A rare find — challenge friends and family to endless matches.
2 bedrooms1+ bathroomSleeps 4
Popular amenities
Hot tub on site
Patio
Swimming pool
Air-conditioning
Pet-friendly
Refrigerator
Explore the area
Cudjoe Key, FL
Upper Sugarloaf Key
Place, Upper Sugarloaf Key
7 min drive
Florida Keys Beaches
Place, Florida Keys Beaches
8 min drive
Upper Sugarloaf Sound
Place, Upper Sugarloaf Sound
8 min drive
Key West, FL (EYW-Key West Intl.)
Airport, Key West, FL (EYW-Key West Intl.)
38 min drive
Rooms & beds
2 bedrooms (sleeps 4)
Bedroom 2
2 Single Beds
Primary Bedroom
1 Queen Bed
1 bathroom, 1 half bathroom
Bathroom 2
Toilet
Primary Bathroom
Bathtub or shower · Toilet
Spaces
Deck or patio
Porch or lanai
Kitchen
Separate dining area
Dining area
About this property
Ground Level Waterfront 2BR in Venture Out - 23' Seawall, Pool, Marina & Pet Friendly
Welcome to Smuggler's Cove #414, a ground level, inviting 2-bedroom, 1.5-bath canal-front retreat located inside the private, gated Venture Out community on Cudjoe Key. Surrounded by swaying palms and laid-back island charm, this comfortable Florida Keys getaway offers the perfect setting for couples, small families, boaters, anglers, and anyone looking to relax near the water. With a 23-foot seawall accommodating boats up to approximately 21 feet, convenient dockside water, a fish-cleaning station, and quick access to the beautiful waters of the Lower Keys, Smuggler's Cove #414 makes it easy to enjoy everything that makes a Florida Keys vacation unforgettable. The Space Step inside to a bright, comfortable living space designed for easy island living. The welcoming living room provides plenty of room to unwind after a day of boating, fishing, or exploring the Lower Keys and features a 65-inch Smart TV for relaxing evenings at home. The dining table comfortably seats five, while the practical kitchen provides everything you need to prepare breakfast before heading out on the water, pack a picnic for the day, or enjoy a casual dinner at home. Start each morning with your favorite brew from the Mr. Coffee 12-cup drip coffee maker before heading outside to enjoy another beautiful day in paradise. Additional conveniences include an in-unit washer and dryer to make longer stays and days on the water even easier. Bedrooms & Sleeping Arrangements The home offers two comfortable bedrooms, each with its own cooling system for added comfort. Primary Bedroom: A cozy retreat featuring a queen-size bed, Smart TV, and quiet mini-split air-conditioning system. Guest Bedroom: Features a twin trundle bed and its own wall-mounted A/C unit, creating a comfortable and flexible sleeping space. Bathrooms The home features 1.5 bathrooms, giving everyone a little extra convenience during their stay. The full bathroom includes a tub/shower combination, perfect for rinsing off after a day at the pool, beach, or on the water. An additional half bathroom provides extra convenience for guests. Waterfront Living, Boating & Fishing Smuggler's Cove #414 is a wonderful home base for boaters and anglers looking to experience the incredible waters of the Lower Florida Keys. The property features a 23-foot seawall that can accommodate boats up to approximately 21 feet, giving you the convenience of keeping your boat just steps from the home. Dockside features include: Water hookup at the seawall Fish-cleaning station Convenient canal-front access After a day of fishing or exploring the surrounding waters, clean your catch right at the dock and settle in for a relaxing evening beneath the palms. Enjoy your meals outdoors at the concrete canal-side picnic table, where you can take in the tropical breeze and laid-back atmosphere that make the Florida Keys so special. Whether you're heading out to fish, cruise the surrounding islands, or simply enjoying the view from the water's edge, this home makes it easy to embrace the Keys lifestyle. Community Amenities at Venture Out Venture Out is one of the most amenity-rich communities in the Lower Florida Keys, offering: Marina store with fuel, bait, and convenience items Boat ramp and wash-down station Beautiful stretch of island along the oceanfront with many thatched roof umbrellas and loungers to take in the clean ocean breezes and relax Massive 80' heated saltwater swimming pool, hot tub, kiddie pool, and saltwater swimming lagoon Tennis courts, basketball, bocce, and pickleball On-site marina store/market and post office Electric Golf cart-friendly streets throughout the community Whether you want to spend the day boating, lounging by the pool, swimming, or enjoying the community amenities, Venture Out offers plenty of ways to enjoy your Florida Keys vacation. Location Smuggler's Cove #414 is conveniently located on Cudjoe Key in the Lower Florida Keys, putting you close to some of the area's favorite restaurants, waterfront hangouts, and attractions. Popular nearby favorites include Square Grouper, Morning Joint, The Bent Prop, Mangrove Mama's, Kiki's Sandbar, and Boondocks Draft House & Miniature Golf, all within approximately a 10-minute drive. Looking for even more dining, nightlife, shopping, and entertainment? Key West is approximately 20 minutes away, making it easy to spend the day exploring everything the Southernmost City has to offer before returning to your peaceful island retreat. Good to Know Pet Friendly: This home welcomes 2 dogs maximum with a $250 non-refundable pet fee per dog. Venture Out Registration Fee: A separate $125 registration fee, subject to change, is charged by Venture Out and paid directly to the community upon arrival. Payment may be made by cash or credit card. A 4% credit card fee may apply to the community registration payment. Guests are required to follow all Venture Out community rules and regulations during their stay. Parking Information Parking is limited to one vehicle per unit. The vehicle must fit completely within the designated driveway and may not extend into the roadway. Driveway measurements: approximately 15'L x 9.5'W. If your vehicle does not fit completely within the driveway, you will need to request an additional parking pass for the overflow lot from the Venture Out guard gate. Overflow parking is approximately $5 per day, subject to availability and community policies. Additional parking permits may be available through the guard station for an additional nightly fee for stays of up to 14 days, depending on availability. Because overflow parking is controlled by Venture Out and availability may change, it is not guaranteed. Age & Booking Requirements The primary guest must be 25 years of age or older. After your reservation has been accepted, the primary guest will be required to provide a copy of a valid government-issued driver's license or identification to the Rental Manager. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance. Payment Requirements A 4% credit card processing fee applies to credit card payments. Whether you're heading out for an early morning fishing trip, spending the afternoon enjoying Venture Out's resort-style amenities, or relaxing canal-side beneath the palms after a day on the water, Smuggler's Cove #414 offers a comfortable and convenient place to experience the laid-back lifestyle of the Lower Florida Keys. Book your stay and make Smuggler's Cove #414 your home base for your next Cudjoe Key getaway.
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Summerland Key
Located in Summerland Key, this holiday home is on the waterfront. Florida Keys Beaches and Upper Sugarloaf Key reflect the area's natural beauty and area attractions include Blue Hole and Big Munson Island. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and horse riding.
Boondocks Grille & Draft House - 10 min drive - 11.7 km
Lower Sugarloaf Sound - 11 min drive - 12.1 km
Getting around
Key West, FL (EYW-Key West Intl.) - 33 min drive
Restaurants
Boondock's Grille & Drafthouse - 9 min drive
Morning Joint - 20 min walk
Kiki's Sandbar - 12 min drive
Looe Key Tiki Bar & Restaurant - 10 min drive
Tonio's Seafood Shack & Tiki Bar - 6 min drive
Frequently asked questions
Does Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Ground Level Waterfront 2BR in Venture Out - 23' Seawall, Pool, Marina & Pet Friendly?
As of 9 Oct, 2026, prices found for a 1-night stay for 2 adults at Ground Level Waterfront 2BR in Venture Out - 23' Seawall, Pool, Marina & Pet Friendly on 13 Oct, 2026 start from S$649, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors pet-friendly?
Yes, pets are allowed at this property.
How much is parking at Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors?
On-site parking is available at the property.
What time is check-in at Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors?
Check-in begins at 4:00 PM.
What time is check-out at Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors?
Checkout is at 10:00 AM.
Where is Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors located?
Situated on the waterfront, this holiday home is within 6 miles (10 km) of Upper Sugarloaf Key, Florida Keys Beaches and Boondocks Grille & Draft House. Lower Sugarloaf Sound and Big Pine Key Flea Market are also within 9 miles (15 km).
Reviews
8.0
Very good
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Thank you so much for your review. We truly appreciate you taking the time to share your feedback. I noticed you rated your stay 4 stars, and we are always striving for a 5-star experience. If there is anything specific that could have made your stay better, we would genuinely love to know. Your feedback helps us improve and ensures future guests have the best possible experience.
Thank you again for staying with us, and we hope to host you again in the future.
About the host
Hosted by Bluescape Vacation Rentals
The Bluescape Vacation Rentals Team Cudjoe Key, Florida
Languages:
English, French
Premier Host
They consistently provide great experiences for their guests