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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.

Just Minutes From Our Beautiful Gulf Of Mexico Beaches & Stunning Sunsets !! - Longboat Key, 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.
Relax And Recharge In This 1br Cottage - Longboat Key, FL
No reviews

Relax And Recharge In This 1br Cottage

cottage, Longboat Key
This bayside cottage on Longboat Key offers bay views and is located 1 mile from Mote Marine Laboratory & Aquarium and 2 miles from Coquina Beach.
This 680 sq ft cottage sleeps 4, featuring 1 bedroom with a king bed, a living room with a queen sofa bed, a full kitchen, a porch, and access to a swimming pool and tennis court.
Recently Renovated Luxury Ground Floor Island Home Close To Beach!o Sleeps 4 - Longboat Key, FL
10 3 reviews

Recently Renovated Luxury Ground Floor Island Home Close To Beach!o Sleeps 4

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.
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.

Best Longboat Key, FL cottages with a garden

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.
6 Mi To Beach: Bradenton Home W/ Private Pool - Longboat Key, FL
9.6 5 reviews

6 Mi To Beach: Bradenton Home W/ Private Pool

cottage, Bradenton
This Bradenton vacation home is conveniently located less than a mile from Blake Medical Center and within six miles of IMG Academy, Riverwalk, De Soto National Memorial, and The Bishop Museum of Science and Nature.
The cottage features a fully equipped kitchen with microwave and dishwasher, two bathrooms, a private patio, an outdoor pool, and an on-site arcade, offering comfortable accommodations for guests near Bradenton's attractions.
Cottage W/ Pickleball Outdoor Oasis 2 Mi To Beach - Longboat Key, FL
10 109 reviews

Cottage W/ Pickleball Outdoor Oasis 2 Mi To Beach

cottage, Cortez
This family-friendly vacation home is located in Bradenton, just a short drive from Anna Maria Sound, Fish Hole Adventure Golf, and arcadeland. The house has received excellent ratings for its location, cleanliness, and overall experience.
This 1500 square foot house comfortably accommodates up to 12 guests in its three bedrooms. It comes equipped with a private pool, a jacuzzi, a terrace, a garden, and a fully-equipped kitchen with a fridge, microwave, and dishwasher.
5 Mi To Riverwalk: Bradenton Family Home W/ Yard - Longboat Key, FL
No reviews

5 Mi To Riverwalk: Bradenton Family Home W/ Yard

cottage, Bayshore Gardens
This cottage in Bayshore Gardens is conveniently located 1 mile from State College of Florida and 2.9 miles from IMG Academy.
This rental offers complimentary Wi-Fi, air conditioning, a full kitchen with a microwave and dishwasher, a garden, and parking, with barbecues available for guest use.

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.

Retro Style Home With Large Pool Close To Downtown Holmes Beach And Walk To Beach! - Longboat Key, FL
10 6 reviews

Retro Style Home With Large Pool Close To Downtown Holmes Beach And Walk To Beach!

cottage, Holmes Beach
This family-friendly cottage is located just a 5-minute walk from Island Gallery West and Bradenton Beach, making it easy to explore the area's art scene and beautiful beaches. The cottage consistently receives excellent reviews from guests who enjoy its comfortable atmosphere and convenient location.
The two-bedroom, three-bathroom cottage comfortably accommodates four guests. Enjoy a private pool, outdoor grill, and patio space, as well as a fully equipped kitchen, DVD player, and convenient access to nearby water activities.
'Uncle Louie's' Gulf Coast Gem W/ Outdoor Oasis - Longboat Key, FL
9.0 2 reviews

'Uncle Louie's' Gulf Coast Gem W/ Outdoor Oasis

cottage, South Bradenton
This South Bradenton cottage is conveniently located near Smugglers Cove Adventure Golf and within a 3-mile radius of State College of Florida and arcadeland, making it an ideal choice for exploring the area. The cottage has earned an excellent user rating, reflecting its comfortable and well-maintained accommodations.
The cottage features two bathrooms and a patio, offering plenty of space and privacy. Guests can enjoy a fully equipped kitchen, free self-parking, and free Wi-Fi in public areas, as well as a peaceful setting in South Bradenton.
Pelican Perch: Tropical Paradise Cottage On The Beach            Vrc17-000167 - Longboat Key, FL
9.0 121 reviews

Pelican Perch: Tropical Paradise Cottage On The Beach Vrc17-000167

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.
Cozy Beachside Cottage At Tradewinds/1br/pool/steps To Beach.unit1 Available Too - Longboat Key, FL
9.8 14 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.
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