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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!!”

  • 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”

  • 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!”

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:₹17,967 / night
PLAYA ESMERALDA/INNATTHEBEACH SUITES #4A BY BRIDGE STREET
SUPERHOSTEntire place
PLAYA ESMERALDA/INNATTHEBEACH SUITES #4A BY BRIDGE STREET
Price:₹6,766 / night
Ohana Beachside Studio - 150 ft from the beach
SUPERHOSTEntire house
Ohana Beachside Studio - 150 ft from the beach
Price:₹8,390 / 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:₹17,441 / night
Cozy Beachhouse 800 steps to beach
SUPERHOSTEntire house
Cozy Beachhouse 800 steps to beach
Price:₹9,698 / 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:₹17,967 / night
2Bedroom Anna Maria condo, only steps from beach!
Entire apartment
2Bedroom Anna Maria condo, only steps from beach!
Price:₹8,270 / night
Gorgeous bayfront house w/ ocean views, private pool - beach nearby!
Entire house
Gorgeous bayfront house w/ ocean views, private pool - beach nearby!
Price:₹23,907 / night
Cancel at Anytime! Beach Side Studio on Anna Maria Island
Entire apartment
Cancel at Anytime! Beach Side Studio on Anna Maria Island
Price:₹4,210 / night
A Cozy Bungalow on the bay.
Entire flat
A Cozy Bungalow on the bay.
Price:₹7,894 / night
5 Star Villa; Great Pool & Patio, Steps to Beach
SUPERHOSTEntire apartment
5 Star Villa; Great Pool & Patio, Steps to Beach
Price:₹12,705 / night
Ohana Beachside 1 Bedroom - 150 feet from beach
SUPERHOSTEntire house
Ohana Beachside 1 Bedroom - 150 feet from beach
Price:₹9,928 / night
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