Villa holiday rentals in Anna Maria Island
Find and book unique villas on Airbnb
Top-rated villa rentals in Anna Maria Island
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 Anna Maria Island
Private villa rentals
Villa in Sarasota
5.0 out of 5 average rating, 21 reviewsVacation Luxury Villa/ Heated Pool -Beach Access
8–15 Nov
Villa in Sarasota
4.91 out of 5 average rating, 22 reviewsBeautiful House w/ Pool, 10 Min to Siesta Beach
9–16 Aug
Villa in Sarasota
5.0 out of 5 average rating, 7 reviewsModern Vacation Villa 4 miles to Siesta Key
3–10 Sep
Villa in Gulfport
5.0 out of 5 average rating, 18 reviewsCozy funky duplex with KING bed
30 Jun – 7 Jul
Villa in Largo
4.97 out of 5 average rating, 36 reviewsClose to Beaches! Basil House
5–12 Jan
Villa in Siesta Key
4.91 out of 5 average rating, 54 reviewsSiesta Key BEACH SIDE villa/Private beach/pool
16–23 Dec
Villa in Bradenton
5.0 out of 5 average rating, 26 reviewsRiver Pointe 3/2 Lakefront Home with Heated Pool
6–13 Nov
Villa in Clearwater
5.0 out of 5 average rating, 7 reviewsNEW! 4 min Walk to Beach, Pool, Roof Deck
25 Sep – 2 Oct
Luxury villa rentals
Villa in Indian Rocks Beach
4.92 out of 5 average rating, 50 reviewsThe Emerald Villa, Eco-Luxury by the Sea
20–27 Aug
Villa in Osprey
5.0 out of 5 average rating, 11 reviewsParadise with a pool, pier and private beach area
2–9 Dec
Villa in Sarasota
5.0 out of 5 average rating, 61 reviewsModern Retreat Close to Beach-4BR/3BA, Pool-Games
6–13 Mar
Villa in Clearwater
5.0 out of 5 average rating, 13 reviewsTake a Break & Escape to Clearwater 6B4B Paradise!
4–11 Oct
Villa in Seminole
4.98 out of 5 average rating, 40 reviews5 BR Luxury Beach Villa: Heated Pool & Games Room
19–26 Oct
Villa in Bradenton Beach
4.7 out of 5 average rating, 37 reviewsShort walk to the beach! Unit B
7–14 Mar
Villa in Tampa
5.0 out of 5 average rating, 4 reviewsLuxury Pool Villa in Upscale Tampa Centrally Loctd
12–19 Dec
Villa in Seminole
4.96 out of 5 average rating, 25 reviewsTuscan Villa*Minutes from Redington Beach
5–12 Feb
Villa rentals with a pool
Villa in Dunedin
4.6 out of 5 average rating, 10 reviewsSeaside Paradise
20–27 May
Villa in Largo
4.91 out of 5 average rating, 90 reviewsPoolside Palms Private Pool & Game Room - 7 Min to Indian Rocks Beach
24–31 Jan
Villa in Sarasota
4.88 out of 5 average rating, 41 reviewsParadise Villa- Sarasota
8–15 Oct
Villa in Largo
4.69 out of 5 average rating, 54 reviewsThe Blue Villa - Luxury Clearwater - Heated pool
4–11 Sep
Villa in Sarasota
4.75 out of 5 average rating, 8 reviewsCharming 2/2 Village des Pins close to Siesta Key
3–10 Sep
Villa in Largo
4.93 out of 5 average rating, 69 reviewsSolar Heated Pool Paradise/5mins 2 beach/Games/BBQ
14–21 Jun
Villa in Dunedin
5.0 out of 5 average rating, 4 reviewsThe Sandy Villa Retreat on Dunedin Causeway
26 Jun – 3 Jul
Villa in Riverview
4.88 out of 5 average rating, 25 reviewsBrand New house with pool and much more
30 Sep – 7 Oct
Destinations to explore
- St Petersburg Holiday rentals
- Sarasota Holiday rentals
- Tampa Holiday rentals
- Key West Holiday rentals
- Naples Holiday rentals
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Boca Raton Holiday rentals
- West Palm Beach Holiday rentals
- Kissimmee Holiday rentals
- Orlando Holiday rentals
- Villa rentals United States
- Villa rentals Florida
- Villa rentals Florida
- Rentals with outdoor seating Anna Maria Island
- Rentals with a firepit Anna Maria Island
- Fitness-friendly rentals Anna Maria Island
- Family-friendly rentals Anna Maria Island
- Rentals with a sauna Anna Maria Island
- Rentals with an EV charger Anna Maria Island
- Rentals with pools Anna Maria Island
- Rentals with a washing machine and dryer Anna Maria Island
- Rentals with a fireplace Anna Maria Island
- Pet-friendly rentals Anna Maria Island
- Cottage rentals Anna Maria Island
- House rentals Anna Maria Island
- Family-friendly rentals Anna Maria Island
- Flat rentals Anna Maria Island
- Beach house rentals Anna Maria Island
- Townhouse rentals Anna Maria Island
- Monthly Rentals Anna Maria Island
- Rentals with a hot tub Anna Maria Island
- Rentals with beach access Anna Maria Island
- Rentals with a patio Anna Maria Island
- Apartment rentals Anna Maria Island
- Waterfront rentals Anna Maria Island
- Rentals with a kayak Anna Maria Island
- Rentals with lake access Anna Maria Island
- Beachfront rentals Anna Maria Island
- Beach apartment rentals Anna Maria Island
- Wheelchair-accessible rentals Anna Maria Island
- Villa rentals Kissimmee
- Villa rentals Tampa
- Villa rentals Manatee 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