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
4.91 out of 5 average rating, 22 reviewsBeautiful House w/ Pool, 10 Min to Siesta Beach
12–19 Nov
Villa in Gulfport
5.0 out of 5 average rating, 19 reviewsCozy funky duplex with KING bed
27 Oct – 3 Nov
Villa in Largo
4.83 out of 5 average rating, 12 reviewsCozy Villa with a Private Pool
13–20 Sep
Villa in Bradenton
5.0 out of 5 average rating, 27 reviewsRiver Pointe 3/2 Lakefront Home with Heated Pool
23–30 Oct
Villa in Siesta Key
4.91 out of 5 average rating, 55 reviewsSiesta Key BEACH SIDE villa/Private beach/pool
8–15 Aug
Villa in Clearwater
5.0 out of 5 average rating, 8 reviewsNEW! 4 min Walk to Beach, Pool, Roof Deck
25 Nov – 2 Dec
Villa in Thonotosassa
5.0 out of 5 average rating, 17 reviewsLakeside Villa
29 May – 5 Jun
Villa in Indian Rocks Beach
5.0 out of 5 average rating, 50 reviewsPrime location on Gulf Blvd in Indian Rocks Beach
5–12 Sep
Luxury villa rentals
Villa in Indian Rocks Beach
5.0 out of 5 average rating, 33 reviewsWater Front! Heated Pool, 6p Golf Cart, 2 Kayaks
9–16 Sep
Villa in Indian Rocks Beach
5.0 out of 5 average rating, 16 reviewsIsland Paradise
31 Oct – 7 Nov
Villa in Sarasota
5.0 out of 5 average rating, 21 reviewsVacation Luxury Villa/ Heated Pool -Beach Access
3–10 Apr
Villa in Indian Rocks Beach
4.92 out of 5 average rating, 51 reviewsThe Emerald Villa, Eco-Luxury by the Sea
16–23 Jan
Villa in Sarasota
5.0 out of 5 average rating, 61 reviewsModern Retreat Close to Beaches |Pool|Game room
7–14 Mar
Villa in Seminole
4.93 out of 5 average rating, 42 reviewsPerfect location 6BR/4BA Pool GameRoom 5 min Beach
4–11 Aug
Villa in Bradenton Beach
4.7 out of 5 average rating, 37 reviewsShort walk to the beach! Unit B
10–17 Jul
Villa in Osprey
5.0 out of 5 average rating, 11 reviewsParadise with a pool, pier and private beach area
4–11 Jun
Villa rentals with a pool
Villa in Dunedin
4.6 out of 5 average rating, 10 reviewsSeaside Paradise
3–10 Jun
Villa in Tampa
5.0 out of 5 average rating, 51 reviewsLuxury home in the heart of South Tampa & POOL!
8–15 Mar
Villa in Bradenton
5.0 out of 5 average rating, 22 reviews'The Gathering Place' Oasis with Huge Heated Pool
12–19 May
Villa in Largo
4.91 out of 5 average rating, 70 reviewsSolar Heated Pool Paradise/5mins 2 beach/Games/BBQ
4–11 Dec
Villa in Largo
4.91 out of 5 average rating, 91 reviewsPoolside Palms Private Pool & Game Room - 7 Min to Indian Rocks Beach
11–18 Jan
Villa in Largo
4.91 out of 5 average rating, 44 reviewsStunning waterfront home w/ pool, all new inside!
23–30 Apr
Villa in Sarasota
4.95 out of 5 average rating, 19 reviewsMid-Century Home with Heated Pool
28 Feb – 7 Mar
Villa in Sarasota
4.88 out of 5 average rating, 42 reviewsParadise Villa- Sarasota
8–15 Nov
Destinations to explore
- St Petersburg Holiday rentals
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