Anna Maria Vacation Homes

A marina with boats, a bridge, and high-rise buildings.

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Our top choices for Anna Maria holiday homes

Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!

Anna Maria

Katherine W.

HK$8,052 total

includes taxes & fees

21 Aug - 22 Aug

3 bedrooms, iron/ironing board, free WiFi, bed sheets

Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

Anna Maria

Chase S.

HK$6,287 total

includes taxes & fees

16 Aug - 17 Aug

Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!

Anna Maria

Terry R.

HK$5,914 total

includes taxes & fees

11 Aug - 12 Aug

Beach nearby, sun-loungers, beach towels

BEST LOCATION! NORTH END OF ANNA MARIA, FL STEPS TO BEACH & DINING - LOWER UNIT

Anna Maria

Chuck M.

HK$6,543 total

includes taxes & fees

29 Jul - 30 Jul

Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

Anna Maria

Lewis E.

HK$5,947 total

includes taxes & fees

14 Aug - 15 Aug

Canalfront Home with Pool, Dock and Putting Green! Close to the Beach!

Anna Maria

Elizabeth F.

HK$11,880 total

includes taxes & fees

25 Jul - 26 Jul

BEST LOCATION! NORTH END OF ANNA MARIA, FL STEPS TO BEACH & DINING - LOWER UNIT

Anna Maria

cara M.

HK$7,092 total

includes taxes & fees

22 Jul - 23 Jul

Do you love the beach?

Anna Maria

Zachary Z.

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Top Anna Maria Hotel Reviews

MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street

10/10 Excellent

"Wonderful place to stay"

Sun and Seader North |Charming Cottage | Steps from the Beach in Anna Maria | 2 bedrooms | 1 king bed + 2 twin beds |

8/10 Good

"Our stay was great. The proximity to the beach was fantastic. The unit was clean and quiet and met our needs as a family of 4."

Waterfront Charm! Walk to Bayfront Park!

8/10 Good

"Cute Rental very comfortable couch! Mattresses not so much super firm woke up sore. Also didn’t realize we’d be sharing a backyard Space with other occupants in the duplex. Didn’t even realize it was a duplex lol other than that, it was a great stay!"

Beautiful, Gulf-Front Home on Bean Point--Halcyon House

10/10 Excellent

"Great beach house. We had everything we needed for a great stay. Great view of the Gulf and on the beach. The host was responsive and made everything easy from check-in to check-out. We'd definitely stay here again and highly recommend it!"

Anna Maria Beach Cottage 110 Traditional beach cottage, moments from the sand!

10/10 Excellent

"The cottage was exactly as described, cute, fun beach gear and close access to the beach, yes it is literally a 1 minute walk! Very clean, which was so important to me and the group of ladies celebrating my daughter’s birthday. Many restaurants within a short drive to choose from as well as a clean grilling area. We could not have asked for more! Thank you Wanda, Hannah and the rest of the cottage family!"

Sea La Vie AM: Bay front, pool, hot tub, rooftop deck, and water sports gear!

10/10 Excellent

"The beach house is as lovely as it is depicted in the photographs. We rented the beach house in late June when the outside temperatures were in the mid-90s F (feels like temps over 100), but the air conditioning and ceiling fans kept the house cool and bedrooms comfortably cool for sleeping. Most of the day we were outdoors as much of the pool deck is shaded. We all swam, kayaked, and our son-in-law caught sea trout from his kayak in front of the beach house. The grill worked perfectly and it was one of the best seafood dinners ever. The pool was in full sun during the afternoon and as all Florida pools do during the summer, the pool water was in the mid-90s F. The water in Tampa Bay was only slightly cooler. We saw dolphins, manatees, and osprey from the deck, and the view of the Skyway Bridge across the bay from the deck is gorgeous (about 8 miles across the water from the beach house). The beach house was immaculate, well appointed, and very comfortable. It has its own parking spot(s) on site which is essential on Anna Maria. It is not suitable for persons who cannot handle stairs. The views are breathtaking. We have already rebooked to stay again."

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