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Anna Maria Island, FL cottages
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178 Best cottages in Anna Maria Island, FL

Best family friendly Anna Maria Island, FL cottages

Among the 178 accommodations in Anna Maria Island, FL, here are the 4 best family friendly cottages

157 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests - Anna Maria Island, FL
No reviews

157 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Bradenton
This waterfront cottage in Bradenton offers prime access to Anna Maria Island, located just 3 miles away, and is within walking distance to Palma Sola Causeway for water sports rentals, with Robinson Preserve also nearby.
This 1690 square foot rental accommodates up to 4 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen with stainless-steel appliances, air conditioning, a swimming pool, and a screened lanai with water views.
Ground Floor Two Bedroom Island Styled Home On Beautiful Anna Maria.  Close To Beaches!! - Anna Maria Island, FL
10 13 reviews

Ground Floor Two Bedroom Island Styled Home On Beautiful Anna Maria. Close To Beaches!!

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 a perfect base for exploring the area. Guests consistently rate this cottage as excellent, highlighting its comfortable and convenient features. This two-bedroom, two-bathroom home comfortably accommodates five guests. Enjoy a private pool, outdoor barbecue grills, a fully equipped kitchen, a DVD player, and a patio for relaxing after a day of beachside fun.
Just Minutes From Our Beautiful Gulf Of Mexico Beaches & Stunning Sunsets !! - Anna Maria Island, FL
10 6 reviews

Just Minutes From Our Beautiful Gulf Of Mexico Beaches & Stunning Sunsets !!

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.
Beautiful Cottage Just Around The Corner From The Beach With Private Pool! - Anna Maria Island, FL
10 14 reviews

Beautiful Cottage Just Around The Corner From The Beach With Private Pool!

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.

Best Anna Maria Island, FL cottages with a garden

Relaxed Luxury · Refined North-side 1 Bedroom - Anna Maria Island, FL
10 1 review

Relaxed Luxury · Refined North-side 1 Bedroom

cottage, Bradenton Beach
This one-bedroom cottage in Bradenton Beach is located minutes from Bradenton Beach and Coquina Beach, offering easy access to island trolley stops for exploration of local shops and restaurants.
This 540 square foot bungalow accommodates up to four guests, featuring a full kitchen, air conditioning, and access to shared amenities like a swimming pool and BBQ area, with a private patio for relaxation.
Island Cottage With Open Living Area, Pool, Ground Floor Very Close To Beach Located In Holmes Beach - Anna Maria Island, FL
10 7 reviews

Island Cottage With Open Living Area, Pool, Ground Floor Very Close To Beach Located In Holmes Beach

cottage, Holmes Beach
This two-bedroom Holmes Beach cottage is located just a mile from Bradenton Beach and Palmetto Avenue Beach, offering easy access to the Gulf of Mexico's white sands and turquoise waters. The cottage features a private pool, a balcony, a fully equipped kitchen with a refrigerator and oven, and a DVD player for entertainment.
Minnow 1 By Duncan Real Estate - Anna Maria Island, FL
9.7 42 reviews

Minnow 1 By Duncan Real Estate

apartment, Anna Maria
Minnow 1 Cabin is located in Anna Maria, just a short walk from the Anna Maria City Pier and the beach. It has received excellent ratings for location, cleanliness, and user experience.
The cozy cottage offers 620 square feet of space with one bedroom and one bathroom, comfortably accommodating two guests. The cabin includes amenities like a fully equipped kitchen, air conditioning, a garden, parking, and free Wi-Fi, making it a convenient and comfortable choice for your Anna Maria vacation.
Charming Ground Level Resort Style 3 Unit Condo  - Unit C - Anna Maria Island, FL
9.8 39 reviews

Charming Ground Level Resort Style 3 Unit Condo - Unit C

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.

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 178 accommodations in Anna Maria Island, FL, here are the 2 best cottages with a jacuzzi

Bridge Street Pier Beach House + Dog-friendly - Anna Maria Island, FL
9.8 33 reviews

Bridge Street Pier Beach House + Dog-friendly

cottage, Bradenton Beach
This Bridge Street Pier Beach House in Bradenton Beach, Florida offers immediate bay access next to the Bridge Street Pier and Anna Maria Oyster Bar.
This 860-square-foot vacation rental boasts three bedrooms, two bathrooms, sleeps six, and includes a private pool, spa, and access to kayaks and paddleboards for exploring Sarasota Bay and the Gulf of Mexico, plus on-site amenities like a grill, firepit, and shuffleboard.
Beautiful New Pool/spa, Steps To Sand & Restaurants, Golf Cart Included - Anna Maria Island, FL
10 13 reviews

Beautiful New Pool/spa, Steps To Sand & Restaurants, Golf Cart Included

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 178 accommodations in Anna Maria Island, FL, here are the 4 best pet friendly cottages

Cozy Cottage Retreat At Tradewind Resort #32 In Bradenton Beach - Anna Maria Island, FL
9.0 22 reviews

Cozy Cottage Retreat At Tradewind Resort #32 In Bradenton Beach

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.
Cozy 1-bed Cottage In Adorable Tradewinds Bradenton Beach, Steps To Beach/pool - Anna Maria Island, FL
10 19 reviews

Cozy 1-bed Cottage In Adorable Tradewinds Bradenton Beach, Steps To Beach/pool

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.
Holmes Beach Cottage Steps To The Beach With Heated Pool! - Anna Maria Island, FL
10 16 reviews

Holmes Beach Cottage Steps To The Beach With Heated Pool!

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.
Charming Cottage In Quiet Area, Close To Beach & Bay. - Anna Maria Island, FL
9.8 319 reviews

Charming Cottage In Quiet Area, Close To Beach & Bay.

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.
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