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Vacation rentals in Anna Maria Island

Vacation rentals in Anna Maria Island

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Anna Maria Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Dog-friendly home with private pool, great location near beach, shopping, dining
    Entire house · 6 guests · 3 beds · 2 bathrooms
    Dog-friendly home with private pool, great location near beach, shopping, dining

    The health and safety of our guests, homeowners, and employees is our number one priority. Many of our vacation rentals minimize person-to-person contact with private amenities and entry via smart locks or lockboxes. Plus, each reservation is backed by 24/7 customer support and expert cleaning in line with current CDC guidelines.

    What guests are saying:

    “Loved this house. My husband and I stayed here for our annual beach trip. I highly recommend it! It was the perfect size for the two of us with two bedrooms and two baths. The place was clean and nice with a great backyard and easy beach access. It does not include laundry detergent, coffee, or extra paper towel or garbage bags. And depending on how long your stay is, you may need to buy extra toilet paper as well. There are plenty of towels, including beach towels and some fun pool floats too! We will definitely be back. I want to buy the place!!”

  • A Cozy Bungalow on the bay.
    Entire flat · 2 guests · 1 bed · 1 bathroom
    A Cozy Bungalow on the bay.

    A comfortable efficiency with a queen size bed, a full kitchen, a private bath, a great location and a lovely view. We are a two minute walk to the beach, restaurants, shopping and nightlife.

    What guests are saying:

    “Deanna’s apartments are beautiful, the location is perfect, 2 mins to the beach and just off the historic bridge street. Plenty of local restaurants within a short walk and close to the free trolley to go up and down the island. The apartment is beautifully presented and certainly very cosy - wonderful views over a private jetty (the sunrise is not to be missed). Only slight issue for us was the height of the bathroom- my husband is 6 ft 4in so struggled slightly in the bathroom but other than that our stay was perfect. Deanna is a very helpful and communicative host. We’ll be back!”

  • Cozy Beachhouse 800 steps to beach
    SUPERHOSTEntire house · 3 guests · 1 bed · 1 bathroom
    Cozy Beachhouse 800 steps to beach

    This beautiful home is only 800 steps from one of the most beautiful beaches in Southwest Florida. Great getaway for couples. Amazing restaurants and entertainment very close. Free trolley, endless things to do: kayaking, sunbathing, and relaxing.

    What guests are saying:

    “A very cozy and clean house with great privacy and location. The size of the place was perfect for a couple who want a comfortable but not overdone place. The strong wi-fi, Roku TV set-up, and very comfy bed made our stay most comfortable. Mario was most responsive to our questions and helped us settle in with information and suggestions. The patio in the back provided a nice place to relax and enjoy quiet time when we were not on the beach or roaming the nice AMI establishment that were so accessible. We particularly enjoyed the quiet beach down the road, the Sandbar restaurant that was so close to view sunsets, Ginny and Jane E.'s for breakfast and bakery, and roaming the island. The trolley is free and handy, but we didn't utilize it since we had rented a car. This was our first visit to AMI, and by luck we selected the perfect place to enjoy one of the more quiet and still more laid back areas on the island.”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Anna Maria Island holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Anna Maria Island

Dog-friendly home with private pool, great location near beach, shopping, dining
Entire house
Dog-friendly home with private pool, great location near beach, shopping, dining
Price:$ 340 SGD / night
PLAYA ESMERALDA/INNATTHEBEACH SUITES #4A BY BRIDGE STREET
SUPERHOSTEntire place
PLAYA ESMERALDA/INNATTHEBEACH SUITES #4A BY BRIDGE STREET
Price:$ 127 SGD / night
Ohana Beachside Studio - 150 ft from the beach
SUPERHOSTEntire house
Ohana Beachside Studio - 150 ft from the beach
Price:$ 158 SGD / night
Cozy Beachhouse 800 steps to beach
SUPERHOSTEntire house
Cozy Beachhouse 800 steps to beach
Price:$ 182 SGD / night
Beach home w/ exquisite backyard - firepit, private heated pool, grill, and TV
Entire apartment
Beach home w/ exquisite backyard - firepit, private heated pool, grill, and TV
Price:$ 326 SGD / night
Dog friendly oasis with private pool and very close to the beach
Entire house
Dog friendly oasis with private pool and very close to the beach
Price:$ 338 SGD / night
NEW LISTING! Pet-friendly home with private pool, short walk to the beach
Entire house
NEW LISTING! Pet-friendly home with private pool, short walk to the beach
Price:$ 335 SGD / night
Ohana Beachside 1 Bedroom - 150 feet from beach
SUPERHOSTEntire house
Ohana Beachside 1 Bedroom - 150 feet from beach
Price:$ 155 SGD / night
Castnetter Beach Resort 10 - Pool Side Studio
SUPERHOSTEntire flat
Castnetter Beach Resort 10 - Pool Side Studio
Price:$ 210 SGD / night
A Cozy Bungalow on the bay.
Entire flat
A Cozy Bungalow on the bay.
Price:$ 148 SGD / night
Gulf-front home with deck and direct beach access - steps to trolley!
Entire house
Gulf-front home with deck and direct beach access - steps to trolley!
Price:$ 349 SGD / night
Gorgeous bayfront house w/ ocean views, private pool - beach nearby!
Entire house
Gorgeous bayfront house w/ ocean views, private pool - beach nearby!
Price:$ 449 SGD / night
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