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Anna Maria Island holiday lettings

We found 4,016 holiday rentals — enter your dates for availability

Discover a selection of 4,000 holiday rentals in Anna Maria Island that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 150 per night, and houses and cottages are popular options for a stay in Anna Maria Island. Either way, you'll find a rental for everyone's needs.
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Find the best place to stay — Anna Maria Island

Visit Anna Maria Island! Relax at Heliconia House, enjoy your own heated pool!

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
£ 150 avg/night
(92)

Best Little Beach House on Anna Maria Island...With a pool

Sleeps 2 · 1 Bedroom · 1 Bathroom
£ 256 avg/night
(142)

BEACHFRONT HOUSE DIRECTLY ON SOFT SUGAR WHITE SANDS

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
£ 474 avg/night
(20)

Literally steps to the beach! Spacious and Light!

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
£ 190 avg/night
(43)

PRIVATE HEATED POOL! 150 Steps to the Beach! Key West Style Cottage

Sleeps 2 · 1 Bedroom · 1 Bathroom
£ 235 avg/night
(23)

Ocean Front ~ No Streets To Cross! Come And Enjoy A Memorable Beach Vacation!

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
£ 205 avg/night
(57)

Search 4,016 holiday rentals

Top rated rentals — Anna Maria Island
Stayed Apr 2021

Perfect

This was the best place I have ever stayed on spring break. We loved the space, the bikes, the pool! I spent almost all of my day sitting by the pool! We tried to book it to return next spring break and couldn’t and we are bummed! It is going to be h...

Erica H.
Erica H.

Grandville

Stayed Mar 2021

Spring break stay

This was our first trip since Covid and we couldn’t have been any happier! The house was amazing and views absolutely beautiful! The kitchen was stocked with anything you could need. Everything was very clean and the owner was very responsive and hel...

Christie K.
Christie K.

pittsburgh pa

Stayed Mar 2021

Anna Maria getaway

We enjoyed our stay over all..I hoped the unit wouldve been cleaner. Unfortunately the mattress had a slight odor of urine and there were crumbs in the kitchen in the corners of the floor also tons of splatter on walls and cabinets in kitchen. And I ...

Gina M.
Gina M.

Glen Ellyn

Stayed Mar 2021

Clean, spacious and great location!

We stayed with our 3 young kids (8,5 and 8 months) and there was plenty of space. Location was perfect and the pools were great! The condo was extremely clean and just like the photos in the listing. The only complaint was about the fold out couch as...

Megan B.
Megan B.
Stayed Mar 2021

What a fabulous place

We are half way through our stay. Couldn’t come down last year because of the pandemic, but everything is as wonderful as we remembered it from years past. Carolyn is a such a great host. She responds quickly. The house has everything you need to go ...

Murray H.
Murray H.

New York, NY

Stayed Mar 2021

Perfect vacation home

We loved this home. It was so clean and was the perfect size for our family of four. It was in the perfect location only about a block to the beach. The home included all the necessities for the beach including a wagon that made things so easy. Our o...

Liz S.
Liz S.
Stayed Mar 2021

Loved our stay!

This property was perfect and had everything we needed!The pool was so nice and the hot tub was a great bonus. The location was perfect and a short walk to the beach, shops, resturaunts and pier. I was suprised to find a collection of stuff we could ...

CHRISTINA L.
CHRISTINA L.
Stayed Mar 2021

Relaxing Retreat

Well appointed outdoor spaces and comfortable interior made for a relaxing family retreat. We enjoyed the pool and spa, ping pong table, beach wagon and accessories, grill, huge deck and covered lower patio, and canal view outdoors. Indoors, we appre...

Elisha K.
Elisha K.
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Can I find a vacation rental around Anna Maria Island?

Yes, our 2021 property listings offer a large selection of 4,016 vacation rentals near Anna Maria Island. From 2,223 houses to 169 cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Anna Maria Island for a holiday or a weekend are on Vrbo.

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