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Anna Maria Holiday Rentals

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Holiday Rentals in Anna Maria

Charming cottage located close to beach - Private heated pool!

Anna Maria
9.4 out of 10, Exceptional, (103)
"Great location. "
United States
Summer J.
Charming cottage located close to beach - Private heated pool!

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

3.0 star property
Anna Maria
9.6 out of 10, Exceptional, (17)
"Had fun "
United States
Otis L.
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

DEC., JAN. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

Anna Maria
9.6 out of 10, Exceptional, (191)
"Bay view was nice "
United States
Steven
DEC., JAN. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Anna Maria
10.0 out of 10, Exceptional, (287)
"Beautiful property in the perfect location to the beach. Dan and Goose were thoughtful and easily accessible. We had a great time! Would absolutely stay here again!"
United States
Hillary D.
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

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

Anna Maria
9.8 out of 10, Exceptional, (124)
"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

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

Sea La Vie Beach House - Luxury Home w/ Pool, Spa, Dock & Canal Access on Anna Maria

Anna Maria
10.0 out of 10, Exceptional, (69)
"Place is amazing "
United States
Eric G.
Sea La Vie Beach House - Luxury Home w/ Pool, Spa, Dock & Canal Access on Anna Maria

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

Anna Maria Island
10.0 out of 10, Exceptional, (31)
"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!

Villa Marisol: Beachfront, Mediterranean style, w/terrace, pool, hot tub!

Anna Maria
10.0 out of 10, Exceptional, (43)
"We had a wonderful time at Villa Marisol. We especially loved the sunset view from the third floor. The house had everything we needed for our stay, and the pool temperature was perfect!"
United States
Yoel S.
Villa Marisol: Beachfront, Mediterranean style, w/terrace, pool, hot tub!

Felicity: Luxury Bayfront Home, Heated Pool, Hot tub and more!

Anna Maria
10.0 out of 10, Exceptional, (42)
"Amazing stay in an amazing property. The pictures can’t do the view justice, truly amazing."
United States
Kenneth S.
Felicity: Luxury Bayfront Home, Heated Pool, Hot tub and more!

Bayfront Escape with Stunning Water Views and Steps to Bean Point

Anna Maria
9.4 out of 10, Exceptional, (13)
"Loved our time there!"
United States
Thomas L.
Bayfront Escape with Stunning Water Views and Steps to Bean Point

The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!

Anna Maria
9.8 out of 10, Exceptional, (198)
"Great location and amenities. Comfortable bed. "
United States
Jennifer T.
The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!

NEW! Meet Me At Sunset! 3 Homes from the Beach!

2.5 star property
Anna Maria
NEW! Meet Me At Sunset! 3 Homes from the Beach!

A Time Out: *Quaint Cottage *Heated Pool *Across the street from the Bay!

Anna Maria
9.4 out of 10, Exceptional, (34)
"Great property for family with kids. Beach in walking distance, pool for bigger kids when little ones nap, 2 separate indoor sitting spaces. Very clean and real estate company came immediately when we had one problem with the door alarm."
United States
Norine P.
A Time Out: *Quaint Cottage *Heated Pool *Across the street from the Bay!

Relaxing Home with Private Pool, High-Speed WiFi, Central AC, & Washer/Dryer

Anna Maria
8.8 out of 10, Excellent, (19)
"We felt very comfortable. The rooms were spacious and comfortable, and the pool and patio were beautiful! We will definitely return in the future. It's only two blocks from the beach!"
United States
DAMARIS L.
Relaxing Home with Private Pool, High-Speed WiFi, Central AC, & Washer/Dryer

NEW~Gorgeous! Arcade!~ Heated pool/spa~North End!

2.5 star property
Anna Maria
NEW~Gorgeous! Arcade!~ Heated pool/spa~North End!

Private Canal Front Home! Heated Pool and 24 ft Boat Dock! - Tarpon Pointe

Anna Maria
9.0 out of 10, Wonderful, (14)
"We spent a lot of time in the pool and hot tub and enjoyed utilizing the backyard. We rented a golf cart and were in close proximity to great restaurants, ice cream shop and the beach. Overall a great stay. "
United States
Kristin K.
Private Canal Front Home! Heated Pool and 24 ft Boat Dock! - Tarpon Pointe

Dog-Friendly 4 Mins to the Beach and Pine Ave - A Place in Paradise Unit B

Anna Maria
9.6 out of 10, Exceptional, (18)
"Very clean, quiet, & walking distance to beach, shopping, & dining! Overall amazing stay. "
United States
Sherri
Dog-Friendly 4 Mins to the Beach and Pine Ave - A Place in Paradise Unit B

Direct Beachfront Home, Steps to the Sand! Private Pool, Amenities for All!

Anna Maria
8.6 out of 10, Excellent, (36)
"We loved staying in the Big Yellow House! The location absolutely could not be beat. The house had everything we needed and we thoroughly enjoyed our stay there. Can't wait to come back!"
United States
Kirsten K.
Direct Beachfront Home, Steps to the Sand! Private Pool, Amenities for All!

Do you love the beach?

Anna Maria
10.0 out of 10, Exceptional, (149)
"Nice place. Clean. Accessible. "
United States
J R.
The price is AU$971
includes taxes & fees
8 Dec - 9 Dec
Do you love the 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 Hotel Reviews

Find out more about Anna Maria

Everything you need to know about Anna Maria 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 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Anna Maria holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Anna Maria. 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 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 holiday rentals we have selected for you start as low as AU$971 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Anna Maria rentals

At Expedia, we put the best Anna Maria 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 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 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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Anna Maria?

Yes, there are holiday rentals close to the most popular sights in Anna Maria, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Anna Maria. Make sure you have time to check out the waterfront while you're in the area.

What are some of the best holiday rentals that Anna Maria has to offer?

Charming cottage located close to beach - Private heated pool!: This highly rated holiday home rental in Anna Maria is located near the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Anna Maria are Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar and Bayfront Escape with Stunning Water Views and Steps to Bean Point.

How many holiday rentals are there in Anna Maria?

With 505 Expedia holiday rentals, you're guaranteed to find just the right place for your Anna Maria stay.

What can I see and do in Anna Maria?

Cultural attractions include Anna Maria Island Museum and Historical Park and Island Players, whereas Anna Maria Beach and Bean Point Beach are a couple of picturesque spots to enjoy the outdoors. While in the area, you can also visit popular places such as Lido Beach and Tampa Bay.

What are holiday rentals like in Anna Maria?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Anna Maria. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip.