Search special places in Anna Maria Island, FL from 100+ sites!
A cabin, a lighthouse, a glamping, your extraordinary stay awaits you
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
345 Unique places to stay in Anna Maria Island, FL
9.7 36 reviews
Anna Maria Island, FL
06/20 – 06/27
$328/nighttotal: $2296 (7 )
Steps To Beach |Heated Pool+spa|direct Pool Access
1 2
bungalow , Holmes Beach
The Captain's Quarters bungalow is located in Holmes Beach, just steps from the Gulf of Mexico beach and one block from the free trolley stop. With excellent user, location, and cleanliness ratings, this one-bedroom, one-bathroom bungalow can accommodate up to four guests. The bungalow features a heated saltwater pool and spa, a gas grill, a spacious layout, and a starter set of supplies. Guests can also enjoy the coastal-inspired interior design, access to shops and restaurants, and the free trolley service nearby.
Anna Maria Island, FL
08/15 – 08/22
$504/nighttotal: $3528 (7 )
Dolphin Cabin! Available For Summer! Screened Pool, Dock & More!
3 1
cabin , Cortez
Dolphin Cabin, located in Bradenton, Florida, offers convenient access to Sarasota attractions, including the Ringling Museum of Art, approximately 12 miles away. This 1980-square-foot vacation home features three bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, screened pool, private dock, free Wi-Fi, and air conditioning.
9.9 244 reviews
Anna Maria Island, FL
08/02 – 08/09
$154/nighttotal: $1078 (7 )
Cabin 2 Spinnakers Cottages - 204 - 56th 2
1 2
cabin , Holmes Beach
This Holmes Beach vacation rental is located just a 10-minute walk from Bradenton Beach and Island Gallery West, and within a mile of Holmes Beach Beaches and Manatee Public Beach. Guests consistently rate this property excellent for its location, cleanliness, and overall experience. The one-bedroom, one-bathroom house has 800 square feet of space and can comfortably accommodate up to four guests. This rental offers a fully equipped kitchen, a private swimming pool, a spa, a garden with barbecue grills, and access to a water park, making it perfect for a relaxing and fun-filled stay.
Anna Maria Island, FL
08/03 – 08/07
$264/nighttotal: $1056 (4 )
Bungalow ∙ 1 Bedroom ∙ 4 Guests
1 3
bungalow , Holmes Beach
This bungalow in Holmes Beach is located less than 200 feet from the Gulf of Mexico beaches and a short walk to the free island trolley service. This rental offers direct gulf views from the living room window, an elevated deck with seating, a gas grill, and accommodates up to 4 guests with 1 bedroom and 2 bathrooms.
Anna Maria Island, FL
01/05 – 01/12
$392/nighttotal: $2744 (7 )
Bungalow ∙ 1 Bedroom ∙ 4 Guests
1 2
bungalow , Holmes Beach
This Holmes Beach duplex, located on Peacock Lane, is a 0.3-mile walk from the beach and close to Holmes Beach's shops and restaurants. The one-bedroom home features a king bed, full-size sleeper sofa (sleeps four), private pool (with optional heating November-April), fully equipped kitchen, outdoor shower, grill, and outdoor dining area.
10 4 reviews
Anna Maria Island, FL
01/05 – 01/12
$359/nighttotal: $2513 (7 )
104 M² Bungalow ∙ 2 Bedrooms ∙ 6 Guests
2 2
bungalow , Holmes Beach
The Blue Haven bungalow is located in Holmes Beach on Anna Maria Island, a seven-minute walk from the pristine sands and near Pine Avenue's shops and restaurants. This 1,110-square-foot vacation home features two bedrooms, two bathrooms, sleeps six, and includes a private heated pool, a fully equipped kitchen with stainless steel appliances, and Tempur-Pedic mattresses.
10 33 reviews
Anna Maria Island, FL
01/05 – 01/12
$154/nighttotal: $1078 (7 )
West Bradenton Cottage
*No Cleaning Fees Or Chores
1 2
cabin , Bradenton
This West Bradenton cottage, located two miles from the Riverwalk and eight miles from Anna Maria Island, offers easy access to downtown Bradenton, beaches, and Sarasota Bradenton International Airport. This 432-square-foot tiny home sleeps two adults and one child, featuring a kitchen, one bedroom, one bathroom, a washer/dryer, a fire pit, an electric grill, and proximity to Publix and The Shake Pit.
Anna Maria Island, FL
08/02 – 08/09
$139/nighttotal: $973 (7 )
Yacht Time
1 2
yacht , Bradenton
The Yacht Time cottage, a pet-friendly boat rental in Bradenton, Florida, is located 5 miles from the city center, offering a quiet escape. This one-bathroom vessel accommodates two guests and features a microwave, air conditioning, a terrace, a garden, barbecue area, and on-site parking.
10 6 reviews
Anna Maria Island, FL
01/05 – 01/12
$242/nighttotal: $1694 (7 )
Steps To The Beach - King Master Suite!
1 2
bungalow , Holmes Beach
This Holmes Beach condo offers direct beach access and is within walking distance to grocery stores, restaurants, shops, and pharmacies. This 1-bedroom, 1-bathroom vacation rental accommodates up to 5 guests and features a newly remodeled kitchen, in-suite laundry, a private patio, and a charcoal grill.
9.0 11 reviews
Anna Maria Island, FL
08/15 – 08/22
$524/nighttotal: $3668 (7 )
Sunkissed Cabin
3 1
cabin , Holmes Beach
Sunkissed Cabin is located in Holmes Beach, Florida, just a 7-minute walk from Anna Maria Island and a short drive from the John and Mable Ringling Museum of Art. The cabin has received very good user ratings, making it a popular choice for travelers. The cozy cabin has 3 bedrooms and 2 bathrooms, providing comfortable accommodation for families and groups. Guests can enjoy features like a private balcony, a fully equipped kitchen with a dishwasher, a swimming pool, and free Wi-Fi.
9.0 169 reviews
Anna Maria Island, FL
01/05 – 01/12
$314/nighttotal: $2198 (7 )
Sea's The Day
2 2
house , Anna Maria
This Anna Maria house is located just steps from the beach and a short walk from the Anna Maria City Pier, offering a peaceful escape in a prime location. The house has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The 2-bedroom house comfortably accommodates 6 guests in its 810 square feet of space. Enjoy a private pool, air conditioning, a fully equipped kitchen, free Wi-Fi, cable TV, and a DVD player for relaxation and entertainment.
Best family friendly Anna Maria Island, FL unique stays
Among the 345 accommodations in Anna Maria Island, FL, here are the 2 best family friendly unique accommodations
10 4 reviews
Anna Maria Island, FL
01/05 – 01/12
$359/nighttotal: $2513 (7 )
104 M² Bungalow ∙ 2 Bedrooms ∙ 6 Guests
2 2
bungalow , Holmes Beach
The Blue Haven bungalow is located in Holmes Beach on Anna Maria Island, a seven-minute walk from the pristine sands and near Pine Avenue's shops and restaurants. This 1,110-square-foot vacation home features two bedrooms, two bathrooms, sleeps six, and includes a private heated pool, a fully equipped kitchen with stainless steel appliances, and Tempur-Pedic mattresses.
10 33 reviews
Anna Maria Island, FL
01/05 – 01/12
$154/nighttotal: $1078 (7 )
West Bradenton Cottage
*No Cleaning Fees Or Chores
1 2
cabin , Bradenton
This West Bradenton cottage, located two miles from the Riverwalk and eight miles from Anna Maria Island, offers easy access to downtown Bradenton, beaches, and Sarasota Bradenton International Airport. This 432-square-foot tiny home sleeps two adults and one child, featuring a kitchen, one bedroom, one bathroom, a washer/dryer, a fire pit, an electric grill, and proximity to Publix and The Shake Pit.
Best Anna Maria Island, FL unique accommodations with a garden
9.0 169 reviews
Anna Maria Island, FL
01/05 – 01/12
$314/nighttotal: $2198 (7 )
Sea's The Day
2 2
house , Anna Maria
This Anna Maria house is located just steps from the beach and a short walk from the Anna Maria City Pier, offering a peaceful escape in a prime location. The house has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The 2-bedroom house comfortably accommodates 6 guests in its 810 square feet of space. Enjoy a private pool, air conditioning, a fully equipped kitchen, free Wi-Fi, cable TV, and a DVD player for relaxation and entertainment.
9.7 36 reviews
Anna Maria Island, FL
06/20 – 06/27
$328/nighttotal: $2296 (7 )
Steps To Beach |Heated Pool+spa|direct Pool Access
1 2
bungalow , Holmes Beach
The Captain's Quarters bungalow is located in Holmes Beach, just steps from the Gulf of Mexico beach and one block from the free trolley stop. With excellent user, location, and cleanliness ratings, this one-bedroom, one-bathroom bungalow can accommodate up to four guests. The bungalow features a heated saltwater pool and spa, a gas grill, a spacious layout, and a starter set of supplies. Guests can also enjoy the coastal-inspired interior design, access to shops and restaurants, and the free trolley service nearby.
10 6 reviews
Anna Maria Island, FL
01/05 – 01/12
$242/nighttotal: $1694 (7 )
Steps To The Beach - King Master Suite!
1 2
bungalow , Holmes Beach
This Holmes Beach condo offers direct beach access and is within walking distance to grocery stores, restaurants, shops, and pharmacies. This 1-bedroom, 1-bathroom vacation rental accommodates up to 5 guests and features a newly remodeled kitchen, in-suite laundry, a private patio, and a charcoal grill.
10 33 reviews
Anna Maria Island, FL
01/05 – 01/12
$154/nighttotal: $1078 (7 )
West Bradenton Cottage
*No Cleaning Fees Or Chores
1 2
cabin , Bradenton
This West Bradenton cottage, located two miles from the Riverwalk and eight miles from Anna Maria Island, offers easy access to downtown Bradenton, beaches, and Sarasota Bradenton International Airport. This 432-square-foot tiny home sleeps two adults and one child, featuring a kitchen, one bedroom, one bathroom, a washer/dryer, a fire pit, an electric grill, and proximity to Publix and The Shake Pit.
Frequently Asked Questions about unique stays in Anna Maria Island, FL
What are some hidden gems to explore on Anna Maria Island, Florida?
For a quieter beach experience than the main stretches, head to Bean Point. It's at the northernmost tip of the island and offers stunning sunset views. The Anna Maria Island Nature Preserve is another great spot for birdwatching and exploring nature trails. For a taste of old Florida, explore the historic Bridge Street, with its charming shops and restaurants, many of which are locally owned.
Are there any notable festivals that take place on Anna Maria Island?
Anna Maria Island doesn't have large-scale, internationally known festivals. However, the island hosts smaller, local events throughout the year. Check local event listings closer to your travel dates for details on these community celebrations. Many events center around the local businesses and the island's laid-back atmosphere.
What types of natural environments are typical on Anna Maria Island, Florida?
Anna Maria Island is known for its beautiful beaches, of course! Beyond that, you'll find coastal dunes, mangrove forests, and salt marshes. The island's natural beauty is a big part of its charm.
Are there popular sporting events or activities on Anna Maria Island?
Fishing is incredibly popular on Anna Maria Island. You can charter a boat for deep-sea fishing or try your luck from the shore. Kayaking and paddleboarding are also popular water activities, allowing you to explore the mangroves and waterways. The island also has several tennis courts and opportunities for biking and walking.
What special gear or clothing is recommended for the climate on Anna Maria Island, Florida?
Pack light, breathable clothing like cotton and linen. Sunscreen is absolutely essential, as is a hat and sunglasses for protection from the strong Florida sun. Comfortable walking shoes are a must, and swimwear is a given! Evenings can be cooler, so a light sweater or jacket might be useful.
What activities allow you to experience local traditions and interact with residents on Anna Maria Island?
Visiting the local farmers markets is a great way to interact with residents and sample local produce. Many of the smaller, independently owned shops and restaurants on Bridge Street and Pine Avenue offer a chance to chat with friendly locals. Taking a guided kayak tour through the mangroves might offer opportunities to learn about local ecology from experienced guides.
Is Anna Maria Island known for any unique natural displays or phenomena during certain seasons?
During the spring and fall, migrating birds pass through, making it a great time for birdwatching. The beaches are also beautiful year-round, though the water temperature varies with the season. There aren't any particularly unique, dramatic natural displays like massive blooms or meteor showers.
What are the best local foods on Anna Maria Island?
Fresh seafood is a must-try! Many restaurants feature locally caught fish and shellfish. The Beach Bistro is known for its upscale dining experience, while other casual eateries offer delicious seafood and American cuisine. Don't forget to try the key lime pie – a Florida classic!
What are the best adventurous activities on Anna Maria Island?
Deep-sea fishing charters are a popular choice for adventure-seekers. Kayaking or paddleboarding through the mangroves provides a unique perspective on the island's natural beauty. For a different kind of adventure, consider renting bikes and exploring the island's scenic paths and beaches.
Nearby regions
Best Anna Maria Island, FL unique stays with a jacuzzi
Among the 345 accommodations in Anna Maria Island, FL, here are the 1 best unique accommodations with a jacuzzi
Anna Maria Island, FL
01/05 – 01/12
$392/nighttotal: $2744 (7 )
Bungalow ∙ 1 Bedroom ∙ 4 Guests
1 2
bungalow , Holmes Beach
This Holmes Beach duplex, located on Peacock Lane, is a 0.3-mile walk from the beach and close to Holmes Beach's shops and restaurants. The one-bedroom home features a king bed, full-size sleeper sofa (sleeps four), private pool (with optional heating November-April), fully equipped kitchen, outdoor shower, grill, and outdoor dining area.
Best pet friendly Anna Maria Island, FL unique stays
Among the 345 accommodations in Anna Maria Island, FL, here are the 4 best pet friendly unique accommodations
Anna Maria Island, FL
08/02 – 08/09
$139/nighttotal: $973 (7 )
Yacht Time
1 2
yacht , Bradenton
The Yacht Time cottage, a pet-friendly boat rental in Bradenton, Florida, is located 5 miles from the city center, offering a quiet escape. This one-bathroom vessel accommodates two guests and features a microwave, air conditioning, a terrace, a garden, barbecue area, and on-site parking.
Anna Maria Island, FL
08/15 – 08/22
$504/nighttotal: $3528 (7 )
Dolphin Cabin! Available For Summer! Screened Pool, Dock & More!
3 1
cabin , Cortez
Dolphin Cabin, located in Bradenton, Florida, offers convenient access to Sarasota attractions, including the Ringling Museum of Art, approximately 12 miles away. This 1980-square-foot vacation home features three bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, screened pool, private dock, free Wi-Fi, and air conditioning.
9.0 169 reviews
Anna Maria Island, FL
01/05 – 01/12
$314/nighttotal: $2198 (7 )
Sea's The Day
2 2
house , Anna Maria
This Anna Maria house is located just steps from the beach and a short walk from the Anna Maria City Pier, offering a peaceful escape in a prime location. The house has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The 2-bedroom house comfortably accommodates 6 guests in its 810 square feet of space. Enjoy a private pool, air conditioning, a fully equipped kitchen, free Wi-Fi, cable TV, and a DVD player for relaxation and entertainment.
9.9 244 reviews
Anna Maria Island, FL
08/02 – 08/09
$154/nighttotal: $1078 (7 )
Cabin 2 Spinnakers Cottages - 204 - 56th 2
1 2
cabin , Holmes Beach
This Holmes Beach vacation rental is located just a 10-minute walk from Bradenton Beach and Island Gallery West, and within a mile of Holmes Beach Beaches and Manatee Public Beach. Guests consistently rate this property excellent for its location, cleanliness, and overall experience. The one-bedroom, one-bathroom house has 800 square feet of space and can comfortably accommodate up to four guests. This rental offers a fully equipped kitchen, a private swimming pool, a spa, a garden with barbecue grills, and access to a water park, making it perfect for a relaxing and fun-filled stay.