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Search results; Over 1,000 places in Siesta Key

Guest favorite
Home in Bradenton
Pool, Mins to Beaches, Shops, Parks
3 beds
May 31 – Jun 5
4.95 out of 5 average rating, 20 reviews
Guest favorite
Home in Sarasota
The Oasis-Heated Private Pool Hot Tub-5mi to beach
3 beds
Apr 26 – May 1
4.96 out of 5 average rating, 189 reviews
Guest favorite
Home in Bradenton
Spa & Pool+By The River+Near Beaches+Gameroom
7 beds
May 8 – 13
4.96 out of 5 average rating, 101 reviews
Guest favorite
Home in Bradenton
Oasis home, 20 min-Anna Maria, Arcade, Bunks
6 beds
Apr 7 – 12
5.0 out of 5 average rating, 9 reviews
Guest favorite
Home in Siesta Key
BOUTIQUE HOTEL STYLE HOME - STEPS FROM THE BEACH!!
3 queen beds
May 11 – 16
4.92 out of 5 average rating, 48 reviews
Guest favorite
Condo in Siesta Key
NO Stairs, beachfront & short walk to the village!
3 beds
Apr 27 – May 2
4.91 out of 5 average rating, 80 reviews
Guest favorite
Home in Siesta Key
Beachfront home with private access, walk to town!
5 beds
Apr 7 – 12
4.95 out of 5 average rating, 85 reviews
Guest favorite
Home in Bradenton Beach
New! Gulf Views/Sunsets/Anna Maria Island Beaches
5 beds
Jun 24 – 29
5.0 out of 5 average rating, 5 reviews
Guest favorite
Home in Sarasota
Hidden Gem in Sarasota
4 beds
Apr 5 – 10
5.0 out of 5 average rating, 13 reviews
Condo in Sarasota
Breathtaking Beachfront Views in Siesta Key
3 beds
May 1 – 6
New place to stay
Guest favorite
Home in Siesta Key
Siesta Key, Private Tropical Waterfront Pool Home
4 beds
May 18 – 25
5.0 out of 5 average rating, 19 reviews
Home in Longboat Key
Longboat Key Beach Bliss Retreat
Jan 24 – 31
5.0 out of 5 average rating, 4 reviews
Guest favorite
Home in Siesta Key
Beachfront 180-Degree View, Walk to Village!
5 beds
Apr 13 – 20
5.0 out of 5 average rating, 18 reviews
Guest favorite
Villa in Siesta Key
Siesta Key Pineapple Beach House Pool Beach view!
4 beds
May 4 – 9
5.0 out of 5 average rating, 40 reviews
Guest favorite
Home in Siesta Key
Siesta Peace Retreat a private home rental
2 king beds
Apr 12 – 17
4.93 out of 5 average rating, 104 reviews
Guest favorite
Home in Anna Maria
ami skyview
4 beds
Sep 2 – 7
5.0 out of 5 average rating, 28 reviews
Guest favorite
Condo in Siesta Key
On the Beach; Siesta Key SunBum Studio
2 beds
Aug 20 – 25
4.96 out of 5 average rating, 267 reviews
Guest favorite
Condo in Siesta Key
Seaside on Siesta Key Beach
3 beds
May 16 – 23
4.98 out of 5 average rating, 66 reviews