Vacation Home Rentals By Owner In Cudjoe Key, FL

Waterfront Getaway in Venture OutbrbrWelcome to your perfect getaway! This beautifully updated vacation home offers comfort, convenience, and stunning canal views.brbrThe primary bedroom features a cozy queen bed, an ensuite bathroom, and plenty of storage space. A second bedroom/flex space includes a queen-size Murphy bed, allowing you to adapt the space to your needs. The family room provides extra sleeping accommodations with a queen-size pull-out sofa.brbrThe kitchen is a chef’s dream, fully updated with stainless steel appliances, including a dishwasher and double ovens, making meal prep a breeze. Enjoy your morning coffee or evening drinks on the back deck overlooking the canal, or relax on the inviting front porch.brbrStay connected with Wi-Fi and multiple smart TVs, allowing you to log in to your favorite streaming services. The home has been freshly painted and features a brand-new stackable washer and dryer for your convenience. Three mini-split AC units keep the space comfortable year-round.brbrOutdoor & Dock AccessbrbrBoaters will love the 35-foot dock, complete with dock posts and cleats, providing easy access to the pristine waters of the Lower Keys. Bring your boat, kayaks, or paddleboards and explore the beautiful surrounding waters.brbrEnhance Your Stay with Exclusive Add-Ons:brbr*Golf Cart Rental- zip to the pool or one of many other areas in the park with ease by renting our convenient 4 seater golf cart! (Available for an additional fee.)br*Concierge Service- Arrive to a fully stocked fridge with all your favorite groceries. Just send us a list, and we'll take care of the rest! (Additional fee applies.)brbrVenture Out offers resort-style amenities, including:brbr*Saltwater pool & kiddie poolbr*Basketball, bocce, pickleball & tennis courtsbr*Playground for the kidsbr*Marina with 2 boat ramps, store, fish cleaning table, pressure washer, ATM br and Fuel.br*24-hour gated securitybrbr***ADDITIONAL DETAILS***brbr* One-time entrance fee of $125 ($116.28 plus tax and CC fee if applicable, payable with CASH or CREDIT CARD ONLY at the Guard Gate. This fee covers everyone in your party and allows you unlimited use of all the amenities.brbr* Only ONE car is permitted at each lot. If you have more than one vehicle you will need to park in the overflow lot and pay a nightly fee: $5.00 for car or trailer under 20 ft or $10.00 for 20 ft or over. OVERFLOW PARKING IS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.brbrBook your stay today and experience the best of the Florida Keys from the comfort of this waterfront gem in Venture Out on Cudjoe Key!

Cottage

Canal front with open water views in Venture Out - Lot 529

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$124.31

RV Lot in Venture Out, Ocean Access & Resort AmenitiesbrWelcome to your perfect Florida Keys RV escape, located inside the private, gated community of Venture Out on Cudjoe Key. This RV lot offers full use of one of the most amenity-rich communities in the Lower Keys. Ideal for boaters, anglers, and anyone looking to experience true island living. **Please note this is for an RV Lot ONLY** There is no RV on this site. Bring your own RV and stay.brThe SpacebrThe 35' x 69' lot features a concrete pad with full hook-ups available, making it ideal for a comfortable and convenient stay in your own RV.brThere is no RV provided with this rental. Guests must bring their own RV.brThe property includes, electric, and sewer connections, allowing for a seamless setup upon arrival. Enjoy the tropical surroundings, ocean breezes, and the simplicity of outdoor island living.brEnjoy quick and convenient access to both:brThe Atlantic Ocean, perfect for offshore and reef fishingbrThe Gulf backcountry, known for flats fishing and calm cruisingbrLocated near Looe Key Reef, one of the most sought-after reef systems in the Florida Keys, offering exceptional snorkeling and diving just a short boat ride away.brAfter a day on the water, relax dockside and take in the peaceful canal views or head out to nearby sandbars for a true Keys experience.brVenture Out also offers a boat ramp and wash-down station, making launching and retrieving your boat easy and efficient.brCommunity Amenities at Venture OutbrVenture Out is one of the most desirable private communities in the Lower Florida Keys, offering:brMarina store with fuel, bait, and essentialsbrBoat ramp and wash-down stationbrOceanfront common area with tiki huts and lounge seatingbrHeated saltwater pool, hot tub, kiddie pool, and swimming lagoonbrTennis courts, pickleball, bocce, and basketballbrPlayground and open green spacesbrPost office and on-site convenience storebrElectric golf cart-friendly streets throughout the communitybrLocationbrYou're just minutes from local favorites including The Square Grouper, Mangrove Mama's, Kiki's Sandbar, and Boondocks Grille & Draft House, all within a short drive.brKey West is only about 20 minutes away, offering world-class dining, nightlife, shopping, and iconic attractions.brGood to KnowbrMinimum stay: 1 night (7-night minimum during Lobster Mini Season)brThis is an RV lot only – no RV, bedrooms, or bathrooms are provided, however community bath houses are located inside of Venture Out. brGuests must bring their own RVbrGolf cart rentals available: Available onsite brVenture Out registration fee: $125 (subject to change), paid directly at arrival (cash or credit card; fees may apply)brParking: 1 vehicle plus 1 RV must fit fully on the lotbrQuiet hours: 10:00 PM to 6:00 AMbrPrimary guest must be 25 years or olderbrPayment & Booking RequirementsbrSigned rental agreement and government-issued ID required after booking. Please reply to the email you receive from us after signing your Rental Agreement with a photo of your ID.brA 4% credit card processing fee applies to credit card paymentsbrWhether you're planning days of world-class fishing, boating out to the reef, or simply enjoying the laid-back island lifestyle, this waterfront RV lot offers a prime home base in the Florida Keys.

Florida Keys RV Lot in Venture Out | Ocean Access, Pool & Boat Ramp

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$281.42

Discover the beauty of Cudjoe Key from this marvelous 3-bedroom house. This delightful property features 1 queen bed, 2 twin bed, and 1 bunk bed, perfect for a cozy stay. With amenities like AC, WiFi, and a washing machine, guests can unwind and feel right at home. Kickback, relax, and enjoy everything Cudjoe Key and our house has to offer.

3 bedroom, 2 bath, canal home with hot tub

Cudjoe Key, Florida, United States

3

Bed

Bath

Sleeps

$160.36

Escape to paradise at this spacious 35' x 69' pull-through RV lot featuring stunning ocean and swimming lagoon views. Perfectly paved with pavers, this site offers easy access for larger rigs while keeping you just steps from the pool and the on-site store. Enjoy the convenience of a concrete picnic table with seating for four—ideal for morning coffee, outdoor dining, or sunset happy hours. A private renter's storage box is included for your gear, and lush tropical greenery lines both sides of the property, adding privacy and a welcoming island vibe. The spacious lot includes full hookups with water, sewer, and 110, 30, and 50 amp electric circuits, making it ideal for a variety of RV setups. With its prime location, refreshing ocean breezes, and close proximity to amenities, this RV lot is the ultimate Florida Keys getaway spot for comfort, convenience, and unforgettable views. This listing is for an RV site only—no RV is provided. The lot is situated within the gated community of Venture Out, which offers a wide array of amenities to enhance your stay. These include a heated pool and jacuzzi, tennis and pickleball courts, playgrounds, and a community boat ramp. There is also an on-site store for your convenience. electrical upgrades within the community, we encourage guests to contact us in advance for the most current information. Please be aware there is no cable or Wi-Fi provided at this site. Nearby, you'll find great dining options and local favorites such as Square Grouper Restaurant, My New Joint Cocktail Lounge, Morning Joint Coffee, the Bent Prop, Tonio's Seafood Shack and Tiki Bar, and family fun at Boondock's Mini Golf and Draft House. This lot offers the perfect balance of waterfront tranquility and easy access to adventure, dining, and entertainment in the Lower Keys. Venture Out charges a $125 registration/check-in fee upon arrival (subject to change). Parking is provided for one vehicle per unit, and an additional permit may be available for a nightly fee depending on availability. Guests must be at least 25 years old to book, and overnight occupancy is limited to six people who must be registered with both the Rental Manager and Venture Out. Up to two dogs are allowed per lot. Check-in time is 4:00 PM, and check-out is at 10:00 AM unless alternate arrangements are made with the Rental Manager in advance. A refundable $150 security deposit is required at the time of booking. There is a 4% credit card processing fee. The main guest must submit a copy of their driver's license and sign a rental agreement within 24 hours of booking. All reservations are subject to final approval from the local Rental Manager.

Oceanview 35'x69' Pull-Through RV Lot- Steps to Pool & Store, Lagoon Views

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$459.0

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, two-bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. The Sun-filled open floor plan allows the family to spend their precious time together cooking and entertaining. Enjoy the tranquil view from our front and back porches. Master Bedroom has KING bed and en- suite bathroom. Guest bedroom has luxury memory foam sleeper bed that sleeps 2. We also offer blow up mattress for the living room area. brbr***4 BIKES, 2 two person kayaks, beach chairs and umbrella included***brbr Community amenities include a large, heated pool, children's pool, hot tub, salt-water swimming area, basketball, pickleball, bocce, and tennis courts. Enjoy your stay within the resort or get out on the water with one of the local fishing, boating, or diving charters. And feel free to bring the family dog along on this vacation!brbr*** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***brParking notes- You may park 1 vehicle under the home. Park rules allow ONLY 1 vehicle, one motorcycle and 1 golf cart parked at any home. Overflow parking for additional vehicles or trailers is available for nightly charge. A pass may be purchased at the guard house. A guest may only bring 1 boat or 2 jet skis on 1 trailer.

Spanish Queen @Venture Out, Cudjoe Key

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$313.68

Cottage #14 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound with 2 swimming pools. Spacious cottage offers a full kitchen, screened patio, two queen bedrooms. The pool, dock and seawall are all available to our guests. A coin laundry is also available on site. Whether you come to the Florida Keys to escape the winters, or enjoy the calm waters and great fishing and diving of the summers, you will find Cudjoe Oceanside Cottage to be your Home Away From Home.

Cottage

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$642.32

Stunning Waterfront Getaway | 56' Dock + Ocean ViewsbrWelcome to Keys to Paradise #95, your perfect Florida Keys escape. This beautiful 2-bedroom, 2-bath waterfront home is tucked away on a quiet cul-de-sac in the gated community of Venture Out on Cudjoe Key, offering breathtaking ocean views, direct boating access, and lots of amenities. Whether you're here for world-class fishing, a family getaway, or simply to relax by the water, this home has everything you need for an unforgettable vacation.brHighlights - Prime Waterfront Location – Overlooks dazzling ocean views with private patio seating for sunrise coffee or evening cocktails.br56' Dock with Deep Water Access – Perfect for large boats or two smaller vessels, with cleats, water, and power. Quick access to the Atlantic and Gulf for fishing or sandbar hopping.brOutdoor Living – Covered balcony with dining set, spacious downstairs patio with loungers, Adirondack chairs, BBQ grill, picnic table, and space to play cornhole or relax in the breeze.brAmenities at Venture Out – Heated Olympic-size pool, hot tub, saltwater lagoon, tennis, pickleball, marina with fuel, store, and more—all within steps of your front door.brInside the Home - Open Living Room – Bright and airy with a wall of windows and sliding glass doors framing the ocean. Includes a 55” TV, leather sofa, and chairs with ottomans.brFully Equipped Kitchen & Dining – Granite island with barstools, seating for six, and everything you need for meals at home. There is a Keurig Single Cup & Mr. Coffee Drip coffee maker at this home for you to enjoy your favorite brew. brSpacious Bedrooms – Primary Suite: King bed, ensuite bath with walk-in shower, TV, and closet space.brGuest Room: Queen bed, private balcony, TV, and easy access to a full bath with tub/shower combo.brAdditional Sleeping: Futon in the living room + queen air mattress.brConveniences – Washer/dryer, high-speed WiFi, and a cargo lift to make moving luggage and groceries easy.brExtra Perks - Kayaks & Bikes – 4 kayaks and 4 bikes included for exploring the Keys by land or water.brFish Cleaning Station & Swim Ladder – Anglers can prep the day's catch with ease, and adventurous guests can take a refreshing dip right from the dock.brRenter's Closet – Extra refrigerator/freezer for bait or fish storage.brWhether you're boating, fishing, kayaking, or simply lounging by the ocean, this Florida Keys waterfront retreat offers the perfect balance of comfort, convenience, and adventure. Just 20 minutes from Key West and close to some of the best restaurants in the Lower Keys, Keys to Paradise #95 is your gateway to an unforgettable island vacation.brVenture Out is a golf cart friendly, private gated community that boasts a plethora of amenities to elevate your stay to the next level. Indulge in resort-style amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, pickleball courts, basketball and bocce courts.brAdventure beyond the gates for a bite to eat at some of Florida Keys favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki's Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away!brWhether you're a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the waters edge, our Florida Keys getaway promises an unforgettable vacation experience. Book your stay now and discover the ultimate blend of luxury, convenience, and coastal charm at our oceanfront retreat in Venture Out on Cudjoe Key.brImportant Notes - Sleeps up to 6 guests. Sorry, no pets allowed. 3 exterior security cameras: two in front (entry & storage) and one rear (dock area).brLocated inside Venture Out on Cudjoe Key. A separate Registration Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. This fee must be paid with cash or credit card (4% credit card fee will apply).Parking for 1 vehicle per Unit. This vehicle must fit on the driveway and not extend out to the road. The driveway measurements are 25'L x 10'W x 8'7H. If your vehicle does not fit when you arrive, you will need to see the guard gate for an additional parking pass for the overflow lot which costs $5/day. Extra parking permit may be available at the Guard Station for an additional nightly fee for a maximum of 14 days depending on availability. Must follow all the Rules and Regulations during your stay. Boat trailer parking is also available on a first come, first serve basis for an additional nightly fee. If the overflow parking is full when you arrive, no worries, we work with several other nearby storage lots.brMain guest must be 25 years of age or older and will need to email a copy of your drivers license to the Rental Manager after booking has been accepted. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance. There is a 4% credit card processing fee. brSocial Media -br@bluescaperealestatebrYouTube Videos @bluescapevacationsbrBook your stay today and experience the beauty of waterfront living!

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$497.33

BOAT RENTAL: We offer to rent our personal boats to our guests, only. We own:brFlats Boat - 17 ft Ranger with E Tech 75brBay Boat - 24 ft Bay Scout with 225 HP YamahabrOpen Fisherman - 29-ft Ocean Runner with twin 300 HP Verrado'sbrThese boats are set up with everything you need to fish the Keys, including spot lock trolling motors, Chart plotters, Depth finders, and everything else including fishing tackle. In the pictures you will see all three boats tied up at the docks. Please call me if you are interested. I get 15 calls a day from insurance scammers from all area codes. You may have to leave a message.br brFISHING AND DIVING. If you are fishermen or divers, Southern Sunset is an excellent property and location. Dockage for two boats. The 38-foot dock has a fish cleaning table, battery charging, and wash down hose. The Tiki Deck has an additional 14-foot dock that will accommodate up to a 24-foot bay boat, or smaller. Located on the ground floor, you will have 2 upright Bait Freezers and a COMMERCIAL GRADE ICE MAKER, 250-lb storage, 17-lb per hour. On the ground floor OUT OF THE SUN you will have plenty of room for all your dive gear, spear guns, fishing rods, coolers and other gear. brbrCruise 100 yards to the end of the canal, follow the markers and you have a straight shot to Looe Key National Marine Sanctuary, or American Shoal and beyond. Adolphus Bush Wreck - 15 miles, Key West Channel-21 miles, Sand Key Light-25 miles, End of the Bar-32 miles, Marquesas- 32 miles, Coal Bin Reef or Half Moon Shoal- 52 miles. If you want to explore the back country, it is 6 miles around the point to the Kemp channel bridge, 11 more miles to the edge of the Gulf.brbrIn front of the house there is parking for four vehicles, and one boat trailer. Until he gets his house built, my most amazing neighbor will allow additional parking for our boat trailers there on his property next door. You will have plenty of privacy here with fences and lush landscaping enclosing the property on both sides. brbrReady to relax Sit on the Sunset Balcony, or Tiki Hut dock at the end of the canal, and watch the amazing sunsets across the bay. Thanks to the prevailing easterly winds, the canal is most often clean and clear. Swim & snorkel right off the dock. Launch our paddle boards from the easy access launch ramp. Paddleboard out to the bay and snorkel for Lobster. Use the outdoor shower to wash off the salt water.brbrFeed the plentiful Mangrove Snapper, Lane Snapper, Small Grouper, angle fish, and baitfish right off your dock. We have a resident 24-inch Barracuda. You will enjoy that for sure. We supply the first bag of fish food!! brbrIf you want nightlife and shopping, it is a 20-mile scenic drive to Key West. Drive over in the evening and watch the breathtaking sunsets over the bridges and bays. brbrFor outdoor dining here at the house, use the outdoor refrigerator and barbeque grill for family gatherings on the shaded ground floor. You have table and bar seating on the ground floor for 18. On the Sunset Balcony there is additional seating for 4 at the glass top table and chairs, plus 2 more at the Sunset Table for 2. Inside you will have a dining table for 6, which can be converted to a table for 10. In the kitchen is seating for 4. brbr If you find time for TV, you will have a living room with three loveseat recliners and a wall mounted 72-inch ROKU smart TV with cable, internet, DVR, and Wi-Fi. Plus, a smart TV (no cable) downstairs behind the bar in the outdoor living area. brbrThe Smith family invites you to turn our house into YOUR house and enjoy your stay in the beautiful Florida Keys.

SOUTHERN SUNSET - As seen on House Hunters-S228 E6 - Family Time in the FL Keys

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$417.98

Mermaid House - VO089brOcean Views 35' Dockagebr2Bd/2Ba Midrise Covered PorchbrThis vacation home is located right off the open water and boasts expansive southeast exposure open water views! Features 35' concrete seawall equipped with dock posts, cleats and swim ladder. Spacious covered porch overlooks the beautiful open water with outdoor table and chairs. Master bedroom features a queen bed, closet storage and private full bathroom. The guest bedroom features a queen bed, closet storage and hallway bath access. brSECURITY DEPOSIT REQUIRED, NO SMOKING, NO PETS,br7 DAY MINIMUM LOBSTER SEASON, WIFI IN REC HALL, OVERFLOWbrPARKING IS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.br brVO REGISTRATION FEE $125**DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE

Mermaid House - Venture Out Lot 089

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$300.12

Pelicans View - VO318 brIsland Gem-Walk to POOL & Marina!brGorgeous Open Water Views! brThis beautifully remodeled midrise 2 bedroom with 1.5 bathrooms offers amazing views of the open water from the main living area and front porch so you can sit back, RELAX and listen to the sounds of palm trees swaying in the breeze, while overlooking the turquoise blue waters, the BEST the KEYS has to offer! You'll never want to leave this Island Home! Features include a spacious open kitchen with stainless steel appliances and large dining table that seats six. The living room features a sleeper sofa, two reclining chairs, flat screen television with DirecTV for expanded channels and free wifi all surrounded by windows and an oversized sliding glass door to bring the outdoors in. For the warmer days, it offers central air conditioning and ceiling fans in every room. This home is within walking distance to the pool, marina and store, and located right across the street from a common area so you'll never lose your view! There is a BBQ Gas Grill to cook your catch, located on the porch in back overlooking a tropical garden. The master bedroom features a queen size bed with private half bath, room darkening curtains and lots of closet space. The guest bedroom features a queen size bed with closet, access to the balcony and hallway full bath, Washer/Dryer. The flooring is easy maintenance laminate flooring, beautifully decorated interior with tropical island flair and gorgeous Aspen wood tongue and groove ceiling. The driveway length is 24' to accommodate oversized vehicles, what a plus! Small to medium size pet allowed with pet fee. brDon't wait, make your reservation today! brSECURITY DEPOSIT REQUIRED, NO SMOKING, 7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL, OVERFLOW PARKING IS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.brVO REGISTRATION FEE $125**DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE*****VEHICLE MAY NOT HANG INTO STREET- GUEST MUST VERIFY PRIOR TO RESERVING*****brONLY.

Pelicans View - Venture Out Lot 318

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$174.49

Captivating Oceanfront Getaway with 35` Durable Seawall! This property is equipped with a robust seawall featuring dock posts, whips, and cleats for secure mooring. Enjoy top-notch facilities including a heated saltwater pool, tennis, basketball, and bocce ball courts, a children`s play area, boat ramp, and a convenience store with a fueling station. Please note, rental RVs are not permitted on-site. A one-time registration fee of $125 is required at check-in.

Empty RV Lot with Amazing Views!

Cudjoe Key, Florida, United States

Bath

Sleeps

Exceptional(14)

$308

CUDJOE NEST WITH ENDLESS AMENITIES …brThis cozy cutie is nestled in the amazing Venture Out Resort! Your clean and comfy abode boasts all the basics to enjoy your Florida Keys lifestyle. A perfect destination for those who seek an active getaway in Paradise!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brYour charming home comes tastefully furnished and equipped for fun and functionality. The living and kitchen areas are a perfect backdrop for enjoyable hours of relaxation and peaceful slumber. The spacious eat-in kitchen is welcoming and invites intimate meals with your loved ones. Unwind with movie nights or rousing card games in this home away from home that soothes your senses with a warm island embrace. The washer/dryer is located in one of the bedroom closets.brbrSLEEPING ARRANGEMENTS…brEnjoy hours of healing sleep in the two plush queen bedrooms that share a bathroom with a walk-in shower. The bathroom is accessed through one of the queen bedrooms, and there is a second entry point through the kitchen (see virtual tour). The couch in the living area pulls out to provide an additional sleeping space.brbrOUTDOOR LIVING…brSoak up the island breeze on the charming back patio equipped with a table and BBQ grill. If you love to be active and close to all the exciting water opportunities, you've found the perfect place. Tennis and pickleball courts, a heated pool, spa, shuffleboard, horse shoes, basketball court, marina with ship store, along with 2 boat ramps, marine grade fuel station, and trailer/boat parking, the possibilities for fun are endless.brbrPARKING...brThis home offers one parking spot and a pet fee is required. There is an overflow parking lot on premises which is first come first serve at $5.-$10/night.brbrPETS...brThis home allows for 2 small dogs under 40 lbs. Please include the size and breed when inquiring. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrYOUR PLAYGROUND IN PARADISE…

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$311.05

Pack your bags and bring your boat! This home is located on the canal with easy access to the Gulf and Atlantic. It is equipped with everything you need for a relaxing resort-like feel with the privacy of a home away from home.brbrThe home features a 1488sqft spacious two-bedroom two-bathroom split open floor plan that comfortably sleeps four people. The Master Bedroom has a king bed, two dressers, large walk-in closet, and en-suite bathroom with shower. The Second Bedroom has a bunk bed with two full beds (175 lbs. weight limit for top bunk), and a pull-out twin. The hall bathroom has a tub/shower combo. The office has a desk, a reading chair, and plenty of books to read. The kitchen is properly equipped with a toaster, coffee maker, french press, coffee grinder, dishwasher, utensils, etc for all your cooking needs. The living room and master bedroom have a Smart TV (No Cable TV) for you to log into your own personal streaming services (Netflix, Amazon, Hulu, Sling, etc) and watch all your favorite tv shows.brbrWhether you want to browse the internet or vacation in the keys while working from home, we have you covered with the fastest internet available in the keys!brbrSnooze off in the hammock. Play some golf in the miniature putting range. Hike, walk or run the trails that extend for miles along the lush mangroves and water flats. Take a ride in the canoe or kayak or try your luck on the paddle boards. Swim in the pool or lounge around with a drink in your hand and soak in the sun. Fish off the dock, or take your boat out to one of the local fishing spots. brbrBring your Boat! 30ft Dock with fish cleaning station, 75ft canal width & 3-4ft draft.brbrMinutes away from some of the greatest eateries in the Keys. The Square Grouper just down the street, Mangrove Mamas 2 mins away, Boondocks 5 mins away, Grocery store 7 mins away. A short 25 min drive to Key West. brbrThings to Note:br* NO SMOKINGbr* NO PARTIESbr* NO PETS OF ANY KIND - (This is a private residence and due to the owner's extreme allergies no animals of ANY kind are permitted in the home or on the premises.) - Violation will result in complete forfeiture of security deposit.br* NO CHILDRENbr* Must be at least 30 years old to book - Copy of valid & current driver's license will be required before check-in date and receiving key/code to property.br* Additional fees and taxes may applybr*Water usage exceeding $100/month will be billed to guest and/or taken from security deposit.br*RV connections not permitted.brbrGuest will have access to the entire house.***brbr***Exceptions include: A locked bedroom closets inside the house. The downstairs garage will be locked as it is used for owners personal storage and not available for guest use. The owners RV/Boat may or may not be parked on the premises and is not available for guest use ***(There are Surveillance Cameras monitoring the RV/Boat and property 24/7 ) *** Please respect the restricted areas.brbr***For your safety and the security of the property, there are security cameras on the premises.***brbr****Any violation of any rule will result in immediate eviction and forfeiture of security deposit.****brbr****We keep the listing updated, however, Furniture and Decor may vary occasionally due to wear and tear****

Waterfront Relaxation and Barefoot Sunsets

Cudjoe Key, Florida, United States

Bed

Bath

4

Sleeps

$250.49

COMPLETELY RENOVATED TOP TO BOTTOM , GOLF CART INCLUDED !,2 BEDROOM , 35' DOCK WITH ALL NEW PAVERS AND 13' UMBRELLA , FISH CLEANING TABLE , HOSE AND ELECTRIC AT DOCK. COMMUNITY STORE , GIANT NEW RAM, ICE, BAIT, AND GROCERY. COMMUNITY POOL AND HOT TUB. DOG FRIENDLY. GATED COMMUNITY WITH FULL TIME GUARDS. brbr****PLEASE NOTE THERE IS A $120 REGISTRATION FEE IMPLEMENTED BY THE ASSOCIATION AND COLLECTED AT THE GATE.

20 MINUTES TO KEY WEST , BOATERS PARADISE

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$670.5

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina.brbrOn the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.brOther things to notebrThere is a community/resort fee of $107.50 that is collected from guests at the security gate upon arrival. The community allows one personal vehicle, one motorcycle and one golf cart on the property.

Cudjoe Key Home with a View

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$379.69

Heavenly Hideaway is a cozy waterfront cottage that provides a picturesque Florida Keys vacation setting. Take in the expansive open water views from inside the home from your covered porch, with outdoor dining or inside watching the sunset. brThe private 35-foot boat slip offers easy access to the beautiful waters. $125.00 registration fee due on arrival!brbrHeavenly Hideaway was recently renovated to a high standard, with Smart TV’s in the living room and both bedrooms. The kitchen is fully equipped with every appliance and tool you’ll need to prepare meals from home. This home accommodates up to 6 people in two bedrooms (a King and a bunk-bed full over twin). You’ll be able to bring your boat to dock on the 35' concrete seawall equipped with dock posts, cleats, fish cleaning table & swim ladder. brbrSister House located next door:brbrbrThere are some wonderful nearby places to explore, from Bahia Honda Beach (voted one of the top 10 beaches in the U.S.) and the American Shoal Lighthouse to snorkeling off Looe Key. For dinner out, consider the Square Grouper, Mangrove Mama’s and Tonio’s Seafood Shack just up the road. Last but not least, we are just a 25-minute drive to either Key West or Marathon, with all their attractions.brbrAmenities: Patio chairs, fish cleaning station, seawall / boat dockage and BBQ Gas Grill. Central Air Conditioning/Heating, High speed internet, WiFi, Smart TVs in living room and both bedrooms, full kitchen, microwave, dishwasher, refrigerator/freezer, cooking utensils, linens provided, beach towels provided, washer, dryer. Gated private community with Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball, bocce courts and ping pong. Vehicles must be under ten feet (10’) in width and must not exceed forty feet (40’) total length.brbrIMPORTANT NOTE: Venture Out Resort charges a one-time Registration/Resort Fee due upon arrival: $116.28 + $8.72 Tax = $125 for up to 6 people (Credit card or cash) PAID DIRECTLY TO VENTURE OUT. If you arrive with more than 6 people which is the maximum allowed in the home, you will not be permitted in the park.

Heavenly Hideaway 284 Charming 2-bedroom house in serene Cudjoe Key w/ WiFi, AC

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$393.94

DREAM COASTAL RETREAT…brIf dazzling open waters and deep draft boating and dockage is what you crave, look no further. Welcome to the coveted Cudjoe Ocean Shores sanctuary, where you'll enjoy premier boating access to world class fishing, snorkeling and diving in both the Atlantic Ocean and the tranquil Gulf of Mexico. Come home to this stunning and serene canal retreat!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brStep into this modern beauty and cast your cares to the inviting breezes of your tropical Paradise. Spread out in all the glorious spaces this home affords you and make priceless memories with your crew in this exquisite 4 bedroom 3.5 bath beauty. An open floor plan with state-of-the-art finishes guarantee an exceptional experience from beginning to end. Immerse yourself in luxury with a high-end chef's kitchen, designer lighting, custom tiled baths with waterfall effects, and California Closets in each bedroom - the love is in the details! brbrSLEEPING ARRANGEMENTS:brThe first bedroom features two twin beds (which can be converted to a king bed upon request) and an en suite shower bathroom. The second bedroom offers a king bed with a desk and an en suite shower bathroom. There is also a queen bedroom and another king bedroom; they share a jack and jill shower bathroom. A sofa sleeper resides in the living room for additional sleeping arrangements with a powder room nearby.brbrOUTDOOR LIVING…brThis is a boater's dream for outdoor spaces. Enjoy a huge covered porch area with a table and plentiful seating adjacent to the sparkling custom pool (comes heated in the cooler months), concrete sea wall, fish station and deep canal with direct Atlantic Ocean access. Tie the boat up (NO BOAT LIFT AVAILABLE) and head out on your boating adventures. Quiet location and close distance to Bahia Honda State Park. Four bikes provided as well! brbrPARKING...brAmple space is provided with covered parking under the home for your cars and boat. brbrPETS...br2 dogs are permitted at this home and a pet fee is required. Please include the size and breed when inquiring. brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrBRING THE BOAT...

ARTIST HOUSE ~ Canal Front 4 BR/3.5 Ba Home w/ Pool & Ocean and Gulf Access!

Cudjoe Key, Florida, United States

4

Bed

3

Bath

8

Sleeps

$152.34

Park your RV and relax in your own slice of paradise! This beautifully landscaped lot is surrounded by mature palm trees, offering shade, privacy, and a true island vibe. Both the driveway and patio area are paved, making it easy to bring your car, set up patio furniture, and enjoy outdoor living in comfort. Expansive lot measuring 69' in length and 35' in widthbrA renter's storage box is included - perfect for stowing away fishing gear, snorkeling equipment, or beach toys. For your RV, you'll find full hookups with water, sewer, and 30-amp/50-amp electrical service, giving you everything you need for a seamless stay.brWhether you're chasing sunny summer days on the water or escaping to milder winter weather, this RV lot is the ideal Keys home base. Please note there is no cable or Wi-Fi service provided at this site. This is for an RV lot only- NO RV is provided! The lot is situated within the gated community of Venture Out, which offers a wide array of amenities to enhance your stay. These include a heated pool and jacuzzi, tennis and pickleball courts, playgrounds, and a community boat ramp. There is also an on-site store for your convenience. brNearby restaurants and bars include Square Grouper Bar & Grill & My New Joint to enjoy some exquisite meals and craft cocktails, Broil Steakhouse is well known for their amazing steaks and service, Boondocks Grille & Draft House is a fun, family friendly huge tiki bar and restaurant with miniature golf, Looe Key Bar has live music nightly and The Bent Prop you can dine on the water! Close by is Murray's Market and Winn-Dixie for your grocery needs. Explore all the Lower Florida Keys has to offer! **No cable or WIFI service is provided at this site** Please note that a Registration/Check-In Fee of $125 (subject to change) will be charged by Venture Out Security upon arrival. Additionally, parking is available for only one vehicle per unit, and extra parking permits may be obtained from the Guard Station for a nominal nightly fee, subject to availability. It is important to adhere to all Rules and Regulations during your stay. Applicable county and state taxes are collected regardless of the booking platform. Renters must be 25 years or older, and overnight occupancy is limited to a maximum of 6 people, all of whom must be registered with the Rental Manager. Furthermore, up to 2 dogs are permitted per Venture Out Regulations. Check-in time is at 4pm, and check-out time is at 10am unless alternative arrangements have been made with the Property Manager prior to arrival. To safeguard both guests and the property owner, a refundable $150 Security Deposit is required at the time of booking. There is a 4% credit card processing fee. Immerse yourself in the laid-back charm of Cudjoe Key and make the most of your vacation by securing this inviting RV Lot. The main guest of the reservation will be required to submit a copy of your driver's license to the Rental Manager for our records. The Rental Agreement is required to be signed within 24 hours from time of booking. All reservations are subject to final approval from the local Rental Manager.

Tropical RV Lot Oasis in the Florida Keys with Paved Patio, Full Hookups & Palm-Tree Privacy

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$281.25

It's Time for some Fun in the Sun here at Venture Out's gated community on Cudjoe Key located at Mile Marker 23 in the Florida Keys!brA cozy 1 bedroom, 1 bath cottage with a 35' concrete seawall that will accommodate up to a 32' boat. brThe bedroom has a Queen size bed. The bathroom is located just outside of the bedroom and is equipped with a tub/shower combo.brIn the living room there is a queen sleeper sofa for additional sleeping accommodations and TV. brThe fully equipped Kitchen will make any Chef happy. There is a Keurig / Drip Coffee Maker at this home for you to enjoy your favorite brew. It also features an island with bar stool seating. There is a laundry closet inside the home with washer and dryer.brOutdoor you will find a BBQ grill and colorful patio table with 4 chairs and a chaise lounge to relax and enjoy your fresh catch dinnersbrTandem kayak and 2 bikes are available for your use to explore the islands. There is a bait freezer inside the home to store your fishing supplies and fresh catches.brWith its seamless blend of style, comfort, and convenience, Blue Mind #225 is the quintessential retreat for those seeking a classic Florida Keys vacation.brYour slice of paradise awaits – book your stay her and prepare to bask in the splendor of the Florida Keys.brThis is a pet friendly home for 1 dog or 2 small dogs with a $250 pet fee per pet . Rental manager must be notified at time of booking. brIf your group is larger than 4 persons, we have another property just 5 doors away on the same canal, which sleeps 6. The Property Name is Big Blue #230 and VRBO property ID is 4358000. These homes are not connected, but a very short, easy walk down the road so your group could stay within steps of each other. brVenture Out is a golf cart friendly, private gated community that boasts a plethora of amenities to elevate your stay to the next level. Indulge in resort-style amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball and bocce courts.brAdventure beyond the gates for a bite to eat at some of Florida Keys favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki's Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away!brWhether you're a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the waters edge, our Florida Keys getaway promises an unforgettable vacation experience. Book your stay now and discover the ultimate blend of luxury, convenience, and coastal charm at our oceanfront retreat in Venture Out on Cudjoe Key.brLocated inside Venture Out on Cudjoe Key. A separate Registration Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. This fee must be paid with cash or credit card (4% credit card fee will apply). Parking for 1 vehicle per Unit. This vehicle must fit on the driveway and not extend out to the road. The driveway measurements are 16'L x 10.5'W. If your vehicle does not fit when you arrive, you will need to see the guard gate for an additional parking pass for the overflow lot which costs $5/day. Extra parking permit may be available at the Guard Station for an additional nightly fee for a maximum of 14 days depending on availability. Must follow all the Rules and Regulations during your stay.brMain guest must be 25 years of age or older and will need to email a copy of your drivers license to the Rental Manager after booking has been accepted. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance. There is a 4% credit card processing fee. brSocial Media -br@bluescaperealestatebrYouTube Videos @bluescapevacationsbrBook your stay today and experience the beauty of waterfront living!

Mobile Home

Blue Mind #225, 35' Seawall Venture Out

Cudjoe Key, Florida, United States

Bed