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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.

  • 5 Star Villa; Great Pool & Patio, Steps to Beach
    SUPERHOSTEntire apartment · 4 guests · 3 beds · 1 bathroom
    5 Star Villa; Great Pool & Patio, Steps to Beach

    OPEN FOR RENTAL!! 5 STAR Rated Villa, Summer time specials. Perfect for QUICK GETAWAY!! Highly Rated & Reviewed Gorgeous 2 Bdrm Villa less than block from Fantastic Beach. Renovated & redecorated, stainless appliances, granite counters, wood cabinets, Super fast WiFi. Smart TV's, Washer/dryer. New furnishings, Fresh paint everywhere. Delightful 4 unit complex, Relaxing pool & tropical patio, including new Tiki Hut for your evening Beverages.

    What guests are saying:

    “Absolutely darling beach cottage nestled in an immaculately well-groomed estate! I think the images do not live up to the actual beauty of the house or the garden (lush tropical plants and flowers!). We’re using airBNB a lot around the world and this home was a truly positive experience! It’s really just across the street from the beautiful beaches and Karen has everything you might need for a perfect day at the beach (towels, the coolest and most comfortable Tommy Bahama beach chairs 😂, umbrella, cooler box, sand toys and even a trolley to transport everything over to the beach)! The house has a beautiful modern and reduced beach-style interior (not as old-school as many other places) and despite its minimalistic interior it still has ALL you might need. The kitchen is fully equipped for cooking or a BBQ with even some basic spices, paper towels and cleaning gadgets and the cottage has a gas BBQ in the patio! This patio is also connected to the pool with a door so you have direct access to the beautiful pool area with plenty of lounge and deck chairs. Karen even surprised us with several little treats like some cool drinks for us and the kids in the fridge as well as coffee and some snacks for the first morning ☀️ It’s all these little treats which are not standard that made our stay outstanding and particularly enjoyable and relaxing! Thank you Karen and family”

  • Walk 2 Beach + PRIVATE Pool + Golf Cart + Boating
    SUPERHOSTEntire townhouse · 6 guests · 3 beds · 2 bathrooms
    Walk 2 Beach + PRIVATE Pool + Golf Cart + Boating

    Welcome to the Loggerhead, a true home away from home. This is a perfect 2 bedroom/2 bathroom on the private and quiet Anna Maria Island. Enjoy your own heated pool in a very lush tropical setting. We are just a few steps to the beach, so no need to fight for beach parking on your trip. All pool and beach essentials are provided as well as 6 beach cruisers and 4 child bikes. Perfect for your next family escape to paradise.

    What guests are saying:

    “Beyond what we ever could have imagined! Our 4 children and ourselves had a complete blast! EVERY thing you could even imagine needing for your stay is at Loggerhead - this made traveling so much easier! It was so apparent that Stephen put so much thought into ensuring his guests had everything they needed to have a great time. Pack light! The beach was SO close (of course the kids “had” to take the golf cart despite us being within walking distance lol). We spent time swimming in the pool - pictures don’t even do it justice as the backyard was a private oasis in itself. We fished with the kids almost daily, spent hours at the beach, explored the island (dreaming of owning a home in the area ourselves lol) and truly made great memories with our children. Stephen was a pleasure to work with and stayed in communication with us during our entire stay ensuring we had everything we needed. We will for sure be back!”

  • 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!!”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
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  • 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

Cozy Beachhouse 800 steps to beach
SUPERHOSTEntire house
Cozy Beachhouse 800 steps to beach
Price:$ 180 SGD / night
Playa Esmeralda/Innatthebeach Suites #1A Amazing Location in Bradenton Beach
SUPERHOSTEntire flat
Playa Esmeralda/Innatthebeach Suites #1A Amazing Location in Bradenton Beach
Price:$ 164 SGD / night
Fall and Snowbird Availability.  Pool & Boat Dock!
SUPERHOSTEntire house
Fall and Snowbird Availability. Pool & Boat Dock!
Price:$ 393 SGD / night
Anna Maria Island Getaway (Beachfront & Dolphins)
Entire apartment
Anna Maria Island Getaway (Beachfront & Dolphins)
Price:$ 183 SGD / night
A Cozy Bungalow on the bay.
Entire flat
A Cozy Bungalow on the bay.
Price:$ 142 SGD / night
Seaside Maison
SUPERHOSTEntire house
Seaside Maison
Price:$ 585 SGD / night
Las Palmas Beach Rentals unit 2
SUPERHOSTEntire flat
Las Palmas Beach Rentals unit 2
Price:$ 151 SGD / night
Happy Island Cottage - Heated Pool
SUPERHOSTEntire house
Happy Island Cottage - Heated Pool
Price:$ 459 SGD / night
Cabin 1 at Spinnakers Vacation Cottages
SUPERHOSTEntire flat
Cabin 1 at Spinnakers Vacation Cottages
Price:$ 263 SGD / night
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
SUPERHOSTEntire house
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
Price:$ 417 SGD / night
Luxury 3BR/3BA, Private Heated Pool, Beach
SUPERHOSTEntire house
Luxury 3BR/3BA, Private Heated Pool, Beach
Price:$ 314 SGD / night
Kayaking Retreat
SUPERHOSTEntire bungalow
Kayaking Retreat
Price:$ 174 SGD / night
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