Updating...
Match: Private pool
All filters matchPrice per night from
$229
Great rentals within 20 miles that match your search
Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool
Bradenton Beach house
- 3 bedrooms
- 2 bathrooms
- sleeps 10
Match: Private pool
All filters matchPrice per night from
$514
Match: Private pool
All filters matchPrice per night from
$995
“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.
Match: Private pool
All filters matchPrice per night from
$530
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.
Match: Private pool
All filters matchPrice per night from
$474
AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS
Bradenton Beach apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 5
Responds fast! avg. 3 hours 22 minutes
Match: Private pool
All filters matchPrice per night from
$195
“Majestic Views” Our family loved our visit to Anna Maria. The house is gorgeous and spacious. My kids enjoyed the pool and eating outside. We hope to return in the near future.
Match: Private pool
All filters matchPrice per night from
$628
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: Private pool
All filters matchPrice per night from
$499
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: Private pool
All filters matchPrice per night from
$512
SNOWBIRDS 25 - 40% OFF 5* Waterfront Canal Pool Home-Dock/Kayak/Bikes/Family fun
Holmes Beach house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Match: Private pool
All filters matchPrice per night from
$229
Responds fast! avg. 3 hours 20 minutes
Match: Private pool
All filters matchPrice per night from
$226
Match: Private pool
All filters matchPrice per night from
$166
Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!
Anna Maria house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
Match: Private pool
All filters matchPrice per night from
$741
Match: Private pool
All filters matchPrice per night from
$367
****Walk to Beach-5min! Waterfront Canal! Private Pool~spa~Kayaks, Bikes!
Siesta Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Match: Private pool
All filters matchPrice per night from
$452
Match: Private pool
All filters matchPrice per night from
$490
Match: Private pool
All filters matchPrice per night from
$284
Match: Private pool
All filters matchPrice per night from
$157
Match: Private pool
All filters matchPrice per night from
$627
Match: Private pool
All filters matchPrice per night from
$406
Responds fast! avg. 1 hour 59 minutes
Match: Private pool
All filters matchPrice per night from
$999
Anna Maria Islands best location Heated pool Best prices!
Anna Maria Island house
- 2 bedrooms
- 2 bathrooms
- sleeps 8
Match: Private pool
All filters matchPrice per night from
$856
Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach
Siesta Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
Match: Private pool
All filters matchPrice per night from
$685
Family Reunion Villa on Anna Maria Island, Florida
Bradenton Beach villa
- 4 bedrooms
- 4 bathrooms
- sleeps 12
Match: Private pool
All filters matchPrice per night from
$571
Responds fast! avg. 3 hours 1 minutes
Match: Private pool
All filters matchPrice per night from
$542
Match: Private pool
All filters matchPrice per night from
$257
Match: Private pool
All filters matchPrice per night from
$480
Responds fast! avg. 1 hour 33 minutes
Match: Private pool
All filters matchPrice per night from
$400
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
Match: Private pool
All filters matchPrice per night from
$2,840
Paradise 3 Bedroom Pool Home Close to Siesta Key Beach and IMG Academy
Braden River house
- 3 bedrooms
- 2 bathrooms
- sleeps 10
Responds fast! avg. 9 minutes
Match: Private pool
All filters matchPrice per night from
$371
Match: Private pool
All filters matchPrice per night from
$1,027
BeautifulHome with Pool - 3 miles from Siesta Key Beach
Gulf Gate Estates house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 1 hour 38 minutes
Match: Private pool
All filters matchPrice per night from
$240
Responds fast! avg. 3 hours 20 minutes
Match: Private pool
All filters matchPrice per night from
$776
Newly remodeled open concept 3 bed, 2 bath with heated pool and screened lanai!
Sarasota house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Match: Private pool
All filters matchPrice per night from
$571
Now Available - Modern Pool Home 1/29-2/26 2022 due to last minute cancellation!
Sarasota house
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Match: Private pool
All filters matchPrice per night from
$273
Elegant HEATED POOL Home. 12 min to Beaches of Anna Maria Island. IMG Academy
Bradenton house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
Match: Private pool
All filters matchPrice per night from
$286
Bird of Paradise Guest House Pool Home 10 Minutes or less to Anna Maria Island
Palma Sola house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
Match: Private pool
All filters matchPrice per night from
$308
Paradise 4 Bedroom Pool Home Close to Siesta Key Beach and IMG Academy
North Sarasota house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
Responds fast! avg. 9 minutes
Match: Private pool
All filters matchPrice per night from
$428