The widest selection of unusual accommodations in Longboat Key, FL

A cabin, a lighthouse, a glamping, your extraordinary stay awaits you

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Longboat Key, FL unique stays
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

39 Unique places to stay in Longboat Key, FL

Luxurious 55-foot Yacht With Captain & First Mate - Longboat Key, FL
Longboat Key, FL
11/01 – 04/01
$2981/nighttotal: $450131 (151 )

Luxurious 55-foot Yacht With Captain & First Mate

2 2
houseboat, Sarasota
This 55-foot Prestige yacht, located in Sarasota near St. Armands Circle and the Mall at University Town Center, offers easy access to Lido Beach and Siesta Key Beach.
The luxury vessel boasts two bedrooms, two bathrooms, and sleeps eight guests, featuring a spacious salon, modern galley, expansive decks, and included captain and first mate service.
Cabin 2 Spinnakers Cottages - 204 - 56th 2 - Longboat Key, FL
9.9 246 reviews
Longboat Key, FL
10/10 – 10/17
$285/nighttotal: $1995 (7 )

Cabin 2 Spinnakers Cottages - 204 - 56th 2

1 4
cabin, Holmes Beach
This Holmes Beach vacation rental is located just a 10-minute walk from Bradenton Beach and Island Gallery West, and within a mile of Holmes Beach Beaches and Manatee Public Beach. Guests consistently rate this property excellent for its location, cleanliness, and overall experience.
The one-bedroom, one-bathroom house has 800 square feet of space and can comfortably accommodate up to four guests. This rental offers a fully equipped kitchen, a private swimming pool, a spa, a garden with barbecue grills, and access to a water park, making it perfect for a relaxing and fun-filled stay.
Sunkissed Cabin - Longboat Key, FL
9.0 11 reviews
Longboat Key, FL
06/27 – 07/04
$607/nighttotal: $4249 (7 )

Sunkissed Cabin

3 2
cabin, Holmes Beach
Sunkissed Cabin is located in Holmes Beach, Florida, just a 7-minute walk from Anna Maria Island and a short drive from the John and Mable Ringling Museum of Art. The cabin has received very good user ratings, making it a popular choice for travelers.
The cozy cabin has 3 bedrooms and 2 bathrooms, providing comfortable accommodation for families and groups. Guests can enjoy features like a private balcony, a fully equipped kitchen with a dishwasher, a swimming pool, and free Wi-Fi.
Yacht Time - Longboat Key, FL
Longboat Key, FL
07/16 – 07/21
$139/nighttotal: $695 (5 )

Yacht Time

1 2
yacht, Bradenton
The Yacht Time cottage, a pet-friendly boat rental in Bradenton, Florida, is located 5 miles from the city center, offering a quiet escape.
This one-bathroom vessel accommodates two guests and features a microwave, air conditioning, a terrace, a garden, barbecue area, and on-site parking.

Top Family Unique Stays in Longboat Key, FL

A unique stay built for families near the water in Longboat Key, FL offers a memorable trip that truly stands out.

Sunkissed Cabin - Longboat Key, FL
9.0 11 reviews
Longboat Key, FL
06/27 – 07/04
$607/nighttotal: $4249 (7 )

Sunkissed Cabin

3 2
cabin, Holmes Beach
Sunkissed Cabin is located in Holmes Beach, Florida, just a 7-minute walk from Anna Maria Island and a short drive from the John and Mable Ringling Museum of Art. The cabin has received very good user ratings, making it a popular choice for travelers.
The cozy cabin has 3 bedrooms and 2 bathrooms, providing comfortable accommodation for families and groups. Guests can enjoy features like a private balcony, a fully equipped kitchen with a dishwasher, a swimming pool, and free Wi-Fi.

Best Longboat Key, FL unique accommodations with a garden

Yacht Time - Longboat Key, FL
Longboat Key, FL
07/16 – 07/21
$139/nighttotal: $695 (5 )

Yacht Time

1 2
yacht, Bradenton
The Yacht Time cottage, a pet-friendly boat rental in Bradenton, Florida, is located 5 miles from the city center, offering a quiet escape.
This one-bathroom vessel accommodates two guests and features a microwave, air conditioning, a terrace, a garden, barbecue area, and on-site parking.
Sunkissed Cabin - Longboat Key, FL
9.0 11 reviews
Longboat Key, FL
06/27 – 07/04
$607/nighttotal: $4249 (7 )

Sunkissed Cabin

3 2
cabin, Holmes Beach
Sunkissed Cabin is located in Holmes Beach, Florida, just a 7-minute walk from Anna Maria Island and a short drive from the John and Mable Ringling Museum of Art. The cabin has received very good user ratings, making it a popular choice for travelers.
The cozy cabin has 3 bedrooms and 2 bathrooms, providing comfortable accommodation for families and groups. Guests can enjoy features like a private balcony, a fully equipped kitchen with a dishwasher, a swimming pool, and free Wi-Fi.
Cabin 2 Spinnakers Cottages - 204 - 56th 2 - Longboat Key, FL
9.9 246 reviews
Longboat Key, FL
10/10 – 10/17
$285/nighttotal: $1995 (7 )

Cabin 2 Spinnakers Cottages - 204 - 56th 2

1 4
cabin, Holmes Beach
This Holmes Beach vacation rental is located just a 10-minute walk from Bradenton Beach and Island Gallery West, and within a mile of Holmes Beach Beaches and Manatee Public Beach. Guests consistently rate this property excellent for its location, cleanliness, and overall experience.
The one-bedroom, one-bathroom house has 800 square feet of space and can comfortably accommodate up to four guests. This rental offers a fully equipped kitchen, a private swimming pool, a spa, a garden with barbecue grills, and access to a water park, making it perfect for a relaxing and fun-filled stay.

Frequently Asked Questions about unique stays in Longboat Key, FL

  • What attractions is Longboat Key, FL famous for?

    Longboat Key is known for its beautiful beaches, like the famous Longboat Key Beach, which is a great place to swim, sunbathe, and enjoy the ocean breeze. There's also the Longboat Key Club, a luxurious resort with a golf course and a spa, and the Mote Marine Laboratory & Aquarium, which features a variety of marine life.
  • What clothing or gear is recommended for the climate in Longboat Key, FL?

    Longboat Key has a tropical climate, so you'll want to pack light, breathable clothing. You'll definitely need swimwear, sunscreen, and a hat. If you plan on doing any outdoor activities, like hiking or biking, bring comfortable shoes and athletic wear. And don't forget a light jacket for the evenings, which can get a little chilly.
  • What are the best ways to travel to Longboat Key, FL eco-consciously?

    The best way to get to Longboat Key is to fly into Sarasota-Bradenton International Airport (SRQ) and then rent a car or take a taxi. If you're looking for a more eco-conscious option, you could consider taking the bus or train to Sarasota and then taking a taxi or rideshare to Longboat Key. You can also try to take a ride-sharing service to the island from the airport.
  • Which neigbourhood offers the best unique stays in Longboat Key, FL?

    The best neighborhood for unique stays in Longboat Key is probably the south end of the island. There are a lot of beautiful beachfront properties and some really unique vacation rentals. You can find everything from cozy cottages to luxurious villas. There is also a great selection of restaurants and shops in the area.
  • What should you know about unique stays in Longboat Key, FL before booking?

    Before you book a unique stay in Longboat Key, it's important to read the reviews and make sure that the property is right for you. You should also check the amenities and make sure that the property has everything you need. And if you're planning on bringing your pet, make sure that the property allows pets.

Destinations nearby

Find the Best Unique Stays with a Hot Tub in Longboat Key, FL

Elevate your trip with a unique stay featuring a private hot tub in Longboat Key, FL, ideal for a private soak after a day of exploring.

Yacht Time - Longboat Key, FL
Longboat Key, FL
07/16 – 07/21
$139/nighttotal: $695 (5 )

Yacht Time

1 2
yacht, Bradenton
The Yacht Time cottage, a pet-friendly boat rental in Bradenton, Florida, is located 5 miles from the city center, offering a quiet escape.
This one-bathroom vessel accommodates two guests and features a microwave, air conditioning, a terrace, a garden, barbecue area, and on-site parking.

Best pet friendly Longboat Key, FL unique stays

Among the 39 accommodations in Longboat Key, FL, here are the 2 best pet friendly unique accommodations

Yacht Time - Longboat Key, FL
Longboat Key, FL
07/16 – 07/21
$139/nighttotal: $695 (5 )

Yacht Time

1 2
yacht, Bradenton
The Yacht Time cottage, a pet-friendly boat rental in Bradenton, Florida, is located 5 miles from the city center, offering a quiet escape.
This one-bathroom vessel accommodates two guests and features a microwave, air conditioning, a terrace, a garden, barbecue area, and on-site parking.
Cabin 2 Spinnakers Cottages - 204 - 56th 2 - Longboat Key, FL
9.9 246 reviews
Longboat Key, FL
10/10 – 10/17
$285/nighttotal: $1995 (7 )

Cabin 2 Spinnakers Cottages - 204 - 56th 2

1 4
cabin, Holmes Beach
This Holmes Beach vacation rental is located just a 10-minute walk from Bradenton Beach and Island Gallery West, and within a mile of Holmes Beach Beaches and Manatee Public Beach. Guests consistently rate this property excellent for its location, cleanliness, and overall experience.
The one-bedroom, one-bathroom house has 800 square feet of space and can comfortably accommodate up to four guests. This rental offers a fully equipped kitchen, a private swimming pool, a spa, a garden with barbecue grills, and access to a water park, making it perfect for a relaxing and fun-filled stay.

Discover Unique Stays by the Sea in Longboat Key, FL

Plan a memorable beach-town holiday at seaside unique stays in Longboat Key, FL, situated short distances from regional shorelines.

Yacht Time - Longboat Key, FL
Longboat Key, FL
07/16 – 07/21
$139/nighttotal: $695 (5 )

Yacht Time

1 2
yacht, Bradenton

Explore Unusual Accommodations with Swimming Pool in Longboat Key, FL

A unique stay in Longboat Key, FL with a pool provides the perfect swim to complement your day by the water.

Cabin 2 Spinnakers Cottages - 204 - 56th 2 - Longboat Key, FL
9.9 246 reviews
Longboat Key, FL
10/10 – 10/17
$285/nighttotal: $1995 (7 )

Cabin 2 Spinnakers Cottages - 204 - 56th 2

1 4
cabin, Holmes Beach
Sunkissed Cabin - Longboat Key, FL
9.0 11 reviews
Longboat Key, FL
06/27 – 07/04
$607/nighttotal: $4249 (7 )

Sunkissed Cabin

3 2
cabin, Holmes Beach
©2026 cozycozy.com