Villa vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Siesta Key villa rentals
Private villa rentals
Villa in Sarasota
4.75 out of 5 average rating, 8 reviewsCharming 2/2 Village des Pins close to Siesta Key
Sep. 3 – 10
Villa in Sarasota
4.88 out of 5 average rating, 42 reviewsParadise Villa- Sarasota
Dec. 12 – 19
Villa in Holmes Beach
5.0 out of 5 average rating, 11 reviewsWaterfront in Paradise
Jun. 27 – Jul. 4
Villa in Sarasota
4.95 out of 5 average rating, 19 reviewsMid-Century Home with Heated Pool
Apr. 22 – 29
Villa in Sarasota
4.91 out of 5 average rating, 44 reviewsSiesta Key Palm Paradise w/ Heated Salt Water Pool
Jul. 13 – 20
Villa in Sarasota
4.98 out of 5 average rating, 52 reviewsNEW Luxury 4/3 Home By Downtown, Beach & Keys
Jan. 8 – 15
Villa in Venice
4.81 out of 5 average rating, 31 reviewsGondola Dr house with private swimming pool
Sep. 13 – 20
Villa in Sarasota
4.81 out of 5 average rating, 64 reviewsParadise Villa on Siesta Key
Jul. 10 – 17
Luxury villa rentals
Villa in Sarasota
4.88 out of 5 average rating, 16 reviewsRelaxation awaits in this bohemian inspired villa
Sep. 5 – 12
Villa in Bradenton
4.5 out of 5 average rating, 4 reviewsBermuda style house on a bayou
May 21 – 28
Villa in Bradenton
New Luxury Home near IMG Academy & Anna Maria Isl
Jun. 30 – Jul. 7
Villa in Longboat Key
Beach Castle Resort, Direct Bay, Walk to Beach
Jul. 23 – 30
Villa in Sarasota
5.0 out of 5 average rating, 16 reviewsCourtyard Villa w/Pool, Spa & Sauna close to Beach
Apr. 13 – 20
Villa in Sarasota
4.5 out of 5 average rating, 8 reviewsLido Villa, steps from the beach, with heated pool
Jan. 18 – 25
Villa in Holmes Beach
4.89 out of 5 average rating, 53 reviewsExclusive Islands West Resort - Villa #3 Seahorse
Jan. 31 – Feb. 7
Villa in Ruskin
4.97 out of 5 average rating, 36 reviewsSunset Paradise -Pool heated. Tampa St Pete Escape
Apr. 13 – 20
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
May 8 – 15
Villa in North Port
5.0 out of 5 average rating, 24 reviewsStunning Retreat: Endless Summer Villa-Heated Pool
Dec. 16 – 23
Villa in Sarasota
4.67 out of 5 average rating, 3 reviewsSarasota Jungle Garden Villa
Apr. 20 – 27
Villa in Venice
5.0 out of 5 average rating, 6 reviewsBeautifully Remodeled Anna-vacation home
Jun. 20 – 27
Villa in Bradenton
4.8 out of 5 average rating, 20 reviewsGulf Coast Retreat - Private Pool, BBQ, Pets OK
May 21 – 28
Villa in Sarasota
5.0 out of 5 average rating, 19 reviewsVilla Siesta, Secret Downtown Treasure-heated Pool
Jan. 1 – 8
Villa in Siesta Key
4.47 out of 5 average rating, 34 reviewsBeautiful property on Siesta Key from bay to beach
Jan. 7 – 14
Villa in Siesta Key
5.0 out of 5 average rating, 5 reviewsModern, Walkable, Updated, Private.
Oct. 25 – Nov. 1
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
$191 CAD before taxes and fees
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