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 villa rentals in Anna Maria Island
Private villa rentals
Villa in Sarasota
4.92 out of 5 average rating, 24 reviewsBeautiful House w/ Pool, 10 Min to Siesta Beach
Villa in Indian Rocks Beach
4.89 out of 5 average rating, 27 reviewsWaterfront Villa, private heated Saltwater Pool
Villa in Sarasota
5.0 out of 5 average rating, 21 reviewsVacation Luxury Villa/ Heated Pool -Beach Access
Villa in Gulfport
5.0 out of 5 average rating, 19 reviewsCozy funky duplex with KING bed
Villa in Siesta Key
4.91 out of 5 average rating, 55 reviewsSiesta Key BEACH SIDE villa/Private beach/pool
Villa in Sarasota
5.0 out of 5 average rating, 61 reviewsModern Retreat Close to Beaches |Pool|Game room
Villa in Bradenton
4.86 out of 5 average rating, 7 reviewsExecutive 2-Bedroom Villa LECOM Park, Anna Maria
Villa in Largo
4.83 out of 5 average rating, 6 reviewsCozy Villa with a Private Pool.
Luxury villa rentals
Villa in Indian Rocks Beach
4.92 out of 5 average rating, 51 reviewsThe Emerald Villa, Eco-Luxury by the Sea
Villa in Sarasota
4.88 out of 5 average rating, 16 reviewsRelaxation awaits in this bohemian inspired villa
Villa in Osprey
5.0 out of 5 average rating, 11 reviewsParadise with a pool, pier and private beach area
Villa in Seminole
4.98 out of 5 average rating, 41 reviews5 BR Luxury Beach Villa: Heated Pool & Games Room
Villa in St. Petersburg
4.95 out of 5 average rating, 66 reviewsHeated Pool! Huge Walk In Shower! 5 min to beach!
Villa in Seminole
4.96 out of 5 average rating, 25 reviewsTuscan Villa*Minutes from Redington Beach
Villa in St. Petersburg
5.0 out of 5 average rating, 3 reviews2 Homes! - 4 MN to Madeira BCH - Hottub - HTD Pool
Villa in Tampa
4.9 out of 5 average rating, 60 reviewsTampa Paradise: 5BR Waterfront Villa with Pool
Villa rentals with a pool
Villa in Tampa
5.0 out of 5 average rating, 52 reviewsLuxury home in the heart of South Tampa & POOL!
Villa in Bradenton
5.0 out of 5 average rating, 22 reviews'The Gathering Place' Oasis with Huge Heated Pool
Villa in Sarasota
4.95 out of 5 average rating, 19 reviewsMid-Century Home with Heated Pool
Villa in Largo
4.91 out of 5 average rating, 70 reviewsSolar Heated Pool Paradise/5mins 2 beach/Games/BBQ
Villa in Largo
4.91 out of 5 average rating, 92 reviewsPoolside Palms Private Pool & Game Room - 7 Min to Indian Rocks Beach
Villa in Sarasota
4.88 out of 5 average rating, 43 reviewsParadise Villa- Sarasota
Villa in Largo
4.91 out of 5 average rating, 45 reviewsStunning waterfront home w/ pool, all new inside!
Villa in Sarasota
5.0 out of 5 average rating, 8 reviewsModern Vacation Villa 4 miles to Siesta Key
Destinations to explore
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- Rentals with pools Anna Maria Island
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