Villa vacation rentals in Siesta Beach
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Top-rated villa rentals in Siesta Beach
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 Beach villa rentals
Private villa rentals
Villa in Bradenton
5.0 out of 5 average rating, 15 reviewsTranquil Tide Villa 1
Apr. 24 – May 1
Villa in Sarasota
4.98 out of 5 average rating, 52 reviewsNEW Luxury 4/3 Home By Downtown, Beach & Keys
Oct. 2 – 9
Villa in Sarasota
4.88 out of 5 average rating, 43 reviewsParadise Villa- Sarasota
Aug. 9 – 16
Villa in Sarasota
4.91 out of 5 average rating, 44 reviewsSiesta Key Palm Paradise w/ Heated Salt Water Pool
Sep. 18 – 25
Villa in Holmes Beach
5.0 out of 5 average rating, 11 reviewsWaterfront in Paradise
Sep. 3 – 10
Villa in Sarasota
4.83 out of 5 average rating, 23 reviewsCheerful 4-bedroom Villa with pool
Aug. 11 – 18
Villa in Bradenton
4.83 out of 5 average rating, 30 reviewsSpectacular waterfront villa on sunny Riverwalk!
Oct. 24 – 31
Villa in North Port
4.88 out of 5 average rating, 17 reviewsCheerful 3-bed villa with heated pool (Car)
Aug. 27 – Sep. 3
Luxury villa rentals
Villa in Osprey
5.0 out of 5 average rating, 11 reviewsParadise with a pool, pier and private beach area
Jul. 31 – Aug. 7
Villa in Holmes Beach
4.98 out of 5 average rating, 52 reviewsCalico - Family Oasis - Steps from the Sand
Nov. 23 – 30
Villa in Bradenton Beach
4.7 out of 5 average rating, 37 reviewsShort walk to the beach! Unit B
Dec. 24 – 31
Villa in Bradenton
4.5 out of 5 average rating, 4 reviewsBermuda style house on a bayou
May 29 – Jun. 5
Villa in Bradenton
New Luxury Home near IMG Academy & Anna Maria Isl
Sep. 17 – 24
Villa in Sarasota
4.5 out of 5 average rating, 8 reviewsLido Villa, steps from the beach, with heated pool
Apr. 25 – May 2
Villa in Anna Maria
4.64 out of 5 average rating, 28 reviewsCondo with Views - Bay Vista at Bayside Bungalow
Dec. 6 – 13
Villa in Holmes Beach
4.67 out of 5 average rating, 6 reviewsModern 3BR 2nd-Floor | Balcony | Pool
Jan. 25 – Feb. 1
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 29 – Jun. 5
Villa in Sarasota
4.67 out of 5 average rating, 3 reviewsSarasota Jungle Garden Villa
Apr. 22 – 29
Villa in Venice
5.0 out of 5 average rating, 6 reviewsBeautifully Remodeled Anna-vacation home
Aug. 16 – 23
Villa in Bradenton
4.8 out of 5 average rating, 20 reviewsGulf Coast Retreat - Private Pool, BBQ, Pets OK
May 18 – 25
Villa in Sarasota
5.0 out of 5 average rating, 19 reviewsVilla Siesta, Secret Downtown Treasure-heated Pool
Apr. 14 – 21
Villa in Siesta Key
4.47 out of 5 average rating, 34 reviewsBeautiful property on Siesta Key from bay to beach
Apr. 26 – May 3
Villa in Sarasota
Pool Home, Pet OK, 2-bed/2-bath
Aug. 9 – 16
Villa in Siesta Key
5.0 out of 5 average rating, 5 reviewsModern, Walkable, Updated, Private.
Nov. 5 – 12
Destinations to explore
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