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Search results; Over 1,000 homes in Siesta Key

Top guest favourite
Apartment in Siesta Key
2 Bed/2 Bath Condo Resort View on Siesta Key Beach
2 bedrooms, 3 beds, 2 private bathrooms
12–17 Aug
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4.94 out of 5 average rating, 155 reviews
Top guest favourite
Home in Sarasota
Luxury Pool Family Paradise-Siesta Key Beach/DT
3 bedrooms, 4 beds, 2 bathrooms
31 Aug – 5 Sept
4.96 out of 5 average rating, 142 reviews
Top guest favourite
Home in Sarasota
NEW Luxe Resort Home*XL Pool/Hot Tub*1 mi to Beach
3 bedrooms, 6 beds, 2 bathrooms
17–22 Aug
4.97 out of 5 average rating, 31 reviews
Guest favourite
Home in Siesta Key
Waterfront Home Pool & Dock 5 Min to Siesta Beach
3 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Sarasota
Private Oasis: Mini Golf and firepit. 2 king beds.
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Home in Sarasota
Palm Tree Haven
2 bedrooms, 2 beds, 2 bathrooms
22–27 Aug
4.99 out of 5 average rating, 100 reviews
Top guest favourite
Cottage in Bradenton Beach
Bradenton Beach Sunsets 2, Anna Maria Island, FL
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 252 reviews
Top guest favourite
Home in Sarasota
Heated pool+near beaches+arcade+hammocks+pooltable
4 bedrooms, 6 beds, 2 bathrooms
25–30 Aug
5.0 out of 5 average rating, 32 reviews
Top 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, 10 reviews
Top guest favourite
Loft in Siesta Key
Siesta Key Dream Inn Rental - Close to Village!
2 beds, 1 bathroom
13–18 Aug
5.0 out of 5 average rating, 64 reviews
Home in Sarasota
Sarasota Silver Oasis - Private Pool Near Downtown
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 3 beds, 2 bathrooms
7–12 Aug
New place to stay
Top guest favourite
Home in Sarasota
Modern 4BR Home *Heated Pool & Spa*
4 bedrooms, 4 beds, 2 bathrooms
26–31 Aug
4.95 out of 5 average rating, 197 reviews
Flat in Siesta Key
Charming 1BR 2nd-Floor | Deck | Pool | Kitchenette
1 bedroom, 2 beds, 1 bathroom
28 Aug – 2 Sept
4.48 out of 5 average rating, 61 reviews
Guest favourite
Home in Sarasota
Private Heated Pool~Yacht Rental~BBQ~Near Water
3 bedrooms, 5 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Sarasota
Private Heated Pool • Near Siesta & Downtown
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 25 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
Home in Sarasota
Private Beach•3 Heated Pools•2BR•Ground Floor
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
New place to stay
Top guest favourite
Home in Sarasota
Siesta Key Tropical Escape | Private Pool Oasis
3 bedrooms, 4 beds, 1 bathroom
12–19 Aug
5.0 out of 5 average rating, 10 reviews