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270 Best cottages in Anna Maria Island, FL
9.4 66 reviews
Anna Maria Island, FL
11/06 – 11/08
$163/nighttotal: $326 (2 )
The "Grouper"
1 2
cottage , Cortez
This Cortez Sunny Shores cottage, located within 3 miles of H2O Watersportz, Anna Maria Sound, Bradenton Beach Marina, Bradenton Beach, and Fish Hole Adventure Golf, offers easy access to Anna Maria Island's beaches and attractions. This one-bedroom, one-bathroom vacation rental sleeps two guests and features a kitchenette with a refrigerator and microwave, air conditioning, a private patio, and free internet access; pets are welcome.
10 8 reviews
Anna Maria Island, FL
07/18 – 07/25
$492/nighttotal: $3444 (7 )
Two Bedroom Ground Floor Island Home Sleeps 5 And Includes Heated Pool.
2 2
cottage , Holmes Beach
This two-bedroom, two-bathroom cottage is located in Holmes Beach, Florida, just a short distance from Bradenton Beach, Palmetto Avenue Beach, and Island Players. The smoke-free cottage features a private pool, a barbecue grill, a balcony, and a fully equipped kitchen, perfect for a relaxing getaway for up to five guests.
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.
Anna Maria Island, FL
10/07 – 10/14
$344/nighttotal: $2408 (7 )
Stay At Pine Key- A Cozy Beach Cottage Retreat!
2 4
cottage , Bradenton Beach
This cottage in Bradenton Beach offers a prime location, a short walk from Canal Anna Maria Sound and Bradenton Beach, and moments from Coquina Beach and Bean Point Beach. Enjoy a private terrace, fenced courtyard, complimentary Wi-Fi, on-site parking, a well-equipped kitchen with an oven and microwave, and an in-unit washer/dryer, plus air conditioning and a barbecue grill for comfortable living.
10 26 reviews
Anna Maria Island, FL
07/18 – 07/25
$446/nighttotal: $3122 (7 )
Orchid Villa By Beach Boutique Rentals
2 2
cottage , Holmes Beach
Orchid Villa is a ground-level cottage in Holmes Beach, just steps from the beach path and within walking distance of shops and restaurants. It has received excellent ratings for location, cleanliness, and overall user experience. This 810 square foot cottage has two bedrooms, two bathrooms, and can accommodate up to five guests. Amenities include a fully equipped kitchen, a spacious living room, a private patio, a botanical courtyard with a fountain, beach essentials, and a shared laundry facility.
10 23 reviews
Anna Maria Island, FL
01/05 – 01/12
$390/nighttotal: $2730 (7 )
Anna Maria Cottage With Golf Cart
2 2
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.
Anna Maria Island, FL
01/05 – 01/12
$243/nighttotal: $1701 (7 )
Dog Friendly Home With Lanai, Internet, And Perfect Location
2 2
cottage , Anna Maria
This Anna Maria cottage, located in the city center, is just steps from the beach and bay, offering convenient access to dining and shopping, and is within walking distance of Bean Point Beach and Coquina Beach. This 840 square foot rental accommodates up to 4 guests with 2 bedrooms and 1 bathroom, featuring a screened-in lanai, a spacious living area with a wall-mounted TV, a well-equipped kitchen with new appliances, and is pet-friendly with parking and internet provided.
9.6 4 reviews
Anna Maria Island, FL
01/05 – 01/12
$504/nighttotal: $3528 (7 )
Tortuga Cottage · 1915 · Pool · Pet-friendly
2 2
cottage , Bradenton Beach
This pet-friendly cottage in Bradenton Beach offers a prime location within walking distance of the historic Bridge Street Pier and Bradenton Beach, with Coquina Beach and Bean Point Beach also nearby. Guests can enjoy a private swimming pool, on-site covered parking, a well-equipped kitchen with an oven and stovetop, and an in-unit washer and dryer, along with outdoor amenities like a barbecue grill and garden.
9.9 222 reviews
Anna Maria Island, FL
07/17 – 07/24
$353/nighttotal: $2471 (7 )
Sailfish Gulf Suites #2, Beachfront, Steps To The Sand
1 2
cottage , Holmes Beach
This Holmes Beach cottage is located directly on the beach, just a 5-minute walk from Bradenton Beach and Manatee Public Beach. Guests consistently rate the cottage excellent for location, cleanliness, and overall experience. This cozy 1-bedroom, 1-bathroom home spans 700 square feet and comfortably accommodates up to 4 guests. Enjoy a full kitchen, private patio, and access to a swimming pool, spa, and free WiFi.
Anna Maria Island, FL
06/27 – 07/04
$538/nighttotal: $3766 (7 )
Charming 1920s Cottage, Waterfront Just 50 Ft Away, Beach Just 1 Minute Stroll!
2 2
cottage , Bradenton Beach
This 1920s-era Bradenton Beach cottage, located on 7th Street South, is a one-minute walk from the beach, the historic pier, and Bridge Street's shops and restaurants. This two-bedroom, one-bathroom vacation home sleeps five, features all-new memory foam beds, a full kitchen, streaming TV, and a large wraparound porch perfect for enjoying waterfront views; nearby attractions include the John and Mable Ringling Museum of Art and Mote Marine Laboratory & Aquarium.
10 3 reviews
Anna Maria Island, FL
01/05 – 01/12
$413/nighttotal: $2891 (7 )
Bridge Street Beach House | Wi-fi | Center Of All
3 2
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.
10 10 reviews
Anna Maria Island, FL
01/05 – 01/12
$371/nighttotal: $2597 (7 )
Cozy 1-bed Cottage In Adorable Tradewinds Bradenton Beach, Steps To Beach/pool
1 2
cottage , Bradenton Beach
This newly renovated 1-bedroom, 1-bathroom cottage in Bradenton Beach is located mere steps from the Bradenton Beach shoreline and community pool, offering convenient access to Bridge Street Bistro, Anna Maria Oyster Bar, Mote Marine Laboratory & Aquarium, and Coquina Beach. This 700 square foot rental accommodates up to 4 guests and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, internet, and private parking, with an option to book an adjacent unit for larger groups.
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
10/07 – 10/14
$610/nighttotal: $4270 (7 )
Newly Renovated Sea Breeze Cottage With Private Dock, Easy Access To Bimini Bay
2 4
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.
Anna Maria Island, FL
08/02 – 08/09
$305/nighttotal: $2135 (7 )
65 M² Cottage ∙ 1 Bedroom ∙ 4 Guests
1 2
cottage , Holmes Beach
This Gulf-front cottage in Holmes Beach offers direct access to the Gulf of Mexico and is steps from Manatee Public Beach, with shopping and restaurants within walking distance. This 700-square-foot, ground-level suite accommodates up to four guests with one bedroom and one bathroom, featuring a full kitchen, air conditioning, a shared patio with grills, and complimentary Anna Maria Trolley access.
10 24 reviews
Anna Maria Island, FL
10/07 – 10/14
$460/nighttotal: $3220 (7 )
Romantic, Cute Cottage On Anna Maria Island. Close To Everything. Pet Friendly!
2 4
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.
9.6 24 reviews
Anna Maria Island, FL
07/18 – 07/25
$492/nighttotal: $3444 (7 )
Two Bedroom Cozy Island Home Right Around The Corner From Gulf Beaches. Lots Of Amenities!
2 2
cottage , Holmes Beach
This two-bedroom, two-bathroom cottage is located in Holmes Beach, less than a mile from Bradenton Beach and Palmetto Avenue Beach. The pet-friendly cottage features a private pool, a fully equipped kitchen, a patio with a barbecue grill, and can accommodate up to five guests.
Best Anna Maria Island, FL cottages with a garden
10 7 reviews
Anna Maria Island, FL
08/02 – 08/09
$194/nighttotal: $1358 (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.
8.6 28 reviews
Anna Maria Island, FL
10/07 – 10/14
$252/nighttotal: $1764 (7 )
Charming, Fully Remodeled Cottage Steps From Beach With Wifi & Central Ac
2 4
cottage , Bradenton Beach
This charming beach cottage is located just a short walk from both Bradenton Beach and Coquina Beach, offering easy access to the beautiful white sands and turquoise waters of the Gulf of Mexico. It has received very good user ratings, making it a popular choice for travelers. This cozy vacation rental has two bedrooms and one bathroom, comfortably accommodating up to four guests. The cottage features a fully equipped kitchen, a washing machine, a sofa bed, a coffee/tea maker, a TV, and free internet access, making it easy to relax and enjoy your stay.
10 49 reviews
Anna Maria Island, FL
07/18 – 07/25
$297/nighttotal: $2079 (7 )
Hibiscus Villa By Beach Boutique Rentals
1 2
cottage , Holmes Beach
This Holmes Beach cottage offers easy access to shops and restaurants, and is just steps from the beach path. It features a botanical courtyard with a fountain and tropical landscape, and a private patio. The cottage has a user rating of excellent, and a location rating of excellent. It has 1 bedroom, 1 bathroom, and a guest capacity of 3. The floor area is 690 square feet. Amenities include air conditioning, a swimming pool, a garden, parking, a kitchen with a fridge, freezer, microwave oven, and dishwasher, and beach supplies (chairs, towels, umbrellas) and bikes.
10 1 review
Anna Maria Island, FL
07/18 – 07/25
$387/nighttotal: $2709 (7 )
Cozy Retro Cottage Located Less Then 2 Blocks From The Gulf Beach - Heated Pool In Private Oasis!
1 2
cottage , Holmes Beach
This one-bedroom cottage in Holmes Beach is located within a mile of Bradenton Beach and Palmetto Avenue Beach, offering easy access to the beautiful shores of the Gulf of Mexico. The cottage is perfect for families or couples looking for a relaxing getaway. The cottage has two bathrooms, a private pool, and a fully equipped kitchen with a refrigerator, microwave, and dishwasher. Guests can enjoy the beautiful Florida weather on the terrace or in the garden, or take advantage of the nearby beaches and activities.
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 2 best cottages with a jacuzzi
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.
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.
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
10 1 review
Anna Maria Island, FL
07/17 – 07/24
$684/nighttotal: $4788 (7 )
Ocean72, 2bed 2bath With Pool
1 2
cottage , Holmes Beach
This Holmes Beach cottage, a short walk from the beach and minutes from local restaurants and shops, offers easy access to Holmes Beach's sugar-white sands and Anna Maria Island's attractions. This two-bedroom, two-bathroom vacation home sleeps six, boasting a private heated pool and spa, a fully equipped gourmet kitchen with granite countertops and stainless steel appliances, beach gear, and a fenced-in backyard with an outdoor BBQ and dining area.
8.8 12 reviews
Anna Maria Island, FL
10/07 – 10/14
$311/nighttotal: $2177 (7 )
Historical Ami 2 Bedroom, Pet Friendly Beach Cottage, Sleeps 6
2 4
cottage , Anna Maria
This Anna Maria Island cottage, near Bradenton Beach, Bean Point Beach, and Anna Maria Beach (all within 1.2 miles), offers easy access to Palmetto Avenue Beach and the Island Players. The 710-square-foot vacation home features three bedrooms, two bathrooms, sleeps six, includes a fully equipped kitchen, and boasts a private fenced yard with barbecue grills, a tennis court, and on-site parking.
9.2 115 reviews
Anna Maria Island, FL
10/07 – 10/14
$370/nighttotal: $2590 (7 )
Tropical Paradise Cottage On The Beach Vrc17-000167
2 4
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.
9.2 19 reviews
Anna Maria Island, FL
08/02 – 08/09
$301/nighttotal: $2107 (7 )
Cozy Cottage Retreat At Tradewind Resort #32 In Bradenton Beach
1 2
cottage , Bradenton Beach
Tradewind Resort #32, a one-bedroom cottage in Bradenton Beach, Florida, offers easy access to nearby attractions like Mote Marine Laboratory & Aquarium and Cortez Beach. This pet-friendly vacation rental sleeps four, features a fully equipped kitchen, a private patio, and access to the resort's pool and hot tub.
