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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Cottage in Siesta Key
Adorable Cozy Silver Sands Cottage on Siesta Key!!
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
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4.88 out of 5 average rating, 200 reviews
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, 7 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, 13 reviews
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Apartment in Siesta Key
The Flamingo's Nest at Sea Club II
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
4.94 out of 5 average rating, 156 reviews
Top guest favourite
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
3 bedrooms, 4 beds, 2.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 12 reviews
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
Top guest favourite
Home in Sarasota
Quiet Family Home w/ Pool Near Pinecraft
3 bedrooms, 4 beds, 2 bathrooms
17–22 Sept
4.84 out of 5 average rating, 43 reviews
Home in Siesta Key
Huge back yard w/heated pool & pet friendly house
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 4 Oct
5.0 out of 5 average rating, 4 reviews
Flat in Siesta Key
Siesta Sandcastle - Egret
1 bedroom, 1 king bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Sarasota
Siesta Breeze ~ Charming Coastal Cottage
2 bedrooms, 2 queen beds, 2 bathrooms
9–14 Sept
4.99 out of 5 average rating, 142 reviews
Guest favourite
Apartment in Siesta Key
Siesta Key condo - short walk to beach - GBB 1219
2 bedrooms, 3 beds, 2 bathrooms
15–22 Sept
5.0 out of 5 average rating, 8 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 Siesta Key
Siesta Key Retreat 1mi to Beach!
3 bedrooms, 4 beds, 2 bathrooms
9–16 Sept
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Flat in Siesta Key
Siesta Premier Location - The 'Calm of Siesta'
2 bedrooms, 2 beds, 2 bathrooms
18–25 Sept
4.94 out of 5 average rating, 142 reviews
Top guest favourite
Home in Sarasota
Private Pool • 10 Min to Siesta Key • 3BR Home
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Home in Sarasota
4BRHeated Pool•Fire Pit•Pool Table Mins Siesta Key
4 bedrooms, 7 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 25 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