Anna Maria Island Vacation Rentals with Pools

21 places to stay · Ad disclosure

Top Deal

Vacation Home

Fall Escape - 4Br+Pool+Img+Anna Maria Island

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4 bedrooms

Pool
$363 per night incl. taxes & fees Rate based on Dec 4 – Dec 11 Free cancellation 64% below similar 4-bedroom vacation homes View Deal Book on Trip.com
Top Deal

Hotel

Tropic Isle at Anna Maria Island Inn

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Pool
$219 per night incl. taxes & fees Rate based on Dec 4 – Dec 11 Free cancellation 38% below similar hotels & resorts View Deal Book on Trip.com

Compare: Vrbo Expedia Hotels.com

Resort

Anna Maria Beach Resort

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Pool • Beachfront
$580 per night incl. taxes & fees Rate based on Dec 4 – Dec 11 View Deal Book on Trip.com

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Anna Maria Island Vacation Rentals with Pools

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.

Anna Maria Island Vacation Rentals with Pools FAQ

How much do Anna Maria Island vacation rentals with pools cost?

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.

How many Anna Maria Island vacation rentals with pools are there?

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.

What else do Anna Maria Island vacation rentals with pools have?

Of these stays, 2 have a hot tub and 8 have four or more bedrooms. Combine the filters above to narrow them down.

What should I check before booking?

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.

How do I book?

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.

About Anna Maria Island

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

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