We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
TripAdvisor
Siesta Key
Post
Inbox
Search

Siesta Key Luxury Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    C$587 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Travellers to Siesta Key are booking February dates now. Secure your vacation rental today, and have the perfect trip.
    144 Matching Rentals in Siesta KeyView all 961 rentals
    Sort by:
    Price (High to low)
    Sandy Toes Siesta Key Florida  (6796)1 / 40
    (23)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Siesta Key -  2bdrm on the beach - amazing views!!1 / 27
    (32)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check-in Check-out
    Show Prices
    Payment Protection
    Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa1 / 38
    (12)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Siesta Key Beachfront 3 Bedroom Home, Sarasota1 / 46
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 1, 2019
    This was our first experience using trip advisor and would highly recommend it! We stayed at this beautiful home on the beach for a week. Along with the fantastic views, the...
    Reviewed September 29, 2018
    We had a wonderful stay at Siesta Keys Florida. David ‘s home is beautiful and well maintained. It does have several bests of steps if you have any kind of handicap. My husband...
    See all reviews
    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 Gulf & beach. The entire back of this house opens...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    Large Modernized Home a Short Walk to Beach1 / 23
    (3)Average
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Children's Pool
    • Balcony
    • Washer
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 27, 2019
    Myself an my family stayed for a week the house was beautiful nice an clean fully equipped with everything you need
    Reviewed July 9, 2019
    Stayed here for 1 week with 12 people (6 adults, 6 kids)PROS: great location which is 5 blocks to Shell Beach, nice sized pool, spa with screen, covered outdoor area great for...
    See all reviews
    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 appliance and modern furnishings! Separate living areas can accommodate one large family or two smaller ones. Each living area has its own living room, kitchen, 2...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Palm Oasis - Relax in Comfort - 1 rental per calendar month1 / 35
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 17, 2018
    This was a family vacation that had been planned for months. We were unaware of the red tide until a few weeks before leaving for our trip. Not spending any time at what was...
    Reviewed August 6, 2018
    For a large family that has not been on vacation sometime, this was ideal. Walking distance to beach and to village as well as the amazing salt water pool. With 3 children under...
    See all reviews
    About this property
    The Palm Oasis is a 4-bed single family home with 2,000 sq. ft. located only 1 block away from Siesta Key Beach. This home is on one level and has all the amenities including a brand new salt-water pool which is the center of the backyard and a outdoor BBQ grill with a bar to enjoy your fabulous...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    The Treehouse1 / 35
    (1)Terrible
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Washer
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy the relaxed vibe of Siesta Key! The beautiful white sand beaches that make Siesta Key the #1 beach in the US are not even a five-minute stroll away. Siesta Key Village and the famous 3 miles of the softest 99.9% quartz sand beaches draws thousands to enjoy the island life. This two...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Patio
    • Waterfront
    • Ocean Views
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    DIRECTLY ON NUMBER ONE RATED BEACH IN THE USA SIESTA BEACH!!! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. Beachfront home on Siesta Key Sunset Point. Siesta Key Beach is the...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    NEW POOL! 3 Bed 2 Bath on Siesta Key   Walk to beach   POOL  Great location1 / 18
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 15, 2019
    I loved that we were just a 2 block walk from the beach, less than a block from Siesta Key Village filled with restaurants, bars, grocery store, etc. Everyone in the Village was...
    Reviewed March 22, 2017
    This three bedroom two bath house is located on Siesta Key near the South Bridge. It has great beach access near several fun restaurants. The owners were very supportive and...
    See all reviews
    About this property
    SIESTA SUN VILLAS - BRAND NEW POOL! 3 Bed 2 bath home on Siesta Key in Sarasota, FL Sleeps 6 people in beds. We are on the beautiful Island of Siesta Key. Walking distance to the number 1 beach in the USA. Full kitchen with oven, microwave, fridge, freezer, coffee maker & toaster. Large HDTV in...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    The Banyan - A Tropical Retreat in Paradise1 / 25
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 19, 2019
    We loved this house and it was stocked with all the amenities that any renter will need for the beach. We especially loved the screened in porch and the cosy set-up of the house.
    Reviewed April 26, 2018
    The Banyon is a remarkably beautiful and comfortable home. There are many private seating areas inside and out. The kitchen is fully equipped; the beds are very comfortable and...
    See all reviews
    About this property
    View of Roberts Bay / Near Beaches / Great Shopping & Dining Get lost in the intoxicating relaxation of Siesta Key, in this luxurious private home. This tropical retreat is a single-family residence located at the end of a secluded dead end street in the opulent neighborhoods of northern Siesta...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Save time - get the best Siesta Key rentals sent straight to your email!
    Get the List
    Luxury Siesta Key Four Bedroom,Five Bathroom Pool Home,180 Yards to Siesta Beach1 / 23
    (7)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 7, 2019
    Amazing. It's so close to the beautiful beach - just a short stroll across the road and a 10/15min walk to the village shops/restaurants. The property was clean, spacious and...
    Reviewed April 22, 2019
    This beautiful house is just the ticket for a large group. The location is within walking distance of the beach and village. It has a nice sized pool and the porch overlooking...
    See all reviews
    About this property
    This Luxury Four Bedroom plus den with a sleeper sofa bed has Four and a Half Bathrooms and 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...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    Sunset Point Siesta Key FL  AWESOME RENTAL !!1 / 27
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Sauna
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 5, 2017
    Could not have a better location. Steps from the sand with the village in walking distance. The beach house is a great place to stay. Everything you need. We very much enjoyed...
    Reviewed July 7, 2017
    This location is absolutely perfect! It is on the most beautiful beach and steps to an adorable village with several restaurants, shops and all the amenities you could need. It...
    See all reviews
    About this property
    Beach and water front on Gulf Of Mexico. A block from Siesta Key Village for lite and fine dinning, fun, shopping and nightlife. Two Master Suite King Bedrooms with Master Bath for each. Sauna, four Mexican tiled decks with panoramic views of the Gulf and beaches. Fishing Pier. Leather, stone...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Exceptional townhouse - Royal Palm Suite - with Gulf Views from all 3 balconies1 / 31
    (24)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 13, 2017
    Great fit for small or large group with two bedrooms and a third semi-private on the top floor with its own balcony. There is a balcony on each of the three levels and all have...
    Reviewed March 30, 2014
    Six of us, ages 7-70, stayed in the Royal Palm Suite, #662 of Gumbo Limbo for 1 week during Spring break. The house is clean, comfortable, has lots of space and views of the...
    See all reviews
    About this property
    The Royal Palm Suite (sleeps 6) is a 3 bedroom luxury townhouse of 1,850 sq/feet over 3 floors, 2 kings and 1 queen size bed, 3 balconies (each has a Gulf View), almost all rooms have a Gulf view, a kitchen with granite counter tops, master bathroom offers a bathtub with Gulf view and a bidet....
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Gorgeous Views of the Gulf Sea Turtle Unit Sunset Beach Resort1 / 24
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Grill
    • Central Heating
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 6, 2019
    The condo was great. Chelly and Shelia were very good to work with. The views from the front window and patio are amazing. The condo was impeccably clean and has been...
    Reviewed July 19, 2018
    This is an amazing location. If you want to step out of your room on to Siesta Key sand this is the spot! We enjoyed our weekend getaway and will definitely be back!
    See all reviews
    About this property
    Directly overlooking the gulf, this designer decorated unit is literally steps to Siesta Beach. This unit has 3 bedrooms each with a queen bed, and couch set up can accommodate 2 and 2 full baths. Open plan living and dining area with spectacular views of the beach. Full size kitchen with...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    The Henry1 / 47
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 29, 2019
    Have you ever been to a place that just feels right? A place where you don’t want to leave and can’t wait to come back again on Siesta Beach? A place where you dream of going...
    See all reviews
    About this property
    The Property Live your travel lifestyle in the luxury stylings of The Henry. This one of a kind private accommodation on Siesta Key, features immaculate hand-picked designer furnishings staged to maximize the comfort, utility, and aesthetic appeal of each living space. From playing cards in the...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for a private home on Siesta Key that's only 460 feet from the Siesta Key Beach Access; then this is your vacation home to come to! It rests on a quiet street in a beautiful upscale neighborhood on Siesta Key just steps from playing in the sand with your kids, or reading a...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Luxury Village Townhouse w/ Gulf and Beach Views1 / 28
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Terrace
    • Washer
    • Balcony
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gorgeous townhouse is located 2 short blocks from Siesta Key Village and a block from the white sands of Siesta Key Beach. VIew the gorgeous sunset and Gulf and beach views from the Master Bedroom on the top level. This unit is immaculately appointed and will make your Siesta Key Vacation...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Patio
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Bedroom Beachfront Pool Home. Closest house to the beach on Siesta Key! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. Siesta Key Paradise is nestled within walking distance of...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Siesta Key private beach access1 / 51
    (35)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Balcony
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 8, 2018
    This place was very well kept, clean and plenty of supplies for the beach and pool as well as fully stocked kitchen for cooking and serving. The accommodations were perfect for...
    Reviewed January 10, 2018
    This well appointed, spacious townhouse is a short walk to the spectacular Crescent Beach. The townhouse is well appointed with EVERYTHING you could possibly need. It had...
    See all reviews
    About this property
    Beachside, spacious 3 bedroom, 2500 square foot, beach townhouse located among the resort community of Sara Sea Circle with direct, private beach access to the world famous (rated #1 in USA) Crescent and Siesta Key Beaches. The Sara Sea Circle community includes a large heated pool, sand...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Sauna
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Grill
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A wonderful 2-bedroom/2-bath fully appointed condo nestled into a the only true resort on Siesta Key. Enjoy the state of the art fitness center, saunas/spas, 3 heated swimming pools, 8 tennis courts (2 converted for pickleball), shuffleboard, basketball/racquetball, tiki huts, grilling areas, 2...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Washer
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this 4 bedroom/4 bath, 1st and 2nd floor Siesta Village Duplex located just half a block away from Siesta Key Village which offers many great restaurants/bars and plenty of wonderful 'beach shopping' for everyone! Only 2 blocks away from our powdery white sandy beach that Siesta Key is world...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    6 Bedroom 4 Bathroom house   New pool  Siesta Key Florida  Walk to the Beach1 / 32
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 12, 2017
    Excellent all-around. Owner was very responsive and friendly. House was clean and in great condition upon arrival, and even bigger than expected! To top it all off, it was...
    See all reviews
    About this property
    Siesta Sun Villa Our home is one large house that has a 3 bed 2 bath unit. A 2 bed 1 bath unit and a 1 bed 1 bath unit. All with connecting doors so you can rent the whole house to sleep 12 guests all in beds. It is perfect for large familys, Weddings and reunions. Private back yard, Overlooking a...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Terrace
    • Washer
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Ocean Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will have a visit to remember in this elegant three bedroom, two and one half bath vacation condo with a path to the famous Siesta Key white sand beaches just out your door! Two levels with tiles lanais and Gulf views from each level. Enjoy the amazing Gulf Coast sunsets right from your own...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Siesta Key Oceanfront on Gulf with western sunsets,  1250 sq ft Townhome1 / 15
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Ocean Views
    • Grill
    • Washer
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gorgeous updated townhouse located right on the Gulf of Mexico’s Big Sarasota Pass with spectacular western views that can be filled with amazing sunsets, fishing boats, dolphins, and more. Great location for fishing or viewing off the community’s private dock. Waterfront views from master bedroom...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    New 6 Bedroom, Luxury Home in Gated Community1 / 22
    (1)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Waterfront
    • Air Conditioning
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 9, 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...
    See all reviews
    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...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Siesta Key’s only luxury hotel. Sitting directly on Siesta’s Quartz Beach that offers the whitest and softest sand in the World that’s always cool to the touch. Relax and make your memories is all that’s required but just minutes to down town’s rich art and cultural community. In the village of...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Beach, Village, Dock, Private Heated Pool... Fantastic Location, No Car Needed!1 / 45
    (6)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Housekeeping Included
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 8, 2019
    My family of four recently stayed at Rad’s Cozy Cottage on Canal. It’s a completely updated ranch style house within close walking distance to both the Village and the beach...
    Reviewed March 18, 2019
    This is a fabulously decorated beachy feel cottage. Beautifully renovated indoor lay out. Updated, stainless steel kitchen with huge island buffet. Located minutes (walking...
    See all reviews
    About this property
    HERE IT IS! This “one of a kind” property is uniquely situated between the beach, canal, village with a private heated pool & dock, one of the best spots on Siesta Key! This charming 1,500 sq. ft. cottage beach home is being offered for the 1st time. If you want a cute, private original bungalow...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Hot Tub
    • Ocean Views
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just across the street from the #1 Beach in the USA!! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. Stunning Three Bedroom Two Bath with Private Pool and jacuzzi on Siesta...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Sauna
    • Cable/satellite TV
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this fabulous 3 bedroom end unit with a direct view from your lanai and living room at the beautiful evening sunsets. This unit has 2 very well furnished enclosed lanais for eating or for lounging with sliding windows for the nice evening gulf breezes. Also for your needs, it is Wi-Fi...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Grill
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and get a slice of heaven in this 3 bedroom penthouse corner unit. The view of the beautiful#1 rated Siesta Key beach on the Gulf of Mexico is nothing less than Spectacular!!! The open floor plan is very spacious and comfortable; it is tastefully decorated and has all the amenities you would...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Small family owned resort that spares nothing to make your vacation one you will remember and want to repeat year after year! We pride ourselves in the details and personalized attention! Views of the gulf can't be beat from this second floor 2 bedroom, 2 bath plus den, beach front unit. Designer...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Washer
    • Patio
    • Ocean Views
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE BEST BEACH HOUSE SIESTA HAS EVER OFFERED, GUARANTEED!! DIRECT GULF FRONT! Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and 7-day week office(s) for your convenience and guest needs. When you dream of a Beach House that sits on the whitest & most soft sand in the...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A wonderful 2-bedroom/2-bath fully appointed condo nestled into a the only true resort on Siesta Key. Enjoy the state of the art fitness center, saunas/spas, 3 heated swimming pools, 8 tennis courts (2 converted for pickleball), shuffleboard, basketball/racquetball, tiki huts, grilling areas, 2...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    636ontheKey - The 'Belle of the Beach'1 / 15
    (7)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Air Conditioning
    • Ocean Views
    • Washer
    • Internet Access
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4,000 SQ FT BEACHFRONT HOME 1/2 mile from Village! 4 Bedroom + Media Room - 5 Bathroom - Sleeps up to 14 and is ON THE BEACH!!! NOTE: Our home is NOT listed on Craig's List. If it is represented there it is fraudulent. Located directly on the beautiful white sands of Siesta Beach! 636...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to your own secluded tropical oasis. Lush island landscaping surrounding the property makes this home a unique and private setting. Private dock on protected cove 2 minutes from Sarasota Bay/ICW. Rent a boat at neighboring marina if you choose. Breathtaking large private pool, with numerous...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Attention serious beach lovers.. paradise has been found at the shores of World-Famous Crescent Beach. Located gulf-side this phenomenal sun-filled ground floor two bedroom vacation home is a treasured jewel located in the highly- sought after private street on Sara Sea Circle. Surrounded within...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Grill
    • Washer
    • Patio
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEWLY CONSTRUCTED MODERN/CONTEMPORARY - SIESTA KEY BEACH RESIDENCE; a must-see, rare new construction on Siesta Key, much sought after modern and contemporary design, 4 Bedrooms/6 Bathrooms-Sleeps 12. Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your vacation in this beautifully decorated beachfront 3 story 4 bed/3.5 bath townhouse! The sparkling blue water and white sand of Crescent Beach is just steps away. The first floor has a full size living room with a TV,DVD,VCR; two bedrooms...one with a queen bed and one with 2 twin beds...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Washer
    • Sauna
    • Internet Access
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautifully updated 2-bedroom/2-bath fully appointed condo nestled into a the only true resort on Siesta Key. Enjoy the state of the art fitness center, saunas/spas, 3 heated swimming pools, 8 tennis courts (2 converted for pickleball), shuffleboard, basketball/racquetball, tiki huts, grilling...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Three bedroom house directly on beach with gulf vi1 / 22
    (2)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Ocean Views
    • DVD Player
    • Waterfront
    • Patio
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We have a 2 week minimum rental period. Tiffany Sands is a group of 9 townhouses directly on Crescent Beach. Our beach house is a stand alone unit(unattached). We have gulf views with 2 decks facing the Gulf of Mexico. It is a spacious 1,800 sq. ft. and newly decorated with a fully appointed...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gorgeous 3 Bedroom/ 2 Bath home located near Siesta Key Village! Offering a beautiful new swimming pool, and just 1 block to the beach! This home offers all the comforts of home, with a large updated kitchen, granite countertops, new bathrooms with quartz vanities! Book your vacation getaway today,...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in luxury while vacationing at the Crescent. This high end gated property offers a garden terrace with poolside seating and fireplace, state of the art fitness center, and it is beachfront with direct beach access where lounge chairs are provided beach side. Crescent is located near the...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Lovely Siesta Key 3BR 2.5BA Condo, Island Paradise1 / 23
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Sauna
    • Parking
    • Internet Access
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 22, 2017
    Perfect location! The pool and beach are within walking distance and downtown Siesta Key is a 5 minute drive or Uber ride away. Close to downtown Sarasota and St. Armond's...
    See all reviews
    About this property
    Beautiful Siesta Key Condo at Peppertree Bay. Gulfside unit just a 2 minute walk to the beach and pool. Crescent Beach was voted #1 most beautiful beach in Florida on Travel Channel. You will never run out of exciting things to do! Fishing, exercise room and Tennis Courts on site. Or just...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BRIGHT, AIRY PENTHOUSE. SLEEPS 6 As you awaken in the morning, open the curtains over your 'wall of glass' in your large master bedroom equipped with king-size bed, FIOS television, new Caribbean-styled furnishings, en suite bath with shower, secured Wi-Fi internet access throughout and unlimited...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Grill
    • Washer
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As you awaken in the morning, open the curtains to your large, carpeted master bedroom equipped with king-size bed, FIOS-television, new Caribbean-styled furnishings, en suite bath with shower, massive closet, high speed Wi-Fi internet access throughout and unlimited domestic calling land-line...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated upper-level home has been meticulously updated and appointed to highlight its open layout and airy entertaining space. A vacation-ready Siesta Key pool & canal residence, the house is elevated on a corner waterfront lot in a prime, quiet neighborhood minutes from the beach....
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A one-of-a-kind beachfront, 2 Bedroom/2 Bath, ground level villa, located ON Crescent Beach in Siesta Key, Florida- with 'The World's Finest, Whitest Sand'. Want to take a quick walk in the surf? Kids want to play in the sand, but you want to relax on the lanai? Since the house is directly on the...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Sauna
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully updated and furnished property with everything you would expect from a resort on Siesta Key. Enjoy the finest beach in America, visit one on the 3 swimming pools on site, get in a workout at state of the art fitness facility, play a game of tennis or pickleball or just relax in this...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Grill
    • Washer
    • Sauna
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unit has had a total remodel and is also Handicap Friendly. The Living Room has been extended to include the Lanai which does have sliding windows to allow you to enjoy the evening or daytime breezes off of the Gulf. Your view is tremendous of the Gulf and also of G&B's lovely courtyard. This...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • Internet Access
    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unit has an exceptional direct 'sunset view' right from your screened lanai and will take your breath away. Unit is newly painted, carpeted and furnished with a tropical flare that affords many comforts. There is a King bed in the Master with 2 Twin beds in the Guest bedroom, eat-in kitchen...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1
    List your property
    Owner log in