Vacation Home Rentals By Owner In Cudjoe Key, FL

$418.07

Upscale Canal-Front Escape w/ Private Pool, Dock & Water Views

Cudjoe Key, Florida, United States

Waterfront 3BR Brand New, Modern Home on Cudjoe Key with a in Venture Out with a 75' Dock, Pool, Ocean Views, World-Class Fishing & Boating AccessbrWelcome to Costa Vida, a freshly built coastal retreat set on a deep-water canal in the Florida Keys, where modern luxury meets effortless island living. This stunning 3-bedroom, 3.5-bath canal front home is designed to impress, offering a private pool, expansive water views, and a 75-foot dock located on Cudjoe Key. This inviting retreat is ideal for couples, boaters, and anglers looking to enjoy the Florida Keys with direct water access, nearby restaurants, and easy island living.brThe SpacebrThis well designed, brand new concrete home offers an open-concept living area filled with natural light and an elegant yet coastal charm. The modern kitchen features gorgeous stone countertops, bar-top seating, and a dining area for six, making it easy to enjoy meals at home. Coffee lovers are well covered with a Keurig coffee maker.brFor added convenience, high-speed Wi-Fi is available throughout the home, and a washing machine and dryer are provided for use during your stay, making longer visits and boating days easy and comfortable. The home is cooled by central air conditioning, allowing for efficient, customizable comfort.brThe living room features an 86'' LG Smart TV and provides a comfortable space to relax after a day on the water.brDownstairs is the place to be to enjoy the gorgeous swimming pool.brBedrooms & Sleeping Arrangements - All Bedrooms offer ensuite bathrooms for exceptional privacy and convenience.brPrimary bedroom: This is a true sanctuary, featuring a King-size bed, 55'' LG Smart TV, and a private balconybrGuest Bedroom #1: This room features a Queen-size bed and 55'' LG Smart TVbrGuest Bedroom #2: This room features a Queen-size bed and 55'' LG Smart TVbrMaximum occupancy: 6 guestsbrBathroombrFull Primary Bathroom: Ensuite spa-inspired bathroom with a walk-in shower and double sinks.brFull Guest Bathroom #1: Features a walk in shower with glass enclosure and a single sink.brFull Guest Bathroom #2: Features a soaking tub and shower and single sink.brHalf Guest Bathroom: Equipped with a sink and toilet for guest convenience.brWaterfront Living, Boating & FishingbrCosta Vida is a true boater and angler-friendly getaway, featuring a 75' concrete dock that can accommodate boats up to approximately 35 feet, with easy access to open water via a very short canal ride. Conveniently located near Looe Key, one of the most famous reef systems in the Florida Keys, offering world-class snorkeling, diving, and vibrant marine life in crystal-clear waters just a short boat ride away. Picnic Island is a nearby local sandbar popular with locals and visitors. A beautiful place to hang out after a day of fishing.brGuests enjoy world-class fishing opportunities, with convenient access to both:brThe Atlantic Ocean, ideal for offshore and reef fishingbrThe Gulf backcountry, known for exceptional flats and inshore fishingbrThe private dock includes a fish cleaning station. brGuests will also enjoy the ocean views from the backyard, calm canal views and effortless days on the water.brAfter a day outdoors, unwind with the propane gas grill, perfect for preparing your fresh catch or an easy island-style dinner.brLocationbrYou're just minutes from popular local favorites including Square Grouper, Morning Joint, The Bent Prop, Broil, Mangrove Mama's, Kiki's Sandbar, and Boondocks Draft House with mini golf, all within a 10-minute drive. Key West is only 15-20 minutes away, offering additional dining, nightlife, and iconic attractions. brGood to KnowbrMinimum stay: 27 nights per Monroe County OrdinancebrStarter supplies provided: A starter supply of toilet paper and paper towels is provided and typically lasts 1–2 daysbrThis is a pet friendly home. Up to 2 housebroken dogs allowed with a paid pet fee of $250 per pet. We must be notified at time of booking. brParking: This home allows parking for up to 2 vehicles plus 1 boat trailer. If you need additional parking please let us know and we can assist in some alternatives. brAge requirement: Primary guest must be 25 years of age 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 paymentsbrThis home is equipped with solar power. Combined utilities of water and electric will allow for up to $600 total for both. Guest weill be responsible for any overages.brWhether you're here for world-class Atlantic and Gulf backcountry fishing, boating adventures, or relaxed evenings by the water, Costa Vida offers a comfortable, well-equipped home base for your Florida Keys vacation.

Bed

Bath

Sleeps

$343.51

/ Nightly

Private Vacation Home

Beautiful, 2100 sq ft 3/2 w/ocean views & easy ocean & gulf access.

Cudjoe Key, Florida, United States

This is your home away from home. Beautiful 3 story home with spacious master bedroom and bathroom located on top floor with breathtaking views on Cudjoe Key. Deep water canal with 60' of bulkhead for your boat. Fish cleaning station. Brand new commercial ice machine makes 300 lbs of ice a day. Plenty of parking with a fully gated yard. Conveniently located just 20 miles north of Key West. A short distance to some of the best restaurants in the lower keys as well as being located close to Looe Key, known as one of the best coral reefs for snorkeling and diving. AT&T U-verse fiber optic 200 channels, Internet 1000MB, Wifi, AC, Washer and Dryer, commercial ice machine, fully equipped, Bait and fish freezer. Heated Pool (Discount December January)

Bed

Bath

Sleeps

$327.41

/ Nightly

Private Vacation Home

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Cudjoe Key, Florida, United States

Escape to this inviting 2-bedroom, 1.5-bath canal-front retreat where tropical charm meets effortless access to the beautiful Lower Keys waters. Smuggler's Cove #414 is set along a 23-foot seawall that accommodates boats up to 21 feet, this home is perfect for boaters and anyone dreaming of smooth, easy trips out to explore the islands. Mature palm trees sway over the lot, creating a relaxed island vibe, while a fish-cleaning station and convenient water hookup at the dock make your fishing days simple and enjoyable. Inside, a bright and comfortable living space welcomes you home with a 65 smart TV, a dining table for five, a practical kitchen setup for preparing meals, and the convenience of an in-unit washer and dryer. There is a Mr. Coffee 12 cup drip coffee maker at this home for you to enjoy your favorite brew. brThe primary bedroom offers a cozy queen bed, its own smart TV, and a quiet mini-split, while the guest bedroom features a twin trundle with its own wall A/C. A full bathroom with a tub/shower combo plus an additional half bath provide plenty of room for everyone. After a day on the water, unwind at the concrete canal-side picnic table and enjoy dinner outdoors as the evening breeze moves through the palms. This is the perfect place to relax, recharge, and enjoy the true spirit of the Florida Keys. This home is dog-friendly with a non-refundable pet fee of $250 per dog.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 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, Kikis 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! Whether 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 15'L x 9.5'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. Main 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.

Bed

Bath

Sleeps

$325.5

/ Nightly

Private Vacation Home

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Cudjoe Key, Florida, United States

Welcome to your ultimate island getaway at at Blue Lobster Lodge #543!! Step into our charming coastal oasis nestled on a spacious corner lot in the sought-after Venture Out community. This 2 bedroom, 1.5 bath retreat is the perfect blend of comfort and style, boasting a vibrant coastal decor that will transport you to a world of relaxation and tranquility.brPrimary Bedroom: King BedbrGuest Bedroom: Full BedbrOther sleeping arrangements: Pull-out sleeper sofa in the Living RoombrAs you enter, you'll be greeted by the cool tile flooring that leads you to a fully stocked kitchen fit for a culinary master. The dining table for 6 provides the perfect spot to savor your creations or gather for a game night with loved ones. There is a Aigostar brand 12-cup drip coffee maker at this home for you to enjoy your favorite brew.brAfter a day of adventure, unwind in the cozy living room featuring a pull-out sleeper sofa and a smart television for your entertainment needs.brNeed a break from the sun Retreat to the primary bedroom with a luxurious king-size bed and your own smart TV, while the guest bedroom offers a full-size bed and smart tv for a restful night's sleep.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 Key s 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 water s 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.brSorry, no pets allowed at this home.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 9'W X 7'H 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 @bluescapevacationsbrbrBook your stay today and experience the beauty of waterfront living!

Bed

Bath

Sleeps

$328.53

/ Nightly

Private Vacation Home

Sea La Vie #197 - Oceanfront, Big Boats Welcome Here!

Cudjoe Key, Florida, United States

Set sail from Sea La Vie! Big boats welcome here - 49' seawall! This tropical oceanfront home showcases modern design, panoramic ocean views, and luxurious amenities.brThis well-appointed 2-bedroom, 2-bathroom oceanfront home has everything you need for a perfect Florida Keys vacation. The open-concept living space seamlessly blends indoor and outdoor areas, while all the windows flood the space with natural light. With a 49' seawall that can accommodate up to a 40' boat comfortably. There is a fish cleaning station, a swimming ladder, and dock posts here. This property offers endless possibilities for relaxation after a day on the water, allowing you to unwind on the deck with your loved ones amidst the refreshing ocean breezes. The views from this home offer uninterrupted ocean views, embodying the essence of coastal living with its prime location and functional design.brOutside is a lovely porch to take in the ocean views and catch up on a good book!brThere is a gas grill waiting to cook up your fresh catch of the day and a nice concrete table for dining. brThe Primary Bedroom has a Queen size bed and the Primary bathroom boasts a glass-tiled walk-in shower for a spa-like feel.brThe Guest Bedroom also features a Queen size bed. The recently renovated Guest bathroom features a walk-in shower and tile floors and walls.brFor extra sleeping accommodations, the living room has a pull out Queen size sleeper sofa and an air mattress in the Guest bedroom closet.brThe kitchen is stocked with all the gadgets you might want on vacation including an air fryer, stainless steel appliances, pressure cooker and Keurig coffee machine. A stackable washer and dryer are inside the home so you can pack light.brWhether you're 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.brAccommodating up to six adults comfortably.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 measures 21'L x 12'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!

Bed

Bath

Sleeps

$373.63

/ Nightly

Private Vacation Home

Paradise Palms in Cudjoe Key #635

Cudjoe Key, Florida, United States

This tropical 2-bedroom, 2 full bathroom home has something for everyone! The kitchen boats new stainless-steel appliances, electric stove and center island making it fun to cook your catch and entertain friends and family. Master bedroom has an en-suite bathroom with full-size shower, large vanity and plenty of storage. The guest bedroom offers a full bathroom with washer and dryer for your convenience. This open floor plan has high ceilings, tropical colors, and plenty of room for your family and friends to relax, or step outside to a private porch surrounded by tropical foliage and sip your morning coffee or unwind at the end of the day with a cocktail. Venture Out has 4 miles of paved secured streets to walk or bike. Amenities include an oceanfront heated saltwater pool, hot tub, marina with fuel dock, boat launch and convenience store, tennis, pickleball, bocce, basketball, playground, fun activities and more! Close to restaurants, shopping, parks and local events, this property has what you are looking for in the Florida Keys! brVO COMMUNITY REGISTRATION FEE OF $125.00 IS DUE UPON ARRIVAL IN CASH OR CREDIT CARD ONLY.

Bed

Bath

Sleeps

$474.48

/ Nightly

Private Vacation Home

Blue Heaven in Cudjoe Key #99

Cudjoe Key, Florida, United States

Spectacular water views from this beautifully maintained 2-bedroom, 2 full bathroom waterfront home located only 4 lots in from the open water and perfect for the avid boater! Step into your boat from the private 35-foot concrete seawall equipped with dock posts, cleats, and swim ladder. Plenty of outdoor seating on your covered porch for a water-front spot to sit and enjoy a cocktail or relax with a book and enjoy the infamous Keys balmy breezes and gorgeous clear blue waters of the Florida Keys! Just bring your swimsuit, your fishing poles and get ready to enjoy all that the Keys have to offer. This home has new kitchen appliances, kitchen island and two new sleeper sofas. Venture Out is an individual owned residential condominium community with 24-hr gated security, only 19 miles from Key West. Venture Out has 4 miles of paved secured streets to walk or bike. Amenities include an oceanfront heated saltwater pool, hot tub, marina with fuel dock, boat launch and convenient store, tennis, pickleball, bocce, basketball, playground for the kids, fun activities and more! Close to restaurants, shopping, parks and local events, this property has something for everyone! VO COMMUNITY REGISTRATION FEE OF $125.00 IS DUE UPON ARRIVAL IN CASH OR CREDIT CARD ONLY.

Bed

Bath

Sleeps

$505.3

/ Nightly

Private Vacation Home

135 Waterfront Property, Boat Dock, Heated Pool, Ocean Views

Cudjoe Key, Florida, United States

Enjoy this fabulous open water vacation home with amazing views of the Atlantic Ocean and some of the best boating access in the Keys! This home offers a covered porch facing the water, 35' seawall to dock your boat, 2 spacious bedrooms, 2 full bathrooms, an updated kitchen with a full line of appliances making this home the perfect for your family vacation spot! Gated Community with Oceanfront Heated Saltwater Pool, Marina with Convenient Store, Fuel Dock, and Boat Launch. Located near restaurants, shopping and nightly entertainment. brbrVO COMMUNITY REGISTRATION FEE OF $125.00 IS DUE UPON ARRIVAL IN CASH OR CREDIT CARD ONLY.

Bed

Bath

Sleeps

$563.62

/ Nightly

Private Vacation Home

Fun in the Sun in Cudjoe Key! #51

Cudjoe Key, Florida, United States

pPanoramic Ocean Views! 35' Concrete Seawall to Dock your Boat! This beautifully updated and well-maintained stilt home offers 2 bedrooms and 2 bathrooms, large kitchen with all the necessities, panoramic ocean views, a private 35' concrete seawall for your boat and off street parking for your vehicle. This home has an open oceanfront deck overlooking the Straits of Florida and a Back screened deck just waiting for you to come and relax. Gated community with Oceanfont Heated Saltwater Pool, Marina with Fuel Dock and Boat Launch, Hot Tub, Pickleball, Tennis, Basketball and Bocce Courts and so much more. Located close to shopping, restaurants and nightly entertainment and only 19 Miles from Key West./pbrbrpstrongVENTURE OUT COMMUNITY REGISTRATION FEE OF $125.00 IS DUE UPON ARRIVAL IN CASH OR CREDIT CARD ONLY./strong/p

Bed

Bath

Sleeps

$585.55

/ Nightly

Private Vacation Home

Tiki Time in Cudjoe Key 136

Cudjoe Key, Florida, United States

Upscale Oceanfront Retreat! This waterfront gem offers amazing views of the Atlantic Ocean and is the perfect getaway for your next vacation in Paradise. Quick access to the Gulf of Mexico and the Atlantic Ocean for your seawall. This 2 bedroom, 2 bathroom vacation home is equipped with everything you need to unwind and relax. Offering a high end kitchen, stainless appliances, three smart tv's and a 54-foot seawall to dock your boat. Gated community with Oceanfront Heated Saltwater Pool, Marina with Convenient Store, Fuel Dock and Boat Launch. Pickleball, tennis, basketball and bocce courts and so much more. VO COMMUNITY REGISTRATION FEE OF $125.00 IS DUE UPON ARRIVAL IN CASH OR CREDIT CARD ONLY.

Bed

Bath

Sleeps

$533.04

/ Nightly

Private Vacation Home

Southern Exposure in Cudjoe Key #49

Cudjoe Key, Florida, United States

pThis 2 bedroom, 1 bathroom home has Panoramic Ocean Views, Southern Exposure, direct oceanfront access with a 45-foot concrete seawall to dock your boat. Seawall with swim ladder and fish-cleaning station. Views of the ocean abound in your large, bright living room, well equipped kitchen, large bathroom, washer and dryer, a covered porch overlooking the Atlantic Ocean and off-street parking for 1 vehicle. Gated community with Oceanfont Heated Saltwater Pool, hot tub, convenient store, marina with fuel dock and boat launch, pickleball, tennis, basketball and bocce courts. Four miles of paved streets to walk or bike and so much more!/pbrbrpstrongVENTURE OUT COMMUNITY REGISTRATION FEE OF $125.00 IS DUE UPDON ARRIVAL IN CASH OR CREDIT CARD ONLY./strong/p

Bed

Bath

Sleeps

$341.25

/ Nightly

Private Vacation Home

Mahi House #440 - 35' seawall

Cudjoe Key, Florida, United States

Welcome to Mahi House #440 brEscape to paradise at Mahi House #440, your perfect getaway nestled along a quiet boating canal with quick access out to the ocean. Ideal for families or friends, this charming 2 bedroom, 2 bathroom home offers the ultimate blend of comfort and adventure. brKey Features:br- Spacious Accommodations: Both bedrooms feature cozy queen-sized beds, perfect for restful nights after fun-filled days.br- The living room has a queen pull out sleeper sofa for additional sleeping accommodations.br- Two Full Bathrooms: Enjoy the convenience of two bathrooms—one with a stand-up shower and the other with a shower/tub combo.br- Entertainment Ready: Relax in the living room or unwind in the bedroom with Smart TVs and high-speed Wi-Fi to keep you connected.br- Fully Equipped Kitchen: Whip up delicious meals in the fully stocked kitchen, then gather around the dining table with seating for six. There is a Drip & Keurig coffee maker at this home for you to enjoy your favorite brew. br- Outdoor Living: Step outside to the patio, where a gas grill awaits your fresh catches, and a table with four chairs provides the perfect spot for alfresco dining under the shade of an umbrella.br- Fun and Games: Enjoy a variety of board games for family nights or lazy afternoons.br- Adventure Awaits: Explore the island with two bicycles or take advantage of the fish cleaning station after a successful day out on the water.br- Convenience: A dedicated laundry room adds to the ease of your stay, and beach towels are provided for your sun-soaked adventures. br- There is a golf cart at the home that can be rented during your stay. The rental rates are $40 per day; $200 per week; $550 per month. If you would like to enjoy the golf cart, please let us know so we can make sure it is charged and ready for your arrival.brBoater's Paradise: With a 35' seawall that accommodates boats up to 32', Mahi House #440 is a dream for boating enthusiasts. Spend your days fishing, cruising, or simply soaking in the stunning Florida Keys waters. brExplore the Area: Nestled in a vibrant community, you'll find easy access to local attractions and restaurants. Whether you're looking for outdoor adventure or a relaxing retreat, Mahi House #440 is your perfect home base.brThis is a pet friendly home. Up to 2 dogs allowed with a paid $250pet fee per pet. Rental manager must be notified at time of booking.brWhether you're 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.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 Key's 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 14'L x 10'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!

Bed

Bath

Sleeps

$223.82

/ Nightly

Private Vacation Home

Cudjoe Key Coastal Retreat

Cudjoe Key, Florida, United States

Welcome to your ideal vacation getaway in the heart of the Florida Keys! Located in the serene Cudjoe Key, this charming home offers luxurious amenities and a perfect blend of comfort and style. Imagine waking up in a cozy, beautifully decorated home and enjoying your coffee on a private deck surrounded by tropical landscaping. Whether you seek relaxation or adventure, this home provides the perfect escape. This newly renovated home has 2 bedrooms and a large sofa that converts to a queen-size bed, comfortably accommodating 6 people. It also includes two full bathrooms and a fully equipped kitchen. Situated on a canal with close and easy ocean access, the home is conveniently located 22 miles from Key West and 15 miles from Bahia Honda State Park which is home to two world class beaches.

Bed

Bath

Sleeps

$535.5

/ Nightly

Private Vacation Home

Open-water home with stunning views, 42' seawall for 40' boat, modern updates, large balcony

Cudjoe Key, Florida, United States

Wake up to uninterrupted open-water views at this beautifully updated 2-bedroom, 2-bath coastal retreat, Paradise #93 Perfectly positioned directly on the open water, this modern Keys escape offers a peaceful setting with all the comforts and amenities you need for a relaxing getaway.brStep inside to find a bright, tastefully furnished living area featuring a 50 smart TV, updated finishes, and a fully equipped kitchen for effortless vacation living. There is a Keurig and Mr. Coffee Drip coffee maker at this home for you to enjoy your favorite brew. brBoth bedrooms include queen beds, smart TVs, and contemporary décor, providing comfort and privacy for couples, families, or small groups.brOutside, your private waterfront area is built for relaxation and adventure. A 42-foot seawall accommodates boats up to 40 feet, and the dock area includes dock posts, a swim ladder, a fish-cleaning station, and an outdoor shower - perfect for fishermen and boaters. Enjoy sweeping water views from the large balcony, ideal for sunrise coffee or sunset cocktails. A Weber propane grill makes outdoor meals easy.brAdditional conveniences include an in-home washer and dryer, central heating and air, and high-speed WiFi throughout.brPerfect for boating adventures, fishing trips, or simply relaxing by the water - this home provides the true Florida Keys experience.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 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, Kikis 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! Whether 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 25L x 10'W x 9'H. 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. Main 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. brbrSocial Media -br@bluescaperealestatebrYouTube Videos @bluescapevacationsbrBook your stay today and experience the beauty of waterfront living

Bed

Bath

Sleeps

$403.1

/ Nightly

Private Vacation Home

Night jasmine oceanfront vacation house

Cudjoe Key, Florida, United States

this is a perfect getaway home to spend your vacation, with open direct Atlantic Ocean view. This spacious new oceanfront construction home offers 4 bedrooms 3.5 bathrooms soap , towels and hair dryers provided ,fenced with private heated pebble tech saltwater pool which thoughtfully designed to allow you to lay back and relax as you watch the sunset across the breathtaking open water view. this new home has a lovely open entertaining feel to the living room, dining and large outdoor spaces! each of the 4 bedrooms has ocean views and own private balcony to enjoy a cup of coffee in the morning as you look out at the magnificent water views! Each coastal designed bedroom also has its own flat screen TV as well as a large flat screen TV in the living room, large state of the art well equipped kitchen and state of the art appliances. Enjoy the spacious outdoor balconies. The first-floor screen balcony has an outdoor dining and seating area, and the upper balcony has also a dining table and lounge chairs. There are 15 kayaks with life vests, a fish cleaning table on dock, large 36 inch Weber BBQ grills and large 36 inch Weber griddle, lounge chairs, large chest freezer, 2 front door freezers, large fridge with freezer on top and tons of open space. You can even swim and snorkel in the clear waters right off your front yard. The large brick paved covered space under the house is for your entertaining pleasure. There is an outdoor shower and 34 feet of private dock. You are about 15 minutes short boat ride to the famous Looe key national reef! Looe key reef offers some of the most spectacular diving and snorkeling in the United States! Some of the species you will likely see will be turtles, goliath groupers, angel fish, parrot fish and puffers to name a few. Just a little further out to deep water and you will encounter some of the best sport fishing only the Florida Keys can offer. You can watch the dolphins from your own balcony, The home has very high-speed WIFI, and printer , streaming thousands of movies and shows through Amazon prime, HBO, HBO max, Starz, show time, paramount (CBS all access), PBS, discovery, Cinemax , Sling TV orange and blue package plus sports package, Netflix and peacock, the home has 5 queen beds and can sleep up to 10. brThe property has also a separate not attached guest house, 2 queen bedrooms, 1 full bathroom, wet bar and family / living room, which is not for rent. the guest house is used only by the owner and will stay vacant during your stay unless in emergency if the owner has to come to do some repair for a day or two. Rentals is preferable from beginning of the month to the end of the month, no subleases allowed no exception to this rule, there is no trespassing in neighboring lots or docs, quiet time from 10:00 pm to 8:00 am, guests can enjoy themselves only with in property lot line. Smoking is not allowed, pets are welcome, hypo -allergenic pets a plus, cats are not allowed under any circumstance due to some of my guests' allergy to dander. no firework allowed, we are on mile marker 23 close enough to key west (15 Min. drive) to enjoy the Mallory square, sights, the famous Duval Street, tour the Hemingway house, Mel fisher's museum, key west lighthouse or take a trolley about town. Experience the exciting nightlife, wonderful restaurants and hundreds of unique shops. yet far enough away from key west to be in a quiet, serene retreat on open water.brYou can head north (5 Min. drive) to big pine key, home of the key deer, (10Min. drive) to Bahia Honda state park, or (20 Min. drive) to marathon to enjoy beautiful dinning.brShops, marinas, boat rentals, banks, gas stations, groceries and restaurants, hardware stores are close by.brThe home is fully equipped, all you need is your groceries and energies to explore the Florida Keys.brWe hope that you have a wonderful time, enjoy your stay at our dream home.brplease inform the owner of any accidental damage small or big that may happen during your stay (include a photo) so he can arrange for replacements.brfor any question you can contact the owner directly at area code nine five four, phone number, four six one five seven three zero. brthe property is equipped with passenger elevator for elderly and whoever (he/she ) can not climb the steps, maximum weight allowed is 750 pound.brA note, your pets are not allowed to jump on furniture or sleep in our house beds and please pick up after your pets and discard in trash. please replace what you use from the house supplies. the house also is equipped with OUTDOOR ONLY security cameras to cover all points of entry for safety and security. All your boat supplies can be found at Cudjoe bay marina on mile marker 21 which is 2 miles away. garbage collection in on Monday and Thursday and recycling is on Wednesday. No recreational vehicle (RV.) allowed to park on the property. Onsite parties or group events are strictly prohibited. 28-day minimum stay per Monroe county.

Bed

Bath

Sleeps

$372.91

/ Nightly

Private Vacation Home

Relaxing Waterfront Escape Near Key West - Venture Out Unit 410

Cudjoe Key, Florida, United States

VO410brRelaxing Waterfront Escape Near Key West – 35' Dock, Kayaks and bikes included. Access to beautiful pool and hot tub at Venture Out Community.br2Bd/2Ba with Covered PorchbrbrRelax and unwind at this inviting canal front retreat in the Venture Out community on Cudjoe Key, just 30 minutes from Key West. Bring your boat or just enjoy the views from your private 35' seawall, complete with heavy-duty dock posts, cleats, a swim ladder, and a fish cleaning station. Guests will have access to storage room to stow your dive and fishing gear, including a bait freezer for added convenience.brbrThis home is a furnished 2 bedroom, 2 bath, with open living and kitchen area, center island with 2 barstools for easy prep work and entertainment. A spacious covered patio overlooks expansive water views with cushioned love seat, 2 chairs and coffee table to create a comfortable outdoor living space. The living room features a sleeper sofa and super comfy reclining chairs and flat screen television and offers views of the water. The master bedroom features a queen bed, double mirrored closet doors and private full bathroom. The guest bedroom features a queen bed with closet storage with access to hallway full bathroom. Covered outdoor living space downstairs set up with hammocks, a BBQ grill and small hightop table.brbrThis home comes fully stocked with everything you need for an unforgettable Keys adventure:brbr Four single kayaks with paddles and life vests. Get ready to explore nearby mangrove islands teeming with wildlife and keep an eye out for dolphins!brbr Four bikes, perfect for cruising along the scenic US-1 bike trail.brbr Four camp chairs, great for fishing trips, beach days, or relaxing on the dock.brbr Beach towels and a Pelican cooler for all your outings.brbrWhether you're paddling the backcountry waters, biking through paradise, or just sipping your morning coffee by the water, this Cudjoe Key gem has everything you need for a laid-back, memorable stay.brbrVideo tour of this vacation home: https://youtu.be/ZmTxuW46lWU si=UNcc74zPl1n_BoMmbrbrSECURITY DEPOSIT REQUIRED, NO SMOKING, NO PETS.br7 DAY MINIMUM LOBSTER SEASONbrPARKING IS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.brbrVO REGISTRATION FEE $125.00- DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE.

Bed

Bath

Sleeps

$197.09

/ Nightly

Private Vacation Home

Paradise Found | Pet friendly, boating on Cudjoe

Cudjoe Key, Florida, United States

Summary:brbrPet-friendly 3 bed/2 bath boating home on Cudjoe KeybrbrbrbrThe Space:brbrCanalfront 3 bedroom/2 bathroom home with excellent oceanside boating access. Open floor plan with a large kitchen, stainless appliances, plank flooring, beautiful tray ceiling over the living area and large windows. French doors out to the covered porch with seating overlooking the canal. Super-comfortable reclining sectional with 55-inch TV in the living room. Satellite TV and high-speed Internet and WiFi. Master suite has a king bed, walk-in closet, double sinks and a shower. Second bedroom (king bed) and third bedroom (queen bed) share the hall bathroom with a shower/tub combo. 30-foot concrete dock. Concrete pad underneath the house. Plenty of off-street parking for your vehicles and trailer. No outside storage.brbrbrbrPlease note:brbrThis home requires a minimum 28-day stay per county ordinance. Proper county and state taxes are collected regardless of booking platform. Primary renter must be 25 or older. Overnight occupancy is limited to 6 people, and all overnight guests need to be registered with the property manager. No smoking. One pet permitted with manager approval and nonrefundable $250 pet fee. There's a cap on electric ($250) and water/sewer ($150).brbrbrbrGuest Access:brbrGuests have the house to themselves.brbrbrbrThe Neighborhood:brbrCutthroat Harbor Estates, a residential neighborhood of mostly single-family homes, is on the ocean side of Cudjoe Key, an island 23 miles from Key West. The famous Square Grouper restaurant is nearby. There`s also a convenience store and two seafood markets on the island. The closest boat ramp is at Cudjoe Marina in the Cudjoe Gardens neighborhood nearby.brbrbrbrGetting Around:brbrA car is recommended. There is a city bus that runs from Key West to Marathon several times a day. The Lower Keys have limited taxi service and Uber/Lyft.brbrbrbrInteraction with Guests:brbrContact-free checkin and checkout are available. We value our guests’ privacy but are always available if needed.

Bed

Bath

Sleeps

$614.16

/ Nightly

Private Vacation Home

Blue Home - Receive 400 dollars towards a BOAT RENTAL!

Cudjoe Key, Florida, United States

Receive a $400 boat rental gift certificate brfrom Nothing Better Boat Rentals, LLC. When you book a full week brat one of our homes staying between the dates ofbrSept 1, 2026 through Dec 19, 2026 Except for Nov 21-28, 2026brbrPlease reach out before booking for brboat availability - 305-587-4565brbrbrYellow House - Blue House - White House br(Except for Nov 22-29, 2025 for all houses)brbrbrbrVacation home has a view over Cudjoe Bay to the Atlantic from the common deck and from the private pool deck. 4 bedroom and 2 bathrooms. Large dock with water access for a small boat. We provide bedding, towels, pots and pans. Vacation home sits far off of the main road for a great quiet vacation. We have 2 other properties with fantastic reviews that sit next to this vacation home.brbrGet 100% money back 48 hours before check in, if the home is in the projection cone of a named hurricane during your stay. Off the beaten path, over 200, 5 star reviews on other platforms. Very spacious, private, heated pool for the guests of this house. Each of our 3 homes on this property have a pool.brbrWe have one of the best restaurants in the Keys just a mile up the road, The Square Grouper.brbrYou can look at our other listings that show our reviews. White Vacation Home listing #3586076 with 166 reviews, Blue Vacation Home listing #7105866 with 105 reviews, and the Yellow Vacation Home listing #7154549 with 100 reviews.brWe require the main renter to provide their ID, home address, and the names of all other guests that will be staying on the property. Any extra, unlisted guests will forfeit this rental immediately with no money back or deposit returned. You will be responsible for any damages caused by you or your guests during your stay. No diving into the pool. No jumping from the deck into the pool. No glassware in or around the pool area. Please keep noise to a minimum after 10 pm.

Bed

Bath

Sleeps

$451.61

/ Nightly

Private Vacation Home

Yellow Home - Receive 400 dollars towards a BOAT RENTAL!

Cudjoe Key, Florida, United States

Receive a $400 boat rental gift certificate brfrom Nothing Better Boat Rentals, LLC. When you book a full week brat one of our homes staying between the dates of brMay 30 - June 13, June 20 - 27th 2026brSept 1, 2026 through Dec 19, 2026 Except for Nov 21-28, 2026brbrPlease reach out before booking for brboat availability - 305-257-9081brbrbrBeautiful house nestled off of US 1. Kayaks included in the rental. Rent one or both of our other properties that are near each other for a great full family vacation. All 3 properties are listed on AirBNB. Private heated pool with seats inside of the pool to enjoy the view. We provide bedding, towels, pots and pans. Home with water access/dock for a small boat.brbrGet 100% money back 48 hours before check in if the home is in the projection cone of a named hurricane during your stay. brbrAddress to the Yellow Vacation Home: 21390 Conch Dr., Cudjoe Key, Fl. 33042brbrYou can look at our other listings that show our reviews. Each of our 3 homes on this property have a private pool. White Vacation Home listing #3586076. Blue Vacation Home listing #7105866, and the Yellow Vacation Home listing #7154549br.brWe require the main renter to provide their ID, home address, and the names of all other guests that will be staying on the property. Any extra, unlisted guests will forfeit this rental immediately with no money back or deposit returned. You will be responsible for any damages caused by you or your guests during your stay. Please keep noise to a minimum after 10 pm. No diving into the pool. No jumping from the deck into the pool. No glassware in or around the pool area. Please keep noise to a minimum after 10 pm.

3

Bed

2

Bath

6

Sleeps

$354.38

/ Nightly

Private Vacation Home

Keys getaway - Relax with the whole family at this peaceful place to stay.

Cudjoe Key, Florida, United States

This marvelous house in Cudjoe Key offers a cozy one bedroom with a queen bed, one and half bathrooms, and an additional living room space with two sofa beds. Guests can enjoy amenities like AC, a hair dryer, and a washing, machine, dryer etc.during their stay. The gorgeous surroundings and excellent comfort of this property make it the ideal retreat for your vacation. We're happy to assist with any questions while you stay at our house.

1

Bed

2

Bath

6

Sleeps

Vacation Home Rentals By Owner In Cudjoe Key, FL

$418.07

$343.51

$327.41

$325.5

$328.53

$373.63

$474.48

$505.3

$563.62

$585.55

$533.04

$341.25

$223.82

$535.5

$403.1

$372.91

$197.09

$614.16

$451.61

$354.38

Rent a place that suits your needs

Most popular vacation rentals in Cudjoe Key

$520.85

$585.55

$582.16

$571.84

$544.46

$534.98

$525.60

$497.33

$487.30

$496.79

Most Popular Cities in Florida