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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Home in Siesta Key
Coastal Luxury*Pool*Hot Tub*Sunsets*Close to Beach
5 bedrooms, 9 beds, 4.5 private bathrooms
19–24 Sept
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4.93 out of 5 average rating, 30 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
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
Flat in Siesta Key
Charming 1BR 2nd-Floor | Deck | Pool | Kitchenette
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
4.48 out of 5 average rating, 61 reviews
Guest favourite
Apartment in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
1 bedroom, 2 beds, 1 bathroom
25–30 Sept
4.94 out of 5 average rating, 68 reviews
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, 10 reviews
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
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
Cottage in Bradenton Beach
Bradenton Beach Sunsets 2, Anna Maria Island, FL
1 bedroom, 2 beds, 1 bathroom
24–29 Sept
4.98 out of 5 average rating, 256 reviews
Top guest favourite
Home in Siesta Key
Walk To Siesta Key Beach & Village ; Renovated 2BR
2 bedrooms, 3 beds, 1 bathroom
1–8 Sept
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Townhouse in Siesta Key
Gulf and Beach Views-Steps from Beach and Village
2 bedrooms, 2 beds, 2.5 bathrooms
26 Oct – 2 Nov
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Home in Sarasota
Modern Home Heated Pool near Siesta & Downtown
3 bedrooms, 6 beds, 2 bathrooms
1–8 Nov
4.96 out of 5 average rating, 46 reviews
Top guest favourite
Home in Anna Maria
Palmetto Beach house hideaway 1 house from beach
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Sarasota
Siesta Sanctuary
2 bedrooms, 4 beds, 1 bathroom
8–13 Sept
4.95 out of 5 average rating, 40 reviews
Apartment in Sarasota
Sarasota Designer Waterfront Retreat * Paddleboard
2 bedrooms, 2 beds, 1.5 bathrooms
1–8 Sept
New place to stay
Top guest favourite
Home in Sarasota
Palm Tree Haven
2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
4.99 out of 5 average rating, 103 reviews
Top guest favourite
Home in Siesta Key
Stroll to the Sea, Steps to the Village, Boat dock
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 23 reviews
Home in Sarasota
Periwinkle House
5 bedrooms, 6 beds, 3.5 bathrooms
1–7 Sept
New place to stay
Flat in Siesta Key
Siesta Sandcastle - Egret
1 bedroom, 1 king bed, 1 bathroom
13–18 Sept
New place to stay