filters

Search results; Over 1,000 homes in Siesta Key

Photo 1 of 29
Top guest favourite
Cottage in Siesta Key
Siesta Key Cozy Cottage across from the beach!
1 bedroom, 2 beds, 1 private bathroom
1–6 Oct
,
4.91 out of 5 average rating, 208 reviews
Photo 1 of 25
Top guest favourite
Apartment in Siesta Key
Private Beach•3 Heated Pools•2BR•Ground Floor
2 bedrooms, 3 beds, 2 bathrooms
28 Nov – 3 Dec
5.0 out of 5 average rating, 10 reviews
Photo 1 of 29
Home in Siesta Key
Your Private Canal front Escape with heated pool
3 bedrooms, 4 beds, 2.5 bathrooms
1–8 Oct
Photo 1 of 25
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds, 1 bathroom
7–12 Nov
5.0 out of 5 average rating, 15 reviews
Photo 1 of 29
Luxe
Home in Siesta Key
7Bedroom Luxury Home W/Private Pool on Siesta Key!
7 bedrooms, 10 beds, 7.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 4 reviews
Photo 1 of 29
Villa in Siesta Key
Private Siesta Key Home minutes from the sand
2 bedrooms, 2 king beds, 2 bathrooms
6–13 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Top guest favourite
Flat in Siesta Key
Beach Walk Bungalow
3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
4.94 out of 5 average rating, 35 reviews
Photo 1 of 22
Flat in Siesta Key
Charming 1BR 2nd-Floor | Deck | Pool | Kitchenette
1 bedroom, 2 beds, 1 bathroom
30 Oct – 4 Nov
4.48 out of 5 average rating, 61 reviews
Photo 1 of 6
Top guest favourite
Room in Sarasota
Siesta Beach 3 Min | Walk to Village + Patio!
1 queen bed, 1 bathroom
13–18 Oct
5.0 out of 5 average rating, 9 reviews
Photo 1 of 29
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 17 reviews
Photo 1 of 29
Top guest favourite
Apartment in Siesta Key
Beachfront Siesta Key | Gulf View + Private Beach
2 beds, 1 bathroom
28 Oct – 2 Nov
4.97 out of 5 average rating, 397 reviews
Photo 1 of 29
Guest favourite
Home in Sarasota
Aloft on Canal – Luxury Beachside Retreat
8 bedrooms, 13 beds, 6.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 11 reviews
Photo 1 of 29
Top guest favourite
Home in Siesta Key
Beach House *Pool*Spa*Walk to Beach and SK Village
4 bedrooms, 5 beds, 2 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 15 reviews
Photo 1 of 29
Top guest favourite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds, 5 bathrooms
31 Dec – 5 Jan
5.0 out of 5 average rating, 13 reviews
Photo 1 of 29
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 Oct
5.0 out of 5 average rating, 23 reviews
Photo 1 of 29
Villa in Siesta Key
Villa Bella Mare
2 bedrooms, 3 beds, 2 bathrooms
1–8 Oct
4.94 out of 5 average rating, 18 reviews
Photo 1 of 17
Flat in Siesta Key
Siesta Sandcastle - Egret
1 bedroom, 1 king bed, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 4 reviews
Photo 1 of 29
Home in Siesta Key
Huge back yard w/heated pool & pet friendly house
3 bedrooms, 5 beds, 2 bathrooms
1–8 Oct
5.0 out of 5 average rating, 4 reviews
Photo 1 of 29
Home in Sarasota
*BRAND NEW* heated pool, golf course views
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
New place to stay