Villa holiday rentals in Anna Maria Island
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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 Anna Maria Island villa rentals
Private villa rentals
Villa in Sarasota
5.0 out of 5 average rating, 22 reviewsVacation Luxury Villa/ Heated Pool -Beach Access
Villa in Gulfport
5.0 out of 5 average rating, 23 reviewsCozy funky duplex with KING bed
Villa in Largo
4.98 out of 5 average rating, 41 reviewsClose to Beaches! Basil House
Villa in Sarasota
5.0 out of 5 average rating, 65 reviewsModern Retreat Close to Beaches |Pool|Game room
Villa in Bradenton
4.84 out of 5 average rating, 31 reviewsSpectacular waterfront villa on sunny Riverwalk
Villa in Siesta Key
4.91 out of 5 average rating, 56 reviewsSiesta Key BEACH SIDE villa/Private beach/pool
Villa in Sarasota
4.95 out of 5 average rating, 19 reviewsMid-Century Home with Heated Pool
Villa in Clearwater
5.0 out of 5 average rating, 10 reviewsNEW! 4 min Walk to Beach, Pool, Roof Deck
Luxury villa rentals
Villa in Indian Rocks Beach
4.92 out of 5 average rating, 53 reviewsThe Emerald Villa, Eco-Luxury by the Sea
Villa in Seminole
4.98 out of 5 average rating, 44 reviews5 BR Luxury Beach Villa: Heated Pool & Games Room
Villa in Seminole
4.96 out of 5 average rating, 26 reviewsTuscan Villa*Minutes from Redington Beach
Villa in Osprey
5.0 out of 5 average rating, 11 reviewsParadise with a pool, pier and private beach area
Villa in Bradenton
4.88 out of 5 average rating, 16 reviewsAmazing views from dock! Short drive to beaches!
Villa in Tampa
5.0 out of 5 average rating, 5 reviewsLuxury Pool Villa in Upscale Tampa Centrally Loctd
Villa in Bradenton
4.5 out of 5 average rating, 4 reviewsBermuda style house on a bayou
Villa in Tampa
5.0 out of 5 average rating, 25 reviews(BAYC) Heated Pool Villa. Boat rental available
Villa rentals with a pool
Villa in Bradenton
5.0 out of 5 average rating, 28 reviewsRiver Pointe 3/2 Lakefront Home with Heated Pool
Villa in Largo
4.87 out of 5 average rating, 15 reviewsCozy Villa with a Pool
Villa in Seminole
4.96 out of 5 average rating, 28 reviewsRenovated 3-bedroom villa with solar heated pool
Villa in Largo
4.92 out of 5 average rating, 97 reviewsPoolside Palms Private Pool & Game Room - 7 Min to Indian Rocks Beach
Villa in Sarasota
Sarasota Resort-Like Living Near Siesta Key For 10
Villa in Sarasota
5.0 out of 5 average rating, 10 reviewsModern Vacation Villa 4 miles to Siesta Key
Villa in Largo
4.92 out of 5 average rating, 75 reviewsSolar Heated Pool Paradise/5mins 2 beach/Games/BBQ
Villa in Dunedin
4.6 out of 5 average rating, 10 reviewsSeaside Paradise
Destinations to explore
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- Rentals with a sauna Anna Maria Island
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