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 Siesta Key
4.82 out of 5 average rating, 65 reviewsParadise Villa on Siesta Key
31 Dec – 7 Jan
Villa in Sarasota
4.95 out of 5 average rating, 19 reviewsMid-Century Home with Heated Pool
18–25 Jul
Villa in Sarasota
5.0 out of 5 average rating, 8 reviewsModern Vacation Villa 4 miles to Siesta Key
18–25 Mar
Villa in Sarasota
4.98 out of 5 average rating, 52 reviewsNEW Luxury 4/3 Home By Downtown, Beach & Keys
17–24 Oct
Villa in Sarasota
4.88 out of 5 average rating, 42 reviewsParadise Villa- Sarasota
18–25 Sep
Villa in HOLMES BEACH
4.94 out of 5 average rating, 35 reviewsSteps from the beach 2BR @Manatee Beach
29 Nov – 6 Dec
Villa in Holmes Beach
5.0 out of 5 average rating, 11 reviewsWaterfront in Paradise
25 Nov – 2 Dec
Luxury villa rentals
Villa in Osprey
5.0 out of 5 average rating, 11 reviewsParadise with a pool, pier and private beach area
16–23 Oct
Villa in Sarasota
4.91 out of 5 average rating, 44 reviewsSiesta Key Palm Paradise w/ Heated Salt Water Pool
14–21 Mar
Villa in Bradenton Beach
4.7 out of 5 average rating, 37 reviewsShort walk to the beach! Unit B
24–31 Dec
Villa in Bradenton
4.5 out of 5 average rating, 4 reviewsBermuda style house on a bayou
27 May – 3 Jun
Villa in Bradenton
New Luxury Home near IMG Academy & Anna Maria Isl
15–22 Jul
Villa in Longboat Key
Beach Castle Resort, Direct Bay, Walk to Beach
15–22 Aug
Villa in Sarasota
5.0 out of 5 average rating, 16 reviewsCourtyard Villa w/Pool, Spa & Sauna close to Beach
17–24 Nov
Villa in Ruskin
4.97 out of 5 average rating, 36 reviewsSunset Paradise -Pool heated. Tampa St Pete Escape
17–24 May
Villa rentals with a pool
Villa in Bradenton
5.0 out of 5 average rating, 27 reviewsRiver Pointe 3/2 Lakefront Home with Heated Pool
8–15 May
Villa in North Port
4.98 out of 5 average rating, 44 reviewsHeated Pool Retreat 3 bed., 2 bath.
30 Nov – 7 Dec
Villa in Bradenton
5.0 out of 5 average rating, 22 reviews'The Gathering Place' Oasis with Huge Heated Pool
15–22 Aug
Villa in North Port
4.88 out of 5 average rating, 17 reviewsCheerful 3-bed villa with heated pool (Car)
9–16 Jan
Villa in North Port
5.0 out of 5 average rating, 24 reviewsStunning Retreat: Endless Summer Villa-Heated Pool
25 Aug – 1 Sep
Villa in Sarasota
4.67 out of 5 average rating, 3 reviewsSarasota Jungle Garden Villa
25 Mar – 1 Apr
Villa in Venice
5.0 out of 5 average rating, 6 reviewsBeautifully Remodeled Anna-vacation home
13–20 May
Villa in Bradenton
4.8 out of 5 average rating, 20 reviewsGulf Coast Retreat - Private Pool, BBQ, Pets OK
17–24 May
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
$189 SGD before taxes and fees
Destinations to explore
- Sarasota Holiday rentals
- Anna Maria Island Holiday rentals
- Tampa Holiday rentals
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