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
14–21 Apr
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
4.95 out of 5 average rating, 104 reviewsSpa & Pool+By The River+Near Beaches+Gameroom
28 Feb – 7 Mar
Home in Bradenton
4.91 out of 5 average rating, 158 reviewsHeated Saltwater Pool near Anna Maria Is.- 6bd/3ba
12–19 Apr
Home in Sarasota
4.79 out of 5 average rating, 85 reviews*Full Bay View Beauty, Private Heated Pool *
9–16 Dec
Home in Sarasota
4.96 out of 5 average rating, 23 reviewsNomadic Abode - heated salt water pool!
24–31 Mar
Home in Siesta Key
4.98 out of 5 average rating, 61 reviewsSiesta Key Seaside Bungalow
25 May – 1 Jun
Home in Siesta Key
5.0 out of 5 average rating, 6 reviewsMid-Century lux pool+canal house -walk to village
17–24 Jul
Pet-friendly mansion rentals
Home in Bradenton
4.99 out of 5 average rating, 132 reviewsBradenton Gem - BRAND NEW POOL!
13–20 Aug
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 Sept
Home in Sarasota
4.91 out of 5 average rating, 186 reviewsModern private getaway heated pool with spa
26 Apr – 3 May
Home in Sarasota
4.82 out of 5 average rating, 51 reviewsS Heated Pool, 5 Min to Siesta Key Beach
30 Jul – 6 Aug
Home in Sarasota
5.0 out of 5 average rating, 45 reviewsLuxury villa near Siesta - heated, screened pool
25 Jul – 1 Aug
Home in Sarasota
5.0 out of 5 average rating, 5 reviewsLovely home with pool Near Siesta Key!
2–9 Nov
Home in Siesta Key
4.91 out of 5 average rating, 45 reviewsPet friendly Home- Blocks from Siesta Key Beach
21–28 Apr
Home in Sarasota
5.0 out of 5 average rating, 17 reviewsCoastal Contemporary Pool Home
6–13 Apr
Mansion rentals with a pool
Home in Sarasota
5.0 out of 5 average rating, 11 reviewsPool + Near Beach + Outdoor Games + Close to DT
5–12 Dec
Home in Anna Maria
5.0 out of 5 average rating, 13 reviewsPier to Pier Paradise by Beach Boutique Rentals
15–22 Sept
Home in Bradenton
4.98 out of 5 average rating, 45 reviewsExecutive Bayside Retreat/Pool/IMG/Sarasota Bay
24 Sept – 1 Oct
Home in Sarasota
5.0 out of 5 average rating, 13 reviewsWaterside Villa - 4BD/2BA with a heated pool
8–15 Oct
Home in Sarasota
4.93 out of 5 average rating, 59 reviewsHeated Pool - Just 1 mile to Beach! Updated/Fun!
26 Jan – 2 Feb
Home in Anna Maria
4.92 out of 5 average rating, 49 reviewsWhite Pearl-New Premier AMI Home with Sunset Views
14–21 Sept
Home in Sarasota
4.88 out of 5 average rating, 49 reviews[The Bay St. Hideaway] Private-Heated Pool, Patio•
17–24 Sept
Home in Sarasota
5.0 out of 5 average rating, 26 reviewsDowntown Sarasota Oasis w/ Heated Pool!
25 Aug – 1 Sept
Destinations to explore
- Sarasota Holiday rentals
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