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Match: Heated pool
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$258
Great rentals within 20 miles that match your search
“Excellent” Our stay at 4638 Runabout way was amazing. We loved that the house was very nice, spacious, and clean for my family and I. We loved swimming in the pool everyday. The service was excellent all around. We would definitely stay there again.
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$194
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$343
“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!
Match: Heated pool
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$451
A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub
Holmes Beach house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.
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$474
2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!
Siesta Key apartment
- 2 bedrooms
- 1 bathroom
- sleeps 5
“Happy Customer” We had an amazing time. The owners were so nice & made us feel so welcomed. I couldnt have been happier with our stay & we look forward to staying there again soon when life slows back down. Highly recommend this home♡
Match: Heated pool
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$240
AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS
Bradenton Beach apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 5
Responds fast! avg. 3 hours 22 minutes
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$196
Responds fast! avg. 1 hour 41 minutes
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$457
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$172
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$160
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$137
Grand accomdation on USA #1 Beach - Siesta Key Fl
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 5
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$205
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$240
Responds fast! avg. 3 hours 25 minutes
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$257
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$408
Luxurious 2 BR Condo-Short Walk to Siesta Beach/1 Small Dog (25 lbs Max) Allowed
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.
Match: Heated pool
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$165
“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!
Match: Heated pool
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$272
A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach
Siesta Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 9
“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!
Match: Heated pool
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$499
“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.
Match: Heated pool
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$507
4 Bedroom with Gulf View Siesta Key FL Beach Fun
Siesta Key apartment
- 4 bedrooms
- 4 bathrooms
- sleeps 10
“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.
Match: Heated pool
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$513
SNOWBIRDS 25 - 40% OFF 5* Waterfront Canal Pool Home-Dock/Kayak/Bikes/Family fun
Holmes Beach house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Match: Heated pool
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$229
“Home away From Home” I've been staying at the Graham's condo once or twice a year for the last 9 years or more. It's always been pristine clean. Accomodations are the best. Rooms large and bright and fully equipped. Decor is so welcoming. Location is the best. Only decisions to make are beach or pool, and where to eat tonight! I consider it my "home away from home." You won't be disappointed, and the value cannot be beat. Don't hesitate to book your reservation.
Match: Heated pool
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$172
Clean comfort in Sarasota-book now for comfort
Sarasota caravan/mobile home
- 1 bedroom
- 2 bathrooms
- sleeps 4
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$134
Cathy's Crescent Condos-Siesta Key, FL GULF FRONT
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
“Great View” We stayed at Kathy’s condo during the 4th of July week. The Condo was great and the view was amazing. We enjoyed the fireworks display and easy access to the beach. We look forward to renting her condo again in the future.
Match: Heated pool
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$313
GULF FRONT ON #1 Beach! Siesta Dunes (by owner)
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
“Perfect, Perfect, Perfect” Nice condo with everything close by! Owners were great to deal with and as stated it would be . We plan on visiting again and would recommend this place to anyone.
Match: Heated pool
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$271
Newly discounted rates! Gorgeous one bedroom across from beach, near village!
Siesta Key condo
- 1 bedroom
- 1 bathroom
- sleeps 3
“Anniversary Trip” Had a wonderful time at LA Siesta Condominiums for our anniversary vacation. Beautifully furnished and do close to the best beach in the USA
Match: Heated pool
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$245
“Great Vacation Rental” We have been coming to Siesta Key for our Vacations for years... We have stayed at a number of Units at Crystal Sands, Crescent arms and El Presidente... Crystal Sands Unit 308 is one of the best Units we have stayed at... It has a great view of the Beach and Pool... You can watch the Sunsets and Moonsets right from the Lanai... The Unit is Roomy, Clean and had all the appliances, Dishes and Linens we needed... The Washer\Dryer in the Unit is very convenient... It has a New 60" Hdtv in the Living Room with an incredible picture... Jim left printed instructions for the Hdtv, Washer and Dryer which made it very easy to use the appliances in the Unit... We are looking forward to staying in Crystal Sands Unit 308 again for our next trip to Siesta Key...
Match: Heated pool
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$428
Responds fast! avg. 3 hours 20 minutes
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$226
Responds fast! avg. 2 hours 27 minutes
Match: Heated pool
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$139
Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.
Match: Heated pool
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$189
Steps to beach and bay on beautiful Anna Maria Island
Bradenton Beach apartment
- 2 bedrooms
- 1 bathroom
- sleeps 5
Match: Heated pool
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$101
Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!
Siesta Key apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 54 minutes
Match: Heated pool
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$265
Pool & Hot Tub-Pine Bay Forest 3-Bedroom Condo, Near AMI Beaches 3 month min
Bradenton condo
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Match: Heated pool
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$107
Sarasota 2BR 2BTH Condo Close to Siesta Key Beach
Sarasota apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
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$60
Direct Beachfront 2 BR Condo on Florida’S Beautiful Gulf Coast!
Holmes Beach apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
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$428
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$182
~ SUPER SPECIAL from $99/night ~ OCEAN FRONT DLX STUDIO
Longboat Key studio
- Studio
- 1 bathroom
- sleeps 3
“Nice Beachfront Location” We stayed there in late June and found it very suitable for our needs. The beach was very accessible. View was awesome. The unit was clean and comfortable for 2 adults.
Responds fast! avg. 1 hour 56 minutes
Match: Heated pool
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$193
Runaway Bay - Bradenton Beach - Bay View Unit 193
Anna Maria Island condo
- 2 bedrooms
- 2 bathrooms
- sleeps 5
“Home away from home” This place is an incredible value. It's spacious and comfortable, and we felt right at home. Sarasota Bay is just steps from the back patio, and it's so lovely to sit outside and watch water--so many fish, dolphins, and birds right there. Everything was in good working order and clean upon our arrival. The beach is a quick walk across the street from the complex, and we spent a lot of time at the heated pool. We would love to rent this unit again! PERFECT LOCATION.
Match: Heated pool
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$208