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Our top choices for Anna Maria holiday rentals

Mint House St. Petersburg Downtown by Kasa

Mint House St. Petersburg Downtown by Kasa
4.0 star property
Downtown St. Petersburg
9.4 out of 10, Exceptional, (800 reviews)
"Great hotel at a relatively low cost. Having a kitchen and a balcony made the stay more enjoyable."
United States
Md Sabbir
The price is £81
includes taxes & fees
7 Jun - 8 Jun
Mint House St. Petersburg Downtown by Kasa

Ocean View: Top-floor Sunset Vistas Condo!

Ocean View: Top-floor Sunset Vistas Condo!
4.0 star property
Sunshine Beach
The price is £425
includes taxes & fees
4 Jun - 5 Jun
Ocean View: Top-floor Sunset Vistas Condo!

Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (3,579 reviews)
"Nice place, I would stay here again"
United States
Jill Michelle
The price is £179
includes taxes & fees
12 May - 13 May
Sunset Vistas Two Bedroom Beachfront Suites

John's Pass Hotel

John's Pass Hotel
2.0 star property
Madeira Beach
8.4 out of 10, Very good, (335 reviews)
"Parking was easy and the shops are right there."
United States
Denice
The price is £84
includes taxes & fees
11 May - 12 May
John's Pass Hotel

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (796 reviews)
"Overall a pretty good spot. Friendly and helping staff, clean area, own parking lot"
United States
Celeste
The price is £240
includes taxes & fees
13 May - 14 May
Bridgewalk Resort

Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort
3.0 star property
Treasure Island
9.2 out of 10, Wonderful, (866 reviews)
"Clean room, convenient location and friendly staff"
United States
Jingjing
The price is £297
includes taxes & fees
17 May - 18 May
Surf Beach Treasure Island Resort

Beach House Suites by the Don CeSar

Beach House Suites by the Don CeSar
3.0 star property
Belle Vista
9.0 out of 10, Wonderful, (1,088 reviews)
"Nice fun hotel "
United States
Kiersten
The price is £257
includes taxes & fees
25 May - 26 May
Beach House Suites by the Don CeSar

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites
3.5 star property
Treasure Island
9.2 out of 10, Wonderful, (1,169 reviews)
"4th time staying here. Still haven’t been disappointed. Highly recommend the terrace to watch the sunrise"
United States
Maurizio
The price is £185
includes taxes & fees
19 May - 20 May
FUSION Resort Waterfront Suites

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, (446 reviews)
"Great location, clean and quiet. "
United States
Sara
The price is £222
includes taxes & fees
10 May - 11 May
Haley's at The Anna Maria Island Inn

Voyager Beach Club

Voyager Beach Club
2.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (111 reviews)
"Very pleasant stay"
United States
Pamela
The price is £234
includes taxes & fees
10 May - 11 May
Voyager Beach Club

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.5 star property
Bradenton Beach
9.2 out of 10, Wonderful, (401 reviews)
"Great location - quiet, private, but just a few blocks from the beach, every eatery and nightlife option. Would definitely stay here again."
United States
Christopher
The price is £223
includes taxes & fees
11 May - 12 May
Pelican Post at Anna Maria Island Inn

South Beach Oceanfront Resort

South Beach Oceanfront Resort
3.0 star property
Sunshine Beach
9.2 out of 10, Wonderful, (1,136 reviews)
"Great staff always helpful and knowledgeable about the area. Enjoy the size of the one bedroom condo "
United States
Bob
The price is £244
includes taxes & fees
11 May - 12 May
South Beach Oceanfront Resort

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (97 reviews)
"Great location!"
United States
Kevin
The price is £253
includes taxes & fees
27 May - 28 May
Seabreeze at Anna Maria Island Inn

Palm Tree Villas

Palm Tree Villas
3.0 star property
Holmes Beach
9.2 out of 10, Wonderful, (173 reviews)
"We had a great stay! The property was located within a short walk to the beach. We will be back!"
United States
Anonymous traveller
The price is £492
includes taxes & fees
10 May - 11 May
Palm Tree Villas

Provident Oceana Beachfront Suites

Provident Oceana Beachfront Suites
3.5 star property
Treasure Island
9.4 out of 10, Exceptional, (635 reviews)
"Great views, great beach access"
United States
Amanda
The price is £173
includes taxes & fees
27 May - 28 May
Provident Oceana Beachfront Suites

Gulfport

Gulfport
3.0 star property
Gulfport
The price is £160
includes taxes & fees
10 May - 11 May
Gulfport

Westwinds Waterfront Resort

Westwinds Waterfront Resort
3.0 star property
Treasure Island
9.0 out of 10, Wonderful, (707 reviews)
"Perfect position, very calm and relaxing. Beautifully clean and well presented, everything you need for great holiday."
United Kingdom
Angela
The price is £239
includes taxes & fees
25 May - 26 May
Westwinds Waterfront Resort

Crystal Palms Beach Resort

Crystal Palms Beach Resort
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (2,376 reviews)
" Clean room very spacious staff friendly "
United States
Cherise
The price is £135
includes taxes & fees
26 May - 27 May
Crystal Palms Beach Resort

FANCY RETREREAT

FANCY RETREREAT
3.0 star property
Bradenton
The price is £475
includes taxes & fees
26 May - 27 May
FANCY RETREREAT

Family Home 10 Mins to Beach Pets Welcome

Family Home 10 Mins to Beach Pets Welcome
2.0 star property
Gulfport
The price is £220
includes taxes & fees
12 May - 13 May
Family Home 10 Mins to Beach Pets Welcome
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, apart-hotels, 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 favorite 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 depends 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 £227 per night. Entering your travel dates in the search wizard you might find 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?

The Wee Cottage | House in Anna Maria: This highly rated holiday home rental in Anna Maria offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind. Other favourite homes for rent in Anna Maria are MAY, JUNE SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog and Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!.

How many holiday rentals are there in Anna Maria?

With 583 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.