358,603 properties available

Located in Cudjoe Key, Florida, United States. Privateer`s Prize | Pet-friendly 3 bed/2 bath boating home on Cudjoe Key Welcome to your perfect waterfront retreat on Cudjoe Key! This pet-friendly 3 bed/2 bath monthly rental is situated on a boating canal, offering you a slice of paradise with endless opportunities for relaxation and adventure.As you step into the spacious living area, you'll immediately feel at home. The well-stocked kitchen and dining area, with seating for six, make mealtime a breeze. The three large bedrooms provide comfort and privacy, while a dedicated desk space is ready for those who need to catch up on work during their stay.Step outside onto the covered porch to soak in the tropical atmosphere. Stay connected with high-speed Internet and WiFi throughout the property. While there's no cable TV, a live streaming service is available upon request for your entertainment needs.The real highlight of this rental, however, is the outdoor haven awaiting you. Relax under the tiki by the canal, or venture out to the

Located in Cudjoe Key, Florida, United States. El Paraiso | Canalfront getaway on Cudjoe Key Welcome to your charming canalfront retreat on Cudjoe Key! This adorable 3-bedroom, 3-bathroom vacation rental offers the perfect blend of comfort, convenience, and waterfront living.Step inside to discover a recently remodeled kitchen and bathrooms, providing a fresh and modern atmosphere for your stay. The fully equipped kitchen ensures all your culinary needs are met, allowing you to whip up delicious meals with ease.The spacious canalfront backyard boasts plenty of seating and lounging opportunities, inviting you to soak up the sunshine and enjoy the tranquil waterfront ambiance. With easy boating access to the Atlantic Ocean from the 55-foot concrete dock, adventure awaits right outside your doorstep.Accommodations include a primary bedroom with 2 queen beds and en-suite bathroom with a shower, offering a comfortable retreat after a day of exploration. The second bedroom features 2 full beds, and there's a full bath down the hall. The

Located in Cudjoe Key, Florida, United States. 4 Bedroom Canal Front Home with Peekaboo Ocean Views Escape to paradise in this luxurious four-bedroom, three-and-a-half-bathroom canal-front home located in the Lower Florida Keys on Cudjoe Key. Perfect for families or groups, this spacious retreat offers everything you need for an unforgettable vacation experience. Step inside to discover a fully stocked and updated kitchen, where you can prepare delicious meals using fresh local ingredients such as your very own catch of the day! The open-concept living and dining area provide ample space for relaxing and entertaining, while large windows offer stunning views of the canal and surrounding tropical landscape. Outside, the expansive outdoor balcony is the perfect spot for enjoying cocktails with friends or dining al fresco. Upstairs, the third level of the home provides a private bedroom balcony, the ideal retreat for sipping morning coffee or soaking in the sunset above the treetops with ocean views. With up to 39 feet available for d

Located in Cudjoe Key, Florida, United States. 2 Bed 2 Bath Pool Home with Sunset views Absolutely stunning 2 bedroom 2 bath home with open water views and great boating access to the Gulf or the Atlantic. Come stay in this completely renovated home with great covered porch, boat dock, heated swimming pool and fully equipped kitchen. Located on a very quiet street, this home is perfect for the fisherman/woman and/or just lounging around. Just a short 25 minute ride to Key West and all of the amenities it has to offer. For the boater this home is located on a short canal with a direct shot into Cudjoe Bay, good draft to the Atlantic and Gulf. Come check in today but beware you may want not want to leave!!

Located in Summerland Key, Florida, United States. Blackbeard`s Hideaway | Cozy canalfront cottage is an angler's dream on Cudjoe Key Welcome to Blackbeard's Hideaway, your perfect monthly vacation rental nestled in a quiet neighborhood on the oceanside of Cudjoe Key. This charming retreat offers a seamless blend of comfort, convenience and coastal living.Step inside to discover an inviting open floor plan with two separate seating areas, warm pine floors and vaulted ceilings, creating a welcoming ambiance throughout. The updated kitchen boasts sleek stainless appliances and elegant quartz countertops, providing the ideal space for culinary adventures and entertaining.Accommodating up to 6 overnight guests, this vacation rental features two main floor bedrooms furnished with luxurious king beds, ensuring restful nights after days of exploration. These bedrooms share a bathroom equipped with a tub/shower combo.Ascend the spiral staircase to find a cozy open loft area with a full-sized bed, offering a private retreat for additional guest

Located in Cudjoe Key, Florida, United States. Looking for a place to stay? Relax in our traditional keys style stilt home. The home is located on a channel with immediate access to the Atlantic Ocean. The concrete dock allows for easy access and quick drive to the open water. With the ocean at your whim, finding your favorite spots for fishing, lobstering, diving, and snorkeling has never been easier. Easy access to Content Islands.The home is conveniently located on Cudjoe Key, MM23, allowing for a 25 minute drive to famous Duval Street in Key West, or Marathon Key to the North. Our home is located far enough to relax and enjoy the serenity of the island life while close enough to take a night on the town.This three bedroom, two bath home features, one king bed, one queen bed, and two twin beds. The home has a beautiful back porch over looking the water where you can enjoy a good book, a glass of wine, or dinner with your loved ones. A spacious, fully equipped kitchen provides the perfect setting to create your favorite dishes or

Located in Cudjoe Key, Florida, United States. Night jasmine oceanfront vacation house this is a perfect getaway home to spend your vacation, with open direct Atlantic Ocean view. This spacious new ocean front construction home offers 4 bedrooms 3.5 bathrooms fenced with private 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 costal 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 loun

Located in Cudjoe Key, Florida, United States. NEW LISTING - Cudjoe Key - Canal with Quick Ocean Access Home is located in a very quiet and nice neighborhood! Home is minutes away from Key West or Big Pine for quick access to great restaurants and shopping! Home sits right on a beautiful, private canal, only 100 yards away from open water! Kemp channel is right in the backyard, so you will have easy access to both the Gulf and Atlantic sides! Marina is right around the corner for easy fuel access. This location is a fisherman’s paradise! It is also located minutes away from great snorkeling, kayaking, long boarding, etc. House also has a commercial ice machine, so fish all day with no worries! Home has been completely remodeled and updated. Enjoy your day out on the water, then come back to clean your fish on the dock! Also, enjoy the beautiful views of the sunrise and sunset - right off the balcony! Enjoy beautiful days in the water, the fast life in Key West, or just come back to your quiet and relaxing getaway!

Located in Cudjoe Key, Florida, United States. Affordable, Adorable home waiting for you in Cudjoe Key Adorable canal front 2 bed/2 bath home for rent in Cudjoe Key. This indoor/outdoor floor plan is complemented by 3 twelve ft sliders that open up to a beautiful porch overlooking the canal. ~Spacious floor plan with modern decor and comfortable amenities. ~Master has King Size bed, cable TV, full bathroom and walk in closet. ~Second bedroom has queen sized bed, cable TV and full bathroom. ~60ft of concrete dock on a beautiful water canal that is less than 5 minutes to open water. ~Outdoor propane grill, bait freezer and cocktail table on canal side.

Located in Cudjoe Key, Florida, United States. Blue Mind - Venture Out Unit 225 BLUE MIND - VO22535' Dockage on Y-shaped CanalSparkling Clean Kayak & WiFiThis beautifully decorated vacation home is located on a WIDE Y-SHAPED CANAL that overlooks a common ground with over 100' plus of expansive water views and easy to turn a boat around! Features many upgrades through out including custom kitchen and bath, central air conditioning, tropical decor and furnishings. Great for boaters, with a full length 35' dock frontage, equipped with dock posts, cleats, fish cleaning table with umbrella and swim ladder. Sit outdoors and RELAX by the water's edge with brightly colored patio table with 4 chairs and 1 lounge chair plus a gas grill to cook your catch. The Located on a gorgeous landscaped lot with mature palms, while the front yard offers partial open water views, with two Adirondack chairs to soak up the afternoon sun! The driveway is concrete and suitable for truck or a larger vehicle. Great tropical breezes enhance this unit, on

Located in Cudjoe Key, Florida, United States. Canal front, dockage, 2 bedroom, 2 bath Open water views from this 2 bedroom, 2 bath stand alone home, 35 foot seawall for docking your boat. Contemporary design with smart TV's and internet in all rooms. Dining indoors and on the porch. Covered porch with lots of sunny spaces. Completely furnished with everything you need to have the best vacation ever. Propane webber grill. Easy dockage, concrete seawall. Marina with boat ramp and security, convenience store. Venture Out charges a fee of $125.00, due at check in for use of the amenities. Parking for one car, one golf cart and one motorcycle, additional vehicles will park in overflow parking. If you are bringing a boat, I have trailer storage for you just down the street. Please let me know.

Located in Cudjoe Key, Florida, United States. Relaxing Home in gated community This 2 bedroom, one bath home is located in Venture Out on Cudjoe Key, FL. 23 miles outside of Key West!. Venture Out is a gated community that features, community pool, hot tub, tennis courts, basketball court, a private ramp, unit is 85 yards from ramp, easy for lunching kayaks. This unit was built in 2017. There is a dishwasher, grill, TV and free WIFI. The unit includes 2 adult bikes, 2 person Kayak and Paddle board at no extra charge. ATTENTION: The community charges a security/registration fee upon arrival to the renter. The fee will be $116.28 plus $8.72 in tax. This fee is not included in your reservation. Also, there are fees for more than one car or trailer storage. Overflow parking is first come, first served basis.

Located in Cudjoe Key, Florida, United States. COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking! CUDJOE CUTIE WITH AMENITIES GALORE…Sweeping views of the dazzling turquoise waters of the Florida Keys will ignite your island soul and pull you away from reality. Come home to this 2 bedroom 2 bath gem that is sure to delight you and your loved ones with endless hours under the sultry island breezes and calming southernmost waters. Located in the Venture Out Resort in Cudjoe Key, you will enjoy all the amenities, such as a heated 80 ft. pool and swimming lagoon with large hot tub, tennis courts, basketball courts, marina, convenience market with fuel on site as well as two double wide boat ramps, a recreation center, patrolled security and so much more!***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEDETAILS AND AMENITIES…You are truly immersed in and surrounded by exquisite tropical waters in this quintessential Lower Keys abode. Enter this new home with its airy 9 ft. ceilings and every modern finish to brin

Located in Cudjoe Key, Florida, United States. Fishermen’s Paradise 🎣 This is a water lover or a Fisherman’s Paradise. This waterfront home can sleep 6. The house is fully furnished with a colorful island vibe Modern 2 bedroom & 1 bathroom.There is a queen bed in the master bedroom along with AC & a flat screen TV. A full bed in second bedroom with AC & flat screen Tv. There is also A full pull out couch (new couch bought 3/9/22) in the Florida room(living room area) with AC and a flat screen TV. 4 ACs units total. New bikes - Two 3/17/22The decoration in all the rooms make it known your home but the feel of paradise. The Florida room has a 4 person dining area. The kitchen has a Microwave,Stove/Oven, Keurig/ Coffee Maker,Fridge,Toaster. Unfortunately the only is no dish washer. There is a picnic table out front to enjoy your morning coffee. The back yard is waterfront with easy access to cut your fish and wash your boat off, outside lighting,power washer,along with a gas grill to enjoying spending extra time outside while making

Located in Cudjoe Key, Florida, United States. Pelican's Paradise - Unit 507 Venture Out 1 Bedroom/1 Bath Canal Front Home Escape to Pelican's Paradise, a charming one-bedroom, one-bath cottage nestled in the private, gated community of Venture Out on beautiful Cudjoe Key. This idyllic vacation rental has undergone a complete renovation, boasting a stunning kitchen adorned with granite countertops and bar top seating, as well as a spacious dining area for four.Boasting a 35-foot concrete dock, Pelican's Paradise is a boater's dream, offering 2 single sit-on-top kayaks & a two person Hobie Cat kayak for guests and easy access to the open water via a serene canal. Within the exclusive Venture Out community, guests can indulge in a plethora of amenities, including a heated pool, a soothing hot tub, tennis court, basketball court, pickleball, playground, on-site store and marina lounge, boat ramp, tiki huts and a swimming area right in the ocean!The thoughtfully designed living room features a convenient queen-size Murphy bed and a pri

Located in Cudjoe Key, Florida, United States. Springs Venture Out Dolphin House (#386) with beautiful open water views This Home has some of the absolute best views of the Ocean; sitting on your deck watching nature at its best. Our 35ft sea wall perfect for fishing or docking your boat.Easy access to either the Atlantic or the gulf; some of the best fishing or lobstering spots located in all of the Keys. Plus one of the most beautiful Light Houses located just a short Boat ride to a awesome light house with great snorkeling opportunities.Also some of best food located just around the corner(Square Grouper and Broil) are Great places to eat and just a short 23 mile drive to downtown Key West. Also have a Local Guide that lives in Venture out if need someone to give you a tour of our beautiful out Islands. (Times and Rates will apply)This Home has been recently been completely updated with a modern updates furniture and all the necessities, you would be looking for a 80 inch smart Tv, two single kayaks two stand up paddle boards a

Located in Summerland Key, Florida, United States. Sunny Hideaway - Venture Out Unit 276 Sunny Hideaway - Venture Out Unit 276This beautifully decorated home is located on the water and is located within walking distance to the pool and marina. Features 35' concrete seawall for docking a boat that equipped with heavy duty dock posts, cleats, swim ladder, whips and fish table and offers quick access to the open water! Main living area features an open floor plan with high ceilings throughout. Living room is surrounded by windows that overlook the water with sleeper sofa and large flat screen television. Kitchen offers full line of appliances with dining room that leads to the covered porch. Master bedroom queen bed features lots of closet storage, flat screen television and private full bathroom. Guest bedroom features a queen bed with closet storage and private entrance. Additional amenities include wireless internet, central air conditioning/heat, washer/dryer, ceiling fans, BBQ grill, dishwasher, microwave. Use of golf cart

Located in Cudjoe Key, Florida, United States. waterfront cottage near key west, sleeps 6 This reimagined vintage style waterfront home is everything! With the ability to tie up to 17f boat right outside your door, you will be able to enjoy the many amenities of the home (kayaks, bikes, beach & snorkel gear, pickle ball, board games, wifi & roku) and of the community (Pools, spa, boat launch, sports courts, even a library and a general store!). You can use this magical location to launch all your Florida keys adventures! Canal patio for drinks? Lush screen porch for coffee? It's on!About this spaceThis reimagined vintage style waterfront home is everything! With the ability to tie up to 17f boat right outside your door, you will be able to enjoy the many amenities of the home (kayaks, bikes, beach & snorkel gear, pickle ball, board games, wifi & roku) and of the community (Pools, spa, boat launch, sports courts, even a library and a general store!). You can use this magical location to launch all your Florida keys adventures! Canal

Located in Cudjoe Key, Florida, United States. Rise-N-Shine with spectacular sunrise views! Perfect spot for fishing, lobstering, and snorkeling with a spectacular sunrise view! There is room to park one vehicle, but we do have a free overflow lot if you need it. Community amenities include tennis, pickle ball, bocce ball, heated pool, hot tub, designated swim area in the cove, pool table, ping pong, and darts. We will also have boat bumpers installed all along the concrete dock that will accommodate a 40' boat. See our other listings that we have managed over the years with 100's of reviews. Get 100% money back if your rental is in the projection cone of a named hurricane.

Located in Cudjoe Key, Florida, United States. 430 Empty RV Lot with 35' Seawall Great Empty Waterfront RV Lot just waiting for you to come visit the beautiful Florida Keys. Private 35-foot seawall, access to both the Atlantic Ocean and the Gulf of Mexico and the added bonus of all that Venture Out gated community has to offer. Bring your RV, your swimsuits and your boat/boating gear and have an amazing family vacation! Venture Out is an individual owned residential condominium community with 24-hr gated security and only 19 miles from Key West. Venture Out has 4 miles of paved secured streets to walk or bike. Amenities include heated pool, hot tub, marina, boat launch, convenient store, tennis, pickleball, bocce, basketball, playground, fun activities and more! Close to restaurants, shopping, parks and local events, this property has something for everyone! ➢ Only commercially manufactured RVs having a current license/registration, in good condition, good appearance, and is self-contained with full hook ups (water, sewer, electric

Located in Cudjoe Key, Florida, United States. Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon This Lobstering paradise is just 2 houses down from open water on a deep 60 foot wide canal, gorgeous open water views, direct access to the Atlantic and the Gulf via Kemp channel, 35' concrete dock/seawall with a fish cleaning station. We are one of only a handful of houses in Venture Out that is secluded with no neighbors directly across the canal. Tropical fish viewing at the seawall and you never know when you will see a manatee swimming by. Fishing for mangrove snapper is also easy from the seawall. Beautiful views of the open water from the living room, dining room, perfect location to tie up your boat. This is a fully furnished 2-bedroom 2 bath home with spectacular sunrise and sunset views. The master bedroom has a king size bed, the second bedroom has a queen bed. New in 2023, a 3 zone mini split A/C and heat, overhead ceiling fans, full kitchen with microwave, washer/dryer, 42" high def flat scr

Located in Cudjoe Key, Florida, United States. Paradise Escape! - VO466 35' Dockage! VO466Paradise Escape!Perfect Location 35' Dockage!It's a wonderful time to enjoy Paradise! Enjoy endless expansive water views (from sunrise to sunset) looking down a wide Y-shaped sparkling blue canal to open water! 35' concrete seawall, perfect for avid boater, open concrete deck as a great gathering spot, swim or fish right off the dock! Dock amenities include fish cleaning table, cleats, swim ladder, dock posts, and storage access with bait freezer. Quick ocean side access to gulf and ocean, near Looe Key Reef. Main living room overlooking water with two sliders off open porch to bring the outdoors in. Large master suite with queen size bed with full bathroom and lots of closet storage and stack washer/dryer. Guest bedroom queen bed, with accordion door to separate living room, and offers closet storage and bathroom with stand up shower plus private entrance. Amenities include central air conditioning, ceiling fans, tile floor, gas gri

Located in Cudjoe Key, Florida, United States. Tree Top Paradise On 7/6/24 I have bought a new oven, microwave, dishwasher, washer and dryer and barbeque to make your vacation very comfortable.Unit #179 - At the “Tree Top Paradise” we have spared no expense to make sure your vacation is not just a vacation but an experience of your life with a peak a boo view of the canal. This home is a fantastic 2 bedrooms (Queen beds) and 2 baths. You have a large lovely screened in porch with comfy furniture to enjoy your morning coffee. A bright open concept kitchen is fully stocked with pots, pans, dishes, etc. Open concept allows you to socialize with those in the living room and dining room while preparing your fresh caught fish. The living room has a sleeper sofa and a new 55-inch flat screen crystal smart tv. The cable/internet is Xfinity Comcast Cable with, Movie channels, News channels. Watching the big game has never been better. There is also a work station with a 27 inch screen that your lap top can connect to if you had to do some

Located in Cudjoe Key, Florida, United States. Crab Shack This cozy home on Cudjoe is exactly what you are looking for if you want good boating. The canal it is on opens up to Kemp Channel, with direct access to either the Gulf or Atlantic. Choose backwater shallows or open ocean, it's all there for you. Perfect for a small family or two couples, with a king-sized bed in the master bedroom and a queen in the second bedroom, this home also has all the amenities needed for a great vacation. The comfortable kitchen also includes a dishwasher and toaster oven. Key West, with its great shopping and dining, is only 20 minutes away. This is a designated non-smoking home. THIS HOME IS A 28-DAY MINIMUM RENTAL PER MONROE COUNTY CODE.