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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Loft in Siesta Key
Cozy Siesta Key Dream Inn Rental < 1/2 Mi to Beach
Studio, 2 beds, 1 bathroom
13–18 Sept
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4.97 out of 5 average rating, 64 reviews
Top guest favourite
Apartment in Siesta Key
Private Beach•3 Heated Pools•2BR•Ground Floor
2 bedrooms, 3 beds
28 Nov – 3 Dec
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Luxe
Home in Siesta Key
7Bedroom Luxury Home W/Private Pool on Siesta Key!
7 bedrooms, 10 beds
5–10 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Apartment in Sarasota
Direct Gulf View - Residence 603
3 bedrooms, 3 beds
5–10 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Flat in Sarasota
Gertrude's Siesta | Bayview Pool Tennis Beach!
1 bedroom, 2 beds
18–23 Sept
New place to stay
Top guest favourite
Apartment in Siesta Key
New listing - Pool Home, 500ft to Beach!
3 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Siesta Key
Two bedroom across from beach, walk to town!
2 bedrooms, 4 beds
12–17 Sept
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Home in Siesta Key
Beach House *Pool*Spa*Walk to Beach and SK Village
4 bedrooms, 5 beds
7–12 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds
12–17 Sept
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Home in Siesta Key
Walk To Siesta Key Beach & Village ; Renovated 2BR
2 bedrooms, 4 beds
19–24 Sept
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Home in Sarasota
SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!
3 bedrooms, 3 queen beds
6–11 Sept
4.98 out of 5 average rating, 119 reviews
Guest favourite
Room in Sarasota
Siesta Beach 3 Min | Walk to Village + Patio!
1 queen bed
12–17 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Sarasota
Coastal Calm
3 bedrooms, 4 beds
6–13 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Apartment in Siesta Key
The Flamingo's Nest at Sea Club II
2 bedrooms, 3 beds
26 Sept – 1 Oct
4.94 out of 5 average rating, 156 reviews
Top guest favourite
Apartment in Siesta Key
Beachfront Siesta Key - 3 night min w/beach gear!
2 bedrooms, 4 beds
13–18 Sept
4.99 out of 5 average rating, 74 reviews
Guest favourite
Home in Sarasota
Spacious | New Pool | 10 Min to Ocean | Quiet Area
3 bedrooms, 5 beds
11–16 Sept
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Home in Sarasota
Coastal Luxe, SaltPool/heatSpa, 5 miles to Siesta
5 bedrooms, 10 beds
7–14 Sept
4.98 out of 5 average rating, 50 reviews