Discover the beauty of Cudjoe Key from this 4-bedroom combined two house listing. Guests find plenty of space to relax and unwind in a peaceful setting. With 4 bathrooms between the two properties, mornings are easy and convenient for everyone. The houses both stay comfortable year-round thanks to air conditioning and heating. Whether you’re gathering for a meal or just hanging out, the excellent layout makes it simple to feel right at home, and to be next door to your friends and family make this listing great to book. Enjoy Fishing Right off the Deck.





Please note- This listing is to rent out both houses that are next to each other to accommodate larger groups, this listing is the nightly rate for both the Unit 386 and Unit 385. I have included their separate VRBO links below to check them out individually as well.

UNIT 386
https://www.vrbo.com/1090660?expediaPropertyId=34110768&chkin=2026-07-09&chkout=2026-07-10&rm1=a2®ionId=6177802&destType=MARKET&sort=RECOMMENDED

UNIT 385
https://www.vrbo.com/5287904?expediaPropertyId=131681789&chkin=2026-07-09&chkout=2026-07-10&rm1=a2®ionId=6177802&destType=MARKET&sort=RECOMMENDED

** Also make note that when you arrive at The Gate, there is a one-time Administration fee of $125 plus Tax, payable upon entry by check or cash.
This fee goes directly Venture Out for the Guard shack with 24 hour maned service and all the services of Venture Out. ie. (equipment for all games on the property)
This is a one time fee and covers your complete stay either three days or 30 days.
Any questions while you are here just walk up the guard shack or call (305)745-1982

ADDITIONAL NOTE ON PARKING:
The following parking rules have been made by the Venture Out Board of Directors. This has been done to improve the appearance of common areas, to discourage long term storage, and to maintain parking in an orderly manner.
The Venture Out (VO) "Overflow parking lot" is designated for short-term (temporary) fee parking only. There is NO guarantee that space can be allocated for tenants during your stay.
Only licensed transportation vehicles, licensed boat trailers (with or without a boat), and licensed recreational vehicles (RVs) are authorized for short-term overnight fee parking in the overflow parking lot.
Commercial vehicles and storage trailers must get approval from management before they can park in the overflow parking lot.
Venture Out can only accommodate (when authorized and available):
a. One (1) licensed transportation vehicle in overflow parking and/or
b. One (1) licensed boat trailer (with or without a boat) -or- one (1) licensed recreational vehicle (RV) in overflow parking.
You may have one licensed transportation vehicle at your unit. All additional vehicles, trailers, and RV's must leave Venture Out property or purchase overflow parking depending upon availability.
Overflow parking may be purchased for a maximum of fourteen (14) days. Once you have reached the fourteen (14) day maximum you will not be able to purchase overflow parking for a six (6) month period.
Overflow parking outside of the designated overflow parking lot (north side of Pavilion) must be specifically coordinated with the Front Gate Security or it will be towed at the owner's expense.
Overflow parking rates are as follows:
a. Transportation vehicles are ten dollars ($10.00) per night.
b. Trailers under fifteen feet (15') are five dollars ($5 .00) per night.
Trailers fifteen feet (15') or longer are ten dollars ($10.00) per night.
RVs need to be evaluated by management.
VEHICLE/BOAT/TRAILER STORAGE (off-site)
Dolphin House at Venture Out provides you with 35 feet of concrete dockage in front of the house. You have your own swim ladder for swimming in the deep, saltwater canal, and there are two stainless steel padded cleats to secure your boat, should you bring one. If you wish not to store your trailer (or boat and trailer before launch) in the Venture Out Overflow Parking Lots, ($5.00 per day up to 15 ft., $10.00 per day 15 ft and over), OR if Venture Out overflow parking is not available, there are other options for storage. Check with any of these options or others you might find online:
Big Pine Storage, 30677 Overseas Hwy., Big Pine, (305) 872-2590
Cudjoe Boat Rentals & Repairs, 447 Drost Dr., Cudjoe Key, (305) 745-2352
Rudy Krause, 26351 Old State Rd. 4A, Ramrod Key, (305) 872-2100
Big Pine Key Industrial Park, 100 Industrial Rd., Big Pine Key, (305) 872-4457
Fanci Seafood, Overseas Hwy., Cudjoe Key, (305) 745-3887
Ryan Construction, 21423 Overseas Hwy., Cudjoe Key, (305) 872-9214