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270 Best cottages in Anna Maria Island, FL
Anna Maria Island, FL
01/05 – 01/12
$547/nighttotal: $3829 (7 )
Castaway Cottage Near Img And Beaches
1 2
cottage , Bradenton
This Bradenton cottage is located 4 miles from the city center and is near Blake Medical Center. This accommodation offers free Wi-Fi, free parking, and a barbeque area, with a guest capacity of 2 and contactless check-in/check-out.
10 23 reviews
Anna Maria Island, FL
07/16 – 07/23
$402/nighttotal: $2814 (7 )
Anna Maria Cottage With Golf Cart
2 4
cottage , Holmes Beach
This Holmes Beach cottage, located in the quiet north end of Anna Maria Island, is within walking or biking distance of shops, the free island trolley, restaurants, beaches, and a boat ramp. This pet-friendly, two-bedroom, one-bathroom home offers an open floor plan, upgraded kitchen and bathroom, front and rear patios with furniture, a backyard grill, and includes beach chairs, umbrellas, and a two-person kayak; it sleeps four and provides a golf cart for exploring the island.
9.6 50 reviews
Anna Maria Island, FL
01/05 – 01/12
$800/nighttotal: $5600 (7 )
The Beach House, Right On Holmes Beach
3 2
cottage , Holmes Beach
This Holmes Beach cottage is directly on the beach, a short walk from Bradenton Beach and Island Gallery West, and less than a mile from both Holmes Beach Beaches and Manatee Public Beach. The 3-bedroom cottage sleeps 6, boasts a private pool, and offers direct beach access, a fully equipped kitchen, and free WiFi.
9.8 83 reviews
Anna Maria Island, FL
07/16 – 07/23
$601/nighttotal: $4207 (7 )
Coastal Cottage On Holmes Beach With Private Heated Pool! 1 Block To Beach.
3 4
cottage , Holmes Beach
This charming cottage is just one block from the pristine white sands of Holmes Beach, offering easy access to the Gulf of Mexico and the laid-back atmosphere of this popular Florida destination. Guests consistently rate this rental as excellent, making it a popular choice for families and groups visiting Holmes Beach. The 1450 square foot cottage comfortably sleeps 6 guests in its three bedrooms and two bathrooms. Guests can enjoy a private pool, a fully equipped kitchen, and a relaxing patio with beautiful sunset views.
9.8 36 reviews
Anna Maria Island, FL
01/05 – 01/12
$406/nighttotal: $2842 (7 )
Charming Ground Level Resort Style 3 Unit Condo - Unit C
2 2
cottage , Holmes Beach
Charming Ground Level Resort Style 3 Unit Condo Unit C is located in Ilexhurst, a 5-minute walk from Anna Maria Sound and Bradenton Beach. It has an excellent user rating. This 900 square-foot, 2-bedroom, 1-bathroom condo has a sofa bed and can accommodate up to 6 guests. It features a private pool, a well-equipped kitchenette, free WiFi, barbecue grills, a garden, and access to nearby wellness and adventure activities.
10 7 reviews
Anna Maria Island, FL
01/05 – 01/12
$195/nighttotal: $1365 (7 )
Coastal Luxury 7mi To Anna Maria Private Cottage
1 2
cottage , Bradenton
This Bradenton cottage is conveniently located near LECOM Park and The Bishop Museum of Science and Nature, a four-minute drive away, offering easy access to Tampa Bay (15 minutes) and Lido Beach (44 minutes). This one-bedroom, one-bathroom home sleeps two guests and includes Wi-Fi, air conditioning, linens, towels, and basic toiletries; nearby attractions include the Mall at University Town Center, St. Armands Circle, and Ellenton's sports complex.
9.2 155 reviews
Anna Maria Island, FL
01/05 – 01/12
$351/nighttotal: $2457 (7 )
Tropical Paradise On The Beach Permit Vrc17-000168
2 2
cottage , Holmes Beach
This charming cottage is located in Ilexhurst, a peaceful neighborhood in Holmes Beach, just a block from the free trolley and a short distance from the shops and restaurants of Bradenton Beach and Anna Maria. This highly rated cottage offers a relaxing escape with direct Gulf views and easy access to the white sand beaches of Anna Maria Island. The cottage features two bedrooms, one bathroom, and 800 square feet of living space, comfortably accommodating up to five guests. Enjoy a private deck with stunning Gulf views, a fully equipped kitchen, a washer and dryer, and a tropical garden with a spa, all just steps from the beach.
9.2 115 reviews
Anna Maria Island, FL
08/15 – 08/22
$379/nighttotal: $2653 (7 )
Tropical Paradise Cottage On The Beach Vrc17-000167
2 1
cottage , Holmes Beach
This charming cottage is located in the quiet Ilexhurst neighborhood of Holmes Beach, just one block from the free trolley and a short distance from the shopping and dining options of Bradenton Beach and Anna Maria. It has received excellent user ratings and offers a peaceful retreat from the hustle and bustle. The cottage has two bedrooms, one bathroom, and sleeps four comfortably, with a total floor area of 700 square feet. Enjoy the convenience of a fully equipped kitchen, a private terrace, a lush garden, and a direct path to the white sand beaches of Anna Maria Island.
9.0 68 reviews
Anna Maria Island, FL
01/05 – 01/12
$417/nighttotal: $2919 (7 )
Beautiful Guest House Near The Beach With Private Pool!
3 2
cottage , Anna Maria
This 3-bedroom Anna Maria Island vacation home is situated just a 15-minute walk from Island Players and Bean Point Beach, and within 5 minutes of Bradenton Beach and the Anna Maria Island Museum and Historical Park. This 1,560 square foot house features a private pool, access to a water park, and a fully equipped kitchen with a refrigerator and oven, perfect for families or groups of up to 8 guests.
9.6 55 reviews
Anna Maria Island, FL
08/02 – 08/09
$318/nighttotal: $2226 (7 )
Seahorse Cottage - With Shared Pool, 200 Feet From The Beach
1 2
cottage , Anna Maria
This charming cottage sits just a short walk from Bradenton Beach and Bean Point Beach on Anna Maria Island, offering easy access to the island's beautiful shores. Guests consistently rate this vacation rental as excellent, making it a popular choice for travelers seeking a relaxing getaway. This cozy one-bedroom cottage comfortably accommodates two guests and features a fully equipped kitchen, a private outdoor barbecue grill, and a refreshing swimming pool. Enjoy the convenience of a washer and dryer, air conditioning, and free Wi-Fi, as well as the peace of mind of knowing your furry friend is welcome.
9.7 152 reviews
Anna Maria Island, FL
01/05 – 01/12
$159/nighttotal: $1113 (7 )
Ty's Canal Cottage
1 2
cottage , Cortez
This charming cottage is just a 10-minute walk from the Blue Water Explorers and the Florida Maritime Museum in the heart of Cortez, a historic fishing village with a relaxed atmosphere. Guests consistently rate the cottage excellent for its location, cleanliness, and overall experience. The cottage has one bedroom and one bathroom, comfortably accommodating up to four guests. Enjoy amenities like air conditioning, a garden, and parking, plus easy access to fishing, boating, kayaking, and other water activities.
10 17 reviews
Anna Maria Island, FL
08/15 – 08/22
$392/nighttotal: $2744 (7 )
Two Bedroom Cottage With Tropical Landscaping Surrounding Private Heated Pool!
2 1
cottage , Holmes Beach
This smoke-free cottage is located in Holmes Beach, just a mile from Bradenton Beach, Palmetto Avenue Beach, and the Island Players theater. Guests rave about the cottage's excellent rating and its convenient location, making it a great choice for a relaxing beach vacation. This two-bedroom cottage comfortably sleeps five guests and features a private pool, outdoor barbecue grills, and a fully equipped kitchen. Enjoy a refreshing dip in the pool, relax on the patio, and explore the nearby beaches and attractions.
Best family friendly Anna Maria Island, FL cottages
Among the 270 accommodations in Anna Maria Island, FL, here are the 4 best family friendly cottages
9.6 250 reviews
Anna Maria Island, FL
08/03 – 08/07
$664/nighttotal: $2656 (4 )
Newly Renovated Sea Breeze Cottage With Private Dock, Easy Access To Bimini Bay
2 3
cottage , Anna Maria
This waterfront cottage is conveniently located on Anna Maria Island, just a 15-minute walk from Bay Boulevard Beach, Anna Maria City Pier, and Bayfront Park, making it easy to access the island's top attractions. Guests rave about the excellent location, cleanliness, and overall experience. The 1100 square foot cottage comfortably sleeps up to 6 guests in its 2 bedrooms and 2 bathrooms. Enjoy a fully equipped kitchen, a relaxing jacuzzi, and a private terrace or balcony for outdoor dining and relaxation.
10 2 reviews
Anna Maria Island, FL
08/15 – 08/22
$424/nighttotal: $2968 (7 )
Recently Renovated Luxury Ground Floor Island Home Close To Beach!o Sleeps 4
2 1
cottage , Holmes Beach
This charming cottage is located in Holmes Beach, just a short walk from Island Gallery West and Bradenton Beach, making it perfect for exploring the area's art galleries, shops, and restaurants. It's also within a 15-minute walk of the beautiful beaches of Holmes Beach and Manatee Public Beach, ideal for enjoying the sun and sand. This rental has received excellent user ratings, so you can rest assured you're in for a comfortable and enjoyable stay. The cottage has two bedrooms and three bathrooms, comfortably accommodating up to four guests. Enjoy a private pool, outdoor barbecue grills, a fully equipped kitchen, a DVD player, and a patio for relaxing and entertaining.
10 23 reviews
Anna Maria Island, FL
08/15 – 08/22
$471/nighttotal: $3297 (7 )
Romantic, Cute Cottage On Anna Maria Island. Close To Everything. Pet Friendly!
2 1
cottage , Bradenton Beach
This Bradenton Beach vacation home is ideally located steps from Fish Hole Adventure Golf, Bradenton Beach, the Historic Bridge Street Pier, and Bridge Street, offering easy access to major attractions. This two-bedroom, three-bathroom rental sleeps six, features a full kitchen with dishwasher, Wi-Fi, a terrace, and is pet-friendly with on-site parking and a tennis court.
10 3 reviews
Anna Maria Island, FL
08/03 – 08/07
$224/nighttotal: $896 (4 )
Just Minutes From Our Beautiful Gulf Of Mexico Beaches & Stunning Sunsets !!
2 3
cottage , Cortez
This Bradenton cottage is located near the Gulf of Mexico beaches, 1.5 miles from the Historical Cortez Fishing Village, and 2 miles from Gulf beaches. This 1000 square foot vacation rental accommodates up to 4 guests and features 2 bedrooms, 1 bathroom, air conditioning, a full kitchen with a fridge and microwave, and allows pets for an additional fee.
Best Anna Maria Island, FL cottages with a garden
10 16 reviews
Anna Maria Island, FL
08/15 – 08/22
$389/nighttotal: $2723 (7 )
Holmes Beach Cottage Steps To The Beach With Heated Pool!
2 1
cottage , Holmes Beach
This charming cottage in Holmes Beach is located just a mile from three beautiful beaches, making it the perfect base for your Florida getaway. Guests consistently rate this property excellent, praising its comfortable accommodations and convenient location. This 2-bedroom, 2-bathroom vacation rental comfortably sleeps 5 guests. Enjoy a private pool, outdoor BBQ, fully equipped kitchen, relaxing patio, and a DVD player for entertainment.
10 1 review
Anna Maria Island, FL
01/05 – 01/12
$602/nighttotal: $4214 (7 )
Beachy Duplex Retreat: Pine Key & Pelicans Nest!
4 2
cottage , Bradenton Beach
This cottage in Bradenton Beach is a short walk from Anna Maria Sound Canal and Bradenton Beach, putting you within 0.2 miles of Coquina Beach and Bean Point Beach. This non-smoking rental offers four bedrooms, 2.5 bathrooms, air conditioning, a full kitchen with a dishwasher and microwave, free Wi-Fi, a private terrace, a fenced yard, and a barbecue grill.
10 14 reviews
Anna Maria Island, FL
08/15 – 08/22
$358/nighttotal: $2506 (7 )
Beautiful Cottage Just Around The Corner From The Beach With Private Pool!
2 1
cottage , Holmes Beach
This charming cottage is located in Holmes Beach, just a short distance from Bradenton Beach, Palmetto Avenue Beach, and Island Players, making it the perfect base for exploring the area. This vacation rental boasts excellent user ratings, making it a popular choice for travelers. The cottage has two bedrooms and two bathrooms, comfortably accommodating up to five guests. It offers a private pool, outdoor BBQ grills, a fully equipped kitchen, and a patio for enjoying the Florida sunshine.
9.6 46 reviews
Anna Maria Island, FL
08/15 – 08/22
$297/nighttotal: $2079 (7 )
Shell Cottage -With Shared Pool, 200 Feet From The Beach
1 1
cottage , Anna Maria
This charming cottage is located on Anna Maria Island, just a short walk from Bradenton Beach and Bean Point Beach, offering a peaceful escape with easy access to the island's beautiful shores. Guests consistently rate this cottage as excellent, highlighting its comfortable accommodations and convenient location. The cottage features one bedroom and one bathroom, comfortably accommodating two guests. Enjoy the fully equipped kitchen, outdoor patio, and access to a swimming pool, making this cottage an ideal choice for a relaxing and enjoyable stay.
Frequently Asked Questions about cottages in Anna Maria Island, FL
What are the top must-see attractions on Anna Maria Island, Florida?
Anna Maria Island boasts beautiful beaches, of course! Bean Point is a must-see for its stunning sunsets and views. The Anna Maria Island Historical Society Museum gives a glimpse into the island's past. For nature lovers, the Anna Maria Island Nature Preserve offers hiking trails and wildlife viewing opportunities. Also, don't miss the charming shops and restaurants in the historic Bridge Street district.
What are the best cottages in Anna Maria Island, FL?
How to spend a 5-day holiday on Anna Maria Island, Florida?
Day 1: Explore Bean Point and enjoy the sunset. Day 2: Visit the Anna Maria Island Historical Society Museum and spend the afternoon relaxing on the beach. Day 3: Rent bikes and cycle the length of the island, stopping at various beaches along the way. Day 4: Take a dolphin watching tour. Day 5: Explore the shops and restaurants in the Bridge Street district and enjoy a final beach day.
What are the best cottages with a pool in Anna Maria Island, FL?
Is Anna Maria Island, Florida a good destination to rent a cottage?
Absolutely! Anna Maria Island has many charming cottages available for rent, offering a quintessential beach vacation experience. They're perfect for families or couples seeking a cozy and relaxing getaway. Many are located within walking distance of the beach.
What are the best cottages with a jacuzzi in Anna Maria Island, FL?
What weather, wildlife, or natural hazards might affect travelers on Anna Maria Island, Florida?
Florida summers are hot and humid, with occasional afternoon thunderstorms. Hurricane season runs from June 1st to November 30th, so travelers should monitor forecasts. Wildlife includes various bird species, dolphins, and occasionally manatees. Be aware of potential jellyfish stings and strong currents when swimming. Mosquitoes can be prevalent, so pack insect repellent.
What are the best cottages for families and kids in Anna Maria Island, FL?
Is Anna Maria Island, Florida pedestrian and cyclist-friendly?
Yes, Anna Maria Island is very pedestrian and cyclist-friendly. There are dedicated bike paths and sidewalks throughout the island, making it easy to explore on foot or by bicycle. Many rent bikes to explore the island at their own pace.
What are the best pet friendly cottages in Anna Maria Island, FL?
Are there any unusual or hidden places to explore on Anna Maria Island, Florida?
The north end of the island, near Bean Point, offers some quieter, less-developed beaches perfect for a secluded escape. Exploring the mangroves by kayak or paddleboard can reveal hidden coves and wildlife. Also, some of the smaller side streets offer charming, unexpected views and hidden gems.
What are the best cottages with parking in Anna Maria Island, FL?
What are some of the best cultural experiences that allow you to meet locals on Anna Maria Island, Florida?
The Anna Maria Island Farmers Market (seasonal) provides a chance to interact with local vendors and residents. Attending events at the Island Players, a local theater group, or checking out live music at some of the bars and restaurants can offer opportunities to meet locals.
What are the best authentic dishes to taste on Anna Maria Island, Florida?
Fresh seafood is a must! Many restaurants offer locally caught fish and shellfish prepared in various ways. Key West Pink Shrimp is a local favorite. Also, try some of the island's casual eateries for classic Florida-style dishes, such as conch fritters or stone crabs (in season).
Are there any recommended items to pack for a stay on Anna Maria Island, Florida?
Sunscreen is essential, along with sunglasses and a hat. Pack light, breathable clothing suitable for warm weather. Swimsuits, beach towels, and flip-flops are also a must. Insect repellent and rain gear are recommended, especially during the summer months. Don't forget a reusable water bottle to stay hydrated.
Nearby regions
Best Anna Maria Island, FL cottages with jacuzzi
Among the 270 accommodations in Anna Maria Island, FL, here are the 4 best cottages with a jacuzzi
10 12 reviews
Anna Maria Island, FL
01/05 – 01/12
$899/nighttotal: $6293 (7 )
Beautiful New Pool/spa, Steps To Sand & Restaurants, Golf Cart Included
2 2
cottage , Holmes Beach
This Holmes Beach vacation home sits a 10-minute walk from Island Gallery West and Bradenton Beach, and less than a mile from Holmes Beach and Manatee Public Beaches. This 1,030-square-foot seaside cottage offers two bedrooms, one bathroom, sleeps six, and boasts a private pool, hot tub, fenced yard, and free Wi-Fi.
Anna Maria Island, FL
07/16 – 07/23
$1805/nighttotal: $12635 (7 )
Serenity Cottage\n
3 4
cottage , Anna Maria
This Anna Maria Island cottage offers a convenient location, less than a 10-minute walk from Bean Point Beach and Anna Maria Beach, and under a 10-minute drive from Bradenton Beach and Bayfront Park. The two-bedroom, one-bathroom house sleeps four guests and includes air conditioning, an on-site fitness center, and proximity to various Anna Maria Island attractions.
10 3 reviews
Anna Maria Island, FL
10/02 – 10/08
$323/nighttotal: $1938 (6 )
Bridge Street Beach House | Wi-fi | Center Of All
3 3
cottage , Bradenton Beach
This cottage is located in the Bridge Street district of Bradenton Beach, just steps from Bradenton Beach and Anna Maria Sound, and a short walk from Mote Marine Laboratory & Aquarium, Bradenton Beach, and Coquina Beach. This 650 sq ft cottage accommodates up to 6 guests with 3 bedrooms and 1 bathroom, featuring a full kitchen, air conditioning, a communal pool, hot tub, garden, spa, tennis court, and on-site parking, with bicycles and water sports equipment available for family-friendly activities.
9.9 359 reviews
Anna Maria Island, FL
01/05 – 01/12
$374/nighttotal: $2618 (7 )
Turtle Cottage - Anna Maria Island
1 2
cottage , Anna Maria
This charming cottage is located on the quiet north end of Anna Maria Island, just two blocks from the beach and a short walk from the intersection of Gladiolus Street and Alamanda Road. The property has earned excellent ratings for location, cleanliness, and overall user experience. The cottage offers 800 square feet of living space with an open floor plan, comfortably accommodating up to four guests. The vacation rental features a private patio with an outdoor dining space, an oversized umbrella, a high-top table, an outdoor shower, an electric grill, a heated pool, and a spa.
Best pet friendly Anna Maria Island, FL cottages
Among the 270 accommodations in Anna Maria Island, FL, here are the 4 best pet friendly cottages
9.8 312 reviews
Anna Maria Island, FL
08/02 – 08/09
$331/nighttotal: $2317 (7 )
Charming Cottage In Quiet Area, Close To Beach & Bay.
2 2
cottage , Anna Maria
This charming cottage is located in Anna Maria, just a short walk from the beach and within a mile of the Anna Maria Island Museum and Historical Park, Bean Point Beach, and Anna Maria Beach. It's rated excellent by previous guests, making it a popular choice for travelers seeking a relaxing beach getaway. The cottage is 800 square feet and can accommodate up to four guests. It offers a fully equipped kitchen, a private yard, a spa tub, and a swimming pool, perfect for enjoying the island's warm weather and beautiful beaches.
9.8 105 reviews
Anna Maria Island, FL
08/15 – 08/22
$462/nighttotal: $3234 (7 )
Blue Agave Villa By Beach Boutique Rentals
2 1
cottage , Holmes Beach
Frangipani Villa is a ground-level cottage located just steps from the beach path in Holmes Beach, offering easy access to the beach, shops, and restaurants. This charming cottage has received excellent ratings for location, cleanliness, and overall experience. The cottage features a private porch with Adirondack chairs and a bistro table, perfect for enjoying the tropical surroundings. Guests can take advantage of beach chairs, towels, and umbrellas provided, along with a fully equipped kitchen, pet-friendly accommodations, and a tranquil garden with a fountain.
9.7 55 reviews
Anna Maria Island, FL
06/20 – 06/27
$351/nighttotal: $2457 (7 )
Newly Renovated Cozy Beach Cottage A1/2 Of A Duplex, 3min Walk To Beach
3 2
cottage , Holmes Beach
This charming cottage is located in a quiet neighborhood just a short walk from Bradenton Beach, offering easy access to the beautiful Gulf Coast. It has received excellent reviews from previous guests, making it a popular choice for travelers seeking a relaxing getaway. This cozy home features two bedrooms and one bathroom, comfortably accommodating up to six guests. Enjoy the private garden, barbecue grill, and free WiFi, along with a fully equipped kitchen.
10 51 reviews
Anna Maria Island, FL
08/15 – 08/22
$552/nighttotal: $3864 (7 )
Welcome To Beach Basket Your Seaside Retreat!"
3 1
cottage , Anna Maria
This charming cottage is located just a short walk from Bradenton Beach, Palmetto Avenue Beach, and the Island Players, offering easy access to the island's best attractions. Guests rave about the cottage's excellent location and amenities, making it a perfect choice for a relaxing beach vacation. The 3-bedroom, 2-bathroom cottage comfortably accommodates up to 6 guests and features a fully equipped kitchen, air conditioning, a private pool, and a spacious terrace. Enjoy the on-site water park, barbecue grills, and free Wi-Fi, making this cottage a perfect choice for families and groups.
