Anna Maria Island Holiday Rentals

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Our top choices for Anna Maria Island holiday rentals

Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn
3.0 star property
Holmes Beach
8.6 out of 10, Excellent, (403)
"Beautiful location. Walking distance to beach. "
United States
Maria
The price is AU$604
includes taxes & fees
26 Dec - 27 Dec
Haley's at The Anna Maria Island Inn

Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!

Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
Anna Maria
9.6 out of 10, Exceptional, (20)
"My fiancé and I stayed at the cottages this past weekend and it was one of most relaxing weekend. Everyone there was so nice and helpful. We can’t wait to book another trip soon!!"
United States
Matthew S.
The price is AU$727
includes taxes & fees
13 Jan - 14 Jan 2026
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.0 out of 10, Wonderful, (61)
"Very great stay will stay again "
United States
Joseph
The price is AU$543
includes taxes & fees
5 Jan - 6 Jan 2026
Seabreeze at Anna Maria Island Inn

Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
10.0 out of 10, Exceptional, (3)
"The location is wonderful for beach access,places to eat and grocery is block away. Small parking area if more than one couple stay. Had a great stay."
United States
Traci
The price is AU$651
includes taxes & fees
4 Jan - 5 Jan 2026
Alamanda Villas

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.2 out of 10, Wonderful, (334)
"Fabulous stay! Super clean!"
United States
Sarah
The price is AU$568
includes taxes & fees
26 Dec - 27 Dec
Pelican Post at Anna Maria Island Inn

Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
Anna Maria
9.8 out of 10, Exceptional, (36)
"Location was perfect"
United States
Michael S.
The price is AU$682
includes taxes & fees
5 Jan - 6 Jan 2026
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

Anna Maria Beach Cottage 109A -Charming beach cottage, pool, steps to the beach!

Anna Maria Beach Cottage 109A -Charming beach cottage, pool, steps to the beach!
Anna Maria
9.6 out of 10, Exceptional, (21)
"Mom and I just stayed for one night and had a lovely trip. "
United States
Brittany B.
The price is AU$746
includes taxes & fees
13 Jan - 14 Jan 2026
Anna Maria Beach Cottage 109A -Charming beach cottage, pool, steps to the beach!

Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!

Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
Anna Maria
9.6 out of 10, Exceptional, (34)
"Great place for a beach stay on Anna Maria!!!"
United States
John F.
The price is AU$710
includes taxes & fees
5 Jan - 6 Jan 2026
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!

Anna Maria Sunsets - studio

Anna Maria Sunsets - studio
Bradenton Beach
9.2 out of 10, Wonderful, (250)
"Condo was great, clean , very comfortable. Great parking. Access to the beach was awesome. Free trollie outside to go up and down the island. Would definitely stay here again. "
United States
Susan
The price is AU$385
includes taxes & fees
2 Jan - 3 Jan 2026
Anna Maria Sunsets - studio

Adorable Cottage moments to beach w/ pool, beach gear, bikes

Adorable Cottage moments to beach w/ pool, beach gear, bikes
Anna Maria
9.8 out of 10, Exceptional, (14)
"Loved how the cottage is wqlking distance to the beach and also restaurants."
United States
Pamela
The price is AU$981
includes taxes & fees
13 Jan - 14 Jan 2026
Adorable Cottage moments to beach w/ pool, beach gear, bikes

Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!

Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
Anna Maria
9.4 out of 10, Exceptional, (24)
"Easy walk to the beach and restaurants. Allowed us to check in early since the place was available. "
United States
Nancy E.
The price is AU$763
includes taxes & fees
13 Jan - 14 Jan 2026
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!

Sunset View Pet Friendly w/Pool Beach Home

Sunset View Pet Friendly w/Pool Beach Home
2.0 star property
Bradenton Beach
10.0 out of 10, Exceptional, (27)
"The cutest little place! We loved how close it was to the beach and that it was pet friendly. Plenty of spots to sleep without feeling on top of each other. It was perfect for what we needed! "
United States
Ashley O.
The price is AU$1,075
includes taxes & fees
7 Jan - 8 Jan 2026
Sunset View Pet Friendly w/Pool Beach Home

Anna Maria Beach Condo 1/1

Anna Maria Beach Condo 1/1
Bradenton Beach
9.8 out of 10, Exceptional, (198)
"Excellent location, great condo, good local restaurants. "
United States
Lloyd
The price is AU$524
includes taxes & fees
4 Jan - 5 Jan 2026
Anna Maria Beach Condo 1/1

Villa #4 Sand Dollar! Pool, Porch, Near the Beach!

Villa #4 Sand Dollar! Pool, Porch, Near the Beach!
Holmes Beach
9.6 out of 10, Exceptional, (47)
"would stay here again"
United States
Richard H.
The price is AU$1,317
includes taxes & fees
1 Jan - 2 Jan 2026
Villa #4 Sand Dollar! Pool, Porch, Near the Beach!

Mello on the Beach - Looney Dunes

Mello on the Beach - Looney Dunes
Holmes Beach
10.0 out of 10, Exceptional, (15)
"The pool is even better in person than in photos. The room is absolutely adorable and immaculate. The location is right on beach. "
United States
LYNN D.
The price is AU$636
includes taxes & fees
5 Jan - 6 Jan 2026
Mello on the Beach - Looney Dunes

Beautiful Bungalow with Pool and Bay Views!

Beautiful Bungalow with Pool and Bay Views!
Anna Maria
9.8 out of 10, Exceptional, (37)
"Great location,great property,spacious,clean everything brand new in the property,beach across the street,my family love it!"
United States
Michel
The price is AU$1,002
includes taxes & fees
13 Jan - 14 Jan 2026
Beautiful Bungalow with Pool and Bay Views!

Anna Maria Beach Condo 1/1

Anna Maria Beach Condo 1/1
Bradenton Beach
9.8 out of 10, Exceptional, (239)
"Beautiful condo. Great location. "
United States
Daniel B.
The price is AU$605
includes taxes & fees
5 Jan - 6 Jan 2026
Anna Maria Beach Condo 1/1

Perfect Bradenton Beach Escape; 2BR Sunset Balcony/Walk to all Restaurants/Shops

Perfect Bradenton Beach Escape; 2BR Sunset Balcony/Walk to all Restaurants/Shops
Bradenton Beach
10.0 out of 10, Exceptional, (10)
"This place was amazing . Best vacation stay so far."
United States
Mark C.
The price is AU$649
includes taxes & fees
7 Jan - 8 Jan 2026
Perfect Bradenton Beach Escape; 2BR Sunset Balcony/Walk to all Restaurants/Shops

Palm Tree Villas

Palm Tree Villas
3.0 star property
Holmes Beach
9.2 out of 10, Wonderful, (172)
"We had a great stay! The property was located within a short walk to the beach. We will be back!"
United States
Anonymous traveller
Palm Tree Villas

Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes

Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
Anna Maria
9.8 out of 10, Exceptional, (30)
"Enjoyed the property, pool, the closeness to the beach"
United States
Susane D.
The price is AU$702
includes taxes & fees
5 Jan - 6 Jan 2026
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Anna Maria Island Hotel Reviews

Find out more about Anna Maria Island

Everything you need to know about Anna Maria Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Anna Maria Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Anna Maria Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Anna Maria Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Anna Maria Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Anna Maria Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Anna Maria Island holiday rentals we have selected for you start as low as AU$385 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Anna Maria Island rentals

At Expedia, we put the best Anna Maria Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Anna Maria Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Anna Maria Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Anna Maria Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.