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Vacation Home
Fall Escape - 4Br+Pool+Img+Anna Maria Island
Bradenton, United States
4 bedrooms
- Pool
4 Bedrooms Private Vacation Home
$363 per night
Rate based on Dec 4 – Dec 11
Free cancellation
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21 places to stay · Ad disclosure
1 / 6
Vacation Home
Bradenton, United States
4 bedrooms
4 Bedrooms Private Vacation Home
$363 per night
Rate based on Dec 4 – Dec 11
Free cancellation
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1 / 6
Hotel
Bradenton Beach, United States
Pool View Terrace King Suite
$219 per night
Rate based on Dec 4 – Dec 11
Free cancellation
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Vacation Home
3 bedrooms
1 / 6
Vacation Home
Manatee County, United States
3 bedrooms
3 Bedrooms Private Vacation Home
$338 per night
Rate based on Dec 4 – Dec 11
Free cancellation
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Vacation Home
3 bedrooms
1 / 6
Vacation Home
Manatee County, United States
3 bedrooms
3 Bedrooms Private Vacation Home
$372 per night
Rate based on Dec 4 – Dec 11
Free cancellation
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Vacation Home
Holmes Beach, United States
1 bedroom
1 Bedroom Private Vacation Home
$460 per night
Rate based on Dec 4 – Dec 11
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Condo
2 bedrooms
1 / 6
Condo
Holmes Beach, United States
2 bedrooms
Two-Bedroom Condo
$434 per night
Rate based on Dec 4 – Dec 11
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Vacation Home
5 bedrooms
1 / 6
Vacation Home
Manatee County, United States
5 bedrooms
5 Bedrooms Private Vacation Home
$762 per night
Rate based on Dec 4 – Dec 11
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Vacation Home
3 bedrooms
1 / 6
Vacation Home
Holmes Beach, United States
3 bedrooms
3 Bedrooms Private Vacation Home
$618 per night
Rate based on Dec 4 – Dec 11
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Villa
3 bedrooms
1 / 6
Villa
Cortez, United States
3 bedrooms
3 Bedrooms Private Vacation Home
$609 per night
Rate based on Dec 4 – Dec 11
Free cancellation
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Vacation Home
5 bedrooms
1 / 6
Vacation Home
Anna Maria, United States
5 bedrooms
5 Bedrooms Private Vacation Home
$1,375 per night
Rate based on Dec 4 – Dec 11
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Vacation Home
2 bedrooms
1 / 6
Vacation Home
Holmes Beach, United States
2 bedrooms
2 Bedrooms Private Vacation Home
$372 per night
Rate based on Dec 4 – Dec 11
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1 / 6
Vacation Home
Holmes Beach, United States
2 bedrooms
2 Bedrooms Private Vacation Home
$305 per night
Rate based on Dec 4 – Dec 11
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Condo
4 bedrooms
1 / 6
Condo
Bradenton Beach, United States
4 bedrooms
4 Bedrooms Private Vacation Home
$1,152 per night
Rate based on Dec 4 – Dec 11
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1 / 6
Condo
Bradenton, United States
4 bedrooms
4 Bedrooms Private Vacation Home
$593 per night
Rate based on Dec 4 – Dec 11
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1 / 6
Resort
Holmes Beach, United States
Oceanfront Pool View King Island Room
$580 per night
Rate based on Dec 4 – Dec 11
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Vacation Home
6 bedrooms
1 / 6
Vacation Home
Bradenton Beach, United States
6 bedrooms
6 Bedrooms Private Vacation Home
$2,809 per night
Rate based on Dec 4 – Dec 11
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1 / 6
Condo
Holmes Beach, United States
2 bedrooms
Two-Bedroom Condo
$353 per night
Rate based on Dec 4 – Dec 11
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1 / 6
Vacation Home
Holmes Beach, United States
6 bedrooms
6 Bedrooms Private Vacation Home
$1,155 per night
Rate based on Dec 4 – Dec 11
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Vacation Home
3 bedrooms
1 / 6
Vacation Home
Bradenton Beach, United States
3 bedrooms
3 Bedrooms Private Vacation Home
$391 per night
Rate based on Dec 4 – Dec 11
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Vacation Home
10 bedrooms
1 / 6
Vacation Home
Holmes Beach, United States
10 bedrooms
10 Bedrooms Private Vacation Home
$1,293 per night
Rate based on Dec 4 – Dec 11
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Vacation Home
3 bedrooms
1 / 6
Vacation Home
Bradenton Beach, United States
3 bedrooms
3 Bedrooms Private Vacation Home
$506 per night
Rate based on Dec 4 – Dec 11
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Stays are booked on our partners’ sites. We may earn a commission when you book, at no extra cost to you. We may earn a commission when you book. Recommended order weighs guest ratings and price against similar stays, and also how much each partner pays us. Recommended order also weighs partner pay. Learn more
We list 21 Anna Maria Island vacation rentals with pools, about 33% of the places to stay we compare in Anna Maria Island. Nightly prices start at $219, and the typical stay is about $506 a night. They range from 1 to 10 bedrooms. They book on Trip.com, and the list above puts their stays side by side so you can compare photos, ratings and prices first.
From $219 a night, and about $506 for a typical stay. These are sample rates for the dates on each stay; open a deal with your dates for the exact price, including fees and taxes.
We compare 21 of them in Anna Maria Island right now. Add your dates above to see which are free when you want to go.
Of these stays, 2 have a hot tub and 8 have four or more bedrooms. Combine the filters above to narrow them down.
Some pools are private and heated indoors, others are a shared resort pool that’s only open in summer. Check the listing for which kind it is and when it’s open.
Pick a stay and choose View Deal. You book directly on Trip.com, which handles payment, confirmation and support. 41 Vacations doesn’t charge you anything; we may earn a commission from the partner.
Anna Maria Island is a seven-mile barrier island on Florida’s Gulf coast, near Bradenton, with soft white sand, calm water and an old-Florida feel. There are no high-rises, just low-rise hotels, beach cottages and vacation rentals.
Where to stay
Anna Maria, at the north end, is the quietest, with rentals near the city pier and Bean Point.
Holmes Beach, in the middle, has the most places to stay plus restaurants and shops.
Bradenton Beach, at the south end, has hotels and rentals near Bridge Street and the historic pier.
Best times to visit
Best overall: April through May and late October through November: warm water, sunshine and fewer visitors than peak season.
Best value: Late summer through early fall usually has the lowest rates and the quietest beaches.
Busiest: February through April, when winter visitors and spring breakers arrive.
Weather to know: Expect hot, humid summers with afternoon storms. Hurricane season runs June through November.
Getting there
Sarasota Bradenton International Airport (SRQ) is about 30 minutes away, and Tampa International (TPA) is about an hour.
Tips for booking
Many island rentals have weekly or minimum-night stays, especially in season, so check the rules and the total price for your dates.
Flying in? Compare flights on CheapOAir
Ratings and review counts come straight from guest reviews on our booking partner.
Each listing shows its nightly rate and the dates it’s quoted for, before you click through.
You book and pay directly on the partner’s site, under their terms.