If you’re ready to visit yet another gorgeous beach destination, you have got to check out Anna Maria Island — a gorgeous barrier island along the Gulf of Mexico to the west and Intracoastal Waterway to the east. And despite what many might think, a spot such as this can be your next vacation destination at a reasonable price! To that end, we’ve gathered 10 amazing Vrbo vacation rentals that all have an average price of $250 or less per night.
You won’t want to waste any time booking your trip at one of these highly rated and differently-sized rentals. Not sure what to do for those rare moments you aren’t on the beach or in the pool? Anna Maria Island offers plenty to do, like boating, great shopping, shelling, fishing, and so much more!
While you could always cook something up in the kitchen, who wants to do that while on vacation? Anna Maria Island has great food options, from great cafe options to a variety of other choices, there are plenty of great food options for everyone.
Ready to book that trip? You’ve come to the right place!
Diamond Surf$329/nightly avg
Diamond Surf, a private ground-level vacation home, is the perfect spot for families, couples, or friends. Walk to the beach in just a few minutes — or take the free Anna Maria Island Trolley. Diamond Surf features a king master bedroom, while the second bedroom comes with a queen bed. With an open floor plan, Diamond Surf comes with a well-equipped kitchen, space for 6 in the dining room, and a washer and dryer for your convenience. Have you seen the photos of the backyard? Take a look! You will love the private pool, gas grill, and chaise lounges.
LaRaya Retreat$404/nightly avg
LaRaya Retreat, located on the second floor of this updated and pet-friendly beach house, features a dog-friendly attitude, a private lagoon pool, and easy access to Bean Point Beach. You’re going to love the updated kitchen and relaxing in the living room, or cooling off on the balcony with an adult beverage. Feel free to pack lightly — a washer and dryer are at your disposal. This one is a beauty, so take a look soon!
Sapphire Surf$392/nightly avg
Perfect for families, couples, or a small group of friends, Sapphire Surf features an open concept floor plan with a well-equipped kitchen, family room, dining room with space for 6, and a cool air-conditioning system. When you’re ready to hit the beach, pack your goodies in the beach wagon and grab the umbrella, beach chairs, towels, and sand toys — all provided for you! Or stay at the Sapphire Surf and enjoy the backyard, complete with a private pool, chaise lounges, a gas grill, and more. This one is gorgeous and reasonably priced, so book soon!
Cute And Cozy Getaway$297/nightly avg
If you’re looking for something for a smaller group, this cute and cozy getaway is exactly what you need. With space for 4 guests, this beautiful vacation home is just a short walk to the beautiful white sand beaches of Bean Point. Relax in the screened-in lanai or on the leather couch in the living room. When you’re ready to hit the beach, take advantage of the provided beach wagon, umbrellas, beach towels, and more. The rental also includes a gas grill, washer and dryer, and fully equipped kitchen — so many amenities with this gorgeous vacation home.
Harmony House$398/nightly avg
Welcome to Harmony House! This Key West style cottage is close to the beach, dining, and Bayfront Park – and comes with a cocktail-style pool right out back! With inviting bedrooms and spacious bathtubs, Harmony House has a full kitchen, private washer and dryer, charcoal grill, and a place to relax – a covered swing right by the pool. The beach at Bean Point is just a few blocks away, or walk to Bayfront Park or 1 of 2 fishing piers. Don’t want to walk? Hitch a ride on the free island trolley! Be sure to check out the gorgeous backyard – Harmony House is as inviting as they come!
MI Oasis Getaway$350/nightly avg
A true oasis on the inside and out, MI Oasis Getaway is appropriately named! This vacation rental comes with a fully stocked kitchen, a dining table for 4, travertine floors throughout, and the feeling that you’re in a luxurious hotel room when entering the master bedroom, complete with a king-sized bed and an incredible view of the rock wall water feature. Just 200 steps from the white sand beaches on the Gulf side of Anna Maria, MI Oasis Getaway is just a block from Pine Street. Don’t want to rent a car? This is a great location for you – everything is within walking distance or accessible via the provided beach bikes or free island trolley. This one is in high demand – don’t wait!
Sea Breeze$269/nightly avg
Sea Breeze is a newly renovated vacation rental with a private dock, an unobstructed view of Bimini Bay, a full kitchen, a washer and dryer, and more! The floor-to-ceiling windows offer spectacular views of the water or wildlife, and being a second-floor unit Sea Breeze gives a fantastic high perspective view of the canal. There’s on the water, and then there is on the water, and Sea Breeze is definitely on the water — check out those pictures! Relax on the balcony where you’ll find an outdoor table, chairs, and barbecue for your use. Would you rather go out? Sea Breeze is within walking distance to multiple restaurants!
The Ballyhoo$180/nightly avg
This ground-floor rental known as The Ballyhoo is on historic Bean Point, just 200 feet from the beach. If you love to fish, you will be thrilled with your proximity to the Rod & Reel Pier! This cozy rental home has space for up to 6 guests and offers you all the privacy you’ll need. Bicycles are provided, making it easy for you to get to any of the 12 local restaurants, historic Pine Avenue, or whatever you choose. It has everything you need at an affordable price!
Quaint And Quiet Northshore Villa$215/nightly avg
This recently updated quaint and quiet Northshore Villa is nestled in the heart of Anna Maria Island. Start the day on the deck enjoying coffee, then make your way to the beach and dip your toes in the Gulf of Mexico. This two-bedroom vacation rental is a perfect getaway for up to five guests and is in a great location for those wanting quick access to Pine Street, the historic city pier, great shopping, theater, and dining. Perfect, subtle beach decor — a true beauty!
Naut 2 Shabby Bungalow$185/nightly avg
Touted as a “cute as a bug bungalow,” the Naut 2 Shabby is located on Anna Maria’s north end, just 1 block from City Pier and Tampa Bay and only 4 blocks from the gulf. With a well-equipped kitchen, a queen-size master, queen sofa sleeper, Naut 2 Shabby is nestled into a garden atmosphere with a private patio and fountain. Bikes, a kayak, beach gear, coolers, beach towels, a grill, and more are provided.
For more fun things to do on Anna Maria Island, check out: