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Search results; Over 1,000 homes in Siesta Key

Superhost
Apartment in Siesta Key
LUXURY BEACH CABANA ON SIESTA KEY!
2 bedrooms, 3 beds, 2 private bathrooms
15–22 Aug
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4.78 out of 5 average rating, 41 reviews
Guest favourite
Home in Siesta Key
Waterfront Home Pool & Dock 5 Min to Siesta Beach
3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 6 reviews
Flat in Siesta Key
Villa with private beach, 3 pools complex on beach
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
New place to stay
Apartment in Siesta Key
2 Bedroom, 1 bath, sleeps 5 in Siesta Key #118
2 bedrooms, 3 beds, 1 bathroom
3–10 Aug
Top guest favourite
Home in Siesta Key
Pool & hot tub -Walk to Beach!
3 bedrooms, 6 beds, 2 bathrooms
2–7 Oct
5.0 out of 5 average rating, 23 reviews
Superhost
Home in Sarasota
New. Luxury Home. Near Siesta Key. Heated Pool.
4 bedrooms, 5 beds, 2 bathrooms
8–13 Aug
New place to stay
Top guest favourite
Apartment in Siesta Key
Private Siesta Key Escape
2 bedrooms, 3 beds, 1 bathroom
1–6 Aug
4.93 out of 5 average rating, 239 reviews
Superhost
Home in Bradenton
The Wabi House
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
New place to stay
Guest favourite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds, 5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Siesta Key
Two bedroom across from beach, walk to town!
2 bedrooms, 4 beds, 1 bathroom
2–7 Aug
4.95 out of 5 average rating, 19 reviews
Guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
4.93 out of 5 average rating, 59 reviews
Home in Siesta Key
Florida Beach House - One Minute to Beach
3 bedrooms, 4 bathrooms
3–8 Aug
Home in Siesta Key
3 bedroom renovated pool home near beach/village
3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Sarasota
Sand & Sea Retreat, Private Heated Pool.
5 bedrooms, 5 beds, 3 bathrooms
17–22 Aug
4.89 out of 5 average rating, 9 reviews
Apartment in Sarasota
Book Me Baby! Esquina Paraiso on Siesta Key
2 bedrooms, 3 beds, 2 bathrooms
11–18 Aug
Home in Siesta Key
Cypress Cottage - Walkable to Siesta Key Beaches
5 bedrooms, 8 beds, 2 bathrooms
1–6 Aug
Home in Bradenton
Modern Farmhouse on the Water |Pool-Kayak-Pontoon
4 bedrooms, 5 beds, 3 bathrooms
4–9 Aug
New place to stay
Superhost
Apartment in Sarasota
Direct Gulf View - Residence 505
4 bedrooms, 4.5 bathrooms
1–6 Sept
Apartment in Siesta Key
Newly Remodeled 2026-Just walk out on to the sand!
2 bedrooms, 3 beds, 2 bathrooms
5–12 Sept