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 Siesta Key
4.82 out of 5 average rating, 65 reviewsParadise Villa on Siesta Key
25 Apr – 2 May
Villa in Sarasota
4.88 out of 5 average rating, 42 reviewsParadise Villa- Sarasota
8–15 Nov
Villa in North Port
4.98 out of 5 average rating, 44 reviewsHeated Pool Retreat 3 bed., 2 bath.
30 Aug – 6 Sep
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
11–18 Apr
Villa in Sarasota
4.95 out of 5 average rating, 19 reviewsMid-Century Home with Heated Pool
28 Feb – 7 Mar
Villa in HOLMES BEACH
4.94 out of 5 average rating, 35 reviewsSteps from the beach 2BR @Manatee Beach
14–21 Dec
Villa in Holmes Beach
5.0 out of 5 average rating, 11 reviewsWaterfront in Paradise
9–16 Aug
Luxury villa rentals
Villa in Osprey
5.0 out of 5 average rating, 11 reviewsParadise with a pool, pier and private beach area
4–11 Jun
Villa in Sarasota
4.91 out of 5 average rating, 44 reviewsSiesta Key Palm Paradise w/ Heated Salt Water Pool
13–20 Mar
Villa in Bradenton Beach
4.7 out of 5 average rating, 37 reviewsShort walk to the beach! Unit B
10–17 Jul
Villa in Bradenton
4.5 out of 5 average rating, 4 reviewsBermuda style house on a bayou
26 May – 2 Jun
Villa in Bradenton
New Luxury Home near IMG Academy & Anna Maria Isl
15–22 Sep
Villa in Holmes Beach
4.89 out of 5 average rating, 54 reviewsExclusive Islands West Resort - Villa #3 Seahorse
31 Dec – 7 Jan
Villa in Anna Maria
5.0 out of 5 average rating, 4 reviews2BR 1st-floor | Patio | Pool | Dog Friendly | W/D
5–12 Jan
Villa in Ruskin
4.97 out of 5 average rating, 36 reviewsSunset Paradise -Pool heated. Tampa St Pete Escape
29 Jan – 5 Feb
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
23–30 Oct
Villa in Bradenton
5.0 out of 5 average rating, 22 reviews'The Gathering Place' Oasis with Huge Heated Pool
12–19 May
Villa in North Port
4.88 out of 5 average rating, 17 reviewsCheerful 3-bed villa with heated pool (Car)
7–14 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
8–15 May
Villa in Bradenton
4.8 out of 5 average rating, 20 reviewsGulf Coast Retreat - Private Pool, BBQ, Pets OK
14–21 May
Villa in Port Charlotte
4.78 out of 5 average rating, 50 reviewsMaine Escape, full refund*, heated pool, Dogs Ok
12–19 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
€ 130 before taxes and fees
Destinations to explore
- Sarasota Holiday rentals
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