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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Cottage in Siesta Key
The Mermaid: Heated Pool, 4 Houses to Beach
1 bedroom, 1 bed, 1 private bathroom
22–27 Sept
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4.94 out of 5 average rating, 146 reviews
Superhost
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 3 beds
18–23 Aug
New place to stay
Flat in Siesta Key
Villa with private beach, 3 pools complex on beach
2 bedrooms, 3 beds
23–28 Aug
New place to stay
Guest favourite
Home in Sarasota
Sarasota Silver Oasis - Private Pool Near Downtown
2 bedrooms, 3 beds
17–22 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Siesta Key
Siesta Key Retreat 1mi to Beach!
3 bedrooms, 4 beds
23–30 Aug
4.96 out of 5 average rating, 47 reviews
Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds
17–24 Aug
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Sarasota
Luxury Pool Family Paradise-Siesta Key Beach/DT
3 bedrooms, 4 beds
31 Aug – 5 Sept
4.96 out of 5 average rating, 146 reviews
Top guest favourite
Home in Sarasota
Books Tide Retreat - minutes from Siesta Beach
2 bedrooms, 2 beds
18–23 Aug
4.95 out of 5 average rating, 59 reviews
Top guest favourite
Cottage in Sarasota
Lido Key Beach Bungalow with Private Heated Pool!
2 bedrooms, 3 beds
17–22 Aug
4.97 out of 5 average rating, 38 reviews
Luxe
Home in Anna Maria
Bridge and Bay Escape - Brand New Listing!
4 bedrooms, 5 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Sarasota
Your Resort •7BR •13 Beds • Pool • Dock • Elevator
7 bedrooms, 13 beds
22–29 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Sarasota
Modern 4BR Home *Heated Pool & Spa*
4 bedrooms, 4 beds
26–31 Aug
4.95 out of 5 average rating, 197 reviews
Home in Sarasota
Private Beach•3 Heated Pools•2BR•Ground Floor
2 bedrooms, 3 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Bungalow in Sarasota
FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay
2 bedrooms, 4 beds
24–31 Oct
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Siesta Key
Completely Remodeled "Beach House on Siesta"
4 bedrooms, 6 beds
22–29 Aug
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Siesta Key
Two bedroom across from beach, walk to town!
2 bedrooms, 4 beds
18–23 Aug
4.96 out of 5 average rating, 24 reviews
Superhost
Home in Sarasota
Sun Coast Oasis-Heated Pool-Pool Table-Arcade
3 bedrooms, 5 beds
9–14 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Bradenton
Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI
5 bedrooms, 6 beds
7–12 Sept
4.96 out of 5 average rating, 148 reviews