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

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

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

Anna Maria

Chase S.

HK$6,289 total

includes taxes & fees

16 Aug - 17 Aug

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

Anna Maria

"This house is in an excellent location halfway between the bay and the gulf, on a street very close to dining, shopping, etc. and yet quiet. Took only four minutes to walk to coffee shop, eight minutes to the beach and restaurants. House was perfect for our family weekend vacation. We all enjoyed the pool. Washer/dryer on site was convenient. Check in was super easy with door code. Property was clean. Everything worked out well, no issues."

Teresa

HK$8,066 total

includes taxes & fees

21 Aug - 22 Aug

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

Anna Maria

Terry R.

HK$5,940 total

includes taxes & fees

10 Aug - 11 Aug

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

4. Coconut Cottage~Private Heated Pool~Block to shops

Anna Maria

Jenny R.

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

Anna Maria

Lewis E.

HK$5,949 total

includes taxes & fees

3 Aug - 4 Aug

6. Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!

Anna Maria

Jane S.

HK$7,470 total

includes taxes & fees

10 Aug - 11 Aug

7. JULY, AUG. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog

Anna Maria

Megan

HK$6,813 total

includes taxes & fees

4 Aug - 5 Aug

8. Anna Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals

Anna Maria

Shea H.

9. 2nd House from the Beach with No Roads to Cross

Anna Maria

Steven W.

HK$7,043 total

includes taxes & fees

4 Aug - 5 Aug

Coffee/tea maker, fridge, microwave, oven

10. Sea Whisper: North End gem w/ pool & dock

Anna Maria

Farah S.

HK$6,497 total

includes taxes & fees

6 Aug - 7 Aug

11. Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite!

Anna Maria

Lisa B.

12. Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach

Anna Maria

Alie P.

HK$8,530 total

includes taxes & fees

14 Aug - 15 Aug

13. Private Pool / Spa Home - Steps to Anna Maria Island Beach

Anna Maria

Erin S.

HK$6,488 total

includes taxes & fees

31 Aug - 1 Sept

14. Tortuga Bay~Canal & Waterslide Putt Putt! TIKI HUT

Anna Maria

Julie D.

HK$13,933 total

includes taxes & fees

22 Aug - 23 Aug

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

Anna Maria

Cheryl L.

HK$6,623 total

includes taxes & fees

10 Aug - 11 Aug

16. Family-Friendly Canal Retreat with Pool and Steps to the Beach

Anna Maria

Jon F.

17. Private Home 1 Block to Beach with Pool and Hot Tub!

Anna Maria

lori jo h.

HK$8,450 total

includes taxes & fees

9 Aug - 10 Aug

18. Palmetto Paradise~Heated Pool/Spa, Steps to the Beach!

Anna Maria

Jonathan S.

HK$11,890 total

includes taxes & fees

16 Aug - 17 Aug

19. Private, Remodeled Home with Pool! 1 Block to Beach, Great for Families!

Anna Maria

Sara V.

20. NEW! Blue Pearl~Heated Pool/Spa~Walkable Pine Ave!

Anna Maria

"Beautiful house! It’s an older home that has been remodeled so it has lots of charm and character with all the modern conveniences of a new house. The backyard is the highlight! We loved the pool and hot tub (just be sure to start the heater in the hot tub an hour prior to use it because it takes time to warm up). The location is absolutely perfect! It’s a short walk to the beach, and the hostess provides nice pool chairs, umbrella and a wagon. Lots of restaurants and stores that are walking...

Ana Cynthia P.

HK$9,290 total

includes taxes & fees

31 Aug - 1 Sept

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Top Anna Maria Hotel Reviews

JULY, AUG. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog

10/10 Excellent

"We have just had the most amazing stay at this beautiful beachfront home on Anna Maria Island. From the moment we arrived, we knew we’d picked somewhere special.The home was spotlessly clean, beautifully furnished and exceptionally well equipped with everything we could possibly need. Waking up each morning to our own private beach and stunning sea views was unforgettable.During our stay we were lucky enough to see dolphins almost every day, along with manatees, pelicans, crabs and even sea turtle nests right on the beach. Hiring a golf buggy and exploring the island like the locals was a real highlight, and the location made it easy to reach fantastic restaurants, shops and some of the most beautiful beaches in Florida.The home itself was comfortable , peaceful and perfect for our family. Communication with the host was excellent throughout, making the whole experience effortless from start to finish.We wouldn’t hesitate to recommend this home to anyone looking for a relaxing, high-quality beachfront escape on Anna Maria Island. It has been one of the highlights of our Florida holiday, and we can’t wait to return!"

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

10/10 Excellent

"We thoroughly enjoyed our stay and would not hesitate to book again. The great parts were location and comfort, but communication was also fantastic. I have stayed places were we don't here a word until an hour before check in and it can be so disconcerting to travel to a distant destination HOPING things are going to go okay at check in. Katy reached out a week before with a very thorough and thought out welcome email and checked on us the day after we checked in to make sure everything was going smoothly. This is a great option if you are headed to AMI."

Ideal Location, Stunning Villa! Close to beach, beach gear provided!

10/10 Excellent

"We had a fantastic stay! Our accommodations were so clean and beautifully decorated, Perfect location to all of the shops, restaurants and beaches! The host was friendly, responsive, and very accommodating. We would definitely stay here again and highly recommend it!"

Moondance- 2 bedrooms- Breathtaking views and beachfront with steps from the bea

10/10 Excellent

"I appreciate how clean the property was. The restaurant that is located next was very convenient. The property has good windows and no noise could be heard inside. I really enjoyed having lunch with my family outside under the house looking at the beach."

Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach

10/10 Excellent

"We loved this property! The location was ideal and everything was as described. The appliances all seemed brand new. The lock wasn’t working when we checked in, but someone was there immediately to get us in and maintenance was called out to fix the problem. It was so nice to know things were taken care of so quickly. We had a great vacation!"

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

10/10 Excellent

"We had a wonderful stay and would absolutely come back! The beach location couldn't have been better, and the views from the back porch were the perfect spot to watch the sunset each evening. The house was stocked with everything we needed, from beach chairs, bikes, and beach towels to all the little extras that made our stay easy and relaxing. The beds were incredibly comfortable, and the home was perfect for our family vacation. Highly recommend!"

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