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Search results; Over 1,000 homes in Siesta Key

Top guest favourite
Apartment in Siesta Key
Gulf Views | Walkable | Spacious
2 bedrooms, 3 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.92 out of 5 average rating, 163 reviews
Superhost
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 3 beds
18–23 Aug
New place to stay
Flat in Siesta Key
Villa with private beach, 3 pools complex on beach
2 bedrooms, 3 beds
16–21 Aug
New place to stay
Top guest favourite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds
24–29 Sept
5.0 out of 5 average rating, 10 reviews
Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds
14–21 Aug
Superhost
Home in Sarasota
Sun Coast Oasis-Heated Pool-Pool Table-Arcade
3 bedrooms, 5 beds
9–14 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Siesta Key
Siesta Key Retreat 1mi to Beach!
3 bedrooms, 4 beds
23–30 Aug
4.96 out of 5 average rating, 46 reviews
Superhost
Home in Siesta Key
Endless Views | Panoramic View of Siesta Beach
3 bedrooms, 3 king beds
23–28 Aug
4.2 out of 5 average rating, 5 reviews
Top guest favourite
Home in Sarasota
Siesta Key Oasis Walk to Beach, Pool, Hot Tub, BBQ
3 bedrooms, 4 beds
23–28 Aug
4.95 out of 5 average rating, 37 reviews
Top guest favourite
Flat in Siesta Key
Two bedroom across from beach, walk to town!
2 bedrooms, 4 beds
15–20 Aug
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Home in Siesta Key
Garage Parking, King beds-NO Bunks, Private Beach
5 bedrooms, 5 beds
24–29 Aug
4.93 out of 5 average rating, 43 reviews
Top guest favourite
Home in Sarasota
Siesta Serenity ~ Pool/Waterslide/Waterfront
4 bedrooms, 5 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 22 reviews
Superhost
Villa in Bradenton
HeatedPool • HotTub • OutdoorKitchen/Theater/Games
6 bedrooms, 7 beds
23–28 Aug
New place to stay
Guest favourite
Home in Sarasota
Private Heated Pool~Yacht Rental~BBQ~Near Water
3 bedrooms, 5 beds
22–27 Aug
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in Sarasota
St Armands Mid Century Rad Pad with Pool
3 bedrooms, 3 beds
14–19 Aug
5.0 out of 5 average rating, 73 reviews
Top guest favourite
Home in Sarasota
SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!
3 bedrooms, 3 queen beds
18–23 Aug
4.98 out of 5 average rating, 119 reviews
Top guest favourite
Home in Sarasota
Coastal Luxe, SaltPool/heatSpa, 5 miles to Siesta
5 bedrooms, 10 beds
23–30 Aug
4.98 out of 5 average rating, 49 reviews
Top guest favourite
Home in Sarasota
Sarasota Paradise/Stunning Home/Heated Pool
4 bedrooms, 6 beds
17–22 Aug
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Home in Sarasota
Your Resort •7BR •13 Beds • Pool • Dock • Elevator
7 bedrooms, 13 beds
22–29 Aug
5.0 out of 5 average rating, 24 reviews