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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Apartment in Siesta Key
Sarasota Surf & Racquet Club Siesta Key Condo
2 bedrooms, 3 beds, 2 private bathrooms
11–16 Sept
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4.83 out of 5 average rating, 151 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
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
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
3 bedrooms, 4 beds
11–16 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Siesta Key
Beach Walk Bungalow
3 bedrooms, 3 beds
3–8 Oct
4.94 out of 5 average rating, 35 reviews
Flat in Siesta Key
Siesta Sandcastle - Egret
1 bedroom, 1 king bed
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Sarasota
Quiet Family Home w/ Pool Near Pinecraft
3 bedrooms, 4 beds
17–22 Sept
4.84 out of 5 average rating, 43 reviews
Top guest favourite
Home in Sarasota
Siesta Breeze ~ Charming Coastal Cottage
2 bedrooms, 2 queen beds
9–14 Sept
4.99 out of 5 average rating, 142 reviews
Top guest favourite
Home in Siesta Key
Siesta Key Retreat 1mi to Beach!
3 bedrooms, 4 beds
9–16 Sept
4.96 out of 5 average rating, 48 reviews
Guest favourite
Apartment in Siesta Key
Siesta Key condo - short walk to beach - GBB 1219
2 bedrooms, 3 beds
15–22 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Siesta Key
Siesta Premier Location - The 'Calm of Siesta'
2 bedrooms, 2 beds
18–25 Sept
4.94 out of 5 average rating, 142 reviews
Top guest favourite
Townhouse in Siesta Key
Gulf and Beach Views-Steps from Beach and Village
2 bedrooms, 2 beds
26 Oct – 2 Nov
5.0 out of 5 average rating, 48 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 Sarasota
Private Pool • 10 Min to Siesta Key • 3BR Home
3 bedrooms, 4 beds
16–21 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Sarasota
4BRHeated Pool•Fire Pit•Pool Table Mins Siesta Key
4 bedrooms, 7 beds
11–16 Oct
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Sarasota
Siesta Sands 1 Mile to Beach
3 bedrooms, 3 beds
14–21 Sept
4.95 out of 5 average rating, 19 reviews
Luxe
Home in Siesta Key
7Bedroom Luxury Home W/Private Pool on Siesta Key!
7 bedrooms, 10 beds
9–14 Sept
5.0 out of 5 average rating, 4 reviews