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Pet Friendly Holiday Rentals in Siesta Key

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    Travellers to Siesta Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    145 Matching Rentals in Siesta KeyView all 910 rentals
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    Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment1 / 16
    (24)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (2)1 / 43
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    The Top  Location on Siesta Key - Gertrude's Village House1 / 100
    (30)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    The Top Siesta Key Location, The Village Studio - Eat Shop Beach!1 / 32
    (15)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Patio
    • Waterfront
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2017
    We loved walking everywhere - the beach, especially every sunset; shops, great food. The condo was lovely, and the setting enriched by the other owners in the complex.
    Reviewed 25 March 2017
    We enjoyed our 3 day stay. A longer stay would require a larger place but it was perfect for this time. Our host was very helpful and had a nice gift awaiting our arrival :)
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    About this property
    A Gertrude Rentals property. Enviable location just steps away from everything! The Siesta Key Village Studio is an accommodating ground floor, one-room efficiency apartment perfectly nestled on a quiet tropical street between the best beaches, shopping and dining on the island. Wander one...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    8 Steps to Sand Path of Siesta's Best Beach! - Old Man and the Sea Inn (4)1 / 94
    (34)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Patio
    • Balcony
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 April 2018
    Great location. Steps away from beach, short walk to restaurants, free shuttles to the village. Clean condo.
    Reviewed 12 September 2017
    We stayed for a long weekend and couldn't have been more pleased. Their team has thought of everything- all you need to do is sit back and enjoy the amazing location and town...
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    About this property
    A Gertrude Rentals Property! Rated 'The World's Finest, Whitest Sand' at the Great International Sand Challenge. Perfect for travelers in search of uncomplicated seclusion. Residing in Siesta Keys most 'private' non-private beach neighborhood and just one marlin's length (5 steps) from yard to...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (3)1 / 42
    (21)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Washer
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2018
    This place was amazing and could not have been more perfect to stay at for an extended vacation!!!! The unit was cozy and comfortable- it had everything that you could possibly...
    Reviewed 9 April 2018
    Great location! Only steps to beach access. Our unit was very clean and had all we needed for 2 people. The owner Daniel, was great to work with. He always replied to any...
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    About this property
    1BR (sleeps 4)- Perfect for travelers in search of uncomplicated seclusion. Brought to you by Gertrude Rentals! Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home located...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This wonderful Florida feel villa features a full self-catering kitchen, a flat screen T.V., dining room, and separate bedroom with a queen size bed. Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Fido Friendly, Saltwater Pool, Only 1 mile to SK Beach, Close to the Village, Sh1 / 42
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 September 2018
    The house was beautiful and very spacious. Great proximity to the beach and town center, and the kids loved Glebe Park, which was located a short walk down the street. We are...
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    About this property
    On Siesta Key we offer a high-end gorgeous, Fido friendly, Key West style 3 bedroom, 2.5 bath custom home. Desire a private saltwater heated pool while vacationing on Siesta Key? Then this vacation home will be your home away from home in tropical paradise…..just minutes from the village and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just cross the street and you are at the entrance to Siesta Key Beach - one of the finest beaches on the Florida Coast and the winner of multiple awards both for its crystal clear waters and its cooling quartz sand. This 2/2 impeccably updated condo is on the first floor and water views...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Sandy Toes Siesta Key Florida  (6796)1 / 40
    (23)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Waterfront
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2018
    Everything was great. The condo was updated, clean and spacious. It had what we needed to really enjoy our week. It was a quick walk to the beach, restaurants and shops. We...
    Reviewed 25 March 2018
    We had so much fun. It was so nice that the kids had their own space , own TV, own bathroom. The beach is amazing. The owner provided beach towels, chairs and umbrellas. I...
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    About this property
    A spacious 2 bedroom 2 bath Townhouse, with a 2 car garage and extra guest parking. Stroll down a private road (about 300 yards) to the #1 Beach in the U,S. You are in the Resorts of Sara Sea and just a couple of blocks from restaurants, grocery, sports rentals and ice cream ! The Great room has...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Shells Villa - Next to Beach & Village1 / 41
    (67)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Air Conditioning
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We booked this vacation home for our family reunion. It was absolutely perfect. All the amenities anyone could ask for were provided. GREAT location...steps away from a...
    Reviewed 27 March 2018
    My family and I just returned from a week at the Shells Villa. We had a wonderful time there and hope to return in the future. Our group consisted of our three grown daughters...
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    About this property
    3 Bedroom, 2.5 Bath Beach Villa (Sleeps 8-10) What makes us different than other homes you may be considering: · The Beach - The home is located on the ocean side of Beach Rd., so you just walk out your door and through our private access path. It’s literally 230 feet to Siesta Key Beach....
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa1 / 38
    (7)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2018
    My family with extended family(total of 8) shared this large home with 5 bedrooms and we had plenty of room and at same time all had our privacy when we wanted it. The kitchen...
    Reviewed 2 April 2018
    Perfect location. Very close to the beach and downtown. The sliding kitchen windows opening to the counter bar in the screened in pool and hot tub area made eating in so fun...
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    About this property
    Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage, Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. This Home Entertains Excellent Because The Pool Area Is...
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    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    Key West Suite next to Siesta Key Beach1 / 32
    (9)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    • Balcony
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2018
    Jus stayed one night and it was really enjoyable. Accommodation was really nice and just across the road from the beach. Hope to return someday.
    Reviewed 24 July 2018
    We loved our week in the Key West Suite at Siesta Key. The apartment is the top half of what probably used to be a garage for the larger house beside it. The suites share a...
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    About this property
    2 apartments to choose from: Key West Suite A relaxed beach experience. This cozy two bedrooms & den apartment, full 2 baths (1 King bed + 2 Twins + 1 Queen) 1,200 sq/ft. suite on second level with two private balconies and partial Gulf view from the den. This apartment is fully furnished and...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs1 / 26
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 January 2018
    I stayed over the winter holiday with my husband and other adult family.It was the perfect place to have a pleasant vacation. Close to all shops and downtown and also a short...
    Reviewed 6 September 2017
    What a beautiful modern and superbly located house. Immaculate and well maintained with everything you could possibly need. Our host Randy was excellent and answered our...
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    About this property
    Steps from the islands best restaurants, shops (in the Village area) and a short walk to the #1 beach in the USA! Great home with 2 car and 1 car private garages. Recently renovated including a screened in patio, hot tub and pool. Brand new appliances making this home a great place for monthly...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (1)1 / 47
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Patio
    • Cable/satellite TV
    • Washer
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2017
    Wonderful, relaxing, perfect location! On the quiet side of the key, easy close access to gorgeous crescent Beach. Easy quick walk to bus stop and local market, restaurants as...
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    About this property
    Old Man and the Sea Inn - 1 marlin to the sand! 2BR (sleeps 8). Brought to you by Gertrude Rentals! Perfect for travelers in search of uncomplicated seclusion. Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Best in Siesta Village! 1.5 blocks to best beaches! - Casa Van Lopik (Canal)1 / 96
    (19)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Grill
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Waterfront
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 April 2018
    This was the perfect place for eight fabulous women who were celebrating life. The beds were comfortable and the rooms spacious. The hot water plenty. It was a plus to have...
    Reviewed 6 March 2017
    Location is the best thing about this condo -- short walk to beach and to Siesta Key Village. Very convenient. Another big "pro" was Daniel. The owner is very...
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    About this property
    A Gertrude Rentals property! Large 3BR home perfectly located between the best beaches, shopping dining and entertainment on Siesta. Leave the car behind. After the beach, you could wander to town for fresh oysters and seafood, drinks, live music or ice cream, or just relax in a tropical garden...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
    • Washer
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the middle of Siesta Key, tucked away on a shaded and quiet canopy lane is this bright and open air 3 bedroom 3 bath home less than one mile from the world famous Siesta Key beach. Plenty of space to spread out and enjoy your vacation, whether it be out on the pool deck, in the hot tub,...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 2 Bed, 2 bath vacation rental with a pool just steps from Siesta Beach Access! 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. There are four different units located on...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Secure Parking
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Directly across from Siesta Beach Access! 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. This darling Florida getaway has 2 king size bedrooms and 1 bedroom with two twin size beds...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Top in Siesta Village at Best Beaches, Food & Entertainment! - Casa Van Lopik(J)1 / 49
    (17)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Waterfront
    • Balcony
    • Patio
    • Wi-Fi
    • Porch
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2016
    While ratings and reviews are subject to personal taste, we found this property average at best. The positives included a nice size home, 3BR, 2BA, 2 blocks to the beach and...
    Reviewed 4 December 2015
    Our extended family of 7 with 4 adults and 3 children, stayed 4 nights at this property. We were thrilled to see that the grocery store was at the end of the street, as were all...
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    About this property
    Casa Van Lopik (jardin), our garden facing suite, is a large 3BR home. Brought to you by Gertrude Rentals! Perfectly located between the best beaches, shopping dining and entertainment on the island. It was named for our father who was a ships captain and sailed the world for 30 years but always...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bd Waterfront Home w/Pool, Close to Siesta Beach1 / 37
    (9)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Cable/satellite TV
    • Parking
    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 April 2018
    This newly renovated, spacious home was ideal for my guests. Best neighborhood on Siesta Key. Loved pool and expansive canal location.
    Reviewed 22 February 2018
    The home we rented on Siesta Key was amazing. It was a perfect fit for my family of 7! It was a quick walk to the beach and or you could spend the day relaxing by the pool...
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    About this property
    Oh what a great feeling you get when you are looking out over the pool to the relaxing waters of the Grand Canal. This home is special with 188 ft. of canal wrapping the back of the home so you get to enjoy the views from three bedrooms, the kitchen, living and two dinning areas. Open all the...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two Bedroom Two Bathroom unit across from Siesta Key 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. Each bedroom has a queen bed, one bedroom has a master bath. Features a...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Dog-Friendly Siesta Key Bungalow, Wifi, Adorable Cottage Close to Siesta Key Bea1 / 32
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Air Conditioning
    • Washer
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2017
    The house was nice, large size, comfortable, nice neighborhood close to the beaches, shopping and restaurants. Perfect for our family and dogs that we brought along on our...
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    About this property
    Totally renovated adorable Siesta Key bungalow nestled on a shaded street just minutes from Siesta Key beach and the village of Siesta Key with a variety of shops, restaurants and nightlife. Drive into the circular driveway and park your car under the covered parking to be away from the 10 minute...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Beach Place is a small group of tropical garden Floridian beach cottages located at Siesta Key Beach - 30 seconds to the sand and 10 - 15 minute walk to Siesta Village. We have a heated pool, tiki cabana wet bar for the guests to entertain at, beachfront picnic and BBQ, poolside BBQ, plenty...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Siesta Key Beachfront 3 Bedroom Home, Sarasota1 / 33
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Cable/satellite TV
    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 September 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...
    Reviewed 30 January 2018
    This is a very nice three story three bedroom house. The first floor includes two separate garages with the house entrance in between. The second floor includes a spacious...
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    About this property
    Description:Walk out the back door to the clean white sand of Siesta Key Beach. This home has private Siesta Key beach frontage on the prime section of beach, there are no homes between you and the beach. Nearly every room has a full view of the beach. The entire back of this house opens with...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand new tiny home near the beach! Why stay in a hotel room or even a boring old house when you can stay in a brand new tiny home. Come check out the only tiny beach hotel in America. We are located less than a mile from the world famous Siesta key Beach rated the number one beach in America by...
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    Location Information
    Siesta Key, Florida 34231
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This condo complex is right on the beach with no crossing of streets. Head out your door and right to your private beach next to Crescent Beach and a short walk from Siesta Key Beach along the crystal clear Gulf of Mexico waters. The world’s finest powder sugar like sand made of 99% quartz makes...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Block to the Beach on Siesta Key Vacation Rental Home with Swimming Pool1 / 28
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Cape Aqua! This single family vacation rental home on Siesta Key has 3 bedrooms 2 1/2 baths and pool. Located on the closest private street to America's #1 named.The two large double doors with decorative frosted glass welcome you into this spacious home. The floor plan offers a very...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Patio
    • Waterfront
    • Ocean Views
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    • 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...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    The Palm Island House - a Shangri-La! 1.5 blocks to Siesta Keys best beaches!1 / 68
    (14)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
    • Balcony
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2017
    Palm Island was a DREAM home for us!! My bf and I were the only ones that went on this vacation so we had the WHOLE house to ourselves!! It was amazing!! A perfect location...
    Reviewed 5 December 2015
    We loved this home! We had a large group and it never felt crowded. The house is lovely and very convenient to everything! Highly recommend this rental!
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    About this property
    Prominently featured in the 2013 and 2014 in NYJL House Tour Magazine and winner Spring of 2014 Top Auction Item. Brought to you by Gertrude Rentals! This Spanish revival home is located on Palm Island, the heart shaped island within the island of Siesta Key, just steps from the beach and one...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    8 Steps to Sand Path! Best Value on Siesta Key! - The Siesta Key Poor Boy1 / 44
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Gertrude Rentals Property! Rated 'The World's Finest, Whitest Sand' at the Great International Sand Challenge! Just 8 steps from the yard to the sand of the beach path! The Poor-Boy unit is perfect for travellers in search of all the best the island of Siesta Key has to offer but on a limited...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Luxurious 2 BR Condo - Short Walk to Siesta Beach1 / 21
    (18)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Grill
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    • Sauna
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2017
    We stayed at the apartment for 2 weeks during Easter holidays with our 2 girls (aged 1 and 4). We had a lovely holiday. We felt there was some positives and negatives with the...
    Reviewed 1 February 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...
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    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...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sandy Toes Siesta Key Florida   (6798)1 / 37
    (22)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
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    • Internet Access
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    • Balcony
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2018
    The house was nice and spacious along with a garage for your car. You are walking distance to restaurants and stores. And just a couple minute walk to white sand beach. They had...
    Reviewed 22 June 2018
    Had everything we needed. We appreciate Joe the maintenance guy checking on us. He was very helpful. Would stsy here again.
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    About this property
    A short stroll down a private road to the #1 Beach in the US. You will love the location - you are located in the Resorts of the SaraSea community and can walk to everything you might need or want... Grocery, restaurants, ice cream, pizza, sports rentals, drugstore or boat rental. You have your...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key 3 Bdrm Private House with Heated Pool minutes from village and beach1 / 20
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2017
    I travelled to Florida with my fiancee for work and decided to extend our stay to enjoy a little R & R. We have used AirB&B in the past and we found this gorgeous home to...
    Reviewed 10 April 2017
    This is a beautiful home a short bike ride to Siesta Beach. It comfortably sleeps 8 on beds in 3 large rooms. 2 of the rooms have a glass door that opens up to the pool and...
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    About this property
    Surrounded by lush, tropical garden, our private villa is situated on a quiet cul-de-sac bordered on two sides by Lake Nancy. A birdwatchers and nature lovers delight! Sip your coffee in your PJs on the private, sunny terrace or enjoy a dip in the large heated pool. Walk for miles on the beach...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sand Dollar is our Amy model’s “big” sister. She has a penthouse suite with an easy spiral staircase found privately on the other side of the bathroom. She also has a sleeping loft above the kitchen that cantilevers over the cute front porch and a modern comfy futon that folds out to a sleeper....
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    Location Information
    Siesta Key, Florida 34231
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Stay on Siesta - SEA - ESTA HOUSE1 / 37
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Outdoor Dining Area
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Patio
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    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2017
    "Avenida Del Mare" was the perfect vacation rental for my family. The home is well appointed, all renovated with comfy beds and amazing bathrooms (love the rainshower...
    Reviewed 9 November 2016
    Convenient location, just a short stroll to beautiful Siesta Beach. Beach gear available, we left some sand toys for the kids.Very well equipped and beautifully decorated. All...
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    About this property
    This Siesta Key 3 Bedroom 2 Bath Home has been completely remodeled. This home is 1 block from the Famous Siesta Key Beach. Granite counter tops, to accent the new white cabinetry. Beautifully tiled bathrooms with all new hardware. All walls beautifully textured. Screened Lanai. Nice back yard. 1...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover Siesta Key at this three bedroom two bathroom vacation rental home located in the heart of Siesta Key tucked away in a quiet neighborhood. Hire one of the many free ride services on the key for a quick trip to visit Siesta Key village where you can find a multitude of restaurants,...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury Siesta Key Four Bedroom,Five Bathroom Pool Home,180 Yards to Siesta Beach1 / 23
    (2)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2018
    We had 4 adults, 5 children and a small dog. What a magnificent home. We were very impressed with the cleanliness, the beauty, and all the amenities the home offered. A...
    Reviewed 7 August 2018
    Our family looked at several homes in Siesta Key and settled on this one due to its convenient location to the public beach entrance along with direct access to the canal. We...
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    About this property
    This Luxury Four Bedroom, Four and a Half Bathroom Home will leave you breathless as you enter. There are not many large rental homes, this close to Siesta Beach, that live like this home. Most Rentals by the beach have their living area 16 feet above the ground level and the pool below, which is...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    PRISTINE SIESTA KEY VILLAGE HOME1 / 28
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Air Conditioning
    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    It was a perfect week for us in a perfect House.Great style and interior and we could use the bikes and kayak. Walk distance to the nice restaurants and the beach. We will...
    Reviewed 29 August 2017
    Beautiful accommodation, superbly located and very well equipped. The new swimming pool is the jewel in the crown, and Cydney was a pleasure to deal with. We would hope to go back.
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    About this property
    Hidden behind a contemporary privacy wall, enter into our front yard oasis. The perfect setting for tanning, dining and entertaining alongside the waterfall feature. Extensive renos offering a stunning gourmet kitchen, updated bathrooms, flat screen tv's in bedrooms and the most appealing Lanai...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Grand White Sands 303 - Walk to beach and village1 / 17
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Sauna
    • DVD Player
    • Wi-Fi
    • Patio
    • Waterfront
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2017
    Enjoyed our stay in this unit , big screen tv was the best. Short walk to the beach, the dog loved it. Everybody in the complex was very friendly and helpful.
    Reviewed 6 January 2016
    Close to all the excellent facilities of Siesta Key and within a comfortable walking distance of the magnificent Siesta beach, Grand White Sands 303 was the ideal place to...
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    About this property
    Please also visit siestakey-whitesands with the usual US ending. There you'll find lots of usedul information on the condo and a travel guide.White Sands Village is located on Siesta Key, just few steps from Siesta Beach and directly on the canal across from Philippee Creek.Highlights of White...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beach House Bungalow #11 / 9
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Parking
    • Balcony
    • Wi-Fi
    • Grill
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 April 2015
    Very nice accommodations. Gulf side of Midnight Pass. Five minute walk to beach. Quiet Crescent Beach.
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    About this property
    Located near the South Village of Siesta Key. This newly updated 2 bedroom duplex has it all. A new dipping pool to cool off the hot summer days, along with a BBQ and fire pit for the winter. Lots of space, all new furnishings throughout the home, the large eat in kitchen has plenty of room for...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Tiny House Siesta - Yellow Lifeguard Stand Tiny House1 / 32
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 May 2018
    We were 4 adults that stayed for 2 nights. The little houses are only five mins drive from the glorious beach.Though compact the houses have everything (except a hairdryer...
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    About this property
    Imagine Yourself At (Tiny) Home: Beach life is best! Enter through the bright yellow, life-sized replica of a Siesta Key lifeguard stand, and drop your beach bags on the two stools beneath our surfboard-shaped breakfast bar. Passing through the living room, decorated with just a touch of...
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    Location Information
    Siesta Key, Florida 34231
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located south Siesta Key with no busy streets to cross, it’s a leisurely stroll to the Gulf of Mexico and to Point of Rocks, the best snorkeling beach on the Key. There are many restaurants, lots of shopping, bike rentals, ice cream shops, beach equipment, etc., in a very beachy atmosphere. It’s...
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    Location Information
    Siesta Key, Florida 34242
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It is a 220-square-foot luxury tiny home, and it offers all of the facilities and conveniences you need for living comfortably The Dragonfly tiny home features a standard-sized bed in the spacious, loft bedroom, as well as a convertible Ikea bed that turns into a couch in the living quarters....
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    Location Information
    Siesta Key, Florida 34231
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 bedroom/1 bath Contemporary Beach Cottage1 / 10
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Balcony
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    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 February 2017
    It was like home away from home. Glad we were able to take our dog and cottage was fully equipped with everything necessary for our stay.
    Reviewed 31 May 2016
    The space seems bigger than the pictures lead it on to be which is a plus! We really enjoyed our stay as the master bedroom was very spacious. We visit Siesta Key almost every...
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    About this property
    Half Mile to the Beach This recently remodeled Beach house has both inside and outside living spaces. There is a combination Kitchen/dining/living area with windows on every wall allowing in loads of the wonderful Florida natural light. The kitchen is all white with stainless appliances and...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Stay on Siesta - Beach Rd -Step out to the Sand1 / 111
    (6)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Patio
    • Waterfront
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 February 2017
    We have visited siesta key many times and loved the location and atmosphere of this condo. It was clean and newly remodeled. The staff was friendly and helpful. Great place to...
    Reviewed 7 February 2017
    Looking forward to coming back. Perfect location for our stay. Nice people and accommodation . Great rates for what you get
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    About this property
    3 bedroom on Beach Rd. with Gulf view This updated townhouse is a one of a kind property. Three bedrooms with king, queen, 2 double beds and living room sleeper sofa. This is a step out to the sand property just north of Siesta Key Beach. Walk to Siesta Village. Views of the Gulf from almost every...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
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    • Wi-Fi
    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...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Beautiful & Modern Condo - Walk to Beach & Village1 / 18
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    White Sands Village is located on Siesta Key, just few steps from Siesta Beach and directly on the canal across from Philippee Creek. Highlights of White Sands Unit 303: Free high-speed WiFi Ground floor unit More than 200 channel cable TV DVR to watch your favorite show when you want to 50 inch...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key Beach Place - Dolphin Cottage -  Sept. Discount $700 per week1 / 28
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2018
    Nestled off a side street from the main beach road, these cottages are quiet but the walk to the beach is less than 3 minutes. The cottages have fully equipped kitchens, so you...
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    About this property
    The Beach Place is a small group of tropical garden Floridian beach cottages located at Siesta Key Beach - 30 seconds to the sand and 10 - 15 minute walk to Siesta Village. We have a heated pool, tiki cabana wet bar for the guests to entertain at, beachfront picnic and BBQ, poolside BBQ, plenty...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bathroom, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You need a vacation and we've got just the place! Not only are we a 5 minute walk to beach, but we're only 2 blocks to the famous Siesta Key Village with all the shops, restaurants and bars. If you don't want to eat out, you have a grocery store right in the village. They have already made...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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