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Siesta Key Vacation Rentals

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    Travellers to Siesta Key are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    31 Reviews
    2 Bedrooms, Sleeps 8Quick View
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    3 Bedrooms, Sleeps 6Quick View
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    Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath villa is approx. 1000 sq. ft., non-carpeted and has a large living area, dining area, full kitchen, all appliances, screened lanai, and covered parking, central ac/heat, 3 tvs, dvd, free wi-fi in unit!....
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    30 Reviews
    3 Bedrooms, Sleeps 10Quick View
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    • Internet Access
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    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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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    10 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    Newly upgraded ( September 2015 ) with new kitchen, new vanities, newly painted and with the tiles steam cleaned this Siesta Key villa is a gem. It comes with a with a lovely heated community salt water pool and private access to the beautiful white sanded Crescent Beach! Crescent Beach on Siesta...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    • Balcony
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    About this property
    Crescent Beach on the Gulf of Mexico. This beautifully maintained complex is located on the widest part of one of the best beaches on the west coast of Florida. This condo offers a view of the turquoise waters of the Gulf of Mexico. The view is picturesque and the sunsets are magnificent. The...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    7 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    Pet friendly
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    Island House Beach Resort, Crescent Beach, Siesta Key Florida! Direct Gulf Front - Panoramic Views! This beautifully maintained complex is located on the widest part of one of the best beaches in central florida. The condo is 1300 sq. ft. and is located on the 2nd floor.KIng, 2 twins, sleeper. It...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    12 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly upgraded ( September 2015 ) with new kitchen, new vanities, newly painted and with the tiles steam cleaned this Siesta Key villa is a gem. It comes with a with a lovely heated community salt water pool and private access to the beautiful white sanded Crescent Beach! Crescent Beach on Siesta...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    9 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    About this property
    Across the street is our Private Access to one of the BEST beaches - Crescent Beach on Siesta Key.Gulf & Bay Club Bayside is a Resort complex of Key West style Town Homes all with one car attached garages. Gulf & Bay Club Bayside offers:* two heated pools* clubhouse with exercise/workout center and...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Review
    2 Bedrooms, Sleeps 8Quick View
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    Pet friendly
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    About this property
    Sophie’s Cottage is a smart, sophisticated upscale waterfront retreat with a private heated pool with sunshelf, boat dock, and a short walk to Siesta Key Beach. Ideally, it accommodates 6, but can easily sleep up to 8 with 2 private bedrooms, and 2 bathrooms and 2 sleeping areas in the living room...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 6Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Gulf & Bay Club Bayside is a Resort complex of Key West style Town Homes all with one car attached garages. Gulf & Bay Club Bayside offers *two heated pools *clubhouse with exercise/workout center and sauna *two lighted tennis courts *fishing pier *walking paths *picnic areas with Weber gas...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    28 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    Siesta Key, Sarasota upscale vacation rental unit within a few steps of the water or a gorgeous pool. Lush, tropical landscaping in well maintained Bay Oaks. Breathtaking views of the intercoastal with fully appointed fishing dock. Accross the street from the beach and there are no beach charges...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Review
    3 Bedrooms, Sleeps 8Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    #1 Happy Hour on the dock #2 Walk to sunset on Shell Beach #3 Enjoy dinner in the Village!! New listing! Offering low rates to get good reviews to get me started on TripAdvisor, HolidayLettings, FlipKey, etc! Wonderful Siesta Key Duplex - Two separate units, upper and lower. Rent one or both....
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large villa is approx. 1000 sq. ft., non-carpeted, has a large living area, dining area, fully equipped kitchen, all appliances, screened lanai, central ac/heat, and covered parking, 3 tvs, dvd, free wi-fi in unit!. It has a king...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island House Beach Resort- Siesta Key Florida, Crescent Beach - The lovely villa is located on the widest part of Crescent Beach. It is approx. 1000 sq. ft. and is 2 bedrooms, 2 baths. The villa has a large living area, dining area, fully equipped kitchen, all appliances, central ac/heat, screened...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Review
    2 Bedrooms, Sleeps 6Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This wonderfully updated island vacation home has a spacious floor plan. There are tropical views from every window. The beautiful, heated private pool includes a spa and a waterfall. You can open the large patio doors to the screened in lanai that overlooks the pool and bring in the sound of...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, Sleeps 4Quick View
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    • DVD Player
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious 1 bedroom, 1 bathroom, turn key furnished condo at Harbor Towers on Siesta Key. The unit has been totally remodeled, kitchen with granite counter tops, new cabinets, new lighting and stainless steel appliances. Bathroom has new shower and granite counter tops. Ceramic tile flooring...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 4Quick View
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    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Heated)
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    • Air Conditioning
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on the widest part of one of the best beaches in Florida. This condo offers a view of palm trees, white sand and the turquoise waters of the Gulf of Mexico. The view is picturesque and the...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    13 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    • Porch
    • DVD Player
    • Grill
    • Waterfront
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    • Washer
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Siesta Key, Sarasota upscale vacation rental unit with a direct view of the inter-coastal water. Lush, tropical landscaping in well maintained Bay Oaks. Breathtaking view of the inter-coastal with fully appointed fishing dock. Across the street from the beach and there are no beach charges on...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    • Private Outdoor Pool (Heated)
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This luxury apartment is part of Island House Beach Resort, which is located on 280 ft. of the award-winning Crescent Beach in Siesta Key Florida. Island House offers a large heated swimming pool with sun deck, shuffleboard courts, and a recreation room with ping pong, pool & air hockey. This 1300...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    About this property
    So close to the beach, but no gulf-front pricing! Short walk to beach, south village (shops, restaurants, etc.) Your perfect home away from home. Over 1250 s.f. to spread out in. New TVs throughout. Drive into town and see the festivities on Sunday evenings at the Drum Circle on the Public...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    About this property
    2 BR. - 2 BA -- 6 Person Max. -- High Rise -- Bay View 1255 - 606 is a Bayside Midrise unit, located approximately 75 yards away from the Bay. 2 Bedroom / 2 Bath unit. Approx. 1250 Sq. Ft. (1375 including the lanai) Bedding: Master Bedroom: King Guest Bedroom: Queen Electronics:...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Reviews
    1 Bedroom, Sleeps 4Quick View
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    Pet friendly
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    About this property
    Island House Beach Resort - Siesta Key Florida - Southwest building, 3rd floor, One bed, 2 bath, King, 2 twins in den area. This unit is 1300 sq. ft. and has fully equipped kitchen, dining area, living area, 2 porches, laundry room. Enjoy spectacular sunsets from this unit. Free Wi - Fi in unit....
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    1 Review
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    • Satellite TV
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    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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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    17 Reviews
    1 Bedroom, Sleeps 4Quick View
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    • Grill
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    Pet friendly
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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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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Modern Clean, Well Appointed Stand Alone Villa, 2 bdrm-2bath. Private Hi-speed internet, 3 tv's , Whole house DVR, Sleeps 4. Fully equipped kitchen, computer desk in living room, dual recliner leather sofa, Lazyboy reckliner, HD TV with DVR 280 channels and free Starz movies, fee free phone to US,...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    18 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    About this property
    A spacious 2 bedroom 2 bath Townhouse, with a 2 car garage and extra guest parking. Stroll down a private road (about 300 yards) to the #1 Beach in the U,S. You are in the Resorts of of Sara Sea and just a couple of blocks from restaurants, grocery, sports rentals and ice cream ! The Great room...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 6Quick View
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    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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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    • Ocean Views
    • Housekeeping Included
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    About this property
    Our Fisherman's Cove condo description Paradise awaits - GORGEOUS, totally renovated in 2016, two bedroom, beach front condo on the Gulf of Mexico with sunset views overlooking the and sunrise views of the lagoon, expansive water views from every window. Beach was restored so it is large...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Newly remodeled! Beautifully and tastefully decorated in a very simple, clean and modern style. Spacious, second floor 3BR/2BA quiet and private corner unit. King bed in master, 2 Twins in the large guest room and a double sized bed in the small guest room. Comfortably accommodates 6 guests. Washer...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    Our 2000 sq ft beautifully renovated 4 bedroom home features a private pool with patio seating and a new Weber BBQ with cast iron grills. The house has been outfitted with new, transitional solid wood furniture throughout including brand new premium mattresses and pillows in every room. The home...
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    Siesta Key, Florida 34231
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    20 Reviews
    Studio, Sleeps 2Quick View
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    About this property
    This Siesta Key Studio was renovated and refurbished in November 2013 it has all new furnishings throughout and is accompanied by a secluded outside area with table and chairs, BBQ and reclining sun loungers surrounded by tropical plants and foliage. Easy access - no stairs. Fully equipped...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    Over 1600 sq. ft. of spacious living space and ceramic tile throughout; beautifully decorated The living area features a large flat screen TV and DVD player, the kitchen is adorned with granite counter tops and stainless steel appliances. The master bedroom features a king bed a flat screen TV;...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    About this property
    Island House Beach Resort, Siesta Key Florida, Crescent Beach - This lovely unit is approx. 1000 sq. ft. It has 2 bedrooms, 2 baths, large living area, dining area, fully equipped kitchen, all appliances, central ac/heat, 3 tvs, dvd, dedicated, non-shared wi-fi in unit, covered parking, screened...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    Island House Beach Resort- Siesta Key Florida, Crescent Beach- This large 2 bedrooms, 2 bath villa is appox. 1000 sq. ft. It has a large living area, dining area, fully equipped kitchen, all appliances, 60" high def tv in living room, 50" high def in master, dvd, free wi-fi in unit, central...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on one of the best beaches in central Florida. This 3rd floor, 2 bedroom, 2 bath condo offers views of palm trees, white sand and the turquoise waters of the Gulf of Mexico. The view is...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Harbor Towers Condo, Enjoy one of the nicest beaches in the world in style, our condo is located on beautiful Siesta Key, completely furnished, accommodations include an additional pull down murphy bed. This third floor unit is completely furnished with all you need to for a great vacation....
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Located in a quiet family neighborhood just minutes to #1 Beach in the USA Siesta Key beach, shopping, dining, golf courses. This is a 1000 square foot two bedroom, two bath house. It offers a Queen size bed in each bedroom and sofa/bed in the Living room. The kitchen has everything you would need...
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    Siesta Key, Florida 34231
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Look at the fabulous intercoastal waterway view from this spacious 3 bedoom/2 bath bayfront unit! Step out back lanai door to the tropical grounds and bay. Only a few minutes to walk to our own little private piece of world famous Crescent Beach! No need to bring your own beach chairs...we have...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Island Reef is located on beautiful Siesta Key, home of the finest, whitest sand in the world. This is a corner unit. It is serenely situated on the bay side with views of the gulf and bay and overlooks the pool. It is a large and spacious end unit which is elegantly furnished with Thomasville...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    For those who prefer to be above ground level this unit is ideal, a bit above the creatures of earth, high enough to catch the view and located perfectly to observe the comings and goings to and from the beach and pool. Additional amenities include: carpet and tile flooring, 2 twin beds in the...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your vacation in this beautifully renovated two bedroom 1.5 bath condo that sleeps 6. Step into the unit and immediately notice the warm open feel, the beautifully tiled floors and the sweeping panoramic views of an inlet off of the intracoastal waterway. The view goes on for acres and acres...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Reviews
    2 Bedrooms, Sleeps 5Quick View
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    • Satellite TV
    • Private Outdoor Pool (Heated)
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island House Beach Resort! Siesta Key, Florida, Crescent Beach. This large 2 bedrooms, 2 bath unit is appox. 1000 sq. ft., non-carpeted and has a large living area, dining area, fully equipped kitchen, all appliances, screened lanai, and covered parking, 3 tvs, dvd, free wi-fi in unit! The unit has...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Luxury King 1 bedroom condo King Size - Double pillow top bed Ground floor Air conditioning Daily, Weekly, Monthly rates. Everything new 2017 Kitchen Coffee maker Toaster Microwave Stainless Steel fridge with ice maker Adults only 21 Years and over Heated swimming pool Free parking...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    About this property
    Beach front and fabulous! Everything is new and remodeled in this unit! Sun yourself on the open balcony and enjoy this 2 bedroom/2 bath in style. The living room is furnished with a LCD TV/VCR, leather sofa and decorated with brilliant colors! The master bedroom offers a king bed and a flat panel...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Enjoy spectacular views of glorious sunsets over the gulf from the comfortable living room, lanai and master bedroom. This third floor unit has everything you need for your beach vacation including ethernet and wifi internet access. Additional amenities include: sofabed, bathtub in guest bathroom,...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Ocean Views
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    About this property
    *New listing! Amazing direct gulf view from this 4th floor condo. Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. We are right on the beach with lounge chairs provided. As close as you can get to the Gulf without...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Hot Tub
    • Patio
    • Washer
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    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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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    6 Bedrooms, Sleeps 12Quick View
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    About this property
    NEWLY LISTED SIESTA KEY WATERFRONT ESCAPE!!!! Brand New , Gated Residence steps from Siesta Key Beach . Perfect location between the village and crystal sands of Siesta Beach!! Bar's, Restaurants, Shopping, Sport Rentals……..EVERYTHING is within walking distance…..NO CAR NEEDED!!! This brand new...
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    Siesta Key, Florida 34242
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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