Luxury Anna Maria Island Vacation Rentals
Book our luxury Anna Maria Island vacation rentals, close to the iconic beaches and near popular attractions, like the Manatee Beach Park.
Destinations in Anna Maria Island
Anna Maria Island Vacation Rentals
This barrier island off the coast of Manatee County, Florida, feels a world away from the thrills and spills of Orlando and the hustle and bustle of Miami.
Anna Maria Island is a place of relaxation, a place to step off the hectic carousel of life and take a breather. One of the biggest draws is the unbroken white sand beach that runs the full 7-mile length of the island, which is the ideal place to kick back and unwind in the soothing rays of the Florida sun. Guests more inclined to an active vacation can rent bikes and cycle around the island, or don diving gear and explore life below the waves.
We have a fantastic selection of beautiful Anna Maria Island vacation rentals, including waterfront homes near all the best attractions, sights, and restaurants on the island. They are perfect for couples and families who are looking for a Florida seaside vacation and with fantastic facilities including private pools, games rooms, and pet-friendly villas all available, your Anna Maria Island villa stay is sure to be luxurious and unforgettable.
Popular Vacation Rentals
Anna Maria Island is in Manatee County, on the coast of Florida.
If you’re coming by air, the nearest airport is Sarasota Bradenton International Airport, which is just 20 miles away from Anna Maria Island. Tampa Airport is also a good option to fly into, just 60 miles away from Anna Maria Island.
Anna Maria Island is 126 miles away from Orlando. It takes just over 2 hours to drive between the two, depending on local traffic conditions.
Red tide is harmful algae bloom present around the Florida coastline. It can damage local ecosystems as well as cause irritation to people that come in contact with it.
Best time to visit Anna Maria Island
The best time to visit Anna Maria Island is March through May and October through early December, when the island enjoys warm sunshine and a calm, relaxed atmosphere.
During these months, temperatures are ideal for beach days without the intense summer heat or humidity. The Gulf waters are clear and inviting, making it perfect for swimming, paddleboarding, and boating.
With fewer crowds and a slower pace, this is also the best time to explore the island’s charming streets, enjoy sunset views along the shore, and dine outdoors while experiencing Anna Maria Island at its most peaceful and picturesque.
Food and drink in Anna Maria Island
Food and drink in Anna Maria Island reflect its laid-back coastal lifestyle, with an emphasis on fresh seafood, casual dining, and sunset views. Many restaurants source local catch daily, serving dishes that are simple, flavourful, and perfectly suited to island living.
Popular seafood options include grouper sandwiches, stone crab claws (in season), shrimp baskets, and blackened or grilled fish tacos. You’ll also find waterfront restaurants offering oysters, lobster rolls, and seafood platters, often enjoyed with views of the Gulf of Mexico.
For drinks, the island is known for relaxed beach bars and open-air patios serving tropical cocktails, frozen margaritas, local craft beers, and crisp wines. Whether enjoying a casual lunch by the water or sunset drinks with your toes in the sand, food and drink on Anna Maria Island are all about easygoing charm and coastal flavour.
Flying to Anna Maria Island is easy, with several nearby airports offering convenient access. The closest airport is Sarasota–Bradenton International Airport (SRQ), located approximately 20 minutes by car from the island.
For greater flight choice, Tampa International Airport (TPA) is around 1 hour to 1 hour 15 minutes’ drive, while St. Petersburg–Clearwater International Airport (PIE) is approximately 45 minutes to 1 hour away. From each airport, visitors can reach Anna Maria Island by rental car, taxi, or private transfer, making arrival simple and straightforward.
Driving in Anna Maria Island is simple and unhurried, perfectly suited to the island’s relaxed pace of life. Visitors drive on the right-hand side of the road, and routes are clearly laid out, making navigation straightforward even for first-time visitors.
The island is compact, so journeys are short, and speed limits are strictly enforced to maintain a calm, pedestrian-friendly environment. Parking is available near beaches, restaurants, and residential areas, though spaces can be more limited during busy periods. With its easy roads and scenic coastal views, driving in Anna Maria Island is a comfortable and convenient way to explore everything the island has to offer.
Arriving at Anna Maria Island by boat is a scenic and enjoyable way to begin your stay, offering beautiful views of Florida’s Gulf Coast and surrounding waterways. The island is accessible via nearby bays and inlets, with several marinas and docking points available for private boats and visiting yachts.
Popular nearby access points include Bradenton, Longboat Key, and Sarasota, all offering marinas with transient slips and services. From the water, Anna Maria Island’s coastline, sandy shores, and laid-back charm make for a memorable approach. For those travelling by boat, arriving this way adds a relaxed and distinctly coastal start to an island getaway.
Relax on the BeachesSpend time on the island’s famous white-sand beaches, including Bean Point, Coquina Beach, and Holmes Beach, known for calm waters and stunning sunsets.
Watch the SunsetGulf Coast sunsets are a highlight, best enjoyed from the beach, a waterfront restaurant, or a sunset cruise.
Explore by BikeCycle the length of the island along quiet roads and coastal paths, an easy and enjoyable way to explore.
Go Dolphin SpottingJoin a boat tour or kayak along the coast to see dolphins and marine life in their natural habitat.
Enjoy Local DiningSample fresh seafood, casual beach cafés, and laid-back bars that capture the island’s easygoing charm.
Anna Maria Island vacation homes with Concierge
When planning a vacation to Anna Maria Island, Florida, consider using our fabulous Concierge service to enhance your stay. Our vacation homes offer a range of added services and amenities that make your experience even more enjoyable.
From private chefs to arranging an Anna Maria Island vacation rental with golf cart, and grocery deliveries to attraction tickets, our Concierge takes your Anna Maria Island vacation rental to the next level, creating custom experiences and services to tailor your trip to your requirements.
Anna Maria Island vacation rentals with private pool
No Floridian retreat is complete without a stunning vacation home with an idyllic pool, where you can simply laze and wile away your day. The properties in Anna Maria Island are varied and crisp, with waterside pools, wrap-around pools, and oblong pools all on offer here. No matter where you stay, the private pools here dominate the grounds of your vacation home, so you are sure to be treated to a stunningly designed outdoor space that you won’t ever want to leave. Explore our Anna Maria Island rentals with pools so you can find the one you’ve been dreaming of.
Whether you're seeking a family-friendly vacation home or a romantic retreat, Anna Maria Island vacation rentals with pools offer the perfect blend of comfort, privacy, and relaxation. After a day of exploring the island's stunning beaches, charming boutiques, and delicious dining options, you can return to your vacation rental and enjoy a refreshing swim or simply unwind by the pool, taking in the beauty of your surroundings.
Explore Anna Maria Island vacation rentals with private pool
Anna Maria Island vacation rentals with game rooms
When planning your vacation to Anna Maria Island, Florida, prepare to be bowled over by our vacation homes with game rooms for added entertainment and fun. Anna Maria Island vacation rentals with game rooms offer a fantastic way to keep everyone in your group entertained, especially during downtime or evenings spent indoors.
The game rooms in these vacation rentals are equipped with a variety of entertainment options. including arcade machines, pool tables, foosball tables, or even home theater systems, providing a range of activities to suit different interests and preferences.
Renting a vacation home with a game room allows you to enjoy friendly competitions, engage in family bonding, or simply relax and have a good time with your travel companions. It's a great way to create lasting memories and make your vacation experience even more enjoyable.
Discover Anna Maria Island vacation rentals with game rooms
Pet friendly vacation rentals Anna Maria Island
Planning a vacation to Anna Maria Island, Florida, and want to bring your furry friend along? Look no further than our pet friendly vacation rentals on Anna Maria Island. These accommodations cater to both you and your beloved four-legged companion, ensuring a memorable and enjoyable stay for the entire family.
Pet friendly vacation rentals on Anna Maria Island provide a comfortable and welcoming environment for both you and your pet. These rentals often feature amenities such as fenced yards or designated pet areas, allowing your furry friend to roam and play freely.
The surrounding area of Anna Maria Island is also pet-friendly, with many parks, trails, and beaches welcoming well-behaved dogs. You and your pet can enjoy long walks along the coastline, explore nature trails, or simply relax and soak up the sun together.
