11 Coolest Beach Rentals on Anna Maria Island

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Anna Maria Island is one of Florida’s top beach destinations, beloved by locals and visitors alike for its white sandy shoreline and laid-back vibes. Ready to plan a beach getaway on this seven-mile-long slice of paradise? We’ve compiled a list of the best Airbnb and Vrbo vacation rentals on Anna Maria Island, offering luxurious perks such as private pools and beachfront locales.

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Old Florida-Style Cottage with Private Pool, Walk to Beach
airbnb.com
Old Florida-Style Cottage with Private Pool, Walk to Beach

Old Florida-Style Cottage with Private Pool, Walk to Beach

You can live the island life at this charming three-bedroom cottage, which embodies the charm of Old Florida. Its private saltwater pool and close proximity to the beach are its biggest highlights, as you can start your mornings here with a quiet stroll along the shore before hopping on the nearby island trolley. It boasts an open floor plan and air conditioning to keep you cool all summer, while flat-screen TVs and free Wi-Fi keep you entertained. Even dogs are welcome for a small fee.

Casa Azul: 3-Bedrooms, Fun Interior, Private Pool, Near Beach
airbnb.com
Casa Azul - 3-Bedrooms, Fun Interior, Private Pool, Near Beach

Casa Azul: 3-Bedrooms, Fun Interior, Private Pool, Near Beach

Casa Azul is a family-friendly Airbnb with 5-star perks, including its location just 600 steps from the Gulf of Mexico. The three-bedroom space has designer furnishings and a chef’s kitchen, while outdoors you’ll find a free-form heated pool with a tiki bar, outdoor shower and grill with al fresco dining. Take in sunset views from one of the several balconies, then visit some of the island’s top restaurants within walking distance.

Top-Rated Anna Maria Vacation Rental
airbnb.com
Top-Rated Anna Maria Vacation Rental

Top-Rated Anna Maria Vacation Rental

It will be tough to peel yourself away from the backyard oasis at the Sassy Seahorse, a 2-bedroom Airbnb just 3-4 blocks from the white sands at Bean Point. Take a dip in the glass-tiled pool or enjoy a soak in the spa, then bask in the sunshine on a sun lounger or retreat indoors to enjoy the home’s cozy and colorfully decorated spaces. When you’re ready to explore, some of the best shops and restaurants are nearby in the North end of the island.

Lazy Palm Cottage - Heated Pool, Steps to Beach
airbnb.com
Lazy Palm Cottage - Heated Pool, Steps to Beach

Lazy Palm Cottage - Heated Pool, Steps to Beach

Located in Holmes Beach, this charming 1930s cottage is just steps from the picture-perfect beach. The three-bedroom property has enough room for your whole gang to stretch out, offering several living areas that lead to a covered area in the backyard with a pool, seating area and chaise loungers. Other perks include a fully-equipped kitchen with a coffeemaker, flat-screen TVs and a master bedroom with a king-size bed.

Gulf-Front Home with Heated Pool
Vrbo.com
Gulf-Front Home with Heated Pool

Gulf-Front Home with Heated Pool

You can’t get any closer to the Gulf than this luxury abode in Anna Maria Island, which sits directly on the sugar-white sands. Accommodating up to 6 guests, the 3-bedroom home boasts an expansive deck with a gas grill and heated pool with plenty of sun loungers. Best of all, indoors you’ll find cozy rooms with beach views where you can fall asleep to the sound of crashing waves. In addition, there are miles of beautiful beach to stroll and collect colorful seashells, while numerous shops and restaurants are just a stone’s throw away.

Heated Salt Pool, Only 200 Steps From Beach
Vrbo.com
Heated Salt Pool, Only 200 Steps From Beach

Heated Salt Pool, Only 200 Steps From Beach

This Anna Maria Island Vrbo is an oasis of tranquility, featuring a heated saltwater pool just 200 steps from the beach. The two-bedroom property boasts a large living room for hanging out, while its outdoor area boasts lush landscaping surrounded by mature palm trees. Kids will love the games available, such as corn hole, while its location is convenient for exploring more of the island. Everything is within walking distance or you can access attractions via the free Trolley, and there are even beach bikes if you want to sightsee on two wheels.

Angie's Place: 2-Bedroom with Heated Pool & Gulf Views
Vrbo.com
Angie's Place - 2-Bedroom with Heated Pool & Gulf Views

Angie's Place: 2-Bedroom with Heated Pool & Gulf Views

Angie’s Place is a two-bedroom Vrbo with a perfect outdoor space for enjoying Florida year-round sunny weather. The cottage is directly across the street from the award-winning Coquina Beach and offers a shared pool area with lounge chairs and a grill. You can actually see the water from the furnished balcony of this property, which offers a relaxing spot to unwind with a cold drink in hand.

Beachfront Condo, Steps from Bridge Street
Vrbo.com
Beachfront Condo, Steps from Bridge Street

Beachfront Condo, Steps from Bridge Street

This two-bedroom beach condo is just steps from Bridge Street, located directly on the Gulf of Mexico. You’ll have access to local restaurants and shops just a short walk away, while most travelers will be content with enjoying the beach views from the large balcony. Stroll the quiet beaches just steps away, or take in the views from the relaxing living room with a flat-screen TV.

Dog-Friendly Home with Private Pool, Near Beach
airbnb.com
Dog-friendly Home with Private Pool, Near Beach

Dog-Friendly Home with Private Pool, Near Beach

Furry friends (under 25 pounds) are allowed in this dog-friendly home, which can host up to six guests. The newly renovated space offers a private outdoor pool, heated spa and spacious backyard that is ideal for hanging out and enjoying a barbecue. There’s a sandy path to the beach that lies at the end of the street while top shopping, dining and beaches are nearby – easily accessed via the nearby trolley stops.

Private Pool & Covered Lanai, 2-Minute Walk to Beach
Vrbo.com
Private Pool & Covered Lanai, 2-Minute Walk to Beach

Private Pool & Covered Lanai, 2-Minute Walk to Beach

This Holmes Beach Vrbo is a two-minute walk to the beach and offers a private heated pool and large covered lanai. Step inside to discover an open floor plan with plenty of light-filled space and coastal decor, then enjoy a meal on the front outdoor deck or enjoy the backyard oasis with a gas grill and shallow pool area for little ones. The hosts provide everything you need for a memorable beach vacation, including towels, chairs, umbrellas and a cooler bag.

4-Bedroom Home, 3-Minute Walk To Beach
Vrbo.com
4-Bedroom Home, 3-Minute Walk To Beach

4-Bedroom Home, 3-Minute Walk To Beach

You can bring the whole gang for a beach vacation in this Vrbo, which offers large living space and four bedrooms. It boasts a heated pool, covered patio and multiple balconies – but its biggest perk is its prime location just 3 minutes from the white sand beach. Other perks include a fully stocked kitchen, high-speed Wi-Fi and kids will love the Playstation 3. If you want to explore Anna Maria’s attractions, a trolley stop is just 1 minute away.