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Holiday Rentals in Siesta Key, FL

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    ₹ 12,016 Average
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    Travellers to Siesta Key are booking April dates now. Secure your holiday home today, and have the perfect trip.
    1 / 24
    5 of 5 bubbles (41) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 28
    Studio, 4 Bathrooms, Sleeps 9 | Quick View
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    1 / 25
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 24
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    Crescent Cottage Welcome to our beautiful and serene vacation home! A gorgeous beach cottage in a dream destination, Crescent Cottage offers a fun-filled activity-packed vacation plan with all of its great amenities, awesome location so close to the beach, and a spacious abode designed around the... View all property information
    Location Information
    Siesta Key, Florida
    1 / 17
    5 of 5 bubbles (9) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This luxurious one story townhouse was newly renovated and has its own private access to the #1 beach in the US merely steps away from the front door. It boasts all the luxury you'd expect from a beach house! Modern kitchen, contemporary bathroom with walk in rain shower, luxurious bedroom and... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 4 February 2017
    Very impressive space and proximity to everything that was important to me. I felt welcomed from the first moment I entered this beautifully appointed beach condo. Steps away are...
    5 of 5 bubbles Reviewed 5 November 2016
    Very well located property. Fixtures and fittings of a high standard. Near all amenities. Definitely to be recommended
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    1 / 32
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    Villa Champagne Welcome to “Villa Champagne”, one of the most fabulous vacation homes in Siesta Key. It’s also one of the most popular favorites among our many guest families. The magic begins as you enter the foyer of this beautiful villa and gaze across the expansive living area, then further out... View all property information
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    Siesta Key, Florida
    1 / 24
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    I have tried to make this apartment as comfortable as your own home only at the beach. This unit has two bedrooms and two baths. It can accommodate six people with a king bed and two double beds. There are plenty of closet and dresser space, a fully-equipped kitchen, color TV's, VCR and/or DVD and... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 28 January 2017
    The condo was everything and more in ad. Very close to the beach. I plan on booking again next year. Rooms were spacious, bedding was comfortable and the kitchen was was awesome...
    5 of 5 bubbles Reviewed 9 August 2016
    This condo was very nice. Steps away from the gorgeous white sandy beach and convenient to shopping and restaurants. We were very impressed with not only the condition of the...
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    1 / 30
    5 of 5 bubbles (11) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • DVD Player
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    • Pet-friendly
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    About this property
    “Pristine sand, blue skies - 'Number 1 Beach'” <BR><BR>The Best Thing to Come Home to after a Day on the Beach Is...<BR> ...a vacation home as comfortable as your own home. <BR><BR>Just a walk across the street to Siesta Key's world famous #1 Beach.<BR><BR> This split-level townhouse, has 2... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 1 week ago
    This is our second year at Our House At the Beach, and we've already booked next year! Siesta Key is rightly called the best beach in the US (and that's being said by a...
    5 of 5 bubbles Reviewed 1 January 2016
    I found this condo on trip advisor when I was researching places to stay in Siesta Key and we couldn't have been happier with our accommodations. My three kids and I spent our...
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    1 / 23
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Casita Coco Welcome to Casita Coco! Sleeps 4: K, SS The units [Casita Bayou & Casita Coco] are rented separately. If combined, these units are called: Coconut Bayou Cottage (Sleeps 10) If one unit is not available, please contact us for the availability of another comparable unit! Casita Coco is... View all property information
    Location Information
    Siesta Key, Florida
    1 / 31
    4.5 of 5 bubbles (11) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    About this property
    Welcome ! Sea Club II is Located steps away from the whitest sand and the # 1 beach in America, Siesta Key. Our location 200 yards away has an easement for private beach access. We are located on the intercoastal waterway of Little Sarasota Bay on the island of Siesta Key . Whether you are keen... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 2 February 2017
    Thank you for allowing me to rent your beach themed condo. It was more than my expectations. Newly remodeled and furnished. The backyard is flat and offers lots of chaise...
    5 of 5 bubbles Reviewed 30 August 2016
    Thank you so much for the chance to stay in your condo. It was clean and had everything we needed for our 5 day stay. Siesta Key is a beautiful beach and we can't wait to...
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    1 / 40
    4.5 of 5 bubbles (5) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Washer
    • Wi-Fi
    • Balcony
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    • Satellite TV
    • Waterfront
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    • Pet-friendly
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    About this property
    Leave your worries behind... If you're looking for a relaxing beachfront condo that's been totally remodeled you've come to the right place. Our ground-level oceanfront condo is the perfect place to unwind unplug and recharge the batteries. Fisherman's Cove is a quiet and relaxed complex on the... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 5 September 2016
    If you are an avid beach goer, you're average rental experience probably includes lifting and lugging a million beach accessories and toys (if you have kids) for what seems like a...
    5 of 5 bubbles Reviewed 16 August 2016
    This unit is literally 200 steps to the water. Fantastic ocean front appeal and it had literally the best master suite mattress that we've had in years for a vacation property...
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    1 / 25
    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Patio
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Sauna
    • Washer
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    5 of 5 bubbles Reviewed 6 January 2016
    THE best spot in the US to see the sunset over the Gulf of Mexico! A starting point for a long beach walk on Siesta Key's white sands as it is just steps to the beach. A short...
    5 of 5 bubbles Reviewed 7 April 2015
    This beautiful beach home had everything you needed to make your stay very enjoyable. Very clean,loved the beautiful view every morning.Enjoyed the shopping and the walks to the...
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    1 / 24
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
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    • Grill
    • Ocean Views
    • Parking
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    If you are looking for the perfect spot for a family vacation, to escape the cold and snow, or a quiet romantic getaway this is the place for you. Recently updated throughout, this 2 bedroom 2 bath condo sleeps 6 comfortably all in real beds. Just outside your door is Crescent Beach, consistently... View all property information
    Location Information
    Siesta Key, Florida 34243
    5 of 5 bubbles Reviewed 20 February 2017
    Don't expect a big ocean view, but this condo on the beach ( it's at a 90 degree angle) is a lovely place to stay. Our unit, 207, had virtually no view and a tiny balcony, but...
    5 of 5 bubbles Reviewed 25 May 2016
    The property is ideally located - i.e on the beach. The owner was extremely friendly and checked a couple of times to make sure that we had everything we needed. The condo has...
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    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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    About this property
    2 bedroom, 2 bathroom on 4th floor, lovely view...<BR><BR>Enjoy the best that beautiful Bay Oaks has to offer. This 4th floor corner condo has been remodeled. With 1101 square feet, this 2BR/2BA condo has a living room, dining room, kitchen and screened lanai where you can enjoy morning coffee or... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 26
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    About this property
    Casita Sol Welcome to Casita Sol of Sol y Mar. This COMPLETELY RENOVATED, single level (2 Bedroom / 1 Bathroom - Master BR/1 Queen & 2nd BR/2 twins -sleeps 4) vacation home features private, gated beach access, a sparkling clean hot tub in a private, lush setting, a communal heated swimming pool... View all property information
    Location Information
    Siesta Key, Florida
    1 / 31
    3.5 of 5 bubbles (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Great first impressions are evident from the moment you enter this lovely condo and enjoy the breathtaking ocean views from our private oversized lanai. We know you'll adore our comfortably decorated oceanfront condo and have the relaxing vacation you've been dreaming of. This unit unfolds as you... View all property information
    Location Information
    Siesta Key, Florida 34242
    3 of 5 bubbles Reviewed 12 February 2017
    This condo is just feet away from waves slapping against the shore. It is well stocked with everything you would need while vacationing. It could use a deep cleaning, But...
    4 of 5 bubbles Reviewed 31 January 2017
    Great week in Siesta Key as always! Thanks! Will visit again in the near future. Would definitely recommend the Key!
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    1 / 24
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    Seaside Cottage Welcome to Seaside Cottage! This lovely and rare 4 bedroom 3 bathroom heated pool home has just gone under extensive renovation, leaving a spectacular beach vacation home that rivals most on Siesta Key! Completed in November 2015, our guests will now enjoy the luxury of a brand new... View all property information
    Location Information
    Siesta Key, Florida
    1 / 23
    Studio, 4 Bathrooms, Sleeps 12 | Quick View
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    Topsail Cottage Welcome to Topsail! Our newly constructed luxury cottage has all the amenities your group [up to 12] can fathom. Inside you’ll enjoy travertine flooring throughout the entire three-story building, garden soaking tub in the master, new appliances, oversized washer/dryer, granite... View all property information
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    Siesta Key, Florida
    1 / 21
    5 of 5 bubbles (5) Excellent
    Studio, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Villa Palma is a stand-alone single story villa located in the beautiful Polynesian Gardens community, on the beautiful barrier island of Siesta Key, Fl. The home is chic and hip in its mid-century modern beach cottage decor and style. The newly renovated kitchen is sleek in design and... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 8 November 2016
    We had a great time at Villa Palma. The villa is very clean and it has everything you need for your stay. It is very close to the beach, we ended up only going to the beach. The...
    5 of 5 bubbles Reviewed 11 August 2016
    What a LOVELY place to stay!!! Sean was flexible, attentive and accommodating, and there was even fresh fruit, sparkling water and a personalized welcome sign waiting on the...
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    1 / 27
    4.5 of 5 bubbles (19) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    About this property
    AVAILABLE After April 16th, 2017 GOING FAST-BOOK NOW! SUMMER SPECIALS - BOOK NOW! One Bedroom with TWO (2) BATHROOMS! PRIVACY of-- 2ND floor END unit! No one walking past door all day and night!! TWO (2) OUTDOOR common areas -BALCONY for morning... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 bubbles Reviewed 4 days ago
    This unit is located just south of Highway 72 on Midnight Pass Road. It's walking distance to some nice restaurants and shopping. The condo itself is located on the second floor...
    5 of 5 bubbles Reviewed 9 February 2017
    The location of the condo couldn't be more convenient--near the beach, with restaurants (don't miss the one offering German food and bakery), a drug store, a grocery story, and...
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    1 / 42
    3 of 5 bubbles (2) Average
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    • Porch
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    • Pet-friendly
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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... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 bubbles Reviewed 23 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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    1 / 39
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Playa y Blanca Welcome to Playa y Blanca. This COMPLETELY RENOVATED, single level and uniquely configured (4 BR/2BA - 2 Master BR/1 Queen each & 2 2nd BR/2 twins each-sleeps 8) vacation home [Casita Blanca and Casita Playa] has 2 kitchens and 2 living areas, the perfect arrangement for families or... View all property information
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    Siesta Key, Florida
    1 / 24
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Pelicans Perch Welcome to Pelicans Perch! Please Note: Sleeps 6 (K,K, AB) This unit is on the 2nd floor, with elevator access. If this unit is not available, please contact us for the availability of another comparable unit! Located on the south end of Siesta Key near Point of Rocks Beach, this... View all property information
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    Siesta Key, Florida
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Just across the street from sun kissed Siesta Beach, acclaimed as the Number One Beach in the United States. Noted for “The Whitest sand in the world”, set your sites for your next vacation at Our House At the Beach! Enjoy spectacular sunsets and Gulf views from 2 over-sized balconies in this... View all property information
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    Siesta Key, Florida 34242
    1 / 14
    5 of 5 bubbles (17) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
    • Smoking allowed
    • x
    About this property
    Newly furnished, newly renovated 2BR (one king size & 2 single beds) + convertible sofa bed, 2 Bathrooms 2nd floor condo (sleeps 4-6), and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings, our air-conditioned condo offers two... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 31 January 2017
    Everything about this condo was fantastic! The beautiful two bedroom/ two bathroom, spacious, quiet, the large swimming pool and two gas grills which we used often, we will...
    5 of 5 bubbles Reviewed 28 June 2016
    This place is as good as the previous reviews say it is. It has everything you need from pool floats to beach chairs to blow dryers to bicycles, dishwashing soap to laundry soap...
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    1 / 24
    5 of 5 bubbles (1) Excellent
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Juicy Mango Cabana Welcome to the Juicy Mango Cabana! This beautiful and vibrant 2 bedroom, 2 bathroom vacation home accommodates up to 6 people. This property is very unique as it is one half of "Mango Manor," which is comprised of the two separate cabanas, Juicy and Honey Mango. This provides a... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 bubbles Reviewed 11 February 2017
    We have a duplex house with a heated swimming pool within two blocks of the beach and four blocks of the causeway between Siesta Key and Sarasota where there is also a small mall...
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    1 / 12
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Jamaica Royale condo #92 on the #1 beach in the USA, This 2 bedroom 2 bath garden view unit is located in the garden area of our beautifully landscaped property. This unit is on the first floor and reserved parking is right outside the front door. This unit has a full size washer and dryer for... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 29 December 2014
    Just returned from our first trip to Siesta Key. Had my wife and two adult sons with us. Unit was very clean and ready upon our arrival. Beds were extremely comfortable...
    5 of 5 bubbles Reviewed 11 May 2014
    My husband and I stayed here with our five children. This place was perfect for us. It was clean and comfortable. I was surprised to find every single thing I needed in the...
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    1 / 23
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The Home Enjoy the luxury and amenities of Siesta Key from the comfort of your own private villa. Exquisitely decorated, encompassing the ambiance and excitement of Siesta Key, the Great Blue Heron provides you with all the luxuries and comforts you will need for the perfect beach getaway.... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 24
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Villa Vista Mare Welcome to Villa Vista Mare! This beautiful and luxurious 3 bedroom, 3 bathroom, heated pool, townhome boasts the best views of the world famous No. 1 Siesta Key Beach Access! With absolutely unobstructed views, this home is part of only a handful of private residences that can... View all property information
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    Siesta Key, Florida
    1 / 25
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Sol y Mar Welcome to Sol y Mar. This COMPLETELY RENOVATED, single level and uniquely configured (4 BR/2BA - 2 Master BR/1 Queen each & 2-2nd BR's w/2 twins each-sleeps 8) vacation home [Casita Mar and Casita Sol] has 2 kitchens and 2 living areas, the perfect arrangement for families or groups that... View all property information
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    Siesta Key, Florida
    1 / 17
    5 of 5 bubbles (3) Excellent
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    Island House Beach Resort, Siesta key, Crescent Beach!New improvements in 2014! 60" tv and entertainment center ( netflix reaady), new ac unit, new dishwasher and ceiling fans in bedrooms. Professionally decorated in October 2011. This large 2 bedrooms, 2 bath unit is approx 1000 sq. ft. It has a... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 11 May 2014
    A wonderful place to stay! Clean and updated. King bed was very comfortable. Problems with the wifi is my only complaint. Wifi is available, but not dependable. Couldn't...
    5 of 5 bubbles Reviewed 24 June 2014
    Our stay was fantastic, very clean, quiet ... the spectacular beaches, pool spotlessly clean condo. We were in town .. 39 is very comfortable and cozy, had everything we needed...
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    1 / 24
    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    - Expansive, panoramic gulf view from every room of this 6th floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the beach with lounge chairs provided. As close as you can get to the Gulf without... View all property information
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    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 3 weeks ago
    We really enjoyed our stay. The unit has been thoughtfully equipped with dishes, containers and beach items. The space was perfect for my husband and I to share with another...
    5 of 5 bubbles Reviewed 13 February 2017
    Second time we have stayed in this unit. Perfect for us and everything continues to be first class. Unit is well appointed and VERY clean. Impressed with the new carports...
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    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
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    Siesta Key, Florida 34242
    1 / 19
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Siesta Key Vacation Condo all new, and an easy walk over to the #1 Beach in America. Complex has Pool, Covered Parking, Clubhouse, Marina. Two Bedrooms, Two full Bathrooms, Completely renovated Kitchen, all new Tile flooring throughout Condo, back Lanai catches glimpse of Sunsets, and front... View all property information
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    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 28 August 2016
    we stayed here in mid July 2016, Sue was very helpful on answering all my questions and I had a few .she's a very nice professional lady and that makes easier to communicate .the...
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    1 / 17
    5 of 5 bubbles (1) Excellent
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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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, central ac/heat, covered parking, screened lanai, free wi-fi in unit! The unit is non-carpeted... View all property information
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    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 5 February 2012
    If you like a beach vacation this is the place. It is rated one of the 10 best beaches in the WORLD! This is my second stay and you have to experience it yourself to really grasp...
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    1 / 22
    4.5 of 5 bubbles (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    LAST MINUTE DEALS NOW AVAILABLE AUGUST - JANUARY at our luxurious Villa#4 (on Crystal Sands, 6300 Midnight Pass Rd, Sarasota, Florida) - sleeps 6 and includes everything your family needs for your stay at the #1 beach in the USA. This Villa has easy access to the beach without leaving the property... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 bubbles Reviewed 7 September 2016
    The two bedroom cottage is nice. Not luxury, but absolutely adequate. The beach is spectacular. The biggest drawback from the rental was the lack of any sort of outdoor...
    4 of 5 bubbles Reviewed 30 November 2015
    Villa was nice. It had all of the amenities needed for a comfortable stay. It was clean. It was only a short walk to the beach. It was close to town center.
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    1 / 25
    4.5 of 5 bubbles (29) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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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... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 bubbles Reviewed 25 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...
    5 of 5 bubbles Reviewed 18 July 2016
    We had 10 people in our group and this cute house perfectly fit us all! It was in the prime location for the beach, restaurants, and beach bars. Daniel was amazing to work with...
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    1 / 19
    5 of 5 bubbles (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    This vacation rental offers a full view of Siesta Key Beach/ The Gulf upon entry; relax and enjoy from your lanai or master bedroom. The property has been newly transformed to accommodate our guests best welcome to Siesta. From the comfort of the home décor to your fully stocked kitchen: cookware,... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 2 weeks ago
    The lanai was our favorite space because of the wide view of the beach and ocean. We even saw dolphins during breakfast one day and twice at lunch time!!! With the beach being...
    5 of 5 bubbles Reviewed 6 March 2015
    What an awesome condo. Unit was furnished beautifully and very up to date. Couldn't have has asked for more. Location was great. Great views of the ocean and less than 20 minute...
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    1 / 19
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Jamaica Royale Condominiums are located directly on the Gulf of Mexico along the white sands of world-famous Siesta Key Beach in Sarasota, Florida. A barrier island on Florida’s West coast, considered the most beautiful of Florida’s barrier islands, Siesta Key’s beach boasts “the world’s finest... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 3 weeks ago
    Truly awesome experience. Quiet garden sid. A home away from home. Nice sheets & new towels. Everything we needed. Very responsive & helpful owner Beach side, 3 pools, helpful...
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    1 / 17
    5 of 5 bubbles (4) Excellent
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath unit is non-carpeted and 1000 sq. ft. It has a large living area, fully equipped kitchen, all appliances, central heat/ac, High Definition Tv, 3 dvds, free wi-fi in unit, covered parking. The unit has a... View all property information
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    Siesta Key, Florida 34242
    1 / 19
    5 of 5 bubbles (7) Excellent
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    GULF FRONT - GROUND FLOOR UNIT!! This spectacular 2 bedrooms, 2 baths unit is 1300 sq. ft. as is located on Crescent Beach. This condo offers a view of palm trees, white sand and turquoise waters of the Gulf of Mexico.Fully equipped kitchen, all appliances. The unit has a king size bed and 2 twins.... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 3 June 2012
    What a great place. It has a wonderful view, great updates, everything you need to entertain, prepare meals, etc. The patio is comfortable with such a nice breeze. The beds...
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    1 / 15
    5 of 5 bubbles (2) Excellent
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Island House Beach Resort! Newly remodeled!! Crescent Beach, Siesta Key Florida! This attractive complex is located on the widest part of one of the best beaches in central florida. This condo is 1300 sq. ft, non-carpeted and is located on the 4th floor. It is 2 bedrooms, 2 baths, King, 2 twins,... View all property information
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    Siesta Key, Florida 34242
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Turtle beach was just re-nourished in March 2016!! Come enjoy the great new beach at Fisherman's Cove! Leave your worries behind... If you're looking for a relaxing beachfront condo that's been totally remodeled you've come to the right place. (all new photos -just uploaded!) Our ground-level... View all property information
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    Siesta Key, Florida 34242
    1 / 29
    5 of 5 bubbles (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    About this property
    Spacious Condo on Siesta Key is so centrally located you won't even need a car! 800 square feet, renovated, new, and super clean! King Bed in Bedroom and Sleeper sofa in living room provides 2 separate bed options with spacious closets ready for your things! Screened Lanai (porch). Central AC and... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles 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!
    5 of 5 bubbles Reviewed 9 June 2016
    Sue B was very helpful leading up to my visit, going out of her way to make sure that I had everything I needed on arrival. The condo was exactly as described, very clean, very...
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    1 / 18
    5 of 5 bubbles (4) Excellent
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Island House Beach Resort - Crescent Beach, Siesta Key Florida. 2nd Floor unit, 2 bedrooms, 2 baths. This beautifully maintained complex is located on 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... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 3 August 2012
    4S was an awesome apartment/condo. It was on the second floor right off the beach . Very clean and stocked with everything you can think of that you would need to stay for a...
    5 of 5 bubbles Reviewed 13 June 2012
    I had an impossible time finding a beachfront condo to rent for just two nights. We would have loved to stay a week but we didn't have the time this trip. All I got from other...
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    1 / 18
    5 of 5 bubbles (10) Excellent
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Island House Beach Resort!!Ground Floor, Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on the widest part of one of the best beaches in central florida. This condo offers views of palm trees, white sand and the crystal blue waters of the Gulf of Mexico. The view... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 5 September 2012
    It was like I was in paradise! Literally steps away from the soft white sand and clear ocean. Very well kept apartment area. This unit was perfect because you could walk out right...
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    1 / 41
    5 of 5 bubbles (58) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
    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.... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 12 January 2017
    Look no further for THE perfect vacation property! We rented this property for grandparents/parents/grandchildren and I don't know who had the most fun! The location is ideal...
    5 of 5 bubbles Reviewed 17 November 2016
    Awesome home for our family of 8. There was a major housekeeping problem, but the owner took care of it immediately. We would definitely stay here again!!
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    1 / 21
    5 of 5 bubbles (1) Excellent
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Island House Beach Resort - Siesta Key Florida - Crescent Beach. This beautifully maintained complex is located on the widest part of one of the best beaches in Central Florida. This 2nd floor condo offers views of palm trees, white sand and the turquoise waters of the Gulf of Mexico. The view is... View all property information
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    Siesta Key, Florida 34242
    1 / 18
    5 of 5 bubbles (4) Excellent
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Enjoy the view of the white sand of Crescent Beach and the azure waters of the Gulf of Mexico from this lovely third floor 2 bedrooms, 2 baths gulf view condo at Island House Beach Resort. This beautifully maintained complex is located on the widest part of one of the best beaches in Florida.This... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 15 May 2014
    We really enjoyed our 9-day visit to Island House and Unit 13 So. This updated unit is one of our favorites! It is beautifully decorated and very comfortable . We were pleased...
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    4.5 of 5 bubbles (11) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    We offer a boutique style property with just 4 units. Close enough to the beach without the congestion of larger properties. Enjoy this newly renovated (2014) apartment, located less than a mile from beautiful Siesta Key Beach. We've fully remodeled in the "Beach Chic" style, with a touch of... View all property information
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    Siesta Key, Florida 34242
    5 of 5 bubbles Reviewed 23 June 2016
    Had the best girls getaway weekend with everthing you need. Great gourmet style kitchen and such a beachy feel with all the cutest decor design Such a great place for a vacation...
    4 of 5 bubbles Reviewed 4 May 2016
    The apartment was lovely and very comfortable. I loved the kitchen. We slept well on the king sized bed. It had all the comforts of home. It was nice having bikes to ride to...
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    Siesta Key Holiday Rentals

    Looking for world class powdery white quartz sand beaches, a relaxed low-rise life style, and about 100 nearby golf courses on Florida’s South Gulf Coast? This plus bay- and ocean-side views can be yours with a money-saving Siesta Key holiday rental. From Siesta Key cross Roberts or Little Sarasota Bay to Sarasota for museums, art, wildlife, circuses, opera, ballet, symphonies, theater, film festivals, botanical gardens, baseball spring training, and polo, cricket, and lawn bowling clubs.

    Lions, Tigers & Circuses

    When you need a break from basking in the sun or seashell collecting around Siesta Key, it’s Ringling Brothers and Barnum & Bailey Circus time at Circus Sarasota (Feb., March) and the Museum of the Circus (year-round) at the old Ringling wintering grounds. Visit the Ringling’s bayside winter mansion, Ca d'Zan, and savor their extensive art collection at the recently expanded John and Mable Ringling Museum of Art. The nearby Big Cat Habitat is a sanctuary for lions, tigers, bears and other animals. Hike or take a swamp buggy eco-tour with the kids at Babcock Wilderness in Punta Gorda, and see Florida’s native plants and animals in their natural habitats.

    Gardens & Aquariums

    Let the whole family enjoy the mazes, pirates ships, colorful flowers, and tropical birds at the Sarasota Children's Garden. Marvel at the orchids, bromeliads, and Sarasota Bay views at Selby Gardens. Enjoy the Parker Manatee Aquarium, plus the Bishop Planetarium’s digital projections of the heavens with Dolby surround sound at the South Florida Museum, near the Manatee River in downtown Bradenton. Schedule a Monday, Wednesday, or Friday morning for Mote Aquarium’s Narrated Shark Training Sessions; and visit Molly the Mollusk, a 27-foot pickled New Zealand giant squid.

    Locomotives & Science

    Learn some science and technology with the family at downtown Sarasota’s bay-front G.WIZ (Gulfcoast Wonder & Imagination Zone). In the evening, treat the family to Broadway theater, dance, or a jazz, pop, or rock concert at the Van Wezel Performing Arts Hall, next door to G.WIZ. Make a weekend visit to the Florida Railroad Museum, 45 minutes north of Siesta Key in Parrish, where you can get hands-on-training, take over the controls, and even rent a locomotive.

    History & Baseball

    From your money-saving Siesta Bay holiday rental home, apartment or condo, take Stickney Point Road across Little Sarasota Bay to the Tamiami Trail (U.S. 41) and Historic Spanish Point. This unusual museum and archaeological site has an intact prehistoric village with middens, as well as a pioneer home, citrus packing house, and old boatyard. In 1924, the New York Giants began a spring training tradition in Sarasota that is being continued by the Baltimore Orioles and the Grapefruit League in Ed Smith Stadium.