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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.

Cozy 2bd+2 Ba Beach Cottage; Scrnd Fl Rm, 5min Thru Dune To Bch; Vr22-00059 - Longboat Key, FL
10 85 reviews

Cozy 2bd+2 Ba Beach Cottage; Scrnd Fl Rm, 5min Thru Dune To Bch; Vr22-00059

cottage, Sarasota
This charming beach house is located a short walk from Lido Beach and St. Armands Circle, offering easy access to Sarasota's vibrant attractions and dining scene. The property consistently receives excellent ratings from previous guests, highlighting its comfortable accommodations and convenient location.
The two-bedroom cottage provides 1000 square feet of space, comfortably accommodating up to six guests. Enjoy the beautiful weather with a private patio, relax in the garden, or take a dip in the pool. A fully equipped kitchen, a fireplace, and free WiFi ensure a comfortable and enjoyable stay.
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.
Adorable 1-bedroom Cottage In Sunny Sarasota - Longboat Key, FL
No reviews

Adorable 1-bedroom Cottage In Sunny Sarasota

cottage, Sarasota
This modern Sarasota cottage is located in Central Sarasota, offering convenient access to St. Armands Circle, Lido Key beaches, and downtown.
This 480 square foot cottage features one bedroom and one bathroom, comfortably sleeping up to 4 guests with two full beds, and includes a fully equipped kitchen, an in-cottage washer and dryer, and a fenced outdoor area for relaxation.
Charming Ground Level Resort Style 3 Unit Condo  - Unit C - Longboat Key, FL
9.8 41 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.

Best Longboat Key, FL cottages with a garden

Quiet Nights Of Quiet Stars On Anna Maria Island - Longboat Key, FL
10 149 reviews

Quiet Nights Of Quiet Stars On Anna Maria Island

cottage, Holmes Beach
This beach house is located in Holmes Beach, a short walk from Bradenton Beach and Island Gallery West, and less than a mile from Holmes Beach Beaches and Manatee Public Beach. It has received excellent user ratings, making it a popular choice for travelers. This two-bedroom vacation rental comfortably accommodates up to four guests. The property offers amenities like a playground, barbecue grills, a private terrace, and a fully equipped kitchen. Enjoy easy access to the beach, nearby attractions, and activities like swimming, sunbathing, and fishing.
Cottage W/ Pickleball Outdoor Oasis 2 Mi To Beach - Longboat Key, FL
10 111 reviews

Cottage W/ Pickleball Outdoor Oasis 2 Mi To Beach

house, 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.
Stay At Pine Key- A Cozy Beach Cottage Retreat! - Longboat Key, FL
8.0 1 review

Stay At Pine Key- A Cozy Beach Cottage Retreat!

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.
Backyard Hangouts: Bradenton Home Near Dining! - Longboat Key, FL
No reviews

Backyard Hangouts: Bradenton Home Near Dining!

cottage, Bradenton
This smoke-free cottage in Bradenton is located 1.9 miles from Blake Medical Center and 2.6 miles from IMG Academy, with Palma Sola Bay and Smugglers Cove Adventure Golf also within 3 miles.
This accommodation offers a fully equipped kitchen with a microwave and dishwasher, air conditioning, a garden, a private patio, and WiFi, making it ideal for self-catering stays and outdoor enjoyment.

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.

Charming Coastal Oasis 2bed/2 Bath Cottage Close To Beach And Downtown-southgate - Longboat Key, FL
9.8 81 reviews

Charming Coastal Oasis 2bed/2 Bath Cottage Close To Beach And Downtown-southgate

cottage, Southgate
This Southgate cottage is conveniently located near Coconuts Family Entertainment Center, Sarasota Memorial Hospital, and Bee Ridge Park, making it a great option for families or groups visiting the area. The cottage has received excellent user ratings, indicating a comfortable and enjoyable stay.
The cottage has two bedrooms and two bathrooms, comfortably sleeping up to six guests. Guests can enjoy amenities like a private pool, spa tub, fully equipped kitchen, and a peaceful garden with barbecue grills.
Beautiful New Pool/spa, Steps To Sand & Restaurants, Golf Cart Included - Longboat Key, FL
10 14 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.
Bridge Street Pier Beach House + Dog-friendly - Longboat Key, FL
9.6 35 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.
Historic Home With Hot Tub, Steps From Lido Beach - Ringling Cottage - Longboat Key, FL
9.8 8 reviews

Historic Home With Hot Tub, Steps From Lido Beach - Ringling Cottage

cottage, Sarasota
This Sarasota vacation home is ideally located a 15-minute walk from Lido Beach and St. Armands Circle, with South Lido Park and Coolidge Park also nearby.
The two-bedroom, two-bathroom house sleeps four guests and boasts a private pool, fenced yard, rooftop terrace, hot tub, and access to an on-site water park, plus a fully equipped kitchen and free WiFi in common areas.

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.

Fabulous 1-bedroom Cottage With Patio In Charming Sarasota - Longboat Key, FL
No reviews

Fabulous 1-bedroom Cottage With Patio In Charming Sarasota

cottage, Gulf Gate Estates
This 1-bedroom bungalow in Gulf Gate Estates, Sarasota, is located 2 miles from Ed Smith Stadium and a short drive to Siesta Key Beach.
This pet-friendly rental accommodates up to 2 guests and offers air conditioning, WiFi, a private patio, and is conveniently situated near St. Armands Circle and The Mall at University Town Center.
Charming 2bed Ami  Beach Cottage  1/2 Of A Duplex, 3min Walk To Beach - Longboat Key, FL
9.6 61 reviews

Charming 2bed Ami Beach Cottage 1/2 Of A Duplex, 3min Walk To Beach

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.
Relaxed Luxury · Refined North-side 1 Bedroom - Longboat Key, 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.
'The City Oasis' Near Img & Anna Maria Island! - Longboat Key, FL
No reviews

'The City Oasis' Near Img & Anna Maria Island!

cottage, Bradenton
This Bradenton vacation home is conveniently located less than 1.2 miles from LECOM Park, Riverwalk Park, and the Bishop Museum, offering easy access to Bradenton's attractions.
The pet-friendly cottage features a fully equipped kitchen with microwave and dishwasher, two bathrooms, a private patio, free Wi-Fi, an outdoor swimming pool, and free on-site parking.
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