta Key, Florida. Come and stay at our serene environment and enjoy and visit all the...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Grand White Sands 303 - Walk to beach and village1 / 17
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Sauna
    • DVD Player
    • Wi-Fi
    • Patio
    • Waterfront
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 February 2017
    Enjoyed our stay in this unit , big screen tv was the best. Short walk to the beach, the dog loved it. Everybody in the complex was very friendly and helpful.
    Reviewed 6 January 2016
    Close to all the excellent facilities of Siesta Key and within a comfortable walking distance of the magnificent Siesta beach, Grand White Sands 303 was the ideal place to...
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    About this property
    Please also visit siestakey-whitesands with the usual US ending. There you'll find lots of usedul information on the condo and a travel guide.White Sands Village is located on Siesta Key, just few steps from Siesta Beach and directly on the canal across from Philippee Creek.Highlights of White...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stay on Siesta - Crescent House1 / 10
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Parking
    • Balcony
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 April 2015
    Very nice accommodations. Gulf side of Midnight Pass. Five minute walk to beach. Quiet Crescent Beach.
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    About this property
    Located near the South Village of Siesta Key. This newly updated 2 bedroom duplex has it all. A new dipping pool to cool off the hot summer days, along with a BBQ and fire pit for the winter. Lots of space, all new furnishings throughout the home, the large eat in kitchen has plenty of room for...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Stay on Siesta,Beach Bungalow PET Friendly1 / 16
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2016
    Very cozy but good for 1-2 people. Walk to private beach and pool. Only thing - can be quite noisy at night with the bar across the street but otherwise great
    Reviewed 5 July 2016
    Old Florida vibe, love it. Short walk to beach! Perfect size place for my husband and I and our 60 lb lab. The private fenced grassy area in backyard was perfect for our dog...
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    About this property
    PET Friendly! This one bedroom and one bathroom beach bungalow is located 150 yards away from the beach. You can walk to restaurants, shops and a great pool area. Queen bed and a sleeper sofa make it possible to sleep four. Enjoy your morning coffee on your private screened porch or while you walk...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Stay on Siesta - SEA - ESTA HOUSE1 / 19
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Outdoor Dining Area
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Patio
    • Parking
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    "Avenida Del Mare" was the perfect vacation rental for my family. The home is well appointed, all renovated with comfy beds and amazing bathrooms (love the rainshower...
    Reviewed 8 November 2016
    Convenient location, just a short stroll to beautiful Siesta Beach. Beach gear available, we left some sand toys for the kids.Very well equipped and beautifully decorated. All...
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    About this property
    This Siesta Key 3 Bedroom 2 Bath Home has been completely remodeled. This home is 1 block from the Famous Siesta Key Beach. Granite counter tops, to accent the new white cabinetry. Beautifully tiled bathrooms with all new hardware. All walls beautifully textured. Screened Lanai. Nice back yard. 1...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Old Man and the Sea Inn #2 - 8 steps to the sand of Siestas best beach!1 / 23
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Internet Access
    • Waterfront
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 February 2017
    What a wonderful stay! To start, Daniel is a very down-to-earth guy....ALWAYS responded promptly to phone calls and emails, and always was always courteous and complete in...
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    About this property
    1BR (sleeps 4)- Perfect for travelers in search of uncomplicated seclusion. Brought to you by Gertrude Rentals! Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home located...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Stay on Siesta - Beach Rd -Step out to the Sand1 / 25
    (6)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Patio
    • Waterfront
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 February 2017
    We have visited siesta key many times and loved the location and atmosphere of this condo. It was clean and newly remodeled. The staff was friendly and helpful. Great place to...
    Reviewed 6 February 2017
    Looking forward to coming back. Perfect location for our stay. Nice people and accommodation . Great rates for what you get
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    About this property
    3 bedroom on Beach Rd. with Gulf view This updated townhouse is a one of a kind property. Three bedrooms with king, queen, 2 double beds and living room sleeper sofa. This is a step out to the sand property just north of Siesta Key Beach. Walk to Siesta Village. Views of the Gulf from almost every...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Large 1br/1ba vacation rental condo (780 Sq.Ft.)1 / 24
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Parking
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2016
    This place is absolutely great. Me and my girlfriend spent two nights over the weekend at this condo. First of all this place has more stuff that we could imagine. It literally...
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    About this property
    Newly renovated 1/1 large (780 Sq.Ft.) 2nd floor condo.Situated a short 5-minute drive from the cool emerald waters of Siesta Key Beach, on the North edge of Palmer Ranch. This tropical resort community is a relaxing oasis under the warm skies of the Gulf Coast. With its swaying palms, shimmering...
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    Location Information
    Siesta Key, Florida 34231
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The Shells Villa - Next to Beach & Village1 / 41
    (65)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Air Conditioning
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 2017
    Owners are quick to respond and great to work with, even after recent hurricane. Spacious, clean, and a great location!
    Reviewed 9 August 2017
    We spent 2 wonderful weeks at Shells Villa. This is a return visit for our family. We loved everything about Shells Villa! The location--- steps away from the beach and the...
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    About this property
    3 Bedroom, 2.5 Bath Beach Villa (Sleeps 8-10) What makes us different than other homes you may be considering: · The Beach - The home is located on the ocean side of Beach Rd., so you just walk out your door and through our private access path. It’s literally 230 feet to Siesta Key Beach....
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bayfront Contemporary Home on Sarasota Bay! This Contemporary Home on Sarasota Bay has Spectacular Views from all 3 stories. Enjoy bayfront living at it's finest with a 2-story great room, bayfront lanai, pool, boat dock and lift. Perfect for Family Gatherings, Wedding Parties, Birthdays and...
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    Location Information
    Siesta Key, Florida 34231
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Old Man and the Sea Inn #1 - 8 steps to the sand of Siestas best beach!1 / 28
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2017
    Wonderful, relaxing, perfect location! On the quiet side of the key, easy close access to gorgeous crescent Beach. Easy quick walk to bus stop and local market, restaurants as...
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    About this property
    Old Man and the Sea Inn - 1 marlin to the sand! 2BR (sleeps 8). Brought to you by Gertrude Rentals! Perfect for travelers in search of uncomplicated seclusion. Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Casa Van Lopik (Canal) – In Siesta Village just 1.5 blocks to the best beaches!1 / 27
    (18)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Outdoor Dining Area
    • Grill
    • Cable/satellite TV
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    • Air Conditioning
    • Waterfront
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 2017
    Location is the best thing about this condo -- short walk to beach and to Siesta Key Village. Very convenient. Another big "pro" was Daniel. The owner is very...
    Reviewed 9 November 2016
    We stayed in unit 360.Pro's-Our extended family of seven stayed at Casa VanLopik in the heart of Siesta Village. The house sleeps 10, and has all the amenities of home. Two...
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    About this property
    Casa Van Lopik (c), our canal facing suite, is a large 3BR. Brought to you by Gertrude Rentals! Perfectly located 1.5 blocks away from the best beaches, shopping, dining and entertainment on the island. It was named for our father who was a ships captain and sailed the world for 30 years but...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Old Man and the Sea Inn #4 - 8 steps to the sand of Siestas best beach!1 / 52
    (33)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 September 2017
    We stayed for a long weekend and couldn't have been more pleased. Their team has thought of everything- all you need to do is sit back and enjoy the amazing location and town...
    Reviewed 3 September 2017
    Fantastic location, a little stroll down a sandy lane to a picture perfect beach. The accommodation was beautifully presented and really clean, it was a little tired in places...
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    About this property
    Old Man and the Sea Inn - 1 marlin to the sand! 2BR (sleeps 8). Brought to you by Gertrude Rentals! Perfect for travelers in search of uncomplicated seclusion. Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Luxury Four Bedroom, Four and a Half Bathroom Home will leave you breathless as you enter. There are not many large rental homes, this close to Siesta Beach, that live like this home. Most Rentals by the beach have their living area 16 feet above the ground level and the pool below, which is...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    Dog-Friendly Siesta Key Bungalow, Wifi, Adorable Cottage Close to Siesta Key1 / 29
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2017
    The house was nice, large size, comfortable, nice neighborhood close to the beaches, shopping and restaurants. Perfect for our family and dogs that we brought along on our...
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    About this property
    Totally renovated adorable Siesta Key bungalow nestled on a shaded street just minutes from Siesta Key beach and the village of Siesta Key with a variety of shops, restaurants and nightlife. Drive into the circular driveway and park your car under the covered parking to be away from the 10 minute...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
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    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the middle of Siesta Key, tucked away on a shaded and quiet canopy lane is this bright and open air 3 bedroom 3 bath home less than one mile from the world famous Siesta Key beach. Plenty of space to spread out and enjoy your vacation, whether it be out on the pool deck, in the hot tub, relaxing...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    The Top  Location on Siesta Key - Gertrude's Village House1 / 25
    (30)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Waterfront
    • Patio
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 May 2017
    My son booked this for his whole family. There were nine of us. The beach was just a half block away. It was beautiful with cool white sand, aqua water with warm rolling...
    Reviewed 24 September 2016
    Stayed there, the location is great. Everything in walking distance. The kitchen was supplied with everything you need. The positives beyond location varied, quiet, lots of room...
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    About this property
    Our Top Location, Gertrude's Village House! Brought to you by Gertrude Rentals and named for our grandmother who traveled the world until age of 91 but always insisted this street on Siesta Key was the place she loved best. Leave the car behind. Gertrude's is richly furnished, perfectly nestled...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Children's Pool
    • Balcony
    • Washer
    • Grill
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    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quiet and serene, but close to local attractions, you will love this large 4 bedroom, family friendly home with 2 kitchens, new appliances, modern furnishings, and beach buggy with all the gear! Separate living areas can accommodate one large family or two smaller ones. Each living area has its...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located south Siesta Key with no busy streets to cross, it’s a leisurely stroll to the Gulf of Mexico and to Point of Rocks, the best snorkeling beach on the Key. There are many restaurants, lots of shopping, bike rentals, ice cream shops, beach equipment, etc., in a very beachy atmosphere. It’s...
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    Location Information
    Siesta Key, Florida 34242
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The Top Siesta Key Location, The Village Studio - Eat Shop Beach!1 / 14
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 March 2017
    We loved walking everywhere - the beach, especially every sunset; shops, great food. The condo was lovely, and the setting enriched by the other owners in the complex.
    Reviewed 24 March 2017
    We enjoyed our 3 day stay. A longer stay would require a larger place but it was perfect for this time. Our host was very helpful and had a nice gift awaiting our arrival :)
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    About this property
    Our favorite location on Siesta Key, The Siesta Key Village Studio, brought to you by Gertrude Rentals! An accommodating ground floor one-room efficiency apartment perfectly nestled on a quiet tropical street between the best beaches, shopping and dining on the island. Wander one block to your...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Beautiful & Modern Condo - Walk to Beach & Village1 / 18
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Sauna
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    White Sands Village is located on Siesta Key, just few steps from Siesta Beach and directly on the canal across from Philippee Creek. Highlights of White Sands Unit 303: Free high-speed WiFi Ground floor unit More than 200 channel cable TV DVR to watch your favorite show when you want to 50 inch...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Old Man and the Sea Inn #3 - 8 steps to the sand of Siestas best beach!1 / 23
    (18)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Cable/satellite TV
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    The rental was perfect for my husband and I with our 2 dogs. Everything you could possibly need is in the cutely decorated unit. A plethora of towels, dishes, cups and even a...
    Reviewed 3 December 2016
    Charming key west style 1 bedroom, owner was extremely helpful in creating same day booking w. minimal extra fees.
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    About this property
    1BR (sleeps 4)- Perfect for travelers in search of uncomplicated seclusion. Brought to you by Gertrude Rentals! Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home located...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Just Minutes from the White Sandy Siesta Beach1 / 28
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Patio
    • Shared Outdoor Pool (Unheated)
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    • DVD Player
    • Grill
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 October 2017
    Bea's condo was so wonderful! It was really spacious and comfy! The location was super close to Siesta Key Beach! Kitchen and bathroom were fully stocked with everything we...
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    About this property
    Situated a SHORT 5 min DRIVE from the cool emerald waters of SIESTA KEY BEACH, Nr.1. Beach in the USA. This tropical resort community of Sienna Park is a relaxing oasis under the warm skies of the Gulf Coast. My condos are good for couples, solo adventurers, business travelers, families (with...
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    Siesta Key, Florida 34231
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    Sand Dollar is our Amy model’s “big” sister. She has a penthouse suite with an easy spiral staircase found privately on the other side of the bathroom. She also has a sleeping loft above the kitchen that cantilevers over the cute front porch and a modern comfy futon that folds out to a sleeper....
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    Location Information
    Siesta Key, Florida 34231
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    New 6 Bedroom, Luxury Home in Gated Community1 / 22
    (1)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
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    • Washer
    • Waterfront
    • Air Conditioning
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2017
    View from master bedroom was fantastic. Plenty of room for the 14 of us. Will defiantly book again. Kitchen had all appliances needed. Grill was old and had to light with a...
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    About this property
    Perfectly located, New, 6 bedrooms 4 1/2 bathrooms private home,in a gated community, combines luxury with convenience of location. We offer you a large 6000sf+ home within a short distance to the pristine beaches of Siesta Key and walking to the Village, Restaurants, shops and nightlife. Privacy...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    directly on the beach, studio apt. 'the Sandbox'
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly remodeled -Queen Murphy Bed -Convenience Kitchen -Laundry Facilities on site -Patio / Grill -VCR/DVD -WiFi -Microwave NOTE: PLEASE CONTACT US FOR AVAILABILITY. We do NOT always keep this calendar current. Thanks. Visit our site to see more photos and descriptions:...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    1 Block to the Beach on Siesta Key Vacation Rental Home with Swimming Pool1 / 24
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Cape Aqua! This single family vacation rental home on Siesta Key has 3 bedrooms 2 1/2 baths and pool. Located on the closest private street to America's #1 named.The two large double doors with decorative frosted glass welcome you into this spacious home. The floor plan offers a very...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Siesta Key Poor Boy - 2BR/1Bath; sleeps 8. Residing in the most 'private' non-private beach neighborhood in Siesta Key just about 8 steps from the sand path of the best beach on the island, our Poor-Boy unit is perfect for travellers in search of all the best the island of Siesta Key has to...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    About this property
    SIESTA KEY DREAM HOUSE!!!!!!!!!!!!!!!! Custom designed home. Open flow. Great for entertaining. Custom Kitchen with island. Eat-in area, granite & 2-tone wood cabinetry. Separate living, dining, family/ great rooms plus 4 bedrooms and 4 1/2 baths. 2 master suites. Heated pool with waterfall -...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Beachfront Bungalow is nestled in a tranquil, natural setting. Relax and listen to the ocean from a spacey private deck, that has sublime views of the marshes and the bay. Located right on the # 1 beach in the USA! Five minute walking distance to the public beach and Siesta Key Village. Close...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Hot Tub
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just cross the street and you are at the entrance to Siesta Key Beach - one of the finest beaches on the Florida Coast and the winner of multiple awards both for its crystal clear waters and its cooling quartz sand. This 2/2 impeccably updated condo is on the first floor and water views overlooking...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Casa Van Lopik (J) – In Siesta Village steps to the best beaches!1 / 27
    (17)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Waterfront
    • Balcony
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    • Porch
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2016
    While ratings and reviews are subject to personal taste, we found this property average at best. The positives included a nice size home, 3BR, 2BA, 2 blocks to the beach and...
    Reviewed 4 December 2015
    Our extended family of 7 with 4 adults and 3 children, stayed 4 nights at this property. We were thrilled to see that the grocery store was at the end of the street, as were all...
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    About this property
    Casa Van Lopik (jardin), our garden facing suite, is a large 3BR home. Brought to you by Gertrude Rentals! Perfectly located between the best beaches, shopping dining and entertainment on the island. It was named for our father who was a ships captain and sailed the world for 30 years but always...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village1 / 48
    (8)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 May 2015
    Great location just steps away from beautiful Siesta Beach. Room a little small but fully kitchen and very clean.
    Reviewed 14 September 2014
    I came down to Florida with my boyfriend and two friends and we pulled up and from the outside it doesn't look like very much, but when we stepped inside the building it was...
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    About this property
    Get the best of both locations with this beach property. Located across the street with direct access to Siesta Key beach and just a few blocks from Siesta Key Village. Enter through the front door and step into the large living area of this beach cottage. Bright and sunny seating area, living...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    This Tiny House was built by Tumbleweed. Once you walk thru the door, you know you are at the beach. Eleanor has bright fun colors and very cozy for your week at the beach. She even has a Washer/Dryer combination unit. Comfortably sleeps 3- single bed on the first floor and queen bed in the...
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    Location Information
    Siesta Key, Florida 34231
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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