Mansion holiday rentals in Siesta Key
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Top-rated mansion rentals in Siesta Key
Guests agree: These mansions are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Siesta Key mansion rentals
Luxury mansion rentals
Home in Bradenton
4.91 out of 5 average rating, 113 reviewsParadise Oasis w/ amazing pool | Near AMI beaches
19–26 Dec
Home in Nokomis
4.88 out of 5 average rating, 147 reviews4/2.5 Oak Bahay, Heated Pool! 5min to Beach,4Acres
23–30 Dec
Home in Bradenton
4.91 out of 5 average rating, 157 reviewsHeated Saltwater Pool near Anna Maria Is.- 6bd/3ba
11–18 Apr
Home in Sarasota
5.0 out of 5 average rating, 10 reviewsFruit /Botanical Garden Estate 2 miles to downtown
14–21 Aug
Home in Anna Maria
4.96 out of 5 average rating, 50 reviewsSteps to the Beach! Pool/spa! Golf Cart Included!!
10–17 Dec
Home in Siesta Key
4.9 out of 5 average rating, 21 reviews*Minutes from beach w/private access, heated pool
19–26 Sep
Apartment in Siesta Key
5.0 out of 5 average rating, 12 reviewsCoastal Luxury Penthouse
7–14 Aug
Home in Sarasota
4.79 out of 5 average rating, 85 reviews*Full Bay View Beauty, Private Heated Pool *
25 Jan – 1 Feb
Pet-friendly mansion rentals
Home in Holmes Beach
4.97 out of 5 average rating, 124 reviewsTwin Palms: Big House Steps to Beach w/Lush Pool
31 Aug – 7 Sep
Home in Bradenton
4.99 out of 5 average rating, 131 reviewsBradenton Gem - BRAND NEW POOL!
13–20 Aug
Home in Bradenton
4.95 out of 5 average rating, 104 reviewsSpa & Pool+By The River+Near Beaches+Gameroom
24–31 Jan
Home in Sarasota
4.91 out of 5 average rating, 186 reviewsModern private getaway heated pool with spa
20–27 Jan
Home in Sarasota
5.0 out of 5 average rating, 17 reviewsCoastal Contemporary Pool Home
11–18 Dec
Home in Sarasota
4.97 out of 5 average rating, 58 reviewsRenovated Ranch near Downtown Sarasota and Siesta
6–13 Oct
Home in Sarasota
5.0 out of 5 average rating, 45 reviewsLuxury villa near Siesta - heated, screened pool
18–25 Aug
Villa in Sarasota
5.0 out of 5 average rating, 61 reviewsModern Retreat Close to Beach-4BR/3BA, Pool-Games
6–13 Mar
Mansion rentals with a pool
Home in Sarasota
4.93 out of 5 average rating, 58 reviewsHeated Pool - Just 1 mile to Beach! Updated/Fun!
10–17 Dec
Home in Sarasota
5.0 out of 5 average rating, 12 reviewsWaterside Villa - 4BD/2BA with a heated pool
15–22 Oct
Home in Anna Maria
5.0 out of 5 average rating, 12 reviewsPier to Pier Paradise by Beach Boutique Rentals
17–24 Sep
Home in Anna Maria
4.96 out of 5 average rating, 56 reviewsMy Private Beach
17–24 Nov
Home in Siesta Key
5.0 out of 5 average rating, 13 reviewsBeautiful House with Heated pool
15–22 Nov
Home in Siesta Key
4.83 out of 5 average rating, 58 reviewsA Family Island Treasure
5–12 Oct
Home in Sarasota
5.0 out of 5 average rating, 28 reviewsFamily Fun House near Siesta Key Beach
31 Mar – 7 Apr
Home in Sarasota
5.0 out of 5 average rating, 10 reviewsPool + Near Beach + Outdoor Games + Close to DT
5–12 Dec
Destinations to explore
- Sarasota Holiday rentals
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