
Long Beach, Big Pine Key
06/22 – 06/30
$275/nighttotal: $2200 (8 )
Updated 2br/2ba Venture Out Home W/ Pool Access, Pet Friendly, Near Key West
2 2apartment , Cudjoe Key
This waterfront vacation rental on Summerland Key is an 8-minute drive to Upper Sugarloaf Key and a 14-minute drive to the National Key Deer Refuge Visitor Center.
This 820-square-foot apartment accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, offering amenities like a full kitchen, Wi-Fi, air conditioning, a swimming pool, hot tub, and on-site parking.
This 820-square-foot apartment accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, offering amenities like a full kitchen, Wi-Fi, air conditioning, a swimming pool, hot tub, and on-site parking.

Long Beach, Big Pine Key
06/22 – 06/30
$290/nighttotal: $2320 (8 )
Relax By Florida Keys Beaches, Just A 7-min Drive Away
2 2apartment , Cudjoe Key
This waterfront vacation home is located in Cudjoe Key, Florida, within a 15-minute walk of Venture Key and Venture Out Keys, and within 6 miles of Upper Sugarloaf Key and Florida Keys Beaches.
This 2-bedroom house comfortably accommodates 5 guests and features a private pool, a spa tub, and a fully equipped kitchen with a refrigerator, oven, stovetop, and microwave.
This 2-bedroom house comfortably accommodates 5 guests and features a private pool, a spa tub, and a fully equipped kitchen with a refrigerator, oven, stovetop, and microwave.

Long Beach, Big Pine Key
06/22 – 06/30
$188/nighttotal: $1504 (8 )
Rv In The Keys | Tropical Retreat
1 2cabin , Big Pine Key
"Rv In The Keys" offers a Big Pine Key campervan rental conveniently located in an RV park, 30 miles from Key West and 20 miles from Marathon, providing easy access to both destinations.
This one-bedroom, one-bathroom toy hauler sleeps four, features a full kitchen with fridge, freezer, and microwave, and boasts on-site amenities including a swimming pool, laundry facilities, and BBQ grills, plus a unique convertible patio for indoor/outdoor living.
This one-bedroom, one-bathroom toy hauler sleeps four, features a full kitchen with fridge, freezer, and microwave, and boasts on-site amenities including a swimming pool, laundry facilities, and BBQ grills, plus a unique convertible patio for indoor/outdoor living.

Long Beach, Big Pine Key
06/22 – 06/30
$237/nighttotal: $1896 (8 )
Island Home In Paradise #624 - Oceanfront Community!
2 2apartment , Cudjoe Key
This Cudjoe Key vacation home, located in the Venture Out gated community, is a 20-minute drive from Key West and 10 minutes from restaurants like the Square Grouper and Morning Joint.
The 700-square-foot property boasts two bedrooms, one bathroom, and sleeps four, featuring a fully equipped kitchen, private patios with a grill, and access to community amenities including an 80-foot heated pool, Jacuzzi, and tennis courts.
The 700-square-foot property boasts two bedrooms, one bathroom, and sleeps four, featuring a fully equipped kitchen, private patios with a grill, and access to community amenities including an 80-foot heated pool, Jacuzzi, and tennis courts.

Long Beach, Big Pine Key
09/03 – 09/08
$886/nighttotal: $4430 (5 )
Waterfront Captain House With Boat Basin & Ramp!
1 3apartment , Big Pine Key
This waterfront home on Little Torch Key is just steps away from the ocean and a short drive from Big Pine Key, offering a peaceful retreat with easy access to the area’s attractions. This property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The home features a spacious floor plan with a cozy queen bedroom, a heated massage recliner chair, and three smart TVs, comfortably accommodating up to 8 guests. Enjoy direct waterfront access, a private boat basin, a full kitchen with modern appliances, and outdoor amenities like a BBQ grill, beach chairs, and a bait freezer.
The home features a spacious floor plan with a cozy queen bedroom, a heated massage recliner chair, and three smart TVs, comfortably accommodating up to 8 guests. Enjoy direct waterfront access, a private boat basin, a full kitchen with modern appliances, and outdoor amenities like a BBQ grill, beach chairs, and a bait freezer.

Long Beach, Big Pine Key
06/22 – 06/30
$320/nighttotal: $2560 (8 )
New Deluxe Duplex Unit, 1 Queen Bed, Unit D-1
1 2apartment , Big Pine Key
This one-bedroom apartment is located in Big Pine Key, just a short drive from the island's beautiful beaches and natural attractions. The area is known for its peaceful and family-friendly atmosphere.
This comfortable rental has a full kitchen and bathroom, perfect for families or groups of up to four people. You'll also enjoy amenities like air conditioning, parking, and internet access.
This comfortable rental has a full kitchen and bathroom, perfect for families or groups of up to four people. You'll also enjoy amenities like air conditioning, parking, and internet access.

Long Beach, Big Pine Key
06/22 – 06/30
$224/nighttotal: $1792 (8 )
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
09/04 – 09/14
$399/nighttotal: $3990 (10 )
Waterfront Bungalow W/ Kitchen, Private Patio & Marina Views Near Snorkel Spots
3 1apartment , Big Pine Key
This waterfront vacation rental on Summerland Key is located just minutes from Looe Key Reef and Bahia Honda State Park, offering prime access to coastal activities.
This 660 sq. ft. condo accommodates up to six guests and features a kitchen, air conditioning, a shared heated pool, complimentary kayaks, paddleboards, and bikes, with pets welcome for an additional fee.
This 660 sq. ft. condo accommodates up to six guests and features a kitchen, air conditioning, a shared heated pool, complimentary kayaks, paddleboards, and bikes, with pets welcome for an additional fee.

Long Beach, Big Pine Key
09/04 – 09/14
$281/nighttotal: $2810 (10 )
2 Bedroom Aqualodge # 14 Yellowtail
1 1boat , Big Pine Key
This Big Pine Key houseboat, named Aqualodge, is located at the Old Wooden Bridge Marina.
The 2-bedroom, 1-bathroom floating home sleeps 6, features a kitchen, air conditioning, and offers access to marina amenities, including a swimming pool and on-site parking; pets are allowed for an extra fee.
The 2-bedroom, 1-bathroom floating home sleeps 6, features a kitchen, air conditioning, and offers access to marina amenities, including a swimming pool and on-site parking; pets are allowed for an extra fee.

Long Beach, Big Pine Key
06/22 – 06/30
$104/nighttotal: $832 (8 )
Luxury Pull Thru Rv Lot With Access To All The Resorts Amenities!
1 2resort , Cudjoe Key
Luxury RV Lot With Access To All The Resorts Amenities! is located in the Venture Out community on Cudjoe Key, mile marker 23, offering ocean views and easy access to Summerland Key attractions. This spacious 2,450-square-foot RV lot features water, sewer, and 50/30 amp electrical hookups, accommodating up to six guests and two dogs, plus access to an 80-foot pool, hot tub, tennis and pickleball courts, and a boat ramp.

Long Beach, Big Pine Key
09/04 – 09/14
$415/nighttotal: $4150 (10 )
Keys Beach Retreat Close To Key West
1 1apartment , Big Pine Key
This Big Pine Key condo offers a prime location, situated 3 miles from Bahia Honda Beach and 27 miles from Key West, with close proximity to the National Key Deer Refuge and Looe Key Reef.
This 3-bedroom, 2-bathroom vacation rental accommodates up to 11 guests and features a full kitchen, air conditioning, garden, and parking, making it ideal for exploring the Florida Keys' natural attractions and fishing spots.
This 3-bedroom, 2-bathroom vacation rental accommodates up to 11 guests and features a full kitchen, air conditioning, garden, and parking, making it ideal for exploring the Florida Keys' natural attractions and fishing spots.

Long Beach, Big Pine Key
06/22 – 06/30
$410/nighttotal: $3280 (8 )
Queen Studio W/ Kitchen, Pool & Beach Access Near Bahia Honda State Park
1 2studio , Big Pine Key
This studio apartment in Summerland Key is located 3 miles from Looe Key Reef and 4 miles from Bahia Honda State Park, offering convenient access to diving and nature exploration.
This pet-friendly unit accommodates up to two guests and features a kitchenette with a fridge and microwave, air conditioning, a private terrace, shared heated pool access, and complimentary kayaks, paddleboards, and bikes for waterfront relaxation.
This pet-friendly unit accommodates up to two guests and features a kitchenette with a fridge and microwave, air conditioning, a private terrace, shared heated pool access, and complimentary kayaks, paddleboards, and bikes for waterfront relaxation.













