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Longboat Key, FL cottages
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29 Best cottages in Longboat Key, FL

Explore Family Cottages in Longboat Key, FL

Kid-friendly cottages in Longboat Key, FL with room for the whole family to spread out make vacations a breeze.

Anna Maria Cottage With Golf Cart - Longboat Key, FL
9.8 26 reviews

Anna Maria Cottage With Golf Cart

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.
The Cottage By Anna Maria Island - Longboat Key, FL
9.4 27 reviews

The Cottage By Anna Maria Island

cottage, Bradenton
This charming cottage is located in central Bradenton, within easy walking distance of restaurants, the Village of the Arts, and the Riverwalk. Guests rave about the cottage's excellent location and cozy atmosphere.
The cottage has three bedrooms and one bathroom, comfortably accommodating up to six guests. Enjoy the fully equipped kitchen, relaxing porches, and a private jacuzzi, perfect for unwinding after a day exploring Bradenton's beaches and attractions.
Beautiful New Pool/spa, Steps To Sand & Restaurants, Golf Cart Included - Longboat Key, 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.
Just Minutes From Our Beautiful Gulf Of Mexico Beaches & Stunning Sunsets !! - Longboat Key, FL
10 5 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.

Best Longboat Key, FL cottages with a garden

Beachy Duplex Retreat: Pine Key & Pelicans Nest! - Longboat Key, FL
10 1 review

Beachy Duplex Retreat: Pine Key & Pelicans Nest!

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.
Spoonbill Lagoon With Fantastic Water Views Of Palma Sola Bay! - Longboat Key, FL
10 7 reviews

Spoonbill Lagoon With Fantastic Water Views Of Palma Sola Bay!

cottage, Bradenton
This waterfront cottage in Bradenton is located 3 miles from Anna Maria Island beaches and provides convenient access to Robinson Preserve, Mote Marine Laboratory & Aquarium, and Palma Sola Causeway for water sports.
This 1690 square foot home features 2 bedrooms, 3 bathrooms, and a guest capacity of 6, with amenities including air conditioning, a full kitchen, a swimming pool, and a screened lanai.
The "Grouper" - Longboat Key, FL
9.4 73 reviews

The "Grouper"

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.
Castaway Cottage Near Img And Beaches - Longboat Key, FL
No reviews

Castaway Cottage Near Img And Beaches

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.

Frequently Asked Questions about cottages in Longboat Key, FL

  • What would be a good 2-days itinerary for visiting Longboat Key, FL?

    On your first day, head to the Longboat Key Beach for some sun and sand. You can rent a chair and umbrella or just spread out your towel. In the afternoon, take a walk or bike ride along the Longboat Key Nature Trail. It's a beautiful trail that winds through mangroves and coastal areas. In the evening, grab dinner at one of the many restaurants on the island. On your second day, visit the Mote Marine Laboratory & Aquarium. It's a great place to learn about marine life and see a variety of animals, including sharks, manatees, and sea turtles. After, go for a walk on the pier at the Longboat Key Club. It's a great spot to watch the sunset. And if you have time, you can also visit the St. Armands Circle for some shopping and dining.
  • What are the best cottages in Longboat Key, FL?

  • What part of Longboat Key, FL is ideal for renting a cottage?

    The north end of Longboat Key, near the Longboat Key Club, is a great place to find cottages. It's a quieter area than the south end, and it's close to the beach and the nature trails. The north end has more of a residential feel, with a mix of single-family homes and cottages. You'll find a lot of options for cottages with private pools and patios.
  • What are the best cottages with a pool in Longboat Key, FL?

  • When is the best time to rent a cottage in Longboat Key, FL?

    The best time to visit Longboat Key is during the shoulder seasons, from April to May and September to October. The weather is still warm, but the crowds are smaller and the prices are lower. You'll also have a better chance of finding a cottage with a pool.
  • What are the best cottages with a jacuzzi in Longboat Key, FL?

  • What are the can't-miss sights in Longboat Key, FL?

    You definitely want to visit the Longboat Key Beach, which is known for its white sand and clear water. Another must-see is the Mote Marine Laboratory & Aquarium. It's a great place to learn about marine life and see a variety of animals. And don't forget to check out the St. Armands Circle, which is a popular shopping and dining destination.
  • What are the best cottages for families and kids in Longboat Key, FL?

  • Why consider renting a cottage in Longboat Key, FL for your stay?

    Renting a cottage in Longboat Key can give you a more relaxed and private experience than staying in a hotel. Many cottages have private pools and patios, which are great for enjoying the Florida sunshine. You'll also have more space to spread out and feel at home.
  • What are the best pet friendly cottages in Longboat Key, FL?

  • Can you easily explore Longboat Key, FL on foot or by bike?

    Longboat Key is relatively flat, so you can easily explore it on foot or by bike. There are bike paths along the beach and through the nature trails. If you want to venture further, you can rent a car. But for getting around the island, you can definitely get by without one.
  • What are the best cottages with parking in Longboat Key, FL?

  • What are the best restaurants in Longboat Key, FL with nature views?

    The Shore restaurant at the Longboat Key Club has beautiful views of the Gulf of Mexico. You can also try the dining room at the Mar Vista Dockside Restaurant, which has stunning views of the Sarasota Bay. Both restaurants are known for their fresh seafood and upscale ambiance.
  • What family-friendly activities are available in Longboat Key, FL?

    Longboat Key is a great place for families. There are plenty of activities for kids, including the Mote Marine Laboratory & Aquarium, the Longboat Key Beach, and the Anna Maria Island Beach. You can also rent bikes and explore the island's nature trails. And don't forget to check out the St. Armands Circle, which has a variety of shops and restaurants that are perfect for families.

Popular destinations

Traveler-Approved Cottages with a Hot Tub in Longboat Key, FL

Experience the ultimate recovery after a day by the water with a private hot tub at these Longboat Key, FL cottages.

Bridge Street Pier Beach House + Dog-friendly - Longboat Key, 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.

Compare Pet-Friendly Cottages in Longboat Key, FL

Bringing your dog to Longboat Key, FL? Every pet-friendly cottage here is set up for success, featuring dog-friendly facilities.

Cozy 1-bed Cottage In Adorable Tradewinds Bradenton Beach, Steps To Beach/pool - Longboat Key, FL
10 17 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.
Cozy Beachside Cottage At Tradewinds/1br/pool/steps To Beach.unit1 Available Too - Longboat Key, FL
9.8 13 reviews

Cozy Beachside Cottage At Tradewinds/1br/pool/steps To Beach.unit1 Available Too

cottage, Bradenton Beach
This renovated 700 sq ft cottage in Bradenton Beach offers 1 bedroom and 1 bathroom, accommodating up to 4 guests, and is located just steps from the Gulf beaches and a community pool, with Bridge Street Bistro and Anna Maria Oyster Bar within walking distance. Guests can enjoy amenities such as a full kitchen with a dishwasher, air conditioning, internet, and parking, with an option to book a second adjacent unit for larger groups.
Cozy Cottage Retreat At Tradewind Resort #32 In Bradenton Beach - Longboat Key, FL
9.2 21 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.
115 M² Cottage ∙ 3 Bedrooms ∙ 6 Guests - Longboat Key, FL
8.0 1 review

115 M² Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage, Holmes Beach
This Holmes Beach cottage is located on a quiet street, just a short walk from the beach. It's highly rated by previous guests, who consistently describe it as "very good". This charming home offers 3 bedrooms and can comfortably accommodate up to 6 guests within its 1230 square feet of space. The cottage provides internet access, is pet-friendly, and features comfortable furnishings, making it a great choice for a relaxing beach getaway.
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