Anna Maria Island Holiday Rentals

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Holiday Rentals in Anna Maria Island

Pelican Post at Anna Maria Island Inn

3.0 star property
Bradenton Beach
9.2 out of 10, Wonderful, (316)
"Great location"
United States
Michael
The price is AU$413
includes taxes & fees
30 Nov - 1 Dec
Pelican Post at Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3.0 star property
Holmes Beach
8.6 out of 10, Excellent, (387)
"Shampoos conditioners and lotions, beach towels, cleanliness freshness, thank you it was a good day"
United States
Karen
Haley's at The Anna Maria Island Inn

Bridgewalk Resort

3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (759)
"Great stay!"
United States
Sufyan
The price is AU$494
includes taxes & fees
11 Nov - 12 Nov
Bridgewalk Resort

Seabreeze at Anna Maria Island Inn

3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (50)
"This property was clean and the staff was professional. Right from the back door to the beach in ten steps. View and the sunsets were magnificent. I would go back there again. "
United States
Larry
The price is AU$516
includes taxes & fees
30 Nov - 1 Dec
Seabreeze at Anna Maria Island Inn

Bayfront Home with Amazing Water Views! Private pool! – Breakaway

Anna Maria
9.4 out of 10, Exceptional, (43)
"Great location, great people, awsome hosts, very prompt and caring. "
United States
Alban K.
Bayfront Home with Amazing Water Views! Private pool! – Breakaway

Tradewinds Beach Resort

2.5 star property
Bradenton Beach
9.2 out of 10, Wonderful, (383)
"It was very quiet and beautiful place to vacation."
United States
David
Tradewinds Beach Resort

Private Pool & Hot Tub - House close to Beach & Bridge Street

Bradenton Beach
10.0 out of 10, Exceptional, (3)
"Wonderful property that is comfortably close to beach. Everything at the property was what we needed and the downstairs area was super nice. This really is a hidden gem next to cortez beach. "
United States
Angel B.
Private Pool & Hot Tub - House close to Beach & Bridge Street

Anna Maria Sunsets - studio

Bradenton Beach
9.0 out of 10, Wonderful, (227)
"Condo was very clean but small. A few issues but nothing major. Worth the price. "
United States
CHRISTY
The price is AU$373
includes taxes & fees
16 Nov - 17 Nov
Anna Maria Sunsets - studio

Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

3.0 star property
Anna Maria
9.6 out of 10, Exceptional, (16)
"Wonderful visit, an excellent venue for a family. Fantastic pool area, with sunshine all day. Enjoyable gulf views.Clean and inviting home."
United States
Jon M.
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

Love Shack on the Water Most desirable location on AMI

Anna Maria
10.0 out of 10, Exceptional, (40)
"Great spot for our last minute vacation! Beautiful views and short walk to anything up Pine Avenue and to the beaches. The place is as nice as pictured. Would definitely stay again!"
United States
Laura H.
Love Shack on the Water Most desirable location on AMI

Bayfront Escape with Stunning Water Views and Steps to Bean Point

Anna Maria
9.4 out of 10, Exceptional, (12)
"Very nice property with a great view great location "
United States
Gerry C.
Bayfront Escape with Stunning Water Views and Steps to Bean Point

Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach

Anna Maria
9.8 out of 10, Exceptional, (70)
"Perfect home for a family getaway "
United States
Michael M.
Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach

Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes

Anna Maria
9.8 out of 10, Exceptional, (122)
"We had so much fun at our stay at AMI. There were so many beautiful beach's (not crowded) and delicious restaurants. A great place to relax and watch sunrise and sunset."
United States
Fran M.
Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes

Palm Tree Villas

3.0 star property
Holmes Beach
9.2 out of 10, Wonderful, (172)
"Liked everything about the property! Great location! "
United States
jane
Palm Tree Villas

Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!

2.0 star property
Bradenton Beach
9.8 out of 10, Exceptional, (10)
"This beach house was everything we hoped for and more! The space was clean and felt like a true home away from home. The kitchen was well-stocked, the beds were comfortable, and the bathrooms are spacious. The location couldn’t have been better—a very short walk to the beach. The hosts were incredibly kind and responsive, making the entire stay seamless from start to finish. We made so many great memories here and can’t wait to come back. Highly recommend!"
United States
Alexis A.
Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!

~ BEACHFRONT ~ YES, THAT'S YOUR VIEW! ~ FALL/WINTER SPECIALS ~

Bradenton Beach
10.0 out of 10, Exceptional, (98)
"Updated and clean place to stay. Located right on the beach."
United States
Amandalee M.
~ BEACHFRONT ~ YES, THAT'S YOUR VIEW! ~ FALL/WINTER SPECIALS ~

Beachfront - 2 Masters with Beachfront Views! Pool - Games!

Anna Maria Island
10.0 out of 10, Exceptional, (30)
"We can't say enough good things about this house and the owners! The location, amenities, cleanliness, and communication were all A.We will definitely stay here again!"
United States
Chad S.
Beachfront - 2 Masters with Beachfront Views! Pool - Games!

Thanksgiving Availability! Amazing 6 bed house on Anna Maria! Putt putt

Anna Maria
10.0 out of 10, Exceptional, (3)
"Beautiful place, host is very responsive and overall fantastic to work with. We had a great time! "
United States
Heather W.
Thanksgiving Availability! Amazing 6 bed house on Anna Maria! Putt putt

NOVEMBER SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

Anna Maria
9.6 out of 10, Exceptional, (190)
"Stayed 4 nights and overall it was fantastic! Roomy, a great patio area and the backyard is literally the beach. Private parking for 4 cars was a great benefit. And for us dog lovers, being able our precious pooch was a huge plus! Highly recommend for your next beach trip…you won’t be disappointed. "
United States
Andre P.
The price is AU$1,160
includes taxes & fees
16 Nov - 17 Nov
NOVEMBER SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

Adorable Cottage ONLY STEPS to Anna Maria Beach, No Roads to Cross! FREE WiFi & Trolley

Anna Maria
9.2 out of 10, Wonderful, (24)
"The location of this property combined with its affordability make it a no brainer. The property itself is basic and cute but it is one house from the beach and withing easy walking distance to the Pine Ave shopping and restaurants. It is perfect for the family that is looking for a place to rest, eat, and clean up between beach time and island time. We would definitely stay there again."
United States
Travis N.
Adorable Cottage ONLY STEPS to Anna Maria Beach, No Roads to Cross! FREE WiFi & Trolley
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$373 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.