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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Resort in Siesta Key
The Haven, with heated pool.
1 bedroom, 1 bed, 1 private bathroom
21–26 Sept
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5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Apartment in Siesta Key
Private Beach•3 Heated Pools•2BR•Ground Floor
2 bedrooms, 3 beds, 2 bathrooms
28 Nov – 3 Dec
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Siesta Key
Beach Walk Bungalow
3 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
4.94 out of 5 average rating, 34 reviews
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Apartment in Siesta Key
Siesta Key Beach front 2 bedroom condo w/ parking
2 bedrooms, 2 queen beds, 2 bathrooms
17–24 Sept
4.97 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Siesta Key
Siesta Key Retreat 1mi to Beach!
3 bedrooms, 4 beds, 2 bathrooms
3–10 Sept
4.96 out of 5 average rating, 48 reviews
Flat in Siesta Key
Siesta Sandcastle - Egret
1 bedroom, 1 king bed, 1 bathroom
13–18 Sept
New place to stay
Guest favourite
Apartment in Siesta Key
The Flamingo's Nest at Sea Club II
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
4.94 out of 5 average rating, 156 reviews
Top guest favourite
Home in Sarasota
Siesta Key Tropical Escape | Private Pool Oasis
3 bedrooms, 4 beds, 1 bathroom
8–15 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Siesta Key
Beach House *Pool*Spa*Walk to Beach and SK Village
4 bedrooms, 5 beds, 2 bathrooms
3–8 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.93 out of 5 average rating, 60 reviews
Guest favourite
Home in Siesta Key
Siesta Key Home: Private Screened Pool
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 9 reviews
Flat in Siesta Key
Villa with private beach, 3 pools complex on beach
2 bedrooms, 3 beds, 1 bathroom
29 Sept – 4 Oct
New place to stay
Superhost
Home in Sarasota
The Aviator | 7 Mins From SRQ | Pool | Giga Wifi
3 bedrooms, 3 queen beds, 2 bathrooms
11–16 Sept
New place to stay
Top guest favourite
Apartment in Siesta Key
New listing - Pool Home, 500ft to Beach!
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Sarasota
Quiet Family Home w/ Pool Near Pinecraft
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.83 out of 5 average rating, 42 reviews
Top guest favourite
Apartment in Siesta Key
❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
1 bedroom, 1 king bed, 1 bathroom
3–8 Sept
5.0 out of 5 average rating, 172 reviews