Holiday rentals in Anna Maria Island

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Top-rated holiday rentals in Anna Maria Island

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Guest favourite

Home in Anna Maria

4.94 out of 5 average rating, 167 reviews

Private 30' Pool and Boat Dock - Rated best on AMI

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. * There's no better way to unwind and forget all your troubles than staying at Sunshine Cottage, located in the City of Anna Maria!

Guest favourite

Home in Holmes Beach

4.97 out of 5 average rating, 128 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

Twin Palms is home to NY Times best-selling food writer and chef and her tech husband. Infant/kid/pet-friendly (to 35 lbs) in a great location 5 min. walk to the beach. Private lagoon-style *heated* pool amid lush landscaping with gorgeous rock waterfall. Fully updated kitchen, 60-inch Sony HDTV, 55'' Samsung Frame TV, Italian leather reclining sofas, BBQ, beach gear, updated bathrooms, three king bedrooms. Classic Florida one-level home - no stairs. Managed directly by owners. No crazy fees!

Guest favourite

Townhouse in Holmes Beach

4.99 out of 5 average rating, 133 reviews

Escape with Us! Gorgeous home 700 ft from beach!

Recently renovated! Less than 2 blocks from the powder white sands of Holmes Beach! Come stay in our well-appointed 3 bedroom 2 bath home with modern decor in a quiet beach community. The main bedroom features a walk-in closet and attached bath. We have a shared heated pool and are within half a mile of restaurants and shopping on the famed Anna Maria Island! Perfect house for families. Saturday to Saturday rental only during peak season (Jan-Aug). 7 night minimum due to city ordinance.

Guest favourite

Bungalow in Anna Maria

4.88 out of 5 average rating, 132 reviews

Bay Breeze Cottages #2 (The Redfish)

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

Guest favourite

Home in Anna Maria

4.99 out of 5 average rating, 99 reviews

1 block to Beach on Pine Ave! Private Heated Pool

Sat-Sat rentals, usually... Our 3 bedroom, 2 bath townhouse, with a private heated-pool oasis, is on Pine Ave in the heart of Anna Maria - 1 ½ blocks from the best white sand beach on the island - 3 blocks in the other direction to the bay - from sunrise at the City Pier to Sunset on the Gulf of Mexico. Walk or ride a bike to all the quaint stores, shopping and restaurants (plus the local doughnut, taco shop and Northshore Cafe next door) without ever getting in your car!

Guest favourite

Home in Holmes Beach

4.95 out of 5 average rating, 87 reviews

Breezy Harbor AMI pool retreat near the Beach

Charming Breeze Harbor boasts a private heated pool and sits on a quaint corner of AMI. Upon arriving you will immediately relax bird watching and enjoying the breeze. You'll love grilling in the lush yard and the 6-min walk to the beach and nearby AMI trolley stop. The supermarket is a couple of streets over. The home is perfect for families, couples, 1x 50Lb pet (fee), and working remotely. Parking for 2 vehicles plus your toys. *Ask us for other calendar blocks

Guest favourite

Home in Anna Maria

4.93 out of 5 average rating, 103 reviews

Charming house w/heated pool,steps to beach-Unit A

Location! North end of Anna Maria Island . This charming two story duplex- each unit has two bedrooms , one bathroom. Rent one unit or both. Perfect for a group of extended family and friends. Steps to the Bean Point Beach . Includes beach chairs, umbrellas and all you need for a perfect day at the beach! Heated pool , private seating, grilling areas, bicycles and much more available.MAX Occupancy - 4 people including children of any age.

Guest favourite

Home in Anna Maria

5 out of 5 average rating, 51 reviews

ami skyview

When you open your door and step out, you will enjoy your own private white sandy beach, with sparkling blue/green, Gulf/Bay water. The location and view are incredible, only two blocks walk to the famous Anna Maria City Pier, Pine Avenue, restaurants boutiques and shops. Enjoy kayaks, paddle boards and bicycles, all FREE, for our guests. Come and enjoy paradise! There is only one camera located at the front entrance (street side).

Guest favourite

Guest suite in Bradenton

5 out of 5 average rating, 206 reviews

Off Anna Maria Island ~10min to beach w/salt pool

Stay close to the beach and like a local at Off Anna Maria, a cozy, private guest suite attached to our home with separate entrance, saltwater pool, and shaded outdoor patio. Located ~10 mins from Anna Maria Island, 45 mins from Siesta Key, 1 hr from Tampa in a quiet suburban neighborhood. Your interior space is completely separate from ours. The pool and patio are shared with us. *Travel time estimates depend on traffic.

Guest favourite

Cottage in Anna Maria

4.97 out of 5 average rating, 222 reviews

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

Guest favourite

Guest house in Anna Maria

5 out of 5 average rating, 18 reviews

The Boathouse

Would you like to feel like you are sleeping in a tree house with all the luxuries and comfort of a high end hotel? Then welcome to our brand new guest house, which accommodates a maximum of two guests and is a completely private tropical oasis. Standing on the edge of Lake LaVista, surrounded by tropical palms where you have use of the private and beautiful pool which we heat during the winter months.

Guest favourite

Home in Holmes Beach

5 out of 5 average rating, 39 reviews

Perfect Hideway- easy 5 min walk to the beach!

You’ll love this updated classic Florida beach house on a quiet, dead-end street and close to everything in Holmes Beach. It’s a perfect home base for you to enjoy the laid back, Old Florida lifestyle of Anna Maria Island. Sandy Palms is managed by the owners who live in FL and are always available if you should need anything during your stay. Follow us! FB: Sandy Palms on AMI INST: @sandypalmsami