If soaking up the sunshine on sugar sand beaches, catching fabulous Gulf sunsets, and eating all the fresh seafood in sight sounds like your kind of vacation, look no further than Anna Maria Island.
This lesser-known Florida getaway just south of Tampa is home to gorgeous white beaches, high-end restaurants, laid-back bars, and unique shops. This is all balanced with the beautiful natural setting provided by the seven-mile strip of beach that lines this barrier island paradise.
Whether you want a taste of the high life or a chill cabana, the top Anna Maria Island Airbnbs have more than enough beachy vibes to make your stay memorable.
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1. Sunsets on Carissa
Why you should stay: A heated pool plus walking distance to the beach.
- Location: Holmes Beach
- Sleeps: 6
- Minimum stay: 5 nights
- Rates from: $415/night
This spacious three-story home is the perfect escape for the entire family. From the tropical vibe of the landscaped backyard to the decked-out game room and great back deck lounge area, you can put your feet up in whichever space calls your name.
The best part of this location is the easy access to the nearby public beach. You can pack up the included chairs, umbrella, towels, and toys and hit the Gulf for the morning or afternoon. Head in the opposite direction and you’re a short walk (or drive) from the dining and shops at the Island Shopping Center. If you’re looking for a unique thrill, book a trip to go parasailing at Bradenton beach.
Check AvailabilityRelated Read: 9 Gorgeous Beachfront Airbnbs in Florida
2. Villa Chez Shell
Why you should stay: A tropical villa with delightful extras whether you are 8 or 80.
- Location: Holmes Beach
- Sleeps: 6
- Minimum stay: 7 nights
- Rates from: $277/night
If you’re looking for a private home that has the added touches of a resort, Villa Chez Shell delivers on the five-star treatment. Adults will love the in-house Tiki bar, and kids will love the full-size ping pong table, foosball, and dedicated kids’ room complete with bunk beds. Everyone will love the luxurious heated pool and the shaded lanai where you can dine and enjoy the tropical outdoor spaces.
When you are ready to head to the beach, you have your choice of activities from fishing to boogie boarding to taking a nap on the beach. The villa includes almost anything you could want for an afternoon out on the beach. The great location is close to it all — catch the free Anna Maria public trolley for a ride to the Anna Maria City Pier or one of the public beaches.
Check AvailabilityRelated Read: 10 Best Cabin Rentals in Florida for a Relaxing Vacay
3. Beachfront Luxury Home
Why you should stay: Take luxury living to the next level.
- Location: Anna Maria
- Sleeps: 16
- Minimum stay: 7 nights
- Rates from: $1,380/night
This jaw-dropping beachfront property looks like it came right out of the pages of a magazine. Not only is this mansion beautiful inside, but the views overlooking the blue-green waters of the Gulf from the back decks, covered pool patio, and pool are truly picture-perfect.
Should you desire to leave the property, you are a short walk from Rod and Reel Pier and Bean Point Beach. The home is located near the northernmost tip of Anna Maria Island where you can enjoy sunsets over the Gulf of Mexico and sunrises over Tampa Bay. You aren’t far from local eateries and shops as well and Bayfront Park. Bring your paddleboard or kayak if you’re feeling adventurous to explore the stunning waters.
Check AvailabilityRelated Read: 10 of the Best Airbnbs in Daytona Beach, Florida
4. Amie’s House
Why you should stay: Soak up the panoramic Gulf views from the rooftop deck.
- Location: Anna Maria
- Sleeps: 8
- Minimum stay: 4 nights
- Rates from: $823/night
This coastal getaway is everything you would expect of a bright, modern home in a killer location. Whether you are taking a few laps in the palm-tree shaded pool, soaking in the hot tub, or enjoying the sunset from the rooftop deck, this home has some truly spectacular outdoor spaces. In addition to the beautiful home, you also get a few great bonuses like the included beach cruisers that you can use during your stay to explore the island by bike.
Located on the northern tip of the island, you are a short walk from the Gulf-side beaches and Pine Street where you can find great shopping and dining. You can pop out to the Donut Experiment for a morning bite and hit up the Sandbar restaurant in the evening. This end of the island doesn’t have any hotels and is a bit more tranquil than some of the busier parts of Anna Maria.
Check Availability“Beautiful house with many extras that make your stay super special. The pool was amazing.”
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5. AMI Boathouse
Why you should stay: Launch your boat, kayak, or paddleboard from your own private dock.
- Location: Anna Maria
- Sleeps: 8
- Minimum stay: 7 nights
- Rates from: $479/night
If you want to cruise the Gulf or Bay in your boat, the AMI Boathouse is the perfect place to stay as you can park your watercraft at the 55-foot dock. The house is built right on a deep water canal just steps from the back patio and an exquisite pool and lounge area. You might even be lucky enough to spot manatees from the dock.
Located on the Tampa Bay side of the island, you are a short walk from the waterfront. From here you have great views of the Sunshine Skyway Bridge and can watch the boats sail in and out of the Bay as well as spot dolphins cruising by. If you aren’t into motorized water travel, bring your canoe, kayak, or stand-up paddleboard. At the end of the day, you can stroll over to Pine Street for fresh seafood and a cold beverage.
Check Availability6. Sunshine Kiss Villa
Why you should stay: Set your watch to “island time” at this private villa.
- Location: Holmes Beach
- Sleeps: 6
- Minimum stay: 4 nights
- Rates from: $105/night
If you’re looking for a budget-friendly option that doesn’t shortchange you on any of the Anna Maria Island experiences, the Sunshine Kiss Villa is a great option. The back deck comes complete with a grill and plenty of seating underneath the sunshade. On the lower level, you get a second sitting area and plenty of room for a game of corn hole or bocce ball.
Centrally located in the middle of the island between the Gulf and the Bay, you can easily catch the free trolley or take a walk to get to your activity of choice. Bring your snorkeling gear for a swim in the Gulf and pack your dancing shoes for an evening out dancing to live music. After a day out on the beach, you can unwind by sampling the local seafood and sipping a daiquiri under the stars.
Check Availability7. Casa Azul
Why you should stay: A nautically-inspired designer getaway.
- Location: Holmes Beach
- Sleeps: 6
- Minimum stay: 7 nights
- Rates from: $185/night
Are you looking for a private tropical paradise within an island vacation? If so, look no further than Caza Azul. This fully-updated beach home has all modern amenities plus some downright luxuries. Tiki bar in a heated pool? Yes, please! The entire property is designed with seclusion and relaxation in mind from the fabulous backyard to the beautiful balconies.
You are a few minutes’ walk from the beach and other amenities of the island. If you’re looking to spice up your laid-back vacation, consider booking a glass-bottom kayak tour, a sunset or dolphin cruise, or a sunset e-bike tour of the area. There are also a variety of kayaking and paddleboard tours available. You can choose from exploring the mangrove tunnels of Shell Key Preserve or doing guided paddleboard yoga on the Bay.
Check Availability8. Casa Mariposa
Why you should stay: A unique retreat with a yard that rivals a tropical jungle.
- Location: Anna Maria
- Sleeps: 8
- Minimum stay: 4 nights
- Rates from: $765/night
As soon as you step off the street and into the yard of Casa Mariposa, you will feel like you’ve entered your own tropical oasis. The beautiful landscaping and mature palm trees set the stage for this retreat which includes, among other amenities, a pool, spa, cabana, lanais, and, uniquely, a butterfly sanctuary.
You are one block away from the shop and eateries of Pine Avenue. A short walk will get you to the beach. Pack the beach chairs and towels and take the kids to the shore to build some sandcastles and collect seashells. Or hop on a cruiser bike for a tour of the island, best recommended at sunrise or sunset to catch Anna Maria in full island glory.
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Seen in: Florida, Southeast, Where to Stay
