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Anna Maria Island, Florida, United States of America

Anna Maria Island rentals with pools

We found 3,148 rentals with pools — enter your dates for availability

Explore Anna Maria Island rentals with pools

Walk to the Beach! Single-level Home w/ Private Pool, Spa, AC & Fast Wifi!

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
$160 avg/night

Single-level Home w/ Private Pool, Spa, Terrace & Fast Wifi - Walk to the Beach!

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
$157 avg/night

Club Bamboo South 122 Studio

Sleeps 4 · Studio · 1 Bathroom
$166 avg/night
(17)

Anna Maria Beach Condo 1/1

Sleeps 4 · 1 Bedroom · 1 Bathroom
$107 avg/night
(80)

Tranquil Anna Maria Island Resort, Unit 1... Only 4 units, all amenities!

Sleeps 4 · 1 Bedroom · 1 Bathroom
$133 avg/night
(69)

Anna Maria Sunsets - Studio

Sleeps 4 · 1 Bedroom · 1 Bathroom
$110 avg/night
(82)

Search 3,148 pool rentals

Recent reviews of Anna Maria Island rentals with pools
Stayed Jul 2021

Summer Paradise

We had such a wonderful time at this home. The beach house was in a perfect location to the beach, just a short 3 minute walk. The house had everything we needed and also included beach items like a beach wagon, floaties, sand pails, beach chairs and...

Jasmine V.
Jasmine V.
Stayed Jul 2021

A True Gem

A fantastic place to stay at a perfect location! The beach is right across the street. Everything was explained perfectly and easy to follow. The room was sparkling clean and we enjoyed the large bathroom with double shower heads. Beach chairs and um...

Janeane C.
Janeane C.
Stayed Jul 2021

Tortuga Inn Unit 269

Had a wonderful time. Pros: close to beach, elevator, 2 pools, beach chairs and umbrellas provided free, close to shops and restaurants, clean, great owner, covered parking, towels and soap provided. Wifi, extremely comfortable bed, keypad accessibi...

James H.
James H.
Stayed Jul 2021

Cute, Clean and So close to the beach

Easy check in, 2 bedrooms, and the sleeper sofa is comfy enough to nap/ sleep on without opening it up. Kitchen is well stocked. And from the front door to the beach is approximately 45 seconds. Having the pool was a bonus we loved. Unit was very cle...

Marty H.
Marty H.

Birmingham, AL

Stayed Jul 2021

Wonderful stay

This little Gem was a wonderful for my family of 4. My husband and 2 girls ages 2.5 and 7. We loved the property was steps to the private beach access, 2 pools and a beautiful dock we fished off of. The shower is huge with 2 working shower heads. C...

Shannon B.
Shannon B.
Stayed Jul 2021

Perfect Vacation Location

The Starfish Cottage is absolutely awesome! This was the perfect destination for our couples vacation. The cottage has everything that you need for a quiet beach vacation. We visited the beach a few times (which is a short walk), but the tropical poo...

Chris H.
Chris H.
Stayed Jun 2021

4th of July Holiday Vacation

We had an amazing time - we love Anna Maria Island. Harbor Lane is a hidden gem. This was our first time staying there and when we return to AMI next summer we plan on staying here again. Joan & Olga are wonderful hosts! I highly recommend staying he...

Sarah H.
Sarah H.
Stayed Jun 2021

Perfect location

Loved every thing about the location to the condo, to the easy walk to resturants and Bridge street to do some shopping. Love that the beach was right across the street. It was the perfect place for my husband and I to stay for our honeymoon. We have...

Jessica S.
Jessica S.
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