Anna Maria Island Holiday Rentals

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Our top choices for Anna Maria Island holiday rentals

Apartment in Bradenton Beach

Seabreeze at Anna Maria Island Inn
3.0 star property
9.0 out of 10, Wonderful, (65)
"Very great stay will stay again "
United States
Joseph
The price is NZ$407
includes taxes & fees
7 Jan - 8 Jan 2026
Seabreeze at Anna Maria Island Inn

Condo in Holmes Beach

Alamanda Villas
3.5 star property
9.6 out of 10, Exceptional, (4)
"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 NZ$788
includes taxes & fees
4 Jan - 5 Jan 2026
Alamanda Villas

Apartment in Holmes Beach

Haley's at The Anna Maria Island Inn
3.0 star property
8.6 out of 10, Excellent, (405)
"Beautiful location. Walking distance to beach. "
United States
Maria
The price is NZ$507
includes taxes & fees
30 Dec - 31 Dec
Haley's at The Anna Maria Island Inn
9.8 out of 10, Exceptional, (36)
"Location was perfect"
United States
Michael S.
The price is NZ$774
includes taxes & fees
4 Jan - 5 Jan 2026
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

Aparthotel in Bridge Street

Bridgewalk Resort
3.5 star property
9.4 out of 10, Exceptional, (768)
"Great stay!"
United States
Sufyan
The price is NZ$445
includes taxes & fees
6 Jan - 7 Jan 2026
Bridgewalk Resort
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 NZ$1,142
includes taxes & fees
13 Jan - 14 Jan 2026
Beautiful Bungalow with Pool and Bay Views!

Apartment in Bradenton Beach

Pelican Post at Anna Maria Island Inn
3.0 star property
9.2 out of 10, Wonderful, (335)
"Easy access to Bridge St... Walk quick to beach. Quiet pool nice ... They can definitely improve the Internet as that was spotty. "
United States
Marc
The price is NZ$704
includes taxes & fees
1 Jan - 2 Jan 2026
Pelican Post at Anna Maria Island Inn
9.6 out of 10, Exceptional, (34)
"Great place for a beach stay on Anna Maria!!!"
United States
John F.
The price is NZ$806
includes taxes & fees
4 Jan - 5 Jan 2026
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
9.8 out of 10, Exceptional, (16)
"Clean, great communication, convenient location. "
United States
Teri
Beach Sunrise Villa! Outdoor Dining, Beach Cart and Gulf Breezes
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 NZ$837
includes taxes & fees
5 Jan - 6 Jan 2026
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill

Apartment in Holmes Beach

Palm Tree Villas
3.0 star property
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
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 NZ$832
includes taxes & fees
6 Jan - 7 Jan 2026
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!

Holiday Home in Anna Maria

Cute Cottage Near Beach and Shops
10.0 out of 10, Exceptional, (4)
"The place was great and as presented on the app. Having a designated parking space was very helpful. Close to many great restaurants, shops, the beach, etc. The north shore cafe and waterfront restaurant were both very good and very close in walking distance "
United States
Justin B.
The price is NZ$999
includes taxes & fees
13 Jan - 14 Jan 2026
Cute Cottage Near Beach and Shops
9.6 out of 10, Exceptional, (102)
"Perfect place to stay, loved it, walking distance to everything you need beach right across the street. Loved it."
United States
jason l.
The price is NZ$518
includes taxes & fees
14 Jan - 15 Jan 2026
Stylish bayside condo with WiFi & pool - close to the beach & restaurants

Holiday Home in Bradenton Beach

Sunset View Pet Friendly w/Pool Beach Home
2.0 star property
10.0 out of 10, Exceptional, (28)
"Great property!"
United States
Jeff W.
The price is NZ$1,225
includes taxes & fees
7 Jan - 8 Jan 2026
Sunset View Pet Friendly w/Pool Beach Home
9.2 out of 10, Wonderful, (34)
"Lived the location so close to the beach and really enjoyed having the pool close by "
United States
nicki h.
Beach Condo with Pool Near Holmes Beach!
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 NZ$872
includes taxes & fees
6 Jan - 7 Jan 2026
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
9.8 out of 10, Exceptional, (30)
"Enjoyed the property, pool, the closeness to the beach"
United States
Susane D.
The price is NZ$799
includes taxes & fees
4 Jan - 5 Jan 2026
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
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 NZ$1,120
includes taxes & fees
6 Jan - 7 Jan 2026
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
9.8 out of 10, Exceptional, (62)
"Place us espectacular , one block to a beautiful beach, nice and clean pool, place was clean "
United States
Enis
The price is NZ$1,363
includes taxes & fees
13 Jan - 14 Jan 2026
Beach Villa! Pool, Porch, and 2-Min Walk to Beach!
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 favorite 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 depends 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 NZ$407 per night. Entering your travel dates in the search wizard you might find 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.