Anna Maria Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Anna Maria holiday rentals

Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (3414)
"The location is EXCELLENT, the staff was welcoming and accommodating, and our room had everything we needed to fulfill our goal of being beach bums and mermaids... We can't wait to come back!"
United States
Jaimie
The price is NZ$331
includes taxes & fees
4 Jan - 5 Jan 2026
Sunset Vistas Two Bedroom Beachfront Suites

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites
3.5 star property
Treasure Island
9.2 out of 10, Wonderful, (1107)
"Clean and spacious"
United States
April
The price is NZ$412
includes taxes & fees
15 Jan - 16 Jan 2026
FUSION Resort Waterfront Suites

Mint House St. Petersburg - Downtown

Mint House St. Petersburg - Downtown
4.5 star property
Downtown St. Petersburg
9.4 out of 10, Exceptional, (697)
"Very clean, conveniently located, and friendly staff."
United States
Carolyn
The price is NZ$248
includes taxes & fees
25 Jan - 26 Jan 2026
Mint House St. Petersburg - Downtown

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 NZ$686
includes taxes & fees
27 Dec - 28 Dec
Pelican Post at Anna Maria Island Inn

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 NZ$693
includes taxes & fees
26 Dec - 27 Dec
Haley's at The Anna Maria Island Inn

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, (1033)
"Great hotel "
United States
sandra
Beach House Suites by the Don CeSar

Provident Oceana Beachfront Suites

Provident Oceana Beachfront Suites
3.5 star property
Treasure Island
9.4 out of 10, Exceptional, (611)
"I believe the pool area the Jacuzzi should be open at least till 9:00 or 10:00 p.m."
United States
GARY
The price is NZ$361
includes taxes & fees
7 Jan - 8 Jan 2026
Provident Oceana Beachfront Suites

Westwinds Waterfront Resort

Westwinds Waterfront Resort
3.0 star property
Treasure Island
9.0 out of 10, Wonderful, (693)
"AWESOME location! Right on the bay and 25 steps to the Gulf! 2 minute walk to Publix; 3 minute walk to Walgreens. 1.5 block to a Treasure Island Beach, where there was a sand castle festival for 3 days. "
United States
susan
Westwinds Waterfront Resort

Shoreline Island Resort - Exclusively Adult

Shoreline Island Resort - Exclusively Adult
3.0 star property
Madeira Beach
9.2 out of 10, Wonderful, (1437)
"Super cute apartment and the view from the balcony, right on the beach and very close to restaurants and shops. "
United States
Walesca
The price is NZ$414
includes taxes & fees
16 Jan - 17 Jan 2026
Shoreline Island Resort - Exclusively Adult

Crystal Palms Beach Resort

Crystal Palms Beach Resort
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (2361)
"Unit size was very nice and the linens were good quality. "
United States
Pamela
The price is NZ$317
includes taxes & fees
6 Jan - 7 Jan 2026
Crystal Palms Beach Resort

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 NZ$637
includes taxes & fees
5 Jan - 6 Jan 2026
Seabreeze at Anna Maria Island Inn

Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort
3.0 star property
Treasure Island
9.2 out of 10, Wonderful, (854)
"Room was clean and the front desk was very nice. We would definitely stay here again!"
United States
Rebecca
The price is NZ$681
includes taxes & fees
4 Jan - 5 Jan 2026
Surf Beach Treasure Island Resort

John's Pass Hotel

John's Pass Hotel
2.0 star property
Madeira Beach
8.6 out of 10, Excellent, (277)
"Great location, staff and room"
United States
Saori
John's Pass Hotel

South Beach Oceanfront Resort

South Beach Oceanfront Resort
3.0 star property
Sunshine Beach
9.2 out of 10, Wonderful, (1123)
"Great place to stay!"
United States
Angela
The price is NZ$556
includes taxes & fees
4 Jan - 5 Jan 2026
South Beach Oceanfront Resort

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

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (767)
"Great stay!"
United States
Sufyan
The price is NZ$494
includes taxes & fees
1 Jan - 2 Jan 2026
Bridgewalk Resort

Coastal Comfort 2BR Getaway St Pete

Coastal Comfort 2BR Getaway St Pete
2.0 star property
Childs Park
The price is NZ$413
includes taxes & fees
6 Jan - 7 Jan 2026
Coastal Comfort 2BR Getaway St Pete

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 NZ$747
includes taxes & fees
4 Jan - 5 Jan 2026
Alamanda Villas

Top-floor Sunset Vistas Condo: Ocean-view Balcony!

Top-floor Sunset Vistas Condo: Ocean-view Balcony!
3.5 star property
Sunshine Beach
The price is NZ$865
includes taxes & fees
27 Dec - 28 Dec
Top-floor Sunset Vistas Condo: Ocean-view Balcony!

Voyager Beach Club

Voyager Beach Club
2.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (108)
"We had a wonderful stay"
United States
Diane
Voyager Beach Club
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.
Save an average of 15% on thousands of hotels when you're signed in

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 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 NZ$1,310 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?

Lazy River! Mini Golf! Sleeps 16 Anna Maria Island - Nautical Situation: This highly rated holiday home rental in Anna Maria has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Other favourite homes for rent in Anna Maria are Bayfront Home with Amazing Water Views! Private pool! – Breakaway and Stunning 5 Bedroom Luxury Home, Pool and Spa, Beach Views!.

How many holiday rentals are there in Anna Maria?

With 500 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.