filters

Search results; Over 1,000 homes

Photo 1 of 24
Top guest favourite
Apartment in Siesta Key
Siesta Key Serenity At The Palm Bay Club
2 bedrooms, 3 beds, 2 private bathrooms
19–24 Oct
,
4.94 out of 5 average rating, 176 reviews
Photo 1 of 25
Top guest favourite
Apartment in Siesta Key
Private Beach•3 Heated Pools•2BR•Ground Floor
10-min drive
28 Nov – 3 Dec
5.0 out of 5 average rating, 9 reviews
Photo 1 of 25
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
3-min walk
26 Sept – 1 Oct
5.0 out of 5 average rating, 14 reviews
Photo 1 of 29
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
14-min walk
20–25 Sept
5.0 out of 5 average rating, 17 reviews
Photo 1 of 29
Top guest favourite
Home in Sarasota
Sun Coast Oasis-Heated Pool-Pool Table-Arcade
20-min drive
21–26 Sept
5.0 out of 5 average rating, 9 reviews
Photo 1 of 29
Top guest favourite
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
3-min walk
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Photo 1 of 29
Guest favourite
Apartment in Siesta Key
Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything
10-min drive
19–24 Sept
4.88 out of 5 average rating, 179 reviews
Photo 1 of 29
Top guest favourite
Apartment in Siesta Key
New listing - Pool Home, 500ft to Beach!
10-min drive
18–23 Sept
5.0 out of 5 average rating, 17 reviews
Photo 1 of 17
Flat in Siesta Key
Siesta Sandcastle - Egret
10-min drive
15–20 Nov
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Top guest favourite
Home in Sarasota
Luxury 3B/3B waterfront home w/ pool + boat access
10-min drive
5–10 Oct
5.0 out of 5 average rating, 11 reviews
Photo 1 of 29
Top guest favourite
Flat in Siesta Key
Beach Walk Bungalow
6-min walk
3–8 Oct
4.94 out of 5 average rating, 35 reviews
Photo 1 of 29
Top guest favourite
Apartment in Siesta Key
Beachfront Siesta Key - 3 night min w/beach gear!
10-min drive
14–19 Nov
4.99 out of 5 average rating, 75 reviews
Photo 1 of 29
Home in Sarasota
*BRAND NEW* heated pool, on golf course
30-min drive
20–25 Oct
New place to stay
Photo 1 of 29
Top guest favourite
Home in Sarasota
Heated Private Pool • 10 Min to Siesta Key • 3BR
20-min drive
19–24 Sept
5.0 out of 5 average rating, 16 reviews
Photo 1 of 8
Guest favourite
Cottage in Sarasota
Cozy Lido Studio by Beach & St Armand's
20-min drive
27 Sept – 2 Oct
4.95 out of 5 average rating, 66 reviews
Photo 1 of 29
Top guest favourite
Home in Sarasota
4BRHeated Pool•Fire Pit•Pool Table Mins Siesta Key
20-min drive
11–16 Oct
5.0 out of 5 average rating, 25 reviews
Photo 1 of 29
Guest favourite
Home in Sarasota
Coastal Calm
10-min drive
26 Sept – 1 Oct
5.0 out of 5 average rating, 10 reviews
Photo 1 of 29
Townhouse in Siesta Key
3 bdrm 4 bath Beachhouse
7-min walk
25 Sept – 2 Oct
5.0 out of 5 average rating, 4 reviews
Photo 1 of 13
Top guest favourite
Flat in Sarasota
Siesta Sanctuary
10-min drive
9–14 Nov
4.95 out of 5 average rating, 43 reviews