
Long Beach, Big Pine Key
06/20 – 07/01
$477/nighttotal: $5247 (11 )
135 Waterfront Property, Boat Dock, Heated Pool, Ocean Views
2 2apartment , Cudjoe Key
This waterfront vacation rental in Summerland Key, near Cudjoe Key, offers easy access to Bahia Honda State Park and other attractions.
The 780-square-foot apartment features two bedrooms, two bathrooms, accommodates four guests, and includes a private boat dock, oceanfront pool access, tennis court, and updated kitchen.
The 780-square-foot apartment features two bedrooms, two bathrooms, accommodates four guests, and includes a private boat dock, oceanfront pool access, tennis court, and updated kitchen.

Long Beach, Big Pine Key
06/20 – 07/01
$210/nighttotal: $2310 (11 )
Seascape Vacation!!!
1 2apartment , Cudjoe Key
This waterfront vacation home is located on Cudjoe Key, just a short walk from Venture Key, Venture Out Keys, and Out Key, with Florida Keys Beaches a quick drive away. Guests have consistently rated this property as very good for cleanliness and location, and excellent overall.
This 1-bedroom, 1-bathroom property offers 730 square feet of space, comfortably accommodating up to 4 guests. Enjoy amenities like a swimming pool, jacuzzi, and a fully equipped kitchen, perfect for relaxing and enjoying the beautiful Cudjoe Key surroundings.
This 1-bedroom, 1-bathroom property offers 730 square feet of space, comfortably accommodating up to 4 guests. Enjoy amenities like a swimming pool, jacuzzi, and a fully equipped kitchen, perfect for relaxing and enjoying the beautiful Cudjoe Key surroundings.

Long Beach, Big Pine Key
10/09 – 10/19
$253/nighttotal: $2530 (10 )
2 Bedroom Aqualodge # 13 Barracuda
1 2barge , Big Pine Key
This barge is located at the Old Wooden Bridge Resort and Marina in Big Pine Key, just a short distance from the beautiful saltwater pool and fish cleaning stations. It has received excellent ratings for its location, cleanliness, and overall user experience.
This charming vessel features two bedrooms and can comfortably accommodate up to six guests. The barge offers a kitchen with a fridge and microwave, air conditioning, a swimming pool, a garden, parking, and internet access.
This charming vessel features two bedrooms and can comfortably accommodate up to six guests. The barge offers a kitchen with a fridge and microwave, air conditioning, a swimming pool, a garden, parking, and internet access.

Long Beach, Big Pine Key
06/20 – 07/01
$342/nighttotal: $3762 (11 )
Our Little Slice Of Paradise
2 2apartment , Big Pine Key
This two-bedroom, two-bathroom condo is located in Breezeswept Beach Estates on Summerland Key, offering 27 miles of access to Key West and proximity to Bahia Honda State Park and the Blue Hole.
This pet-friendly rental accommodates up to six guests and features a private dock, a screened-in porch, air conditioning, internet, and a full kitchen with a microwave and dishwasher.
This pet-friendly rental accommodates up to six guests and features a private dock, a screened-in porch, air conditioning, internet, and a full kitchen with a microwave and dishwasher.

Long Beach, Big Pine Key
10/09 – 10/19
$532/nighttotal: $5320 (10 )
Starfish - Ocean Front With Dock And Pool
3 2apartment , Big Pine Key
This vacation home is located in Summerland Key, just 20 minutes from Key West and 15 minutes from Bahia Honda State Park, offering a convenient location for exploring the Florida Keys. The property has received excellent user ratings, indicating a comfortable and enjoyable stay for guests.
The 1400 square foot home features three bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a private pool, a dock for boat access, kayaks, a fully equipped kitchen, central air conditioning, a screened-in porch, a propane BBQ grill, a hammock, and breathtaking ocean views.
The 1400 square foot home features three bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a private pool, a dock for boat access, kayaks, a fully equipped kitchen, central air conditioning, a screened-in porch, a propane BBQ grill, a hammock, and breathtaking ocean views.

Long Beach, Big Pine Key
06/20 – 07/01
$404/nighttotal: $4444 (11 )
Sir David Waterfront
1 2apartment , Big Pine Key
This two-bedroom, two-bathroom waterfront townhome is located off US-1 on Big Pine Key, offering direct canal access and is approximately 20 minutes from Key West.
The 2-guest unit features a kitchen, air conditioning, parking, internet access, and provides opportunities for swimming, boating, and jet skiing rentals nearby.
The 2-guest unit features a kitchen, air conditioning, parking, internet access, and provides opportunities for swimming, boating, and jet skiing rentals nearby.

Long Beach, Big Pine Key
09/03 – 09/08
$385/nighttotal: $1925 (5 )
New Deluxe Duplex Unit, 2 Queen Beds, Unit I-6
1 3apartment , Big Pine Key
This Big Pine Key apartment rental sleeps six guests in two bedrooms and one bathroom, offering a fully equipped kitchen with a fridge, microwave, and dishwasher.
The property features air conditioning, a swimming pool, a garden, and parking; further details regarding its precise location within Big Pine Key and proximity to specific landmarks are unavailable.
The property features air conditioning, a swimming pool, a garden, and parking; further details regarding its precise location within Big Pine Key and proximity to specific landmarks are unavailable.

Long Beach, Big Pine Key
09/03 – 09/08
$582/nighttotal: $2910 (5 )
The Hideaway - Private Paradise At Its Best!
1 3apartment , Big Pine Key
This Big Pine Key vacation rental is located in a tranquil setting, just 5 minutes from a boat ramp and offering distant ocean views. The property has received excellent ratings for location, user experience, and cleanliness.
The home comfortably accommodates up to 6 guests in 3 bedrooms, each with a comfortable bed. Enjoy amenities like a fully equipped kitchen, air conditioning, a private garden, and a wrap-around porch with breathtaking sunset views.
The home comfortably accommodates up to 6 guests in 3 bedrooms, each with a comfortable bed. Enjoy amenities like a fully equipped kitchen, air conditioning, a private garden, and a wrap-around porch with breathtaking sunset views.

Long Beach, Big Pine Key
10/09 – 10/19
$280/nighttotal: $2800 (10 )
2 Bedroom Aqua Lodge # 15 Porgie
1 2boat , Big Pine Key
This houseboat at the Old Wooden Bridge Resort and Marina in Big Pine Key, Florida, offers convenient access to resort amenities.
The one-bedroom, one-bathroom Aqua Lodge sleeps six guests and features a kitchen, air conditioning, and access to a swimming pool and parking; wet and dry slips are available for an additional fee.
The one-bedroom, one-bathroom Aqua Lodge sleeps six guests and features a kitchen, air conditioning, and access to a swimming pool and parking; wet and dry slips are available for an additional fee.

Long Beach, Big Pine Key
10/09 – 10/19
$334/nighttotal: $3340 (10 )
New Deluxe Duplex Unit, 2 Queen Beds, Unit H-5
1 2apartment , Big Pine Key
This two-bedroom apartment is peacefully situated in Big Pine Key, just a short distance from the beach and close to local shops and restaurants. The tranquil atmosphere makes it ideal for families seeking a relaxing getaway.
The rental sleeps up to six guests and offers a well-equipped kitchen with a refrigerator, microwave, and dishwasher. Enjoy the tropical climate in the garden, take a dip in the swimming pool, or simply relax in the air-conditioned apartment.
The rental sleeps up to six guests and offers a well-equipped kitchen with a refrigerator, microwave, and dishwasher. Enjoy the tropical climate in the garden, take a dip in the swimming pool, or simply relax in the air-conditioned apartment.

Long Beach, Big Pine Key
10/09 – 10/19
$534/nighttotal: $5340 (10 )
Old Florida Style, Wrap Around Porch, Boat Basin For Dockage, Open Water
3 2apartment , Big Pine Key
This waterfront Big Pine Key vacation home boasts stunning views and direct water access, situated within three miles of Florida Keys Beaches and the Big Pine Key Flea Market, and six miles from the Key West Visitor Center.
This 1700-square-foot house features three bedrooms, two bathrooms, and accommodates six guests, offering a fully equipped kitchen, in-house laundry, and a terrace—perfect for enjoying the Key's natural beauty.
This 1700-square-foot house features three bedrooms, two bathrooms, and accommodates six guests, offering a fully equipped kitchen, in-house laundry, and a terrace—perfect for enjoying the Key's natural beauty.

Long Beach, Big Pine Key
06/20 – 07/01
$744/nighttotal: $8184 (11 )
Tiki Time In Cudjoe Key 136
2 2apartment , Cudjoe Key
This Cudjoe Key waterfront home offers stunning views and direct access to the water, located within nine miles of Upper Sugarloaf Key, Florida Keys Beaches, Lower Sugarloaf Sound, the Big Pine Key Flea Market, and the National Key Deer Refuge Visitor Center.
This 860-square-foot vacation rental boasts two bedrooms, two bathrooms, and accommodates four guests, featuring a fully equipped kitchen, swimming pool, Jacuzzi, tennis court, and laundry facilities.
This 860-square-foot vacation rental boasts two bedrooms, two bathrooms, and accommodates four guests, featuring a fully equipped kitchen, swimming pool, Jacuzzi, tennis court, and laundry facilities.













