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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.

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

  • Cozy Beachhouse 800 steps to beach
    SUPERHOSTEntire house · 3 guests · 1 bed · 1 bath
    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.”

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

Holiday rentals for every style

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Popular amenities for Anna Maria Island holiday rentals

  • Kitchen
  • Wi-Fi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Anna Maria Island

PLAYA ESMERALDA/INNATTHEBEACH SUITES #4A BY BRIDGE STREET
SUPERHOSTEntire place
PLAYA ESMERALDA/INNATTHEBEACH SUITES #4A BY BRIDGE STREET
Price:$140 NZD / night
A Cozy Bungalow on the bay.
Entire apartment
A Cozy Bungalow on the bay.
Price:$171 NZD / night
Kayaking Retreat
SUPERHOSTEntire bungalow
Kayaking Retreat
Price:$194 NZD / night
Las Palmas Beach Rentals unit 2
SUPERHOSTEntire apartment
Las Palmas Beach Rentals unit 2
Price:$168 NZD / night
#4 HTD POOLSIDE 1 BR QUEEN-20 sec TO BCH-SLEEPS 4
SUPERHOSTEntire cottage
#4 HTD POOLSIDE 1 BR QUEEN-20 sec TO BCH-SLEEPS 4
Price:$155 NZD / night
Cabin 2 at Spinnakers Vacation Cottages
SUPERHOSTEntire apartment
Cabin 2 at Spinnakers Vacation Cottages
Price:$263 NZD / night
Becker's Beach Bungalow
SUPERHOSTEntire cottage
Becker's Beach Bungalow
Price:$233 NZD / night
Ohana Beachside 1 Bedroom - 150 feet from beach
SUPERHOSTEntire house
Ohana Beachside 1 Bedroom - 150 feet from beach
Price:$171 NZD / night
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:$384 NZD / night
Castnetter Beach Resort 10 - Pool Side Studio
SUPERHOSTEntire apartment
Castnetter Beach Resort 10 - Pool Side Studio
Price:$232 NZD / night
Happy Island Cottage - Heated Pool
SUPERHOSTEntire house
Happy Island Cottage - Heated Pool
Price:$511 NZD / night
BEACH NEST *Pool*Hot Tub*Dock*Steps to Gulf Beach!
SUPERHOSTEntire house
BEACH NEST *Pool*Hot Tub*Dock*Steps to Gulf Beach!
Price:$603 NZD / night
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