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“Very comfortable, nice amenities and well run.” Loved the beach and the nearby restaurants. The free trolly ride was easy to use and a great way to go into the village.
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$224
Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach
Siesta Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
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$685
2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach
Siesta Key house
- 2 bedrooms
- 2 bathrooms
- sleeps 6
“Great Location, Very Well Appointed” This house is perfectly located right in Siesta Key Village within an easy walk to shops and restaurants. It is also just a block from the beach. No parking hassles! The house is very well appointed. The owner has thoughtfully provided more than enough coffee for the Keurig, lots of towels, and all needed kitchen utensils, dishes, containers, and cooking supplies, in addition to a beach wagon and chairs. Although not luxurious, this is a very comfortable rental. We also liked the privacy of having our own house. The only negatives were the lack of towel racks in the bathrooms and the lack of hot water in the bathroom with the tub (it remained only warm, even after running for a very long time). The water in the other bathroom was fine.
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$315
“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.
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$507
Luxury Romantic Oceanfront Siesta Beach Condo #304
Siesta Key apartment
- 1 bedroom
- 1 bathroom
- sleeps 4
“What a View!” This is a very nicely decorated 1 bedroom and bath on Siesta Key Beach. You have an unobstructed view of the beach the minute you look into the condo. There's a great view from the bedroom as well! Very easy walk fo the beach..chairs and umbrella provided as well as all the amenities of home. We'd stay here again!
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$183
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!
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$499
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$441
Responds fast! avg. 3 hours 1 minutes
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$542
“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!
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$271
“Beautiful inside and out. Perfect location” My family and I stayed in this beautiful rental during February 2015. We could not have asked for a more perfect spot. The rental is just steps away from the beach and has a wonderful view of the beautiful sunsets. Siesta Key Village is an easy walk away and has great restaurants and shops. We are hoping to go back as soon as we can!
Responds fast! avg. 3 hours 50 minutes
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$799
Beach, Village, Dock, Private Heated Pool... Fantastic Location, No Car Needed!
Siesta Key house
- 2 bedrooms
- 3 bathrooms
- sleeps 6
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$457
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$223
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$257
Responds fast! avg. 1 hour 59 minutes
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$999
Lovely Siesta Key house with heated pool - A block away from Siesta beach!
Siesta Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$490
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$1,202
Beautiful house for rent at siesta key beach with pool, theater and game room
Siesta Key house
- 7 bedrooms
- 3 bathrooms
- sleeps 15
Responds fast! avg. 1 hour 59 minutes
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$2,840
Responds fast! avg. 16 minutes
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$216
****Walk to Beach-5min! Waterfront Canal! Private Pool~spa~Kayaks, Bikes!
Siesta Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$452
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$331
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$410
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$343
Responds fast! avg. 1 hour 26 minutes
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$326
Great rentals within 20 miles that match your search
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$194
TROPICCAL, 4 min from the beaches! Meticulously cleaned and sanitized!
Bradenton house
- 3 bedrooms
- 2 bathrooms
- sleeps 5
“Lovely home in an awesome location!” Literally a minute's drive from the beach, this very clean and welcoming home is also convenient to great restaurants and shopping opportunities. It really is in a perfect location, especially considering the affordable price. Walking to restaurants and a rental shop is easy thanks to the sidewalk on Cortes. We even enjoyed a morning run to the beach - biking to the beach would also be a great option (3.5 mi one way.) The home might appear small at first, but we fit 6 comfortably, including 4 teenagers! The best part is the lovely décor that greets you after a long day at the beach or running around. Two thumbs up!
Responds fast! avg. 2 hours 33 minutes
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$143
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$143
Responds fast! avg. 2 hours 17 minutes
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$314
Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool
Bradenton Beach house
- 3 bedrooms
- 2 bathrooms
- sleeps 10
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$514
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$211
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$154
“Beautiful little cottage” We stayed at this lovely little cottage on Siesta Key mid-April. The cottage is very nice, with all the amenities, even a washer/dryer for extended stays. It's cozy, with high ceilings, a nice bathroom and kitchen/living room. The bed seemed a little small (only a double), but it was very comfortable. The wireless internet was not working when we were there, which was a little frustrating. There is a beautiful pool and nice garden areas. The private beach was also very nice. All of the staff and the owner were extremely pleasant and welcoming. We enjoyed our time there.
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$530
2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!
Bradenton Beach cottage
- 3 bedrooms
- 2 bathrooms
- sleeps 8
“Best home away from home at the beach.” I spent a lot of time searching for a bungalow at the beach and my expectations were surpassed when I opened the door! The owners were thoughtful in design, layout and furnishings to provide a laid back experience at the beach. I wished I could have stayed forever - it was that nice. I especially enjoyed the fully stocked kitchen which included colorful dishes to match the colorful walls and great blue floor! Best of all - location - you can walk everywhere as you are right in the historic Bridge Street neighborhood.
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$245
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
Responds fast! avg. 1 hour 41 minutes
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$457
Vacation Home on Alligator Drive . Winter 2025 Special !
Venice house
- 3 bedrooms
- 2 bathrooms
- sleeps 5
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$149
Responds fast! avg. 43 minutes
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$206
Clean comfort in Sarasota-book now for comfort
Sarasota caravan/mobile home
- 1 bedroom
- 2 bathrooms
- sleeps 4
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$134
BAY VIEW. SUNSETS. CLOSE TO ANNA MARIA ISLAND AND IMG ACADEMY
Bradenton house
- 3 bedrooms
- 2 bathrooms
- sleeps 4
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$365