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Fruitville Pet Friendly Rentals

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    Don't let other travelers get your favorite Fruitville area vacation rental. You're so close to securing your perfect getaway. Book today.
    168 Matching Rentals in the Fruitville AreaView all 971 rentals
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    Fruitville
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Fruitville
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    The following rentals are within 10 miles of Fruitville.
    Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment1 / 16
    (24)Excellent
    Siesta Key
    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
    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Grill
    • Air Conditioning
    • Waterfront
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 19, 2017
    What a wonderful stay! To start, Daniel is a very down-to-earth guy....ALWAYS responded promptly to phone calls and emails, and always was always courteous and complete in...
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    About this property
    1BR (sleeps 4)- Perfect for travelers in search of uncomplicated seclusion. Brought to you by Gertrude Rentals! Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home located...
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    Siesta Key, Florida 34242
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The Top Siesta Key Location, The Village Studio - Eat Shop Beach!1 / 32
    (15)Very good
    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Patio
    • Waterfront
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 28, 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 March 24, 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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (3)1 / 84
    (21)Excellent
    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Washer
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 26, 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 April 9, 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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Lovely 2 BR Beach Cottage at Lido Key Villas across from Lido Beach1 / 21
    (3)Very good
    Lido Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Yard
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed yesterday
    I highly recommend vacationing here and staying at this charming Villa. We stayed seven days for the F18 Worlds Regatta that David and Mark were in! We enjoyed the cleanliness...
    Reviewed yesterday
    We had an excellent time at this rental which is convenient to everything Lido Key has to offer. While there we enjoyed a kayak tour around the corner, dined at the local...
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    About this property
    Our spacious fully furnished two-bedroom cottage is directly across the street from the beach (600 ft, a 2 min walk). It offers everything you need to enjoy a memorable beach vacation. It features all the conveniences – full kitchen, full bath and a lovely tree-shaded back yard. There is also a...
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    Location Information
    Lido Key, Sarasota 34236
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs1 / 26
    (2)Excellent
    Siesta Key
    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 January 29, 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 September 5, 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa1 / 38
    (7)Excellent
    Siesta Key
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 31, 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 April 1, 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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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    Sandy Toes Siesta Key Florida  (6796)1 / 40
    (23)Very good
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Waterfront
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 9, 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 March 25, 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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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 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
    Siesta Key
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Patio
    • Cable/satellite TV
    • Washer
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 16, 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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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    8 Steps to Sand Path of Siesta's Best Beach! - Old Man and the Sea Inn (4)1 / 47
    (34)Very good
    Siesta Key
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Balcony
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 12, 2018
    Great location. Steps away from beach, short walk to restaurants, free shuttles to the village. Clean condo.
    Reviewed September 12, 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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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Key West Suite next to Siesta Key Beach1 / 96
    (9)Very good
    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    • Balcony
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 25, 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 July 23, 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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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beach Studio at Lido Key Villas - your own home at the beach1 / 23
    (2)Very good
    Lido Key
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Yard
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 20, 2018
    The screened in porch was equipped with seating and dining so greatly expands the space. The kitchen is harder to cook in because of space.. The bed and amenities were very nice...
    Reviewed October 7, 2017
    Such a great place to be. The location is paradise, right across from the beach and walking distance to St. Armand’s circle for shopping and dining. The studio is a perfect...
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    About this property
    Imagine waking up in this cute studio apartment just steps away from the beach on Lido Key. Our spacious studio apartment offers everything you need to enjoy a relaxing beach vacation away from home. This unit features all the conveniences you’re used to at home – full kitchen, full bath and a...
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    Location Information
    Lido Key, Sarasota 34236
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Family friendly house with pool/spa1 / 29
    (2)Very good
    Lido Key
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Air Conditioning
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 18, 2016
    The owners are great, very friendly and helpful. The house was clean and almost everything needed was supplied. The rooms are nice and clean. The pool was the main focus of the...
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    About this property
    We want you to enjoy, staying here this year & be back with your friends/family. Beautiful house on 1 acre lot, close to everything located in one of the best and desirable area in south Sarasota. This property offers easy access to all local attractions and beaches. Only a short drive to the...
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    Location Information
    Lido Key, Sarasota 34233
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Dog-Friendly Siesta Key Bungalow, Wifi, Adorable Cottage Close to Siesta Key Bea1 / 26
    (2)Very good
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 25, 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Top in Siesta Village at Best Beaches, Food & Entertainment! - Casa Van Lopik(J)1 / 49
    (17)Very good
    Siesta Key
    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 June 12, 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 December 4, 2015
    Our extended family of 7 with 4 adults and 3 children, stayed 4 nights at this property. We were thrilled to see that the grocery store was at the end of the street, as were all...
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    About this property
    Casa Van Lopik (jardin), our garden facing suite, is a large 3BR home. Brought to you by Gertrude Rentals! Perfectly located between the best beaches, shopping dining and entertainment on the island. It was named for our father who was a ships captain and sailed the world for 30 years but always...
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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    The Top  Location on Siesta Key - Gertrude's Village House1 / 50
    (30)Very good
    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Waterfront
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 13, 2017
    My son booked this for his whole family. There were nine of us. The beach was just a half block away. It was beautiful with cool white sand, aqua water with warm rolling...
    Reviewed September 24, 2016
    Stayed there, the location is great. Everything in walking distance. The kitchen was supplied with everything you need. The positives beyond location varied, quiet, lots of room...
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    About this property
    A Gertrude Rentals property! Our Top Location! Leave the car behind. Richly furnished, perfectly nestled between the best beaches, shopping and dining on the Island, and sure to provide a combination of fun and rejuvenation you won't find in other getaways. Our living room, master bedroom and...
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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Lido Key
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Washer
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Sarasota City, just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach and more. This is a 1000 square foot two bedroom apartment with 1 car garage, offers a...
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    Location Information
    Lido Key, Sarasota 34236
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Sandy Toes Siesta Key Florida   (6798)1 / 37
    (22)Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Grill
    • Internet Access
    • Air Conditioning
    • Balcony
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 17, 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 June 21, 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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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key
    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
    Rental Home - 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 / 36
    (1)Excellent
    Siesta Key
    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 August 31, 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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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    • Parking
    • Grill
    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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    Lido Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Secure Parking
    • Air Conditioning
    • Washer
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Sarasota City, just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach and more. This is a 1000 square foot two bedroom apartment with 1 car garage, offers a...
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    Location Information
    Lido Key, Sarasota 34236
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Best in Siesta Village! 1.5 blocks to best beaches! - Casa Van Lopik (Canal)1 / 144
    (19)Excellent
    Siesta Key
    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 April 16, 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 March 6, 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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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just cross the street and you are at the entrance to Siesta Key Beach - one of the finest beaches on the Florida Coast and the winner of multiple awards both for its crystal clear waters and its cooling quartz sand. This 2/2 impeccably updated condo is on the first floor and water views...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Siesta Key Beachfront 3 Bedroom Home, Sarasota1 / 33
    (4)Excellent
    Siesta Key
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    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 January 29, 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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    Siesta Key, Florida 34242
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Siesta Key
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Hot Tub
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    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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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    The Palm Island House - a Shangri-La! 1.5 blocks to Siesta Keys best beaches!1 / 34
    (14)Very good
    Siesta Key
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 29, 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 December 4, 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
    Rental Home - 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
    Siesta Key
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
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    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Siesta Key 3 Bdrm Private House with Heated Pool minutes from village and beach1 / 20
    (3)Excellent
    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Grill
    • Private Outdoor Pool (Heated)
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 11, 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 April 10, 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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    Siesta Key, Florida 34242
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Pinecraft
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in a wonderful family neighborhood just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Siesta Key, Longboat beach and more. This is a 1650 square foot newly renovated 3 bedroom, 2 bath plus...
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    Location Information
    Pinecraft, Florida 34232
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    New 6 Bedroom, Luxury Home in Gated Community1 / 22
    (1)Excellent
    Siesta Key
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Heated)
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    • Air Conditioning
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 9, 2017
    View from master bedroom was fantastic. Plenty of room for the 14 of us. Will defiantly book again. Kitchen had all appliances needed. Grill was old and had to light with a...
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    About this property
    Perfectly located, New, 6 bedrooms 4 1/2 bathrooms private home,in a gated community, combines luxury with convenience of location. We offer you a large 6000sf+ home within a short distance to the pristine beaches of Siesta Key and walking to the Village, Restaurants, shops and nightlife. Privacy...
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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    PRISTINE SIESTA KEY VILLAGE HOME1 / 28
    (5)Excellent
    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Air Conditioning
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    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 29, 2017
    Beautiful accommodation, superbly located and very well equipped. The new swimming pool is the jewel in the crown, and Cydney was a pleasure to deal with. We would hope to go back.
    Reviewed July 20, 2017
    I can't say enough wonderful comments about this house. It's charming, comfortable, gorgeous, adorable, lovely....I could go on and on. My family has enjoyed walking to...
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    About this property
    Hidden behind a contemporary privacy wall, enter into our front yard oasis. The perfect setting for tanning, dining and entertaining alongside the waterfall feature. Extensive renos offering a stunning gourmet kitchen, updated bathrooms, flat screen tv's in bedrooms and the most appealing Lanai...
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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pet friendly paradise with heated pool close to Sarasota-Osprey-Nokomis-Venice1 / 17
    (2)Very good
    Osprey
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Private Yard
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 18, 2017
    We had a great stay for the month and plan to come again. Great location midway between our favorite beaches, Caspersen, Casey Key and Siesta Key. Very private lanai and pool...
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    About this property
    Absolutely the best value for your vacation dollar in the Sarasota-Osprey-Nokomis-Venice area ! This newly renovated pet friendly paradise is a single family 3 br - 2 bath home with heated pool that has it all. Large, extremely well equipped kitchen with granite countertops, double convection...
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    Location Information
    Osprey, Florida 34229
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Tiny House Siesta - Yellow Lifeguard Stand Tiny House1 / 32
    (1)Excellent
    Siesta Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed May 27, 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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    Siesta Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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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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    Lido Key
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a 1000 square foot newly renovated 2 bedroom, 1 bath, 1 car garage town-home located in Sarasota downtown, walking distance to restaurants, theaters, night clubs, marina and stores. It offers a King size bed in Master bedroom and two Twin size beds in Guest bedroom, and two sofa's-bed...
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    Location Information
    Lido Key, Sarasota 34236
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Luxurious 2 BR Condo - Short Walk to Siesta Beach1 / 14
    (18)Very good
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Sauna
    • DVD Player
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    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 20, 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 January 31, 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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    Luxury Siesta Key Four Bedroom,Five Bathroom Pool Home,180 Yards to Siesta Beach1 / 46
    (2)Excellent
    Siesta Key
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
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    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    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 August 7, 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
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    1 Block to the Beach on Siesta Key Vacation Rental Home with Swimming Pool1 / 24
    (1)Excellent
    Siesta Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Cape Aqua! This single family vacation rental home on Siesta Key has 3 bedrooms 2 1/2 baths and pool. Located on the closest private street to America's #1 named.The two large double doors with decorative frosted glass welcome you into this spacious home. The floor plan offers a very...
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    Siesta Key, Florida 34242
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Lido Key
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a 1000 square foot newly renovated 2 bedroom, 1 bath, 1 car garage town-home. It offers a Queen size bed in Master bedroom, two twin size beds in second bedroom and two sofa's beds (Full size) in the Living room. The kitchen has everything you would need to cook. 32' LED TV, WiFi internet,...
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    Location Information
    Lido Key, Sarasota 34236
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    4 Bd Waterfront Home w/Pool, Close to Siesta Beach1 / 37
    (9)Excellent
    Siesta Key
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 19, 2018
    This newly renovated, spacious home was ideal for my guests. Best neighborhood on Siesta Key. Loved pool and expansive canal location.
    Reviewed February 22, 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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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    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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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Siesta Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just over the bridge from Siesta Key and minutes away from Sarasota’s thriving dining and arts districts, our sunny and cheerful tiny house, Red Lifeguard Stand, sleeps four. With the convenience of a hotel, the comfort of a vacation home, and the cool factor of a tiny house, make staying...
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    Location Information
    Siesta Key, Florida 34231
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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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    Just Minutes from the White Sandy Siesta Beach1 / 28
    (4)Excellent
    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Patio
    • Shared Outdoor Pool (Unheated)
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    • DVD Player
    • Grill
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 3, 2017
    Condo has plenty of dishes, towels and wash rags. You will need laundry soap and toilet paper. Bed is very comfortable, Nice TV's and furniture to set in. It is not luxury but...
    Reviewed October 8, 2017
    Bea's condo was so wonderful! It was really spacious and comfy! The location was super close to Siesta Key Beach! Kitchen and bathroom were fully stocked with everything we...
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    About this property
    Situated a SHORT 5 min DRIVE from the cool emerald waters of SIESTA KEY BEACH, Nr.1. Beach in the USA. This tropical resort community of Sienna Park is a relaxing oasis under the warm skies of the Gulf Coast. My condos are good for couples, solo adventurers, business travelers, families (with...
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    Location Information
    Siesta Key, Florida 34231
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Stay on Siesta - SEA - ESTA HOUSE1 / 74
    (2)Very good
    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Outdoor Dining Area
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 10, 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 November 8, 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Siesta Key
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Patio
    • Waterfront
    • Ocean Views
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    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
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Siesta Key
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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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