Vacation Home Rentals By Owner In Cudjoe Key, FL

Welcome to your Florida Keys getaway! Unit #22 is a beautifully updated 2-bedroom, 2-bath home in Venture Out offers modern comforts and coastal charm, all just a short stroll from the community's top amenities.brStep inside to find a bright, open living area with a comfortable sofa, two recliners, and a smart TV for all your favorite streaming platforms. The fully equipped kitchen features stainless steel appliances, ample counter space, and everything you need to enjoy meals at home. There is a Keurig Single Serve coffee maker at this home for you to enjoy your favorite brew. brRelax in the spacious master suite with a plush queen bed, mirrored closets, and smart TV, or retreat to the inviting guest bedroom with a queen bed and smart TV. There is also a Queen size air mattress located in the Guest bedroom closet for additional sleeping options. With two full bathrooms, this home is ideal for families, couples, or friends traveling together. Cheerful coastal décor and tile floors throughout add to the fresh, modern feel.brEnjoy Florida's sunny weather on the screened-in porch, complete with wicker seating and string lights for cozy evenings. This outdoor space is perfect for morning coffee, evening cocktails, or simply soaking in the laid-back Keys lifestyle. Fire up the propane Nexgrill for family cookouts after a day of adventure.brThis home is conveniently located within walking distance to all of the community's amenities, making it easy to enjoy everything Venture Out has to offer. A golf cart is also available at the home for $40 per day or $200 per week with a signed golf cart waiver. Whether you're here to fish, boat, explore, or just relax, this home has everything you need for an unforgettable stay.brOne small dog is welcome with a non-refundable pet fee of $250. Standard occupancy is up to 6 guests.brVenture Out is a golf cart friendly, private gated community that boasts a wide variety of amenities to elevate your stay. Enjoy amenities such as a marina store with onsite fuel, bait and convenience market, boat wash-down station, an 80-foot heated pool, Jacuzzi, large kiddie pool, saltwater swimming lagoon, post office, two lighted tennis courts, basketball courts, and bocce.brJust beyond the gates, you'll find some of the Florida Keys' best restaurants, including Square Grouper, Morning Joint, The Bent Prop, Mangrove Mama's, Kiki's Sandbar, and Boondocks Draft House & Miniature Golf—all within a 10-minute drive. For even more fun, head 20 minutes south to Key West. Whether you're a seasoned angler eager to explore world-class fishing grounds or simply seeking relaxation by the water's edge, this Keys retreat promises an unforgettable experience.brThe driveway measures 11.2 feet wide by 18 feet long. Parking is limited to one vehicle per unit, and the vehicle must fit entirely within the driveway. If your vehicle does not fit, you will need to obtain an additional parking pass for the overflow lot for $5/day, available at the guard gate (maximum 14 days, subject to availability).brA separate registration fee of $125 (subject to change) is charged by Venture Out upon arrival. This fee must be paid with cash or credit card (4% credit card fee applies). Guests must follow all community rules and regulations during their stay.brThe main guest must be 25 years of age or older and provide a copy of their driver's license to the rental manager after booking. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance.brThere is a 4% credit card processing feebrFollow us on social media @bluescaperealestate and find property videos on YouTube at @bluescapevacations. Book your stay today and experience the beauty of waterfront living!

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Cudjoe Key, Florida, United States

Bed

Bath

6

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

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

$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

$249.48

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

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

6

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

Bed

3

Bath

8

Sleeps

$318.04

Beautiful Florida Keys Home located in a Gated Community with Lots of Amenities!brWelcome to Casa del Mare #42 - Your perfect getaway! This beautiful 2-bedroom, 2-bath home offers everything you need for a relaxing and enjoyable Florida Keys vacation. Open living room to the fully equipped kitchen and dining area.brKey Features:br*Open Kitchen Dining: The fully equipped kitchen opens to a welcoming dining area that comfortably seats up to 4, perfect for family meals or entertaining friends. There is a Kenmore drip drip Coffee Maker at this home for you to enjoy your favorite brew.br*Spacious Bedrooms: Two cozy bedrooms designed for comfort, ensuring restful nights after your adventures.brThere is a Queen size bed in the primary bedroom and an ensuite full bathroom for privacy equipped with a stand up shower.brThe Guest bedroom has a full size bed and the full guest bathroom is located just steps away in the hallway for your guests convenience. There is also an attached balcony for your guests to use in the morning to enjoy the views and a cup of coffee or sit out there at night to do a little stargazing.brThere is also a pull out sleeper sofa bed in the living room for additional sleeping accommodations.br*Outdoor Oasis: Enjoy the expansive covered patio downstairs with plenty of seating. A BBQ grill is here for you to cook up your fresh catches too.br*Laundry Facilities: A washer and dryer are available within the home, so you can pack light and keep your clothes fresh throughout your stay.brWhether you are here for a weekend getaway or an extended vacation, our waterfront retreat promises a unique blend of relaxation and adventure. Explore the local attractions, enjoy the water activities, or simply kick back and enjoy the stunning views from your patio.brThis home has a 4 person maximum occupancy. 4 guests allowed plus 1 child.brSorry, no pets allowed at this home.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 25'L x 10'W x 8'6H. 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 @bluescapevacations

Casa del Mare #42 - Oceanfront, Gated Community!

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$341.45

Beautiful and cozy 4 bedroom, pool home located on Cudjoe key with excellent boating access to the Atlantic or the Gulf. Nice and quiet location. With no one directly across the canal, this home is ready for you to enjoy. Located just 23 miles from Key West, this home is great for extended stays. The interior features an open living area with eat-in island, fully equipped kitchen, 65 inch flat screen TV, great screen porch that over looks the canal, elevated decks, 85ft dock and pool area. The Upstairs bedrooms both have King size beds, and Master offers a spacious closet and 1/2 bath en-suite. Downstairs features 2 bedrooms with 3 queens and futon, outdoor shower with hot and cold water, storage shed for fishing equipment, patio and outdoor dining area. Call and book this property today for a vacation you will remember for years to come!!

Spectacular 4 bedroom 2 bath pool home with great boating

Cudjoe Key, Florida, United States

3

Bed

1

Bath

6

Sleeps

$817.26

If you are looking for the ultimate Keys vacation, your search is over!! This private 4 bedroom 3.5 bath luxury estate home boasts a custom heated pool with spa, fire feature, huge outdoor living area with TV, pool table, beautiful wood table with seating for 8-10, covered garage and entryway, excellent boating with immediate access to the Atlantic and the Gulf, paddle boards and kayaks available for exploring the bay area. The breathtaking interior features an open living area with hotel quality elevator which services all 3 floors perfect for groceries and/or persons that have trouble with stairs, Sonos surround sound system through out the entire house and outdoor area, gorgeous fully equipped kitchen, top of the line appliances, eat in bar, and dining area. The main floor consists of 3 bedrooms (2 queen beds and 2 full size beds) and 2.5 baths. The master features a kings size bed with a stunning master bath with custom glass and marble walk in shower and walk in closet. Enjoy the southern breezes from the private balcony off of the master bedroom with endless views of the Atlantic.This home is by far one of the nicest homes in the Florida Keys!! Come experience it for yourself!!

Stunning 4 bedroom 3.5 bath Open Water home with great boating

Cudjoe Key, Florida, United States

Bed

3

Bath

8

Sleeps

$280.84

Welcome to Pirate’s Paradise – your ideal tropical escape in the Lower Keys! brbr brbrThis 3-bedroom canal front home on Cudjoe Key offers the perfect mix of relaxation, adventure, and island charm. brbr brbrStep into a bright, breezy living space with coastal decor and an open layout that brings everyone together. The well-equipped kitchen makes meal prep a breeze, and the comfortable furnishings invite you to unwind after a day on the water. brbr brbrOutside, you’ll find a private heated and chilled pool for year-round comfort, surrounded by lush landscaping and space to soak up the sun or sip cocktails in the shade. Boaters will love the convenient dockage with easy access to both the Atlantic and the Gulf, making this the perfect home base for your Florida Keys adventures. brbr brbrWhether you’re reeling in the catch of the day, exploring nearby islands, or simply enjoying canal views and island breezes, Pirate’s Paradise is your ultimate Cudjoe Key retreat. brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1: King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 2: Queen Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 3: Queen Bed, Smart TV (no cable/satellite TV) brbr brbrLiving Room: Sofa W/ Pull Out Queen Bed, Two Chairs, Smart TV (no cable/satellite TV) brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- 60' seawall (maximum 36' boat/trailer) brbr brbr- Private Heated/Chilled Saltwater Pool (heated/chilled to ~85-87 degrees) brbr brbr- Outdoor Seating brbr brbr- Propane BBQ Grill brbr brbr- Linen's and towels provided brbr brbr- Parking for up to 4 vehicles, including boat trailers. RV's are not permitted. brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrMinimum Rental Period: County of Monroe zoning requires a minimum rental period of 28 nights, and no exceptions can be made. brbr brbrAge and Occupancy Requirements: Booking tenant must be 25 years of age or older and must occupy the property for the entire duration of the booking. Furthermore, this property is exclusively available as a vacation rental and is not available for worker housing. brbr brbrNo Smoking: Smoking is strictly prohibited within the property. For the comfort and safety of all guests, please refrain from smoking indoors. brbr brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. brbr brbrBoating Safety: Due to bridges and varying water depths, it is your responsibility to verify that your boat can safely navigate the local waters, access the canal, and fit the listed dockage before booking this property. Please ensure that your boating activities are conducted safely and in compliance with local regulations. brbr brbrWildlife & Pest Advisory: The Florida Keys are home to various insects, including mosquitoes, no-see-ums, termites, etc. While routine pest control is in place, complete elimination is not possible. Additionally, guests may encounter geckos, lizards, iguanas, frogs, and chickens, which are part of the natural environment. We encourage guests to take necessary precautions, such as using insect repellent and keeping doors closed, to minimize exposure. Enjoy the beauty of the Keys with an understanding of its unique ecosystem! brbr brbrConstruction Notice: The Florida Keys are resort islands where renovations, new construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by construction in the area. brbr brbrImage Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and owners frequently update their properties. Additionally, photos are taken in different lighting conditions, and screen settings may affect how colors appear. For the most accurate information, please refer to the written description and feel free to reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time.

Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$462.32

Step onto the spacious covered porch and take in the stunning open water views that seem to go on forever. With plenty of outdoor space, it’s perfect for relaxing in the ocean breeze or entertaining with a view. Just 19 miles from the excitement of Key West. VO REGISTRATION FEE $125.00DUE UPON ARRIVAL. Overflow parking for boat trailers and extra vehicle is available for an additional fee and is available on a first come first serve bases and is not guaranteed.

Salty Kisses in Cudjoe Key

Cudjoe Key, Florida, United States

Bath

Sleeps

Exceptional(4)

$475.21

Welcome to the Blue Pearl – Cudjoe Key, FloridabrbrSpacious Canal-Front Home | Private Pool | Boat Lift | 4 Bedrooms + Bonus RoombrbrExperience tropical living at its finest at The Blue Pearl, a beautiful 2,693 square foot canal-front home in Cudjoe Key. Perfect for large families, boaters, and entertaining, this well-appointed property offers comfort, space, and stunning waterfront amenities in the heart of the Florida Keys.brbrHome Highlightsbrbr4 Bedrooms | 4 Full BathroomsbrbrOptional Bonus Room with 2 additional bedsbrbrPrivate Pool (heating available seasonally)brbr16,000 lb Boat Lift (with approval)brbrFish Cleaning Station & Canal Accessbrbr4 Spacious Balconies with Water ViewsbrbrCovered Outdoor Entertaining Areabrbr2 Ocean Kayaks & 2 Bicycles for Guest UsebrbrInterior FeaturesbrbrThe Blue Pearl blends luxury and comfort with custom design features throughout, including crown molding, tray ceilings, and stone/tile finishes in every bathroom. The open-concept layout includes:brbrA large living room with ample seating, oversized windows, and a custom entertainment wall with flat-screen TVbrbrA gourmet kitchen with wood cabinetry, hammered copper sink, GE Café appliances, and a built-in microwave drawerbrbrA dedicated wet bar with a built-in ice machine, ideal for entertainingbrbrBedroom LayoutbrbrPrimary SuitebrbrKing bed, sitting chair, chest of drawers, flat-screen TVbrbrEn-suite bathroom with glass-enclosed shower and vanitybrbrGuest Suite 1brbrQueen bed, dresser, flat-screen TVbrbrEn-suite bathroom with shower and vanitybrbrGuest Suite 2brbrQueen bed, dresser, flat-screen TVbrbrEn-suite bathroom with shower and vanitybrbrBunk RoombrbrTwo sets of twin bunk beds (4 total), flat-screen TV, large closetbrbrShares a full bathroom with shower and vanitybrbrBonus Room (Optional Add-On)brbrLocated on the ground floor with 2 additional twin bedsbrbrAvailable for guests 11 and 12 at $125.00 per nightbrbrMust be reserved in advancebrbrOutdoor AmenitiesbrbrPrivate pool (heating available from October 1 – May 15 at $20.00 per day, 7-day minimum)brbr16,000 lb boat lift (center consoles under 28 feet only; registration, insurance, and signed waiver required)brbrLarge covered area under home for shaded entertainingbrbr4 spacious balconies with open water viewsbrbrFish cleaning station for anglersbrbr2 kayaks and 2 bicycles available for guest use (waivers required)brbrGuest Access and Use GuidelinesbrbrBoat LiftbrbrAvailable to guests with prior approvalbrbrRequires proof of insurance, vessel registration, and signed liability waiverbrbrOnly center consoles under 28 feet permittedbrbrFlats boats and catamarans are not allowed on the liftbrbrKayaks and BicyclesbrbrTwo ocean kayaks and two bicycles includedbrbrLiability waivers must be signed before arrival to receive access codesbrbrLife jackets must be worn at all times when using kayaksbrbrGuests born after 1984 must present a valid Florida Boater Safety Course certificatebrbrParkingbrbrMaximum parking: 2 vehicles and 1 boat or boat trailerbrbrNo additional vehicles allowed on propertybrbrPet PolicybrbrOne dog permitted (under 50 lbs) with prior approval onlybrbr$20.00 per day pet feebrbrPet reduces total guest occupancy by one personbrbrPet arrangements must be made prior to check-inbrbrAdditional Fees and NotesbrbrBonus Room: Optional at $125.00 per night (for guests 11 and 12)brbrPool Heating: $20.00 per day (October 1 to May 15 only; must be arranged before check-in)brbrPool heat is not included in standard rental ratebrbrMinimum rental age: 25brbrNo parties or events permittedbrbrYour Keys Getaway AwaitsbrbrWhether you're boating, relaxing poolside, or enjoying the views from one of the balconies, The Blue Pearl is the perfect setting for your Florida Keys escape. Comfortably designed with upscale finishes and thoughtful amenities, this home is ready to welcome you.

BLUE PEARL - 5 Bedroom/ 4 Bathroom Pool, Kayak, Bike, Canal Front w/ Boat Lift

Cudjoe Key, Florida, United States

5

Bed