Vacation Rentals By Owner In Cudjoe Key, FL

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

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

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$403.1

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.

Night jasmine oceanfront vacation house

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$328.28

Sea Breeze CottagebrVO066br 2Bd/2Ba South End of Park Walk to Ocean!brbrThis delightful 2 bedroom, 2 bathroom cottage sleeps 4 in comfort. New smart Tv's, phone/device charging stations along with cable tv and Wi-Fi. New Queen bed in the master and new bedding and pillows. The guest bedroom has twin beds with new bedding and pillows. Pet friendly..2 pets allowed, under 25 lbs. Short driveway...large trucks/SUVs may not fit. Verify vehicle length before booking.brbrVO REGISTRATION FEE of $125.00- DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE.When you arrive at Venture Out , you will go to the Venture Out Office (or the Guard Gate if it is after hours) to pay the fee and to receive your parking pass. Cash or CC only is accepted for this fee.brOVERFLOW PARKING IS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.

Sea Breeze Cottage - Venture Out Unit 066

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$372.91

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.

Relaxing Waterfront Escape Near Key West - Venture Out Unit 410

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$197.09

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.

Paradise Found | Pet friendly, boating on Cudjoe

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$614.16

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.

Blue Home - Receive 400 dollars towards a BOAT RENTAL!

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$451.61

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.

Yellow Home - Receive 400 dollars towards a BOAT RENTAL!

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$358.91

**We Have Everything You Need For A lovely Getaway**brWe welcome you to our Beautifully Furnished 2 bedroom, 2 bath home located in Cudjoe Key Florida. (Also Known As Venture Out & It's Gated Community ) br Located just 23 miles from downtown key west, with a 30 minute drive to either key west or marathon, This house Has direct ocean access for the serious fisherman & is located on a 60 ft Wide Canal, with a 35ft dock space at your backdoor & an outdoor cleaning station. Washer & Dryer available. The 2 bedrooms include 2 Queen size beds with both having access to the bathrooms.brBoth bathrooms have stand up walk-in showers, Kitchen includes all the necessity's.brLiving room has a sleeper sofa & a 55 inch smart Tv with over 5000 channels to choose from. The resort has a beautiful large Olympic size Swimming pool, or a area marked for swimming if you prefer salt water & snorkeling, hot tub, tennis courts, basketball court, Children's playground, Pool Tables, & a marina with two boat ramps, snacks & fuel. There is room to park one vehicle in the driveway at the property anything else isbr ** A VENTURE OUT REGISTRATION FEE**br**Per Registration for no more than 6 guest (MAX) ($125.00) payable at the gate upon arrival br via cash or credit card. This Fee is Paid directly to venture out;brbrOnly one car is permitted at each unit. Transportation vehicles must fit in the driveway or will have to be moved into overflow parking for a small nightly fee. If you have an extra car you will need to park in the overflow parking lot and pay the appropriate nightly fee up to 14 days maximum pending availability.brbrThere is no jet ski trailer parking available. Boat trailer parking may be available, subject to availability and for a fee. The rates are $5-$10 per night depending on size.

water at your back door

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$251.57

VO035brSparkling Clean 2Bd/1Ba w/ Free WiFi brLarge Patio For GREAT Outdoor Enjoyment. This home is sparkling clean with all linens and features two bedroom with 1 full bathroom and is located on the south end of the park close to an open water common area. Living room offers a queen sleeper sofa with flat screen television, Free Wiress Internet, reclining chair and additional comfortable seating. Dining room adjoins the kitchen and offer table and chairs for plus two bar stools. Master bedroom features a queen size bed with flat screen television and hallway bath access. Adjacent the bathroom is a large closet with sliding doors with a full size washer and dryer. Guest bedroom features a full size bed and offers access to the private backyard courtyard with table, chairs and two lounge chairs to soak up the sun or gaze up at the starry night sky. Additional amenities include Central Air Conditioning, full size washer and dryer, 2 flat screen tv's for streaming, BBQ grill, DVD player, FREE IN HOUSE WIRELESS INTERNET and outdoor patio furniture. SECURITY DEPOSIT REQUIRED, NO SMOKING, NO PETS, 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 $113.00- **EFF 71-23 new fee is $125**DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE.br****PLEASE NOTE, THIS PROPERTY HAS A SHORTER DRIVEWAY/PARKING SPACE AND WILL NOT FIT TRUCKS OR SUV'S- GUEST MUST VERIFY PRIOR TO RESERVING****

ISLE BE BACK To The Sunny Keys

Cudjoe Key, Florida, United States

Bed

1

Bath

4

Sleeps

$354.38

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.

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

Cudjoe Key, Florida, United States

1

Bed

Bath

6

Sleeps

$298.3

Cottage #11 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound with 2 swimming pools. Spacious cottage offers a full kitchen, screened patio, two queen bedrooms. This cottages is only steps away from our pool. The pool, dock and seawall are all available to our guests. A coin laundry is also available on site. Whether you come to the Florida Keys to escape the winters, or enjoy the calm waters and great fishing and diving of the summers, you will find Cudjoe Oceanside Cottage to be your Home Away From Home.

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

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$642.34

Boater’s Paradise: Your Dream Waterfront Escape in Cudjoe Key.brbrLooking for the perfect blend of adventure and relaxation Welcome to your newly built custom home in the heart of the Florida Keys. Situated directly on the water in Cudjoe Key, this is the ultimate getaway for boating enthusiasts, nature lovers, and those seeking a peaceful retreat.brbrUnmatched LocationbrStep outside and take your boat from the nearby Cudjoe Marina—just a short walk away—and head straight to the famous sandbars, or discover hidden spots for a fresh lobster catch. Whether you're cruising the waters or relaxing by the shore, you'll feel like you're in your own private slice of paradise.brbrStylish & Spacious LivingbrThis 3-bedroom, 3.5-bath home offers generous living space with luxurious finishes throughout. From the moment you step inside, you'll feel at ease with open-concept living, perfectly designed for family gatherings or laid-back evenings. The bedrooms are spacious and comfortable, while the expansive balconies provide breathtaking sunset views over the water—a perfect place to unwind with a cocktail in hand.brbrOutdoor OasisbrRelaxation comes naturally here. Spend your afternoons floating in the private pool, or lounge on the deck while soaking in the Florida sun. Whether you're hosting a lively evening by the pool or enjoying a peaceful retreat, this home offers it all.brbrYour Ideal GetawaybrWhether you’re seeking a fun-filled boating adventure or a quiet spot to enjoy the serene surroundings, this is the perfect home away from home. Our team is always available to assist with any questions during your stay, ensuring a seamless and memorable experience.brbrBook now and make unforgettable memories in Cudjoe Key!

Gorgeous new build on Cudjoe Marina Basin with 80 ft boat dock and private pool

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$339.41

Cottage #15 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound with 2 swimming pools. Spacious cottage offers a full kitchen, screened patio, two queen bedrooms. The pool, dock and seawall are all available to our guests. A coin laundry is also available on site. Whether you come to the Florida Keys to escape the winters, or enjoy the calm waters and great fishing and diving of the summers, you will find Cudjoe Oceanside Cottage to be your Home Away From Home.

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

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$675.11

Neptune’s End – Your Private Island Getaway in the Florida KeysbrbrWelcome to Neptune’s End, the ultimate island escape. This stunning oceanfront retreat offers unobstructed views of Cudjoe Bay and the Atlantic Ocean and is perfectly designed as a multi-family compound or luxurious group getaway. With a private beach, resort-style amenities, and only 20 minutes from Key West, Neptune’s End is the perfect blend of seclusion and adventure.brbrProperty OverviewbrbrThis split-level home features spacious indoor and outdoor living areas, a total of 4 bedrooms, 3 full bathrooms, and a wide array of entertainment and relaxation spaces. Whether you’re watching sunsets from the screened patio, lounging by the pool, or enjoying your own private tiki bar, every moment here feels like a vacation.brbrMain Floor (Upstairs)brbrLiving Room: Large, comfortable couches, 55” flat-screen TV, cathedral ceilings, and oversized windows with sweeping bay views. Binoculars in the foyer for dolphin or boat watching.brbrDining Area: Formal dining table with seating for 8, plus a bench for extra guests.brbrKitchen: Fully equipped with stainless steel appliances, granite countertops, custom cabinetry, and everything you need to cook and serve.brbrScreened Patio: Perfect for morning coffee, an afternoon nap, or sunset cocktails, furnished with cushioned chairs and a rocker.brbrBedrooms (Upstairs):brbrPrimary Suite: King bed, 37” flat-screen TV, dresser, nightstands, closet, and en-suite bathroom with walk-in shower.brbrBunk Room: Two sets of single bunk beds, two full-size dressers, and a closet—ideal for kids or groups.brbrGuest Room: Queen bed with full-size closet and dresser.brbrShared Bathroom: Full bath with shower/tub combo in the hallway.brbrLower Level (Downstairs)brbrBedroom 4: King-size bed, dresser, large closet, and ocean views.brbrEntertainment Area: Sleeper sofa and love seat, 55” flat-screen TV, wet bar with mini fridge, and direct access to the pool and patio.brbrFull Bathroom: Includes walk-in shower.brbrLaundry Room: Washer/dryer, pool towels, 2 bicycles, cooler, and beach chairs.brbrOutdoor AmenitiesbrbrHeated Pool & Spa: Resort-style pool with spill-over hot tub, surrounded by chaise loungers and conversation seating.brbrPrivate Sandy Beach: Lounge in the hammock or stroll along your own stretch of sand.brbrTiki Bar: Added in 2019 – features bar seating, built-in lounge area, ceiling fan, lighting, and power. Your private resort awaits!brbrDining & Grill Area: Outdoor table for 6, gas grill for barbecues under the stars.brbrDock & Kayaks: Private pier with dockage for boats up to 30’ (low-draft boats only), plus two kayaks for exploring the bay.brbrLocationbrbrWalk to The Square Grouper or 420 Lounge, local favorites for dining and drinks. Just a 20-minute drive south and you're in Key West, home to:brbrDuval Street nightlifebrbrThe Historic SeaportbrbrMallory Square sunsetsbrbrThe Hemingway HousebrbrAnd so much morebrbrAdditional DetailsbrbrParking: Space for 3 cars or 2 cars and 1 boat trailer. (Note: Owner’s boat trailer is stored on-site and not available for guest use.)brbrWiFi & Cable: High-speed internet and cable TV throughout the home.brbrPerfect For: Large families, group vacations, multi-generational trips, or anyone seeking the privacy of a full resort experience in their own backyard.brbrNeptune’s End is more than a vacation rental – it’s your own private paradise in the Florida Keys. Book your escape today!

NEPTUNES END - 4 Bedrooms / 3 Bathrooms Waterfront Retreat- Pool & Sunset Views

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$207.97

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to Wahoo Waterway! brbr brbrExperience the perfect blend of comfort and convenience at Wahoo Waterway, a charming 3BR canal front home in picturesque Cudjoe Key designed with an inverted floor plan. Enjoy stunning views and abundant natural light with the kitchen and living room located on the second floor. This unique layout provides a serene and spacious atmosphere for your gatherings. All three bedrooms are situated on the first floor, ensuring a cool and restful night’s sleep after a day of adventure. With boat dockage right at your doorstep, you can embark on quick trips to the Atlantic or Gulf waters, making fishing and boating excursions incredibly convenient. Just 30 minutes away from the vibrant cities of Key West and Marathon, you’re never far from exciting activities, dining, and entertainment options. Whether you’re seeking a tranquil escape or an adventure-filled getaway, Wahoo Waterway offers the best of both worlds. Book your stay today and create unforgettable memories in the heart of the Florida Keys! brbr brbrSLEEPS MAXIMUM OF 8 GUESTS: brbr brbrBedroom 1 (1st Floor): Queen Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 2 (1st Floor): Queen Bed brbr brbrBedroom 3 (1st Floor): Queen Bed brbr brbrLiving Room (2nd Floor): Sofa w/ Pull-Out Queen Bed, Two Chairs, Smart TV (no cable/satellite TV) brbr brbrKitchen (2nd Floor): Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- 75' of Seawall (35' available for dockage, boat lift not available for guest use) brbr brbr- Fish Cleaning Station brbr brbr- Outdoor Seating brbr brbr- Propane BBQ Grill brbr brbr- Parking for a maximum of 3 vehicles, including boat trailers. Recreational Vehicles may not be parked on the property. brbr brbr- Linen's and towels provided brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrPet Policy: Up to two friendly and well-behaved dogs or cats 75 LBS or less will be considered with a $10/night pet fee. To help maintain a safe and welcoming environment for all, we require every guest to submit pet or assistance animal information through BetterPet Passport. Guests will simply submit household pet information, request an accommodation for an assistance animal, or confirm they are not bringing a pet/animal. It's free, and only requires creating an account if you're bringing a pet or animal. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrBoating & Dockage Advisory: Due to bridges and varying water depths, it is your responsibility to ensure that your boat can safely navigate local waters, access the canal, and fit the listed dockage before booking. While we are happy to provide general information based on our knowledge of the area, guests must exercise extreme caution when boating and ensure all activities comply with local regulations. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, 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 nearby construction. brbr brbrPhoto 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 updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time.

Wahoo Waterway: Charming 3BR Canal Front Home in Cudjoe Key with Dockage & Pet-Friendly Amenities!

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$136.7

Welcome to your ideal RV lot in the vibrant Venture Out community on Cudjoe Key! This dry lot, measuring 35' x 69', offers a perfect base for your Florida Keys adventure with 30 and 50amp hookups, a picnic table and is surrounded by tropical landscaping for added privacy. The Venture Out community boasts an array of amenities, including laundry facilities, bathhouses, a pool, Jacuzzi, boat ramp, marina, and store. Stay active with tennis courts and playgrounds, ensuring fun for the whole family. Located just 25 minutes from the excitement of Key West, you'll also find yourself near a variety of popular restaurants. Enjoy delicious meals and entertainment at the Square Grouper Bar and Grill, Boondocks Miniature Golf and Draft House, Tonio's Seafood Shack and Tiki Bar, and the Bent Prop. Experience the best of the Florida Keys from this prime RV lot in the welcoming Venture Out community. Book your stay today and start making unforgettable memories!br**No cable or WIFI service is provided at this site** Please note that a Registration/Check-In Fee of $125 (subject to change) will be charged by Venture Out Security upon arrival. Additionally, parking is available for only one vehicle per unit, and extra parking permits may be obtained from the Guard Station for a nominal nightly fee, subject to availability. It is important to adhere to all Rules and Regulations during your stay. Applicable county and state taxes are collected regardless of the booking platform. Renters must be 25 years or older, and overnight occupancy is limited to a maximum of 6 people, all of whom must be registered with the Rental Manager. Furthermore, up to 2 dogs are permitted per Venture Out Regulations. Check-in time is at 4pm, and check-out time is at 10am unless alternative arrangements have been made with the Property Manager prior to arrival. To safeguard both guests and the property owner, a refundable $150 Security Deposit is required at the time of booking. Additionally, a 4% credit card processing fee will be applied if paying with a credit card. The main guest of the reservation will be required to submit a copy of your driver's license to Rental Manager for our records. Venture Out security requires Bluescape Vacation Rentals to pre-register all guests prior to your arrival. The main guest of the reservation will be required to email Bluescape Vacation Rentals all guest's first and last names who will be joining you for your stay at time of booking. The Rental Agreement is required to be signed within 24 hours from time of booking. All reservations are subject to final approval from the local Rental Manager.

Caravan Park/Campsite

RV Lot 40 Venture Out, Lot dimentions - 35'x69'

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$431.5

brbrIf you are looking for a great place to kick back and enjoy the easy Keys lifestyle, then Blue Heaven is just for you. brbrThis ground-level three-bedroom two bath home is located on the ocean side of Cudjoe Key with a great deep canal and a marina just around the corner. The home features eclectic and colorful decor with a mix of antiques and Caribbean/Keys colors and art. Inside there is a bright and comfortable living room area with an adjacent dining area as well. There is also a large Florida Room which opens out to a huge screened and covered dining/party area. brThe three bedrooms feature a queen in one bedroom, another queen in the second bedroom, two double beds in the third, plus a sofa sleeper in the Florida room. The kitchen is well equipped and ready for you. Amenities include central AC, five TVs, , stereo with CD, dishwasher, washer/dryer, and barbecue grill. brbrFrom the full-length concrete seawall/dock and boat lift, you have excellent boating access to the ocean, Gulfstream and coral reefs, or the backcountry and Gulf. There is built-in step-down access to the canal for swimming or snorkeling. brbrNearby there are excellent restaurants, a dive shop, and a marina. Within a short drive, there are also groceries, banks, a post office, bait and tackle, boat rentals, kayak rentals, and shopping. Key West and its unusual nightlife, world-class dining, and unique shopping are 20 miles south. The airport in Miami is about a three-hour drive. This is a non-smoking home. Ask about our pet policies.brbrMINIMUM 28 DAY RENTAL PER MONROE COUNTY CODEbr

3/2 Cudjoe Key waterfront single level house.

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$333.85

VO466brParadise Escape!brPerfect Location 35' Dockage!brIt'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 grill, outdoor patio furniture and dishwasher, Keurig coffee maker with Keurig refill cup. brbrWe are located in a spotlessly clean gated community with 24 hr. security, marina, ship store, boat ramps, picnic garden, heated pool, hot tub, tennis, basketball, playground, pickle ball, bocce ball and tennis, pavilion and club house for activities, over 4 miles of paved streets. brIt's a wonderful community with full time residents and vacation renters alike! brSECURITY DEPOSIT REQUIRED, NO SMOKING, br7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL,brOVERFLOW PARKING IS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.brVO REGISTRATION FEE $125.00- DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE.br****VEHICLE MAY NOT HANG INTO STREET- GUEST MUST VERIFY PRIOR TO RESERVING****

Paradise Escape - VO466 35' Dockage

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$362.95

SUNNY GENSbrTurn Key 2Bd/2Ba with Canal Views!br35' Dockage Quick Ocean Access!brbrBeautiful turn key stilt 2Bd/2Ba home in desirable community featuring 24 hr. gated security, pool, marina, tennis, pickle ball + more! This home is being offered furnished with all the household items and TV's. Features a 35' Concrete seawall with heavy duty dock post, fish table, patio furniture, covered parking. Many upgrades to include hurricane impact windows, metal roof, laminate flooring, new refrigerator. Designer decorated with gorgeous furnishings, newly upholstered living room sofa, love seat and chair with ottoman. brbrSECURITY DEPOSIT REQUIRED, NO SMOKING, NO PETS, 7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL,brOVERFLOW 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.br*****VEHICLE MAY NOT HANG INTO STREET- GUEST MUST VERIFY PRIOR TO RESERVING***

Sunny Gens - Venture Out #606

Cudjoe Key, Florida, United States

Bed