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38 Best cottages in Longboat Key, FL
10 3 reviews
Longboat Key, FL
07/15 – 07/24
$416/nighttotal: $3744 (9 )
Bridge Street Beach House | Wi-fi | Center Of All
3 6
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 23 reviews
Longboat Key, FL
08/22 – 09/05
$483/nighttotal: $6762 (14 )
Romantic, Cute Cottage On Anna Maria Island. Close To Everything. Pet Friendly!
2 3
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.
9.8 105 reviews
Longboat Key, FL
08/22 – 09/05
$415/nighttotal: $5810 (14 )
Blue Agave Villa By Beach Boutique Rentals
2 3
cottage , Holmes Beach
Frangipani Villa is a ground-level cottage located just steps from the beach path in Holmes Beach, offering easy access to the beach, shops, and restaurants. This charming cottage has received excellent ratings for location, cleanliness, and overall experience. The cottage features a private porch with Adirondack chairs and a bistro table, perfect for enjoying the tropical surroundings. Guests can take advantage of beach chairs, towels, and umbrellas provided, along with a fully equipped kitchen, pet-friendly accommodations, and a tranquil garden with a fountain.
9.6 9 reviews
Longboat Key, FL
08/22 – 09/05
$273/nighttotal: $3822 (14 )
Cottage In The Shade, 3 Min Walk To Beach, Restaurants, And Pickleball Crt.
2 3
cottage , Bradenton Beach
This 2-bedroom, 1-bathroom bungalow in Bradenton Beach offers on-site parking and is located just a short walk from Bradenton Beach and the historic Bridge Street Pier. This pet-friendly cottage accommodates up to 4 guests and includes air conditioning, Wi-Fi, a television, in-unit laundry, a dishwasher, a microwave, and a barbecue for outdoor enjoyment.
10 7 reviews
Longboat Key, FL
12/26 – 12/31
$208/nighttotal: $1040 (5 )
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.
Longboat Key, FL
08/20 – 08/21
$438/nightfor 1 night
Lido Key Getaway - Bikes & Beach Gear
2 2
cottage , Sarasota
This Sarasota cottage is located a short walk from Lido Beach and is near St. Armands Circle. This 2-bedroom, 1-bathroom accommodation with a private heated pool sleeps 4 guests and includes a screened lanai, outdoor shower, and provided beach essentials for your stay.
9.9 222 reviews
Longboat Key, FL
08/22 – 09/05
$393/nighttotal: $5502 (14 )
Sailfish Gulf Suites #2, Beachfront, Steps To The Sand
2 3
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.
10 22 reviews
Longboat Key, FL
08/22 – 09/05
$491/nighttotal: $6874 (14 )
Palm Villa By Beach Boutique Rentals
2 3
cottage , Holmes Beach
Palm Villa is a charming cottage located in Holmes Beach, just steps from the beach path and within walking distance of local shops and restaurants. It has excellent user, location, and cleanliness ratings. The cottage features two bedrooms and two full baths, accommodating up to five guests comfortably. It has a floor area of 810 square feet. The fully equipped kitchen allows guests to prepare meals and enjoy the convenience of home while on vacation. The cottage also has a private back patio with loungers, a fan, and an outdoor shower, providing a tranquil retreat for relaxation.
9.4 31 reviews
Longboat Key, FL
08/22 – 09/05
$245/nighttotal: $3430 (14 )
Stay At Sun Daze: Private Pool, 3 Minutes To The Beach!
2 3
cottage , Holmes Beach
This 2-bedroom, 2-bathroom vacation home is located in Holmes Beach, Florida, just a 10-minute walk from Island Gallery West, Bradenton Beach, and Holmes Beach Beaches. The 1,120 square foot home features a private pool, a water park, and can accommodate up to 4 guests, making it perfect for families seeking a relaxing beach getaway.
10 23 reviews
Longboat Key, FL
08/22 – 09/05
$389/nighttotal: $5446 (14 )
Anna Maria Cottage With Golf Cart
2 3
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.
9.8 7 reviews
Longboat Key, FL
12/26 – 12/31
$397/nighttotal: $1985 (5 )
Cozy Beachside Cottage At Tradewinds/1br/pool/steps To Beach.unit1 Available Too
1 2
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.
10 12 reviews
Longboat Key, FL
08/22 – 09/05
$593/nighttotal: $8302 (14 )
Beautiful New Pool/spa, Steps To Sand & Restaurants, Golf Cart Included
2 3
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.
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.
10 3 reviews
Longboat Key, FL
07/11 – 07/17
$215/nighttotal: $1290 (6 )
Just Minutes From Our Beautiful Gulf Of Mexico Beaches & Stunning Sunsets !!
2 3
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.
9.4 25 reviews
Longboat Key, FL
08/22 – 09/05
$125/nighttotal: $1750 (14 )
The Cottage By Anna Maria Island
3 3
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.
9.8 36 reviews
Longboat Key, FL
08/22 – 09/05
$330/nighttotal: $4620 (14 )
Charming Ground Level Resort Style 3 Unit Condo - Unit C
2 3
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.
10 2 reviews
Longboat Key, FL
08/22 – 09/05
$399/nighttotal: $5586 (14 )
Recently Renovated Luxury Ground Floor Island Home Close To Beach!o Sleeps 4
2 3
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.
Best Longboat Key, FL cottages with a garden
9.4 66 reviews
Longboat Key, FL
08/20 – 08/21
$211/nightfor 1 night
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 1 review
Longboat Key, FL
07/11 – 07/17
$791/nighttotal: $4746 (6 )
Beachy Duplex Retreat: Pine Key & Pelicans Nest!
4 3
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.
Longboat Key, FL
07/11 – 07/17
$484/nighttotal: $2904 (6 )
Stay At Pine Key- A Cozy Beach Cottage Retreat!
2 3
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 7 reviews
Longboat Key, FL
08/22 – 09/05
$371/nighttotal: $5194 (14 )
Spoonbill Lagoon With Fantastic Water Views Of Palma Sola Bay!
2 3
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.
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 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.
Destinations nearby
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.
10 3 reviews
Longboat Key, FL
07/15 – 07/24
$416/nighttotal: $3744 (9 )
Bridge Street Beach House | Wi-fi | Center Of All
3 6
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 12 reviews
Longboat Key, FL
08/22 – 09/05
$593/nighttotal: $8302 (14 )
Beautiful New Pool/spa, Steps To Sand & Restaurants, Golf Cart Included
2 3
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.
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.
10 29 reviews
Longboat Key, FL
08/22 – 09/05
$408/nighttotal: $5712 (14 )
Charming Ground Level Resort Style 3 Units Condo Of A Triplex- Unit A
2 3
cottage , Holmes Beach
The Charming Ground Level Resort Style 3 Units Condo Of A Triplex- Unit A is located in Bradenton Beach, just a short walk from Island Gallery West and a 5-minute drive from Holmes Beach Beaches. This smoke-free vacation rental is highly rated by guests and offers a comfortable and convenient stay. This ground-level condo has 2 bedrooms, 1 bathroom, and can accommodate up to 6 guests. The 990 square foot space includes a private pool, a fully equipped kitchen, a terrace, and a garden, making it ideal for families or groups seeking a relaxing retreat.
9.6 4 reviews
Longboat Key, FL
12/26 – 12/31
$917/nighttotal: $4585 (5 )
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.
9.2 19 reviews
Longboat Key, FL
07/11 – 07/17
$340/nighttotal: $2040 (6 )
Cozy Cottage Retreat At Tradewind Resort #32 In Bradenton Beach
1 3
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.
10 10 reviews
Longboat Key, FL
08/22 – 09/05
$314/nighttotal: $4396 (14 )
Cozy 1-bed Cottage In Adorable Tradewinds Bradenton Beach, Steps To Beach/pool
1 3
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.
