Anna Maria Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Anna Maria holiday rentals

Aerial view

Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (3,537 reviews)
"Spacious rooms, clean, beautiful beach, nice pool. Great having a cafe and tiki bar available."
United States
Kimberly Sue
The price is S$325
includes taxes & fees
27 Apr - 28 Apr
Sunset Vistas Two Bedroom Beachfront Suites
Interior

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is S$3,916
includes taxes & fees
17 Apr - 18 Apr
3716 7th Ave W
Private kitchen

Gulfport

Gulfport
3.0 star property
Gulfport
The price is S$340
includes taxes & fees
10 May - 11 May
Gulfport
Outdoor dining

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, (762 reviews)
"Very nice place "
United States
Mark
The price is S$141
includes taxes & fees
10 May - 11 May
Mint House St. Petersburg Downtown by Kasa
Poolside bar

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, (1,079 reviews)
"Great place, would absolutely stay again."
United States
Malik
The price is S$522
includes taxes & fees
11 May - 12 May
Beach House Suites by the Don CeSar
3 bedrooms, Internet

Family Home 10 Mins to Beach Pets Welcome

Family Home 10 Mins to Beach Pets Welcome
2.0 star property
Gulfport
The price is S$400
includes taxes & fees
16 Apr - 17 Apr
Family Home 10 Mins to Beach Pets Welcome
2 restaurants, lunch, dinner served; seafood

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (789 reviews)
"So nice to walk to restaurants and shops. Very walkable. Clean. Updated and relaxing atmosphere. Parking was really convenient and accessible. Would stay again."
United States
Deborah
The price is S$439
includes taxes & fees
22 Apr - 23 Apr
Bridgewalk Resort
Premium bedding, pillow-top beds, minibar, free cots/infant beds

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.0 out of 10, Wonderful, (91 reviews)
"The view was beautiful! "
United States
Jennifer
The price is S$640
includes taxes & fees
20 Apr - 21 Apr
Seabreeze at Anna Maria Island Inn
Water view

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites
3.5 star property
Treasure Island
9.2 out of 10, Wonderful, (1,156 reviews)
"Beautiful clean rooms , beautiful view "
United States
Misty
The price is S$360
includes taxes & fees
16 Apr - 17 Apr
FUSION Resort Waterfront Suites
Exterior

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, (389 reviews)
"Love this place "
United States
Leeanne
The price is S$349
includes taxes & fees
12 May - 13 May
Pelican Post at Anna Maria Island Inn
Living area

Stylish Treasure Island Escape

Stylish Treasure Island Escape
3.0 star property
Sunshine Beach
The price is S$2,322
includes taxes & fees
20 Apr - 21 Apr
Stylish Treasure Island Escape
Interior

Artsy Getaway With Vibrant Design Flair

Artsy Getaway With Vibrant Design Flair
3.5 star property
Arlington Park
The price is S$394
includes taxes & fees
21 Apr - 22 Apr
Artsy Getaway With Vibrant Design Flair
Beach

Anna Maria Island Beach Palms 8B

Anna Maria Island Beach Palms 8B
3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (3 reviews)
"Clean, convenient, and affordable stay on AMI. It had everything we needed and the host was very communicative and open to feedback but we had no complaints. "
United States
Emily
The price is S$1,272
includes taxes & fees
26 Apr - 27 Apr
Anna Maria Island Beach Palms 8B
Beach nearby, white sand, sun-loungers, beach towels

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, (443 reviews)
"Incredible location, great room! Loved everything! Would def come back!"
United States
Laís Fernanda
The price is S$369
includes taxes & fees
16 Apr - 17 Apr
Haley's at The Anna Maria Island Inn
Exterior

John's Pass Hotel

John's Pass Hotel
2.0 star property
Madeira Beach
8.4 out of 10, Very good, (324 reviews)
"Love the food and shopping options."
United States
Ann
The price is S$257
includes taxes & fees
16 Apr - 17 Apr
John's Pass Hotel
Room

Sarasota Family Home Private Heated Pool Relax

Sarasota Family Home Private Heated Pool Relax
2.0 star property
Whitfield Estates
The price is S$629
includes taxes & fees
5 May - 6 May
Sarasota Family Home Private Heated Pool Relax
On the beach

Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort
3.0 star property
Treasure Island
9.2 out of 10, Wonderful, (863 reviews)
"Clean room, convenient location and friendly staff"
United States
Jingjing
The price is S$621
includes taxes & fees
3 May - 4 May
Surf Beach Treasure Island Resort
Exterior

Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and the perfect location! Close to the beach, restaurants, and the grocery! We loved the heated pool in February. "
United States
Robert
The price is S$616
includes taxes & fees
14 May - 15 May
Alamanda Villas
Front of property

Walk to Everything! Johns Pass Gem w/ Dock Access

Walk to Everything! Johns Pass Gem w/ Dock Access
3.0 star property
Madeira Beach
The price is S$623
includes taxes & fees
26 Apr - 27 Apr
Walk to Everything! Johns Pass Gem w/ Dock Access
Exterior

Voyager Beach Club

Voyager Beach Club
2.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (109 reviews)
"Everything about this resort was perfect! Can't wait to go back!"
United States
Rocco
The price is S$377
includes taxes & fees
16 Apr - 17 Apr
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Anna Maria Hotel Reviews

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.

How many holiday rentals are there in Anna Maria?

With 560 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.