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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Apartment in Siesta Key
The Honeymoon Suite on Siesta Key Beach
1 bedroom, 1 bed, 1 private bathroom
24–29 Oct
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4.91 out of 5 average rating, 128 reviews
Superhost
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
New place to stay
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Apartment in Siesta Key
Penthouse 20ft to Beach Access, 500ft from Village
3 bedrooms, 7 beds, 2 bathrooms
19–24 Sept
4.89 out of 5 average rating, 47 reviews
Top guest favourite
Bungalow in Sarasota
FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay
2 bedrooms, 4 beds, 1 bathroom
24–31 Oct
5.0 out of 5 average rating, 11 reviews
Villa in Siesta Key
Aloha Kai Villa 52S - Premium Siesta Key Beach
3 bedrooms, 6 beds, 2 bathrooms
1–6 Sept
Flat in Siesta Key
Villa with private beach, 3 pools complex on beach
2 bedrooms, 3 beds, 1 bathroom
13–19 Sept
New place to stay
Apartment in Siesta Key
Jamaica Royale 099 Nice Gulf side unit!
2 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
Top guest favourite
Home in Sarasota
Modern 4BR Home *Heated Pool & Spa*
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.95 out of 5 average rating, 197 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, 11 reviews
Top guest favourite
Home in Sarasota
The Palms Away
2 bedrooms, 2 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 38 reviews
Flat in Siesta Key
Palm Bay Club on Siesta Key New bathroom
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
4.75 out of 5 average rating, 28 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, 11 reviews
Top guest favourite
Home in Sarasota
NEW Luxe Resort Home*XL Pool/Hot Tub*1 mi to Beach
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Home in Siesta Key
New Villa on Siesta Key! Pool & Walkable to Beach
2 bedrooms, 3 beds, 2 bathrooms
1–8 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Sarasota
Luxury 3B/3B waterfront home w/ pool + boat access
3 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 9 reviews
Apartment in Siesta Key
Newly Remodeled 2026-Just walk out on to the sand!
2 bedrooms, 3 beds, 2 bathrooms
5–12 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Siesta Key
Two bedroom across from beach, walk to town!
2 bedrooms, 4 beds, 1 bathroom
1–6 Sept
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Home in Sarasota
Luxury Pool Family Paradise-Siesta Key Beach/DT
3 bedrooms, 4 beds, 2 bathrooms
30 Sept – 5 Oct
4.96 out of 5 average rating, 147 reviews