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Longboat Key, FL cottages
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38 Best cottages in Longboat Key, FL

Charming, Fully Remodeled Cottage Steps From Beach With Wifi & Central Ac - Longboat Key, FL
8.6 28 reviews
Longboat Key, FL
09/16 – 09/19
$293/nighttotal: $879 (3 )

Charming, Fully Remodeled Cottage Steps From Beach With Wifi & Central Ac

2 2
cottage, Bradenton Beach
This charming beach cottage is located just a short walk from both Bradenton Beach and Coquina Beach, offering easy access to the beautiful white sands and turquoise waters of the Gulf of Mexico. It has received very good user ratings, making it a popular choice for travelers.
This cozy vacation rental has two bedrooms and one bathroom, comfortably accommodating up to four guests. The cottage features a fully equipped kitchen, a washing machine, a sofa bed, a coffee/tea maker, a TV, and free internet access, making it easy to relax and enjoy your stay.
Beachy Duplex Retreat: Pine Key & Pelicans Nest! - Longboat Key, FL
10 1 review
Longboat Key, FL
10/10 – 10/17
$468/nighttotal: $3276 (7 )

Beachy Duplex Retreat: Pine Key & Pelicans Nest!

4 4
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.
Orchid Villa By Beach Boutique Rentals - Longboat Key, FL
10 26 reviews
Longboat Key, FL
10/10 – 10/17
$464/nighttotal: $3248 (7 )

Orchid Villa By Beach Boutique Rentals

2 4
cottage, Holmes Beach
Orchid Villa is a ground-level cottage in Holmes Beach, just steps from the beach path and within walking distance of shops and restaurants. It has received excellent ratings for location, cleanliness, and overall user experience.
This 810 square foot cottage has two bedrooms, two bathrooms, and can accommodate up to five guests. Amenities include a fully equipped kitchen, a spacious living room, a private patio, a botanical courtyard with a fountain, beach essentials, and a shared laundry facility.
Charming Ground Level Resort Style 3 Unit Condo  - Unit C - Longboat Key, FL
9.8 37 reviews
Longboat Key, FL
10/10 – 10/17
$431/nighttotal: $3017 (7 )

Charming Ground Level Resort Style 3 Unit Condo - Unit C

2 4
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.
Palm Villa By Beach Boutique Rentals - Longboat Key, FL
10 22 reviews
Longboat Key, FL
10/10 – 10/17
$464/nighttotal: $3248 (7 )

Palm Villa By Beach Boutique Rentals

2 4
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.
Spoonbill Lagoon With Fantastic Water Views Of Palma Sola Bay! - Longboat Key, FL
10 7 reviews
Longboat Key, FL
07/01 – 07/08
$582/nighttotal: $4074 (7 )

Spoonbill Lagoon With Fantastic Water Views Of Palma Sola Bay!

2 2
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.
Private Historical Completely Renovated Cottage With  60 Ft Dock On Sarasota Bay - Longboat Key, FL
10 105 reviews
Longboat Key, FL
07/16 – 07/21
$219/nighttotal: $1095 (5 )

Private Historical Completely Renovated Cottage With 60 Ft Dock On Sarasota Bay

1 2
cottage, Cortez
This golf cottage in Cortez is conveniently located within walking distance of the Florida Maritime Museum at Cortez and Anna Maria Sound. With excellent user ratings, this 1-bedroom, 1-bathroom cottage accommodates up to 4 guests comfortably.
The cottage features a fully equipped kitchen, a comfortable living space with a sofa bed and a balcony, and a garden with barbecue grills for outdoor relaxation and dining. The cottage also offers free WiFi, laundry facilities, and proximity to golf courses for added convenience.
The Beach House, Right On Holmes Beach - Longboat Key, FL
9.6 50 reviews
Longboat Key, FL
10/10 – 10/17
$946/nighttotal: $6622 (7 )

The Beach House, Right On Holmes Beach

3 4
cottage, Holmes Beach
This Holmes Beach cottage is directly on the beach, a short walk from Bradenton Beach and Island Gallery West, and less than a mile from both Holmes Beach Beaches and Manatee Public Beach. The 3-bedroom cottage sleeps 6, boasts a private pool, and offers direct beach access, a fully equipped kitchen, and free WiFi.
Stay At Pine Key- A Cozy Beach Cottage Retreat! - Longboat Key, FL
Longboat Key, FL
10/10 – 10/17
$351/nighttotal: $2457 (7 )

Stay At Pine Key- A Cozy Beach Cottage Retreat!

2 4
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.
Romantic Island Getaway! Just Steps From The Beach - Longboat Key, FL
8.6 4 reviews
Longboat Key, FL
07/16 – 07/21
$349/nighttotal: $1745 (5 )

Romantic Island Getaway! Just Steps From The Beach

1 2
cottage, Bradenton Beach
This Bradenton Beach cottage, a five-minute walk from Anna Maria Sound and Bradenton Beach, offers convenient access to the Aluna Wellness Center & Spa and Bradenton Beach Marina within a 15-minute drive.
The 540-square-foot vacation home includes one bedroom, one bathroom, sleeps four guests, and features a fully equipped kitchen, a swimming pool, and barbecue grills.
Tropical Paradise On The Beach               Permit Vrc17-000168 - Longboat Key, FL
9.2 156 reviews
Longboat Key, FL
10/10 – 10/17
$373/nighttotal: $2611 (7 )

Tropical Paradise On The Beach Permit Vrc17-000168

2 4
cottage, Holmes Beach
This charming cottage is located in Ilexhurst, a peaceful neighborhood in Holmes Beach, just a block from the free trolley and a short distance from the shops and restaurants of Bradenton Beach and Anna Maria. This highly rated cottage offers a relaxing escape with direct Gulf views and easy access to the white sand beaches of Anna Maria Island.
The cottage features two bedrooms, one bathroom, and 800 square feet of living space, comfortably accommodating up to five guests. Enjoy a private deck with stunning Gulf views, a fully equipped kitchen, a washer and dryer, and a tropical garden with a spa, all just steps from the beach.
Quiet Nights Of Quiet Stars On Anna Maria Island - Longboat Key, FL
10 144 reviews
Longboat Key, FL
06/27 – 07/04
$136/nighttotal: $952 (7 )

Quiet Nights Of Quiet Stars On Anna Maria Island

2 2
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.

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; Screened Florida Rm, Sleep Porch; Vr22-00059 - Longboat Key, FL
10 80 reviews
Longboat Key, FL
06/27 – 07/04
$365/nighttotal: $2555 (7 )

Cozy 2bd+2 Ba Beach Cottage; Screened Florida Rm, Sleep Porch; Vr22-00059

2 2
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.
Historic 1930s Cottage + Heated Pool + 12mi To Beaches & 1 Mi To Downtown - Longboat Key, FL
9.9 153 reviews
Longboat Key, FL
10/08 – 10/12
$331/nighttotal: $1324 (4 )

Historic 1930s Cottage + Heated Pool + 12mi To Beaches & 1 Mi To Downtown

4 6
cottage, Palmetto
This charming cottage is located in Palmetto, just half a kilometer from the Manatee County Agricultural Museum and within a 5 kilometer radius of other popular attractions. The cottage enjoys excellent user ratings for location, cleanliness, and overall experience.
The home features three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Amenities include a private pool, spa tub, barbecue grills, a fully equipped kitchen, and free WiFi.
Just Minutes From Our Beautiful Gulf Of Mexico Beaches & Stunning Sunsets !! - Longboat Key, FL
10 3 reviews
Longboat Key, FL
07/16 – 07/21
$219/nighttotal: $1095 (5 )

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

2 2
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.
The Cottage By Anna Maria Island - Longboat Key, FL
9.4 26 reviews
Longboat Key, FL
10/10 – 10/17
$145/nighttotal: $1015 (7 )

The Cottage By Anna Maria Island

3 4
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.

Best Longboat Key, FL cottages with a garden

Sailfish Gulf Suites #2, Beachfront, Steps To The Sand - Longboat Key, FL
9.9 223 reviews
Longboat Key, FL
10/10 – 10/17
$319/nighttotal: $2233 (7 )

Sailfish Gulf Suites #2, Beachfront, Steps To The Sand

2 4
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.
Recently Renovated Luxury Ground Floor Island Home Close To Beach!o Sleeps 4 - Longboat Key, FL
10 2 reviews
Longboat Key, FL
10/10 – 10/17
$523/nighttotal: $3661 (7 )

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

2 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.
The "Grouper" - Longboat Key, FL
9.4 70 reviews
Longboat Key, FL
09/16 – 09/19
$150/nighttotal: $450 (3 )

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.
Retro Style Home With Large Pool Close To Downtown Holmes Beach And Walk To Beach! - Longboat Key, FL
10 6 reviews
Longboat Key, FL
10/10 – 10/17
$523/nighttotal: $3661 (7 )

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

2 4
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.

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.

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.

Bridge Street Beach House | Wi-fi | Center Of All - Longboat Key, FL
10 4 reviews
Longboat Key, FL
09/16 – 09/19
$346/nighttotal: $1038 (3 )

Bridge Street Beach House | Wi-fi | Center Of All

3 2
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.

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 Cottage Retreat At Tradewind Resort #32 In Bradenton Beach - Longboat Key, FL
9.2 19 reviews
Longboat Key, FL
07/14 – 07/16
$428/nighttotal: $856 (2 )

Cozy Cottage Retreat At Tradewind Resort #32 In Bradenton Beach

1 4
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 Beachside Cottage At Tradewinds/1br/pool/steps To Beach.unit1 Available Too - Longboat Key, FL
9.8 10 reviews
Longboat Key, FL
10/10 – 10/17
$405/nighttotal: $2835 (7 )

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

1 4
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.
Blue Agave Villa By Beach Boutique Rentals - Longboat Key, FL
9.8 105 reviews
Longboat Key, FL
10/10 – 10/17
$403/nighttotal: $2821 (7 )

Blue Agave Villa By Beach Boutique Rentals

2 4
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.
Cottage In The Shade, 3 Min Walk To Beach, Restaurants, And Pickleball Crt. - Longboat Key, FL
9.6 10 reviews
Longboat Key, FL
10/10 – 10/17
$349/nighttotal: $2443 (7 )

Cottage In The Shade, 3 Min Walk To Beach, Restaurants, And Pickleball Crt.

2 4
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.
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