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Search results; Over 1,000 homes in Siesta Key

Top guest favourite
Apartment in Siesta Key
Private Beach with Loungers · 2 Pools & Bay View
2 bedrooms, 3 beds, 2 private bathrooms
13–18 Aug
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4.97 out of 5 average rating, 132 reviews
Top guest favourite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5.0 out of 5 average rating, 9 reviews, 5 bedrooms, 7 beds, 5 bathrooms
27 Sept – 2 Oct
Guest favourite
Home in Siesta Key
Waterfront Home Pool & Dock 5 Min to Siesta Beach
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
27 Aug – 1 Sept
Top guest favourite
Home in Sarasota
Luxury 3B/3B waterfront home w/ pool + boat access
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 3 bathrooms
11–16 Aug
Flat in Siesta Key
Villa with private beach, 3 pools complex on beach
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds, 2 bathrooms
9–16 Aug
Home in Siesta Key
3 bedroom renovated pool home near beach/village
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Home in Sarasota
Luxury Pool Family Paradise-Siesta Key Beach/DT
4.96 out of 5 average rating, 142 reviews, 3 bedrooms, 4 beds, 2 bathrooms
31 Aug – 5 Sept
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
Apartment in Siesta Key
Private Siesta Key Escape
4.93 out of 5 average rating, 239 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Home in Sarasota
Siesta Key Oasis| Hot tub| Fire Pit| BBQ| Games
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 5 beds, 2 bathrooms
13–18 Aug
Home in Siesta Key
Cypress Cottage - Walkable to Siesta Key Beaches
5 bedrooms, 8 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Sarasota
NEW Luxe Resort Home*XL Pool/Hot Tub*1 mi to Beach
4.97 out of 5 average rating, 30 reviews, 3 bedrooms, 6 beds, 2 bathrooms
17–22 Aug
Guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
4.93 out of 5 average rating, 59 reviews, 2 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
Top guest favourite
Home in Anna Maria
Magnolia Palms: Family Retreat w/ Backyard Oasis
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 6 beds, 2 bathrooms
29 Aug – 3 Sept
Superhost
Apartment in Sarasota
Direct Gulf View - Residence 505
4 bedrooms, 4.5 bathrooms
1–6 Sept
Superhost
Home in Siesta Key
Gertrudes Siesta, Beach-view, Pool,1 min to Beach
4.6 out of 5 average rating, 5 reviews, 3 bedrooms, 5 beds, 2 bathrooms
8–13 Aug
Home in Bradenton
Pool, Hot Tub, PickleBall, Firepit, 5 min to IMG
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
17–22 Aug