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Siesta Key Beach Rentals

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    All 1,223 Rentals in Siesta Key
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    Midnight Cove #532 in Siesta Key, FL- Sun, Sand & *Save 14% to 40% per Week*1 / 48
    (39)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Midnight Cove #714 in Siesta Key, FL- Sun, Sand & *Save 14% to 40% per Week*1 / 24
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & *Save 14% to 40% per Week*1 / 24
    (27)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Jamaica Royale #92 on the #1 Beach in the USA!1 / 12
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Porch
    • Patio
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 16, 2018
    After reading some of the reviews we were somewhat nervous. The resort was clean and staff was friendly. Our condo in Tower II was found clean and had a great view of the gulf...
    Reviewed August 12, 2017
    We came in around 5pm. I thought its ok not to call because they said in the email that the key will be left in the lockbox. No key when we got there. We had to call and after...
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    About this property
    Jamaica Royale condo #92. Located at the #1 BEACH IN THE USA, this 2 bedroom, 2 bath garden view unit has everything you need! It is located in the garden area of our beautifully landscaped property. It has new furniture and is freshly painted, with tile floors in the living areas and carpet in...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Siesta Key Beachfront Condo with Gulf View!1 / 16
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Sauna
    • DVD Player
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 27, 2018
    We found the facility to be very nice. Rooms were clean, attractive with everything you could think of provided. Everything you would need for a day at the beach provided...
    Reviewed April 1, 2018
    This was our first time visiting Siesta Key and our condo stay made it the perfect vacation. Okay - the beautiful weather helped!! The condo was well equipped for our stay...
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    About this property
    Beautiful one bedroom condo on 4th floor. Come to the beach and enjoy a relaxing vacation with plenty to do and see. Recently updated with new furniture. The view from the 4th floor balcony is incredible. Watch the sailboats and para sails go by as you sip your morning coffee. The bedroom has...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Walk to the beach from this adorable condo. Beachside. Perfect location.1 / 12
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Washer
    • Grill
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    • Air Conditioning
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 18, 2019
    The unit was so clean and lovely to stay at. The walk to the beach is quick and very beautiful. Angel was always quick to response and hospitable. I would definitely come again!
    Reviewed July 17, 2018
    Great home feel, cute place! Very clean and great accommodations. Comfortable bed and furniture, just like home, except at the beach! Love that it is a short walk to the beach...
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    About this property
    Upper floor. Walk to Siesta Key beach, only 0.2 mi from beach access 13. Clean, updated, with all the amenities you have at home. Fully equipped kitchen. Quiet and peaceful getaway and close to shopping, dining, grocery, pharmacy, bars, pubs, bike, boat, & kayak rentals. Park your car and use free...
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    Siesta Key, Florida 34242
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Jamaica Royale #100-Peaceful Gulf Side Condo1 / 44
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 12, 2019
    My first visit to the Gulf side of FL was a great surprise. Our condo owner was amazing. Rene has thought of everything imaginable to include her little piece of Heaven...
    Reviewed February 11, 2019
    Rene provided everything we could need for our stay in the condo and surprised us with much appreciated gifts on arrival. She was always available and pleasant to work with...
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    About this property
    Unlike many rental properties on Siesta Key, Unit #100 was recently renovated! This condo is a 2 bedroom, 2 bath garden view unit located in the quiet area of Jamaica Royale Condominiums! If you want peace and quiet, a relaxing environment to enjoy, this is the condo for you. Jamaica Royale is...
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    Siesta Key, Florida 34242
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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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    • Porch
    • Parking
    • Patio
    • Air Conditioning
    • Washer
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 24, 2018
    My boyfriend and I stayed here last week. Great location! It's only a mile from the beach. Nice and quiet. Very clean and cozy. You can even call for a shuttle, (that only...
    Reviewed October 3, 2017
    Siesta key is a wonderful place to stay ,And this apt was the cherry on top, minutes from the beach and village area,Not only where the accommodations great , they have bikes...
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    About this property
    This lovely 2BD/1BA apartment is located just 1 mile from beautiful Siesta Key Beach. Siesta Key was rated the #1 Beach in the United States by Dr. Beach (2011) and the #2 Beach in the U.S. in the 2013 TripAdvisor Travelers Choice Awards. Siesta Key was listed in 2014 by Smarter Travel.com as...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Beachfront Getaway in Siesta Key1 / 24
    (23)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Parking
    • Private Yard
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 16, 2019
    We just Returned today from spending 4 nights at Seacrest Beach front getaway. It’s the Perfect Little Getaway! Dior, the owner is excellent to deal with. We booked this back in...
    Reviewed April 24, 2019
    Nice beachfront getaway only steps away from the white sand and ocean!! Clean !!! We enjoyed our stay!!
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    About this property
    This luxurious one story townhouse was newly renovated and has its own private access to the #1 beach in the US merely steps away from the front door. It boasts all the luxury you'd expect from a beach house! Modern kitchen, contemporary bathroom with walk in rain shower, luxurious bedroom and...
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    Siesta Key, Florida 34242
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Remodeled 2br 2ba with private patio, beautiful water views, walk to #1 beach1 / 45
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Children's Pool
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Patio
    • Sauna
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 31, 2019
    Enjoyed our vacation here at Harbor Towers in Ruth's condo. We had previously stayed in higher floor condos with lanai, so the 1st floor apt with patio gave great outside space...
    Reviewed June 19, 2019
    Loved the place! Loved the beach. It was just perfect for our family. Was worth every penny! Would love to go back.
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    About this property
    This is a large, bright and clean 2 bedroom and 2 bath first floor Condo. Being first floor gives you extra entrance through patio or lobby. Also one of the few condos with a private patio with new furniture to enjoy the beautiful weather and view. Condo clean and bright and beautifully decorated....
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Washer
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Light, bright & airy, and facing west over the beach - directly in front of one of the best beaches in the world. Siesta Key Beach has quartz sand that never gets hot and is famous for making the most spectacular sand sculptures. Come and try your hand at creating a sand masterpiece, enjoy...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Washer
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Step out onto your private balcony and watch the boats docked in a small cove just off the intercoastal. - Completely redone 2 bedrooms, kitchen, baths, living room in a beautiful beach theme with predominantly white colors with pops of turquoise, teal and calming sea blue. -...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Gorgeous Direct gulf Front 2 Bedroom Condo on Siesta Keys... JUST REMODELLED1 / 58
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Housekeeping Included
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 26, 2019
    This condo was absolutely perfect. Sweeping ocean front, and water views in every room. It was very comfortable, so clean, and had absolutely everything we needed - great...
    Reviewed July 22, 2019
    The beach and docks were amazing! We rented kayaks for the week and took them out 6 of the seven days we were there. There is a kayak rack to store your kayak right by the...
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    About this property
    Our Fisherman's Cove condo description Paradise awaits - GORGEOUS, totally renovated in 2017, two bedroom, beach front condo on the Gulf of Mexico with sunset views overlooking the and sunrise views of the lagoon, expansive water views from every window. Beach was restored so it is large...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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 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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    Siesta Key, Florida 34242
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beachfront- Gulf View! 2 BR/BA Crescent Arms 603S, #1 Beach in the US.1 / 24
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 25, 2018
    Such a well appointed condo, with a fabulous location right on the beach.Easy walking distance to some great restaurants. Our owner was very attentive and answered all...
    Reviewed November 13, 2017
    We loved this condo. The beach was wonderful. Siesta Key Village was so close with great restaurants to choose from... Pavan was very nice to work with. What more can you ask...
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    About this property
    - Expansive, panoramic gulf view from every room of this 6th floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the beach with lounge chairs provided. As close as you can get to the Gulf without...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Siesta Key -  2bdrm on the beach - amazing views!!1 / 27
    (32)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 27, 2019
    Just finished up our week stay and couldn’t be more happy with this condo. It was beautifully decorated, clean and comfortable. The proximity to the beach could not be any...
    Reviewed June 22, 2019
    We just finished up our stay at this beautiful property. Heading home and already missing it! This condo is comfortably and tastefully furnished and has everything necessary...
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    About this property
    The condo benefits from its own private pool. The living room, master bedroom, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is also a comfortable couch to...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vacation on Siesta Key in this newly built 4 bedroom custom pool & spa home just a 600 ft. away from Shell Beach. Across the street and down the small drive is the gulf. Shell Beach has a very small sandy beach. It's on Big Pass and looks out to Lido Key. Here the water has a current so little...
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    Siesta Key, Florida 34242
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy an incredible sunset on Siesta Key's Crescent Beach and walk back to your private villa on Siesta Key in Polynesian Gardens. Plan your get-a-way at our two bedroom, two bath villa where you have a screened-in lanai looking into the grassy back yard with your own personal BBQ grill. The...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Fido Friendly, Saltwater Pool, Only 1 mile to SK Beach, Close to the Village, Sh1 / 38
    (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 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 with Prior Approval, 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...
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    Siesta Key, Florida 34242
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly remodeled, modern and beautiful 3 bedrooms, plus a den, 3 full bath condo right on Siesta Key, in a complex overlooking the intracoastal waterway and close to the beach!! Fabulous powdery white sands of Siesta Key Beach are just a short stroll away!! You won't be disappointed! Take a look...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs1 / 20
    (4)Excellent
    2 Bedrooms, 3 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 February 18, 2019
    We had such a great experience with this rental. The house was beautiful, perfect for a family with a small child (ours was about 15 months old). And you can't beat the location...
    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...
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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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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Siesta Key- Beach Chic Retreat,  Siesta Key 3 Bedroom 2 Bath Apartment1 / 20
    (16)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
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    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 16, 2018
    This place has everything! So spacious and decorated in tasteful beach chic. 3 bedrooms 2 baths, plenty of room for our family, plus laundry facilities, barbecue grill, and...
    Reviewed March 27, 2018
    The home we rented had all the amenities we needed. The location to the beach was awesome and the beach was perfect for long walks and soaking up the sunshine.
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    About this property
    We offer a boutique style property with just 4 units. Close enough to the beach without the congestion of larger properties. Enjoy this newly renovated (2014) apartment, located less than a mile from beautiful Siesta Key Beach. We've fully remodeled in the 'Beach Chic' style, with a touch of...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this beautiful updated two bedroom, two bath condo which has all of the amenities you are looking for in a luxurious and relaxing atmosphere. Bay Oaks is set among tropical foliage and beautiful walkways throughout. Enjoy a stroll along the tropical palm trees and tall shade oaks that line...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Cable/satellite TV
    • Patio
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Be the first to book this brand new completely remodeled unit right across the street from the Best Beach in the USA - Siesta Beach. You have a view of the gulf across the street from this beautifully and lovingly renovated condo with everything done with the most discriminating guest in mind....
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa1 / 38
    (12)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 August 15, 2019
    The house at Siesta Key was perfect for our family. There was plenty of space for everyone to spread out and enjoy the week. The pool and fishing dock worked wonders for the...
    Reviewed July 14, 2019
    The house was perfect for our large family! The Pool was a huge hit with the little ones on those cloudy/rainy days, well really the whole week. The walk to the beach is maybe 5...
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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
    Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front1 / 20
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Waterfront
    • Air Conditioning
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    • Balcony
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 5, 2019
    The location and views were great. The shuttle is easy to catch and the beach is pristine. The condo itself was not very clean when we arrived. We found candy wrappers on the...
    Reviewed August 14, 2018
    This condo is right on the beach. If you are looking for a family friendly place this is it. We absolutely loved this place and the view ..OMG is AMAZING!!! The place was well...
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    About this property
    Description Details Features Inquires Similar Listings google-map-thumb Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front USD 160 Per day 6312 Midnight Pass Rd., Siesta Key slider PreviousNext Property Description Relax in this beautiful fifth floor beach front Condo...
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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Canal Home on Siesta Key w/ Pool, Wifi, Renovated 1950 Style Sarasota School of1 / 37
    (2)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 18, 2019
    This is a large nice home. But it needs basic maintenance. Many light bulbs out, pool deck paint peeling, caulking painting needed, etc. In addition,not enough bath towels...
    Reviewed November 15, 2018
    This house is perfect for your Siesta getaway!Close to Village and #1 beaches great pool on the CanalI would defiantly stay here again!
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    About this property
    You will Never Want to Leave this Upscale, Mid-Century Modern, 4 bedroom Pool home with Salt-Water Canal Views and seawall on Siesta Key!!! This unique 1950's built, partially renovated, 4 bedroom, 3 full bath, 'Sarasota School of Architecture style' pool home is conveniently located...... only a...
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    Siesta Key, Florida 34242
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    WOW Factor Siesta Key Beach Gulf Front Condo in Siesta Dunes on #1 Beach in USA1 / 55
    (21)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Ocean Views
    • Housekeeping Included
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 1, 2019
    Absolutely enjoyed the condo. Well maintained and stocked with everything you would need. The owner was very nice and always responded to my questions immediately. The pool and...
    Reviewed January 16, 2019
    This is a high class condominium resort ON THE BEACH of Sarasota's Siesta Key. The resort itself is first rate, plus it fills it's beachfront with chairs and chaise recliners...
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    About this property
    Our condo has 1,200 sq ft of living area, two bedrooms and two baths and sleeps 6. 2 twin size Aerobeds for the kids. It is in Building 5 Unit 202- 2nd floor - Elevator in building-laundry facility in building by elevator...just two doors away. The first picture on this website was taken from...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    The Shells Villa - Next to Beach & Village1 / 41
    (69)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 28, 2019
    We stayed here with our family, seven of us all together, including 3 children (5, 8 & 11). Big place! Lots of rooms and never felt crowded at all. Lots of stairs too but...
    Reviewed May 15, 2019
    This was a lovely place to stay! Very spacious and charming place. It was well stocked with towels and we loved having a washer/dryer on site. There were 5 beach chairs that...
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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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    New furnishings complete an already fabulous condo! Enjoy this newly painted, newly furnished adorable & quaint ground floor two bedroom, one bath condo with water views and all of the amenities you are looking for in a fun yet relaxing atmosphere. This particular unit is located only about 30...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    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
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
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    About this property
    Got Paradise!? Well now you do..... This oasis on Siesta Key is just that. The condo is only a couple of blocks away from the beach and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and more, all a short walk away. With everything you could...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Quiet and Comfortable Condo Near Turtle Beach1 / 42
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 15, 2018
    We really enjoyed our stay at Dana Z's condo. It was close to all the amenities on Siesta Key. The condo was quiet and peaceful. The water front gave us many enjoyable evenings...
    Reviewed February 21, 2018
    Great place, but needs some attention to the bed in master bedroom also a updated tv in the living room. I would recommend this place for older adults.
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    About this property
    Cozy Cove is a small condominium complex of six total units, located on the south end of Siesta Key in Sarasota, Florida. The complex sits on the Gulf side of the Key along Blind Pass. The complex itself is on the inlet with a dock at the back of the property where you will often see fish jump and...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Honeymoon Suite - Gulf views - next to Siesta Key Beach1 / 25
    (6)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 30, 2018
    The suite was lovely, and the bed was very comfortable. The grounds and pool were very well maintained. Great Beach access.
    Reviewed August 2, 2016
    Me and 2 friends booked this wonderful appoartment very short-term (the day before) and the owner Virginia was just amazing. She helped us with the booking, welcomed us...
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    About this property
    Gumbo Limbo Vacation Rentals: Honeymoon Suite, 60 steps to the BEACH. NEWLY REMODELED AND REFURBISHED. Spacious 1 bedroom / 2 full baths townhouse (850sq/ft) over 2 floors, with 1 King size bed, and a luxury Queen self inflating air bed for max. comfort. This townhouse also offers 2 balconies...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Beachy Chic Condo in Siesta Key - Waterfront - Free wifi - Sleeps 4 !1 / 30
    (21)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 9, 2019
    Nice location and pool was great. Bedroom TV never worked the whole time. Owners are from Canada and my cell phone couldn't make international calls. Had to email and never got...
    Reviewed July 1, 2018
    Nothing negative to say here. Location was great, condo was spacious and had everything we needed. I would definitely book to stay here again!!
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    About this property
    Welcome to our Condo in Siesta Key ! Located on the inter-coastal Waterway and a short walk to the whitest sand and the # 1 beach in the USA. This 1 bedroom Condo is a great retreat for anyone looking for a beautiful Island getaway! Our condo is on the 2nd floor (sleeps 4) We are on Siesta...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the most amazing #1 rated Siesta Key beach views on the Gulf of Mexico from the 15th floor of the Terrace Building in Siesta Key Village! Hands down, best location with the best views! This home away from home 2 bedroom 2 bath condo with almost 1,187 sq. ft. being almost 1/4 of the...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    Walk to Crescent Beach! This is a darling 2 bedroom, 1 bath updated and newly furnished condo in the very popular Bay Oaks on Siesta Key, Florida. The amazing amenities include access to a private fishing pier, private tennis court, billiard room, clubhouse, BBQ area, sauna, a heated swimming...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    SIESTA KEY Gulf side 2 Bed 2 Bath at Jamaica Royale  #104!1 / 20
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Reviewed October 26, 2019
    This Siesta Key condo is an excellent value. The proximity to the ocean is a short, simple walk on the sidewalk from your back patio. There are several strategically placed...
    Reviewed June 22, 2019
    All was great at the bill We had all we needed and were within a quick walk to the beachThe only thing I would change is the beach cart that is a little old and rundown...
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    About this property
    Jamaica Royale Condominiums are located directly on the Gulf of Mexico along the white sands of world-famous Siesta Key Beach in Sarasota, Florida. A barrier island on Florida’s West coast, considered the most beautiful of Florida’s barrier islands, Siesta Key’s beach boasts “the world’s finest...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Luxury Villa, Sleeps 6 Comfortably Located on Siesta Key Beach, Sarasota Florida1 / 26
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 13, 2019
    The villa was great very clean and fully equipment with everything you would have at home. Great week would book next time.
    Reviewed August 26, 2018
    The house was spotlessly clean and up to date with tasteful decor. There were plenty of cleaning supplies, towels etc provided which made our stay with children very easy. In...
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    About this property
    This is a Luxurious Villa on Siesta Key Beach Florida on Crystal Sands - Experience why Siesta Key, Sarasota Florida has been rated the #1 beach in the USA (#5 in the world by TravelAdvisor) for so many years. Siesta Key is one of the only beaches in the world with 99% Pure Quartz powdery white...
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    Siesta Key, Florida 34242
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Got Paradise!? Well now you do..... This oasis on Siesta Key is just that. The condo is only a couple of blocks away from the beach and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and more, all a short walk away. With everything you could want...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Excellent Location - Gulf/Beach View - Siesta Key1 / 26
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Ocean Views
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 13, 2017
    The condo at Sunset was fantastic. The location is right across the street from the Siesta Key beach and you have a view from the condo as well. The white sand is beautiful...
    Reviewed October 24, 2017
    We thoroughly enjoyed our stay at this beautiful condo unit. The location was fabulous, directly across the street from the beach! The condo was very clean, beautifully...
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    About this property
    This vacation rental offers a full view of Siesta Key Beach/ The Gulf upon entry; relax and enjoy from your lanai or master bedroom. The property has been newly transformed to accommodate our guests best welcome to Siesta. From the comfort of the home décor to your fully stocked kitchen: cookware,...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Beach Walk Townhouse1 / 16
    (5)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Reviewed July 22, 2018
    We had a great time. Very close to beach and within walking distance to many restaurants. The place was clean and as advertised.
    Reviewed May 20, 2018
    The space was great. Very close to Siesta Key Beach. The only thing is that it is a 3 floor duplex and it makes it kind of difficult bringing your stuff up the stairs.
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    About this property
    Spacious Beach Getaway (sleeps 6), Calle del Otoño unit D, a 3 bedroom / 2.5 baths townhouse of 2,000sq/feet which is located right next to Gumbo Limbo. It offers 1 king, 2 twins and 1 queen size bed, brand new carpeting (January 2016), a balcony with partial Gulf view and a heated pool. This...
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    Siesta Key, Florida 34242
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    Siesta Key, Florida 34242
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Sea Club II1 / 41
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Reviewed October 14, 2018
    We thoroughly enjoyed our visit to siesta key this conveniently located two bedroom unit only moments from the glistening sands and sunsets made our stay most memorable… The...
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    About this property
    Siesta Key has grown in popularity over recent years due to its beautiful miles of pure white quartz sand beaches, vibrant nightlife, artistic culture, and plethora of things to do on and off the emerald waters. This property sits centrally on the island, just minutes form Siesta Key Village and...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Beach Across the Street, Partial Gulf Views, Wifi, Tennis Courts, Community Pool1 / 42
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 11, 2019
    This big, roomy condo is right across the street from Siesta Key beach! Owners had beach towels, coolers, an umbrella and chairs for beach use. Two balconies with different sun...
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    About this property
    Looking for fantastic location? This 2 bedroom, 2 bath condo on Siesta Key sits right across from the Siesta Key Beach voted #1 Beach in USA. This large condo is light and bright with large wrap around balcony and great view of the pool. It is clean and comfortable with everything you need for a...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Holiday House 11 / 28
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed October 19, 2016
    Pros; Great location, super quiet-depending on situation of who's above you, very clean, 7-eleven and some great Restaurants walking distance from the Beach house. Also my wife...
    Reviewed December 27, 2015
    The best part of this rental was the location! It is less than a 5 min walk from the beach access and wasn't too far to be able to easily carry our beach gear to the beach. The...
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    About this property
    Walk the soft sandy shores of Siesta Key beach from this 1 bedroom1 bath vacation rental on Siesta Key. The unit offers an open floor plan with full kitchen, dining area, and living room with flat screen TV. Through the large sliding doors you can sit out and enjoy the pool area on the screen...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Crescent Arms 703S, Beachfront Penthouse, Gulf View from Every Room! 2BR-BA1 / 36
    (15)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
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    Reviewed July 27, 2019
    Our stay at Crescent Arms 703S was terrific. The room came well furnished with beachy vibes and colors. Plenty of beach toys, ice chests, and rafts stocked in the condo was a...
    Reviewed July 7, 2019
    This is our 3rd year renting at Crescent Arms and with Pavan. The location of this condo is perfect. The bathrooms have been updated and the condo is very clean. Walking...
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    About this property
    -Accommodations: Condo, 2 Bedrooms + Convertible Bed, 2 Baths (Sleeps 4-6) -Expansive, panoramic gulf view from every room of this 7th (top) floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Siesta Key Beachfront 3 Bedroom Home, Sarasota1 / 46
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
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    Reviewed July 1, 2019
    This was our first experience using trip advisor and would highly recommend it! We stayed at this beautiful home on the beach for a week. Along with the fantastic views, the...
    Reviewed September 29, 2018
    We had a wonderful stay at Siesta Keys Florida. David ‘s home is beautiful and well maintained. It does have several bests of steps if you have any kind of handicap. My husband...
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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 Gulf & beach. The entire back of this house opens...
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    Siesta Key, Florida 34242
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Sea Spray #123 is a spacious 900 sq.ft. one bedroom ground floor condo with French doors opening out to a private patio that overlooks the secret tropical garden. The bedroom has king bed with flat screen TV. The bathroom has a walk-in shower. The dining/Living room has a 42” Flat Screen TV w/ HD...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    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 - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Local time: 04:18 PM (EST)
    • Peak travel: March - April
    Siesta Key Vacation Rentals

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

    Lions, Tigers & Circuses

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

    Gardens & Aquariums

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

    Locomotives & Science

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

    History & Baseball

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

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