Villa holiday rentals in Siesta Key
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Top-rated villa rentals in Siesta Key
Guests agree: these villas are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for villa rentals in Siesta Key
Private villa rentals
Villa in Sarasota
4.75 out of 5 average rating, 8 reviewsCharming 2/2 Village des Pins close to Siesta Key
3–10 Sep
Villa in Sarasota
4.88 out of 5 average rating, 41 reviewsParadise Villa- Sarasota
12–19 Dec
Villa in Holmes Beach
5.0 out of 5 average rating, 11 reviewsWaterfront in Paradise
27 Jun – 4 Jul
Villa in Sarasota
4.91 out of 5 average rating, 44 reviewsSiesta Key Palm Paradise w/ Heated Salt Water Pool
13–20 Jul
Villa in Sarasota
4.95 out of 5 average rating, 19 reviewsMid-Century Home with Heated Pool
22–29 Apr
Villa in Sarasota
4.98 out of 5 average rating, 52 reviewsNEW Luxury 4/3 Home By Downtown, Beach & Keys
8–15 Jan
Villa in Venice
4.81 out of 5 average rating, 31 reviewsGondola Dr house with private swimming pool
13–20 Sep
Villa in Sarasota
4.81 out of 5 average rating, 64 reviewsParadise Villa on Siesta Key
10–17 Jul
Luxury villa rentals
Villa in Sarasota
4.88 out of 5 average rating, 16 reviewsRelaxation awaits in this bohemian inspired villa
5–12 Sep
Villa in Bradenton
4.5 out of 5 average rating, 4 reviewsBermuda style house on a bayou
21–28 May
Villa in Bradenton
New Luxury Home near IMG Academy & Anna Maria Isl
30 Jun – 7 Jul
Villa in Longboat Key
Beach Castle Resort, Direct Bay, Walk to Beach
23–30 Jul
Villa in Sarasota
5.0 out of 5 average rating, 16 reviewsCourtyard Villa w/Pool, Spa & Sauna close to Beach
13–20 Apr
Villa in Sarasota
4.5 out of 5 average rating, 8 reviewsLido Villa, steps from the beach, with heated pool
18–25 Jan
Villa in Holmes Beach
4.89 out of 5 average rating, 53 reviewsExclusive Islands West Resort - Villa #3 Seahorse
31 Jan – 7 Feb
Villa in Ruskin
4.97 out of 5 average rating, 36 reviewsSunset Paradise -Pool heated. Tampa St Pete Escape
13–20 Apr
Villa rentals with a pool
Villa in Bradenton
5.0 out of 5 average rating, 22 reviews'The Gathering Place' Oasis with Huge Heated Pool
8–15 May
Villa in North Port
5.0 out of 5 average rating, 24 reviewsStunning Retreat: Endless Summer Villa-Heated Pool
16–23 Dec
Villa in Sarasota
4.67 out of 5 average rating, 3 reviewsSarasota Jungle Garden Villa
20–27 Apr
Villa in Venice
5.0 out of 5 average rating, 6 reviewsBeautifully Remodeled Anna-vacation home
20–27 Jun
Villa in Bradenton
4.8 out of 5 average rating, 20 reviewsGulf Coast Retreat - Private Pool, BBQ, Pets OK
21–28 May
Villa in Sarasota
5.0 out of 5 average rating, 19 reviewsVilla Siesta, Secret Downtown Treasure-heated Pool
1–8 Jan
Villa in Siesta Key
4.47 out of 5 average rating, 34 reviewsBeautiful property on Siesta Key from bay to beach
7–14 Jan
Villa in Siesta Key
5.0 out of 5 average rating, 5 reviewsModern, Walkable, Updated, Private.
25 Oct – 1 Nov
Quick stats about villa rentals in Siesta Key
Total rentals
90 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Rentals with a pool
80 properties have a pool
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
440 reviews
Nightly prices starting at
€ 131 before taxes and fees
Destinations to explore
- Sarasota Holiday rentals
- Anna Maria Island Holiday rentals
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