Villa holiday rentals in Siesta Key
Find and book unique villas on Airbnb
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
5.0 out of 5 average rating, 8 reviewsModern Vacation Villa 4 miles to Siesta Key
21–28 Mar
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 Siesta Key
4.82 out of 5 average rating, 65 reviewsParadise Villa on Siesta Key
17–24 Apr
Villa in Sarasota
4.88 out of 5 average rating, 42 reviewsParadise Villa- Sarasota
14–21 Jan
Villa in Sarasota
4.98 out of 5 average rating, 52 reviewsNEW Luxury 4/3 Home By Downtown, Beach & Keys
8–15 Apr
Villa in Sarasota
4.95 out of 5 average rating, 19 reviewsMid-Century Home with Heated Pool
22–29 Apr
Villa in Holmes Beach
5.0 out of 5 average rating, 11 reviewsWaterfront in Paradise
30 Jun – 7 Jul
Villa in HOLMES BEACH
4.94 out of 5 average rating, 35 reviewsSteps from the beach 2BR @Manatee Beach
14–21 Apr
Luxury villa rentals
Villa in Osprey
5.0 out of 5 average rating, 11 reviewsParadise with a pool, pier and private beach area
6–13 Oct
Villa in Bradenton
4.5 out of 5 average rating, 4 reviewsBermuda style house on a bayou
24–31 May
Villa in Bradenton
New Luxury Home near IMG Academy & Anna Maria Isl
22–29 Jul
Villa in Longboat Key
Beach Castle Resort, Direct Bay, Walk to Beach
31 Dec – 7 Jan
Villa in Sarasota
4.5 out of 5 average rating, 8 reviewsLido Villa, steps from the beach, with heated pool
12–19 Dec
Villa in Holmes Beach
4.82 out of 5 average rating, 33 reviewsBeautiful Islands West Resort - Villa #6 Starfish
2–9 Apr
Villa in Holmes Beach
4.67 out of 5 average rating, 6 reviewsDarling 4BR Gulffront | Patio | W/D
15–22 Mar
Villa in Holmes Beach
4.79 out of 5 average rating, 14 reviewsSand Dollar Beach Side Villa
25 Mar – 1 Apr
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
25 Oct – 1 Nov
Villa in Bradenton
5.0 out of 5 average rating, 22 reviews'The Gathering Place' Oasis with Huge Heated Pool
10–17 May
Villa in North Port
4.88 out of 5 average rating, 17 reviewsCheerful 3-bed villa with heated pool (Car)
5–12 Jan
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
7–14 Dec
Villa in Bradenton
4.8 out of 5 average rating, 20 reviewsGulf Coast Retreat - Private Pool, BBQ, Pets OK
15–22 May
Villa in Sarasota
5.0 out of 5 average rating, 19 reviewsVilla Siesta, Secret Downtown Treasure-heated Pool
26 Mar – 2 Apr
Villa in Siesta Key
4.47 out of 5 average rating, 34 reviewsBeautiful property on Siesta Key from bay to beach
19–26 Nov
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
£112 before taxes and fees
Destinations to explore
- Sarasota Holiday rentals
- Anna Maria Island Holiday rentals
- Tampa Holiday rentals
- Naples Holiday rentals
- Kissimmee Holiday rentals
- Orlando Holiday rentals
- West Palm Beach Holiday rentals
- Boca Raton Holiday rentals
- Fort Lauderdale Holiday rentals
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Key West Holiday rentals
- Villa rentals United States
- Villa rentals Florida
- Villa rentals Florida
- Villa rentals Kissimmee
- Villa rentals Tampa
- Rentals with beach access Siesta Key
- Rentals with pools Siesta Key
- Pet-friendly rentals Siesta Key
- House rentals Siesta Key
- Rentals with a fireplace Siesta Key
- Beach apartment rentals Siesta Key
- Flat rentals Siesta Key
- Beachfront rentals Siesta Key
- Rentals with a washing machine and dryer Siesta Key
- Townhouse rentals Siesta Key
- Rentals with a firepit Siesta Key
- Monthly Rentals Siesta Key
- Family-friendly rentals Siesta Key
- Rentals with a kayak Siesta Key
- Bungalow rentals Siesta Key
- Cottage rentals Siesta Key
- Mansion rentals Siesta Key
- Rentals with a patio Siesta Key
- Fitness-friendly rentals Siesta Key
- Rentals with a hot tub Siesta Key
- Wheelchair-accessible rentals Siesta Key
- Rentals with a sauna Siesta Key
- Apartment rentals Siesta Key
- Waterfront rentals Siesta Key
- Rentals with outdoor seating Siesta Key
- Beach house rentals Siesta Key
- Family-friendly rentals Siesta Key
- Villa rentals Sarasota County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom