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Search results; Over 1,000 places in Siesta Key

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 Sarasota
Bamboo Bungalow - Ideal Location
3 beds
Apr 9 – 14
5.0 out of 5 average rating, 13 reviews
Guest favorite
Home in Siesta Key
One-of-a-kind*Beach, Village, Dock & Private Pool!
4 beds
Apr 6 – 11
5.0 out of 5 average rating, 122 reviews
Superhost
Home in Sarasota
Modern Beach House, Short Drive to Siesta!
3 beds
May 16 – 21
4.78 out of 5 average rating, 74 reviews
Guest favorite
Island in Sarasota
*MAY SALE! Sarasota #1 Luxury Villa Pool/Beach!*
3 beds
Apr 27 – May 2
4.97 out of 5 average rating, 298 reviews
Guest favorite
Vacation home in Siesta Key
Siesta Beach View : Pineapple Bungalow Efficiency
2 beds
Apr 11 – 16
5.0 out of 5 average rating, 55 reviews
Guest favorite
Home in Sarasota
Hidden Gem in Sarasota
4 beds
Apr 5 – 10
5.0 out of 5 average rating, 13 reviews
Guest favorite
Home in Sarasota
Urban Oasis, Pool, 6mi>Beach
5 beds
Apr 22 – 27
5.0 out of 5 average rating, 8 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
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
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 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 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 Bradenton
Coastal Oasis: Cheerful 3Bedroom, Pool, Large Yard
4 beds
May 2 – 7
5.0 out of 5 average rating, 44 reviews
Guest favorite
Home in Sarasota
Sarasota Escape
4 beds
May 14 – 19
4.95 out of 5 average rating, 21 reviews
Guest favorite
Home in Sarasota
Bahia Vista Retreat🌴large home, sleeps 8-9
5 beds
Apr 21 – 26
4.96 out of 5 average rating, 70 reviews
Guest favorite
Condo in Bradenton
Bradenton Beach, Anna Maria Island, IMG Academy!
2 king beds
May 22 – 27
4.93 out of 5 average rating, 54 reviews
Guest favorite
Home in Bradenton
Large 4 BD heat pool near Anna Maria Island + IMG
5 beds
Apr 23 – 28
4.96 out of 5 average rating, 28 reviews