Villa vacation 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.
Vacation 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, 21 reviewsVacation Luxury Villa/ Heated Pool -Beach Access
Sep 18 – 25
Villa in Sarasota
4.91 out of 5 average rating, 22 reviewsBeautiful House w/ Pool, 10 Min to Siesta Beach
Sep 8 – 15
Villa in Gulfport
5.0 out of 5 average rating, 18 reviewsCozy funky duplex with KING bed
Dec 2 – 9
Villa in Largo
4.83 out of 5 average rating, 12 reviewsCozy Villa with a Private Pool.
Aug 3 – 10
Villa in Bradenton
5.0 out of 5 average rating, 27 reviewsRiver Pointe 3/2 Lakefront Home with Heated Pool
Aug 30 – Sep 6
Villa in Sarasota
5.0 out of 5 average rating, 8 reviewsModern Vacation Villa 4 miles to Siesta Key
Oct 27 – Nov 3
Villa in Siesta Key
4.91 out of 5 average rating, 55 reviewsSiesta Key BEACH SIDE villa/Private beach/pool
Dec 22 – 29
Villa in Largo
4.97 out of 5 average rating, 38 reviewsClose to Beaches! Basil House
Feb 12 – 19
Luxury villa rentals
Villa in Indian Rocks Beach
5.0 out of 5 average rating, 16 reviewsIsland Paradise
Sep 15 – 22
Villa in Indian Rocks Beach
5.0 out of 5 average rating, 33 reviewsWater Front! Heated Pool, 6p Golf Cart, 2 Kayaks
Jan 16 – 23
Villa in Indian Rocks Beach
4.92 out of 5 average rating, 51 reviewsThe Emerald Villa, Eco-Luxury by the Sea
Jan 15 – 22
Villa in Sarasota
5.0 out of 5 average rating, 61 reviewsModern Retreat Close to Beaches |Pool|Game room
Mar 28 – Apr 4
Villa in Clearwater
5.0 out of 5 average rating, 14 reviewsTake a Break & Escape to Clearwater 6B4B Paradise!
Sep 13 – 20
Villa in Seminole
4.93 out of 5 average rating, 42 reviewsPerfect location 6BR/4BA Pool GameRoom 5 min Beach
Aug 4 – 11
Villa in Largo
4.96 out of 5 average rating, 57 reviewsLakeside Retreat-4plex Sleeps 20
Jan 25 – Feb 1
Villa in Bradenton Beach
4.7 out of 5 average rating, 37 reviewsShort walk to the beach! Unit B
Jul 10 – 17
Villa rentals with a pool
Villa in Dunedin
4.6 out of 5 average rating, 10 reviewsSeaside Paradise
Jul 12 – 19
Villa in Bradenton
5.0 out of 5 average rating, 22 reviews'The Gathering Place' Oasis with Huge Heated Pool
May 12 – 19
Villa in Largo
4.91 out of 5 average rating, 91 reviewsPoolside Palms Private Pool & Game Room - 7 Min to Indian Rocks Beach
Jan 11 – 18
Villa in Tampa
5.0 out of 5 average rating, 51 reviewsLuxury home in the heart of South Tampa & POOL!
Sep 10 – 17
Villa in Largo
4.91 out of 5 average rating, 44 reviewsStunning waterfront home w/ pool, all new inside!
Sep 8 – 15
Villa in Sarasota
4.95 out of 5 average rating, 19 reviewsMid-Century Home with Heated Pool
Apr 22 – 29
Villa in Largo
4.91 out of 5 average rating, 70 reviewsSolar Heated Pool Paradise/5mins 2 beach/Games/BBQ
Jan 13 – 20
Villa in Sarasota
4.88 out of 5 average rating, 42 reviewsParadise Villa- Sarasota
Dec 5 – 12
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