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Anna Maria Island rentals with pool

We found 5,170 rentals with pool — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to stay in a holiday rental with a pool in Anna Maria Island?
If you'd love to grab a deal on your holiday rental with a pool, our filters can help. After finishing your initial search, narrow your results based on your preferences, including price, location and features and amenities. We've got holiday homes in Anna Maria Island to suit any budget, so make the most of our filters to find the perfect stay.
When is the best time to book a holiday rental with a pool in Anna Maria Island?
Consider arriving in January, when the mercury ranges from around 14ºC to 19ºC. This is the most popular month to splash out on a holiday rental with a pool in Anna Maria Island.
What holiday rentals with a pool in Anna Maria Island have nice views?
If you want to make your trip to Anna Maria Island extra special, stay in one of Stayz's holiday rentals with a pool — and a gorgeous view to boot. Once your initial search is done, use our filters to tailor your results by area and the vistas you want to look out on.
Can I book a cabin with a pool in Anna Maria Island?
Yes. Search for a cabin with a pool in or around Anna Maria Island and create fun new memories with friends or family. Some may offer a private pool, so you can go for a swim whenever you like, while at others you may have to share. Use our "Pool" or "Private pool" filters to find the right cabin for you.
Are there holiday rentals with a private pool in Anna Maria Island?
Book a holiday rental with a private pool in Anna Maria Island and enjoy a refreshing morning swim or late-night dip — or whenever you're in the mood! You'll be able to keep the little ones easily occupied, and you won't have to worry about sharing with anyone else. Use our "Private pool" filter to find your perfect holiday rental.
What are the top things to do in Anna Maria Island?
Venture out and experience all that Anna Maria Island has to offer from the comfort of your holiday home rental. It pays to do a bit of research on what you'd like to see and do, so you can plan the perfect getaway.
Why should I book my holiday rental with a pool with Stayz?
Booking your holiday rental with a pool with Stayz means you get the entire place for your exclusive use — your own private oasis to relax poolside with no interruptions or distractions from anybody else. Also, our easy payment and cancellation policies allow you to change your plans if required.