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Search results; Over 1,000 places

Guest favorite
Condo in Siesta Key
2 BR condo in Siesta Key w/ Private beach access
7 min drive
Apr 27 – May 4
4.97 out of 5 average rating, 36 reviews
Guest favorite
Apartment in Siesta Key
Renovated beachside condo-direct beach access
5 min drive
May 26 – 31
4.95 out of 5 average rating, 37 reviews
Guest favorite
Condo in Siesta Key
Seaside on Siesta Key Beach
3 min drive
May 16 – 23
4.99 out of 5 average rating, 67 reviews
Guest favorite
Tiny home in Sarasota
@Tiffanythetinyhome| island | netflix|bike|hammock
13 min drive
Apr 21 – 26
4.89 out of 5 average rating, 169 reviews
Guest favorite
Place to stay in Sarasota
King bed, private studio with a private entrance
18 min drive
Apr 24 – 29
5.0 out of 5 average rating, 54 reviews
Superhost
Cottage in Siesta Key
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
5 min drive
Apr 27 – May 2
4.88 out of 5 average rating, 214 reviews
Guest favorite
Guest suite in Sarasota
Beach & Town Posh Location! Jungle Paradise Studio
10 min drive
May 29 – Jun 3
4.94 out of 5 average rating, 284 reviews
Home in Sarasota
Luxury House Walking Distance to Ocean - Sleeps 12
16 min drive
Apr 21 – 26
New place to stay
Superhost
Home in Sarasota
Salt Life Villa with heated pool & outdoor dining
18 min drive
Jun 3 – 8
New place to stay
Guest favorite
Cottage in Sarasota
"Honeybee Hideaway" Cozy Cottage Near SIESTA KEY
11 min drive
May 27 – Jun 1
4.9 out of 5 average rating, 174 reviews
Guest favorite
Condo in Siesta Key
Renovated Siesta Key Condo, beach/pool access
5 min drive
Apr 28 – May 3
4.94 out of 5 average rating, 52 reviews
Guest favorite
Home in Sarasota
Tropical Oasis Heated Pool Hot Tub Near Siesta Key
12 min drive
May 27 – Jun 1
5.0 out of 5 average rating, 48 reviews
Guest favorite
Condo in Siesta Key
On the Beach; Siesta Key SunBum Studio
5 min drive
Aug 26 – 31
4.96 out of 5 average rating, 273 reviews
Guest favorite
Apartment in Siesta Key
Siesta Key #1 Beach, pickle ball & tennis paradise
5 min drive
Aug 2 – 7
4.99 out of 5 average rating, 139 reviews
Guest favorite
Home in Sarasota
The Palms-Private Heated Pool Hot Tub-5mi to beach
13 min drive
May 4 – 9
4.97 out of 5 average rating, 159 reviews
Guest favorite
Bungalow in Sarasota
*Waterfront house with dock and heated pool
11 min drive
Apr 22 – 27
4.98 out of 5 average rating, 59 reviews
Guest favorite
Island in Sarasota
*NEW May SALE! last min CX! Sarasota #1 Luxury *
28 min drive
Apr 27 – May 2
4.97 out of 5 average rating, 301 reviews
Guest favorite
Condo in Sarasota
#1 Beach Siesta Key Village w heated pool & arcade
12 min walk
Apr 26 – May 1
5.0 out of 5 average rating, 7 reviews