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
4.88 out of 5 average rating, 42 reviewsParadise Villa- Sarasota
12–19 Oct
Villa in Sarasota
4.98 out of 5 average rating, 52 reviewsNEW Luxury 4/3 Home By Downtown, Beach & Keys
1–8 May
Villa in Sarasota
4.91 out of 5 average rating, 44 reviewsSiesta Key Palm Paradise w/ Heated Salt Water Pool
3–10 Aug
Villa in Holmes Beach
5.0 out of 5 average rating, 11 reviewsWaterfront in Paradise
29 Jun – 6 Jul
Villa in Siesta Key
4.81 out of 5 average rating, 64 reviewsParadise Villa on Siesta Key
9–16 Oct
Villa in Sarasota
4.95 out of 5 average rating, 19 reviewsMid-Century Home with Heated Pool
22–29 Apr
Villa in Venice
4.81 out of 5 average rating, 31 reviewsGondola Dr house with private swimming pool
13–20 Sep
Villa in North Port
4.88 out of 5 average rating, 17 reviewsCheerful 3-bed villa with heated pool (Car)
21–28 Aug
Luxury villa rentals
Villa in Sarasota
4.88 out of 5 average rating, 16 reviewsRelaxation awaits in this bohemian inspired villa
22–29 Sep
Villa in Osprey
5.0 out of 5 average rating, 11 reviewsParadise with a pool, pier and private beach area
14–21 Nov
Villa in Bradenton
4.5 out of 5 average rating, 4 reviewsBermuda style house on a bayou
23–30 May
Villa in Bradenton
New Luxury Home near IMG Academy & Anna Maria Isl
24–31 Jul
Villa in Sarasota
4.5 out of 5 average rating, 8 reviewsLido Villa, steps from the beach, with heated pool
17–24 Feb
Villa in Anna Maria
4.57 out of 5 average rating, 14 reviewsNorthshore Beauty w/pool 5 bed 4bath July deal
9–16 Oct
Villa in Holmes Beach
4.89 out of 5 average rating, 53 reviewsExclusive Islands West Resort - Villa #3 Seahorse
2–9 Apr
Villa in Ruskin
4.97 out of 5 average rating, 36 reviewsSunset Paradise -Pool heated. Tampa St Pete Escape
17–24 Apr
Villa rentals with a pool
Villa in Bradenton
4.83 out of 5 average rating, 136 reviewsElegant private home 3Bdr/3bth
11–18 Apr
Villa in North Port
4.98 out of 5 average rating, 44 reviewsHeated pool, King bed, Beach 25 minutes away
17–24 Aug
Villa in Bradenton
5.0 out of 5 average rating, 27 reviewsRiver Pointe 3/2 Lakefront Home with Heated Pool
3–10 Sep
Villa in North Port
4.73 out of 5 average rating, 11 reviews"Nature Escape" Modern Villa with Heated Pool
24–31 May
Villa in Bradenton
5.0 out of 5 average rating, 22 reviews'The Gathering Place' Oasis with Huge Heated Pool
9–16 May
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
24–31 Mar
Villa in Venice
5.0 out of 5 average rating, 6 reviewsBeautifully Remodeled Anna-vacation home
11–18 Jul
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
₹11,681 before taxes and fees
Destinations to explore
- Sarasota Holiday rentals
- Anna Maria Island Holiday rentals
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