Home Vacation Home Rentals By Owner In Cudjoe Key, FL

Showing 199 Of 199 Vacation Rentals
Slider Thumb
Exceptional(3)

$534.98

/ Nightly
Private Vacation Home

Magnificent Ocean views, privacy abounds on this well appointed mini estate.

Cudjoe Key, Florida, United States

Welcome to “COCOLOCO”! Ocean breezes and a mesmerizing view of open water compliment this mini estate, the ultimate destination for your relaxation. This property has deep water dockage just steps away from your front door. World renowned fishing accessible in minutes. The waters off shore are teaming with sailfish, tuna, mahi mahi, wahoo, grouper, snapper and many other sought after fish for sport or making a scrumptious dinner. The full service “Cudjoe Gardens Marina” is located within the community for your convenience and all of your boating needs. The Bent Prop Bar and Grill within the marina is an eclectic waterfront restaurant that offers indoor and outdoor dining while overlooking the scenic harbor. Key West and Marathon are just short drives away. Unwind in the comfort of your spacious living room, where you can enjoy spectacular ocean views or watch a favorite movie on the 80” Samsung Smart TV. Your well appointed kitchen has everything needed to craft your own culinary creations. The four bedrooms have been meticulously decorated for your relaxation. Indulge in leisurely moments by the beautiful new in-ground pool while basking in the sun’s warmth. Sipping cocktails in the luxurious hot tub or under the alluring Tiki Hut is a must. COCOLOCO has bicycles available to cruise the island and kayaks that can be launched right from the backyard sandy beach. Fish tales can be told by the fire pit or simply relax while gazing at the star lit sky. Your furry family member is welcome, making it a pet friendly haven with a fenced backyard. Bring up to two friendly well behaved dogs. We love cats but for a variety of reasons NO cats please. There is a total pet fee of a mere $200.00 for the length of your stay. Secure your natural beauty getaway at COCOLOCO where adventures, relaxation and fun await.
Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(43)

$435.0

/ Nightly
Private Vacation Home

Shangri-la in the Keys! Enjoy the water views and a 45' dock space!

Cudjoe Key, Florida, United States

Shangri-la in the Keys! Enjoy the water views and a 45' dock space!br VO unit 413 - 2Bd/2Ba Stilt HomebrNewly renovated stilted 2Bd/2Ba furnished vacation home features an oversized 45' concrete seawall perfect for those with larger boats! The dock amenities include dock posts, cleats, swim ladder, outdoor shower, water, electric and fish cleaning table plus and enclosed storage room to store your dive and fishing gear as well as a bait freezer for added convenience. The main living room is bright and airy and overlooks lovely long range canal views on a 60' wide canal. The living room features an open floor plan with sleeper sofa, flat screen TV and reclining chair that leads out to a covered porch with table and chairs. The kitchen features full line of appliances with lots of countertop space for cooking and entertaining guests with a connecting dining room with table that seats six. The master bedroom features a queen bed with full size bathroom, flat screen television with Direct TV. The guest bedroom features a queen bed, closet storage with access to private balcony and access to the full size hallway bathroom. Additional amenities include central air conditioning, ceiling fans, osculating fans, 3 bicycles, WIFI, covered porch, covered balcony and covered parking. brSECURITY DEPOSIT REQUIRED, NO SMOKING, 7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL, OVERFLOW PARKING IS NOT GUARANTEED.IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.brbrVO 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*****brONLY.
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(5)

$336.13

/ Nightly
Private Vacation Home

Treasure Isle at Parks End - Venture Out 062

Cudjoe Key, Florida, United States

Treasure Isle at Parks End - Venture Out 062brSouthern Location Walk to Ocean!brThis sparkling clean and bright 2 Bedroom with 1 full bathroom vacation home, is situated at southern tip of Venture Out where land meets the sea, on the southern tip of Venture Out! A large oversized landscaped lot, offers a spacious concrete patio perfect for outdoor gatherings, plus an additional brick paver patio in the backyard for peaceful enjoyment. brbrThe interior is well appointed, with travertine flooring, a natural waterproof stone that covers the lower level and extends to a half wall with chair rail, adds a designer touch unparalleled by any other. Freshly painted interior, adds color and richness to the homes décor,brbrThe master bedroom Palm Cove boasts a queen size bed with closet storage and washer and dryer. The guest bedroom Coral Castle, is away from the main, features a full size bed with closet storage. brbrThe kitchen is well equipped with full line of appliances, beautiful white oak colored kitchen cabinets, with a spacious dining area and breakfast nook with bar stools that doubles as small office work space. Custom Travertine tile bathroom and exquisite shower details and Caribbean blue walls promote an over-the-top spa like experience. brAttention to detail prevails, from clean finishes to drywall and uplifting fixtures, this home has it all! brThis is your time to Enjoy Life and Live in this Tropical Diamond in Paradise! brbrSECURITY DEPOSIT REQUIRED, FREE WI-FI IN THE REC HALLbrOVERFLOW PARKINOVERFLOW 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. 7-1-23 fee is $125** DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE.br****VEHICLE MAY NOT HANG INTO STREET-brGUEST MUST VERIFY PRIOR TO RESERVING****
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(2)

$571.84

/ Nightly
Private Vacation Home

Slow M'Ocean #54 - Oceanfront Home - Cudjoe Key

Cudjoe Key, Florida, United States

Did you say you wanted something with a view Look no further because this home has the most gorgeous, turquoise ocean water views you have to see to believe!brEscape to paradise here at Slow M'Ocean #54 ~ This stunning, direct ocean front home located in the private, gated community of Venture Out is located on Cudjoe Key.brThis 2 bedroom, 2 bath home is the ideal location with dazzling views of the ocean and nearby islands. Boasting a prime boating location with a 35-foot concrete dock that can accommodate up to a 32' boat, this waterfront retreat offers unparalleled access to both the Atlantic Ocean and the Gulf of Mexico, each just a five minute boat ride away. **Please note - the boat in the photos is for illustrative purposes only and will not be at the home when you arrive.brThis modern home has recently been updated with new leather furniture in the living room. Slow M'Ocean features two cozy bedrooms, perfect for accommodating up to four guests comfortably.brThe Primary Bedroom has a comfortable King size bed and features an ensuite bathroom for privacy. There is also a porch connected to this room so you can wake up and have a cup of coffee or sit out here at night and do a little stargazing.brThere is a Keurig coffee maker at this home for you to enjoy your favorite brew.brThe Guest bedroom has a Queen size bed with ample closet space. This bedroom also has a connecting full bathroom for your guests privacy.brBoth bathrooms are equipped with stand up showers. brLaundry Facilities: A washer and dryer are available within the home, so you can pack light and keep your clothes fresh throughout your stay.brWake up to breathtaking views of the sunrise over the shimmering waters, or unwind on the spacious deck while soaking in the salty breeze. You'll likely see pelicans and egrets soaring by. Keep an eye out by the seawall and you might spot a manatee swimming by. Downstairs has plenty of outdoor seating and is complete with a bait freezer for your fishing trips & a BBQ grill awaits your fresh catch upon your return. br​​​​​​​Sorry, 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 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.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 11' W x 8 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 @bluescapevacationsbrBook your stay today and experience the beauty of waterfront living!
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(6)

$414.38

/ Nightly
Private Vacation Home

**DOLPHIN DAYDREAMS @ VENTURE OUT** New Home & Golf Cart + LAST KEY SERVICES…

Cudjoe Key, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrDOLPHIN DAYDREAMS is a freshly built 2-bedroom tropical home specifically designed to be the perfect antidote to the stresses of everyday life. Substitute zoom meetings and rush hour traffic for slow mornings on the patio and afternoons in the sun. Nestled within Venture Out, a popular resort community on Cudjoe Key, this prime location puts you right in the heart of the Lower Keys. Included with the rental is use of 4 bicycles and a 6-seat Golf Cart - a fun and convenient way to get around the community. Venture Out also offers wonderful on-site amenities including a heated 80-foot pool with large Jacuzzi and Kiddie Pool, tennis courts, basketball court, bocce courts, swimming lagoon, marina and convenience market with fuel on site and two double wide boat ramps, Recreation Center with billiards, darts, and ping pong, post office and a library. Venture Out Resort enjoys 24 Hour Patrolled Security.brbrTHE HOME…brbrEntering through the large sliding glass doors, the warm pastel colors of the open living area welcome you to DOLPHIN DAYDREAMS. The living room features a 75 inch flat screen TV and offers plenty of comfortable seating options. The fully equipped kitchen has new stainless-steel appliances and every tool needed to prepare home cooked meals. The kitchen bar provides indoor dining. Step out to the covered patio for a BBQ of your fresh catch using the propane grill and dining set with seating for 4. DOLPHIN DAYDREAMS is elevated 12 feet off the ground, which requires the use of stairs for entry. However, a unique feature of this home is the exterior lift, allowing for easy cargo access to the home without having to carry heavy items up the stairs.brbrTHE ACCOMMODATIONS…brbr** Master Bedroom: King bed, flat screen TV, closet, private balcony, and an en-suite bathroom with a walk-in shower.brbr** Second Bedroom: Two Twin beds OR One King bed, flat screen TV, closet, and access to the hall bathroom with a walk-in shower.brbrTHE AREA…brbrThere are some wonderful places to explore nearby, from Bahia Honda Beach (voted one of the top 10 beaches in the U.S.) and the American Shoal Lighthouse to snorkeling off Looe Key. For dinner out, consider the Square Grouper, Mangrove Mama’s and Tonio’s Seafood Shack just up the road. Finally, DOLPHIN DAYDREAMS is just a 25-minute drive to either Key West or Marathon, with all their attractions.brbrALL LAST KEY VACATION HOMES INCLUDE: brbr** Washer and Dryer br** Central Heat and A/C br** Ceiling Fans Throughoutbr** Flat Screen Cable TVs in Living Room & Bedrooms br** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels provided br** Wireless high-speed Internet access and full cable is included br** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list: brbr** 6-Seat Electric Golf Cart br** 4 Bicyclesbr** Covered Patiobr** Propane BBQ Grillbr** Community Pool Accessbr** Community Jacuzzi Spabr** Marina Store with Fuel onsitebr** Bait and Convenience Marketbr** Boat Wash Stationbr** Salt Water Swimming Lagoonbr** Post Officebr** Lighted Tennis, Basketball, and Bocce Courtsbr** Ping Pongbr** Off-Street Parking for 1 Vehiclebr** Exterior Lift (for cargo use only)brbrOther notes: brbr** Interim housekeeping provided upon request br** This property will accommodate up to 4 adultsbr** Pets Allowed (Dogs Only. Max of 2)br** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.brbrIMPORTANT NOTE: Venture Out charges a one-time Registration/Resort Fee due upon arrival: $116.25 +7.5% Tax = $125 for up to 4 people (Credit card, check or cash) PAID DIRECTLY TO VENTURE OUT. If you arrive with more than 4 people which is the maximum allowed in the home, you will not be permitted in the park. Overflow parking is available for $5/night and trailer parking for $10/night.brbrVenture Out guests are required to submit additional paperwork in advance of arrival, which Last Key will collect and coordinate within the week of your arrival. Guests should be prepared to submit all guest information to comply with HOA requirements.
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(5)

$330.51

/ Nightly
Private Vacation Home

Sunny Escape - Venture Out Unit 128

Cudjoe Key, Florida, United States

VO128brLovely 2Bd/2Ba with Covered Porchbr35' Dockage with Open Water Views!brCanalfront furnished vacation home featuring 2 bedrooms and 2 full bathrooms and offers quick access to the ocean or gulf! Great for boaters featuring 35' concrete seawall with cleats, dock posts, fish table, swim ladder and outdoor shower. Main living room overlooks the water with double sliding glass doors that lead to the covered porch. Living from offers a pull out sleeper sofa with chair and ottoman and flat screen television and desk with high speed internet access. Dining room features a glass top table with 4 chairs plus outdoors on the patio is additional seating for 4. Kitchen offers full line of appliances and gas top stove. Master bedroom queen bed with flat screen TV and full bathroom with combo shower/tub. The guest bedroom offers a queen bed with full bath access and a flat screen TV. Additional amenities include high speed internet, basic cable, central cooling/heat, dishwasher, microwave, washer, dryer and gas grill,2 bicycles and 2 single person kayaks brSECURITY DEPOSIT REQUIRED, NO SMOKING, br7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL,brOVERFLOW PARKING ADDITIONAL FEE 14 DAYS MAX,brVO REGISTRATION FEE $125 DUE UPON ARRIVAL CASH OR CHECK ONLY.br****PLEASE NOTE, THIS PROPERTY HAS A 14 FT. DRIVEWAY/PARKING SPACEbr AND WILL NOT FIT TRUCKS OR SUV'S- GUEST MUST VERIFY PRIOR TO RESERVING****
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb

$258.75

/ Nightly
Private Vacation Home

Oceanview at 372, Venture Out Cudjoe Key

Cudjoe Key, Florida, United States

Welcome to Oceanview at 372. Escape to a serene oasis with our charming Oceanview rental in the picturesque Florida Keys, perfect for a cozy winter retreat for two. This delightful one-bedroom, one-bathroom haven is designed to offer you a peaceful and rejuvenating getaway.brStep inside to find a bright and airy space, tastefully decorated with coastal-inspired decor that complements the stunning ocean views. The bedroom features two comfortable twin beds, dressed in soft linens to ensure a restful night's sleep. Large windows fill the room with natural light, creating a warm and inviting atmosphere.brThe bathroom is well-appointed, providing all the essentials you need, including fresh towels and complimentary toiletries. The fully equipped kitchenette allows you to prepare your favorite meals and enjoy them at the small dining area or outside on the private balcony, where you can savor your morning coffee while gazing out at the sparkling blue waters. There is a Cuisinart Drip & Keurig single cup coffee maker at this home for you to enjoy your favorite brew. brDuring your stay, you can marvel at the impressive 35-foot seawall and enhance your experience by either bringing your own boat or renting one from a local provider to fully enjoy the scenic waterways.brOur rental is conveniently located near popular attractions, local eateries, and water activities, making it easy to explore the vibrant culture and natural beauty of the Florida Keys. Whether you're looking to unwind on the sandy shores, embark on a snorkeling adventure, or simply bask in the tranquil ambiance, this ocean view retreat offers the perfect setting for a memorable winter escape.brWe kindly ask - NO PETS at this home due to severe allergies.brVenture Out is a golf cart friendly, private gated community that boasts a plethora of amenities to elevate your stay to the next level. Dive into the massive heated saltwater pool next to the ocean, let the little ones splash around in the kiddie pool, or relax in the bubbling spa. Stay active with a game of tennis, bocce, basketball, or pickleball on the community courts. Need fishing supplies or fuel for your watercraft The ship store and dock fueling station have got you covered! Don't miss out on this incredible opportunity to experience the best of island living at our slice of paradise on Cudjoe Key. Book your stay today and experience the magic of the Florida Keys from the comfort of our cozy and inviting ocean view rental.brA Registration/Check-In Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. Parking for 1 vehicle per Unit. This vehicle must fit on the driveway and not extend out to the road. The driveway measurements are 13.5'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.brProper county and state taxes are collected regardless of booking platform. Main guest must be 25 years or older. Overnight occupancy is limited to a maximum of 2 people, and all guests need to be registered with the rental manager. No smoking. Check-In is at 4pm, Check-Out is at 10am, unless otherwise arranged with the Rental Manager prior to arrival. To ensure that you are protected, as well as the owner, we offer a $55 Damage Waiver Insurance. If you chose to opt out of the Damage Waiver a refundable $1,500 Security Deposit will be collected. There is a 4% credit card processing fee.brPlease submit a copy of your driver's license to the Rental Manager for our records.brAll reservations subject to final approval from the local Rental Manager. Online bookings accepted with approval from the Rental Manager within 24 hours. The vacation rental contract must be signed and returned after speaking with the Rental Manager for the reservation to be confirmed.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Slider Thumb
Exceptional(3)

$496.79

/ Nightly
Private Vacation Home

Breezy Palms: Exquisite Open Water Keys Paradise W/ Spectacular Views, Dockage, Pool & Dog-Friendly!

Cudjoe Key, Florida, United States

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to Breezy Palms, where the allure of island life and breathtaking vistas converge in a tropical oasis that promises an unforgettable getaway! brbr brbrDelight in the gentle caress of island breezes as you immerse yourself in endless views that stretch to the horizon. With private dockage at your disposal, swift access to world-renowned fishing is merely minutes away. Embrace the thrill of casting your line into these legendary waters, where fishing dreams come true. Indulge in the inviting pool (construction to begin Dec 2023), offering a refreshing haven for playful splashes and relaxation alike. As the sun sets, elevate your experience by sipping cocktails against the backdrop of expansive open water views, where every moment is a picture-perfect memory in the making. While Breezy Palms presents a wealth of opportunities on its premises, the enchanting allure of the Florida Keys beckons. A mere 25-minute journey transports you to the vibrant energy of Key West, while 40 minutes away, the charm of Marathon awaits your exploration. Secure your stay at Breezy Palms today, where a harmonious blend of relaxation, adventure, and natural beauty creates a haven unlike any other. brbr brbrSLEEPS MAXIMUM OF 8 GUESTS: brbr brbrBedroom 1: King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 2: Queen Bed brbr brbrBedroom 3 (apartment with inside access): King Bed, En-Suite Bathroom, Sofa with Queen Pull-Out Bed, Two 36 Smart TV's (no cable/satellite TV), Kitchen, Laundry brbr brbrLiving Room: Sofa, Smart TV (no cable/satellite TV) brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- 40' of Private Protected Dockage on separate lot across the street (~3-4' depth at low tide, no water or electric) brbr brbr- Saltwater Heated Pool (heated to ~85 degrees Nov-Apr) brbr brbr- Propane BBQ Grill brbr brbr- Outdoor Seating brbr brbr- Keurig, Drip Coffee Maker, Toaster, Blender brbr brbr- Laundry (2 sets of Washer and Dryer) brbr brbr- Parking for a maximum of 5 vehicles (including boat trailers) on the property. 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 one friendly and well-behaved dog 40 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 brbrNo Smoking: 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. brbr brbrSecurity Cameras: For the safety and security of our guests and property, three exterior security cameras monitor the property. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.
Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps

Slider Thumb

$256.58

/ Nightly
Private Vacation Home

Waterfront w/15lb Boat Lift 2-bedroom house in charming Cudjoe Key

Cudjoe Key, Florida, United States

Available for short-term rental (1 to 6 months), this waterfront property on Cudjoe Key features a 15,000-pound boat lift, offering direct access to the Atlantic Ocean along with ample parking for both your boat trailer and vehicles. The residence boasts a beautifully furnished split floor plan that includes two spacious bedrooms, two bathrooms, and an open layout enhanced by a cathedral ceiling with exposed beams and abundant natural light, making it an ideal retreat for fishing enthusiasts, boaters, or anyone just wanted to relax. Situated in the serene and sought-after Cudjoe Key community, this remarkable canal-front home combines luxury with convenience and peace. The expansive screened patio presents a perfect venue for enjoying morning coffee or evening cocktails while taking in the stunning views. Additionally, its proximity to Key West ensures easy access to a lively selection of dining, shopping, and entertainment opportunities.brbrThe kitchen is thoroughly outfitted with a refrigerator, smooth-top stove, dishwasher, microwave, garbage disposal, coffee maker, toaster, blender, and all the essentials you could require. The dining area and living room are elegantly designed, featuring retractable sliders that lead to a screened-in deck, effectively merging indoor and outdoor spaces. The expansive Master Bedroom is furnished with a new organic king-sized bed and includes a walk-in closet along with a sizable television. By sliding open the door, one can step onto the lovely screened deck to savor morning coffee. The Master Bathroom features a new king organic mattress, tub/shower combination, toilet, and a separate vanity area.brbrThe second bedroom includes a queen-sized adjustable bed and a walk-in closet.brbrRates are subject to variation based on the length of stay, with options for shorter terms available.
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

Slider Thumb

$388.55

/ Nightly
Private Vacation Home

Spectacular Views & Amenities in Gated Community

Cudjoe Key, Florida, United States

Our comfortable, beautifully decorated two bedroom/one bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment.brbrAmenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.brbrInside you will find a peaceful, tastefully decorated home with attention to detail, comfort and cleanliness. It contains all the basics for your comfort. br br- Bedrooms: Two bedrooms. Each bedroom is equipped with a queen sized bed, pillows, comfortable, clean, and professionally washed linen. brbr- Bathroom: One bathroom with a tub/shower combination. Clean, professionally washed towels are provided, as well as basic toiletries that should cover guests needs upon arrival. For longer stays, please plan accordingly.brbr- Laundry Closet:Washer and dryer in the hallway closet.brbr- Kitchen: The kitchen is equipped with the basics: stove with electric countertop, refrigerator with ice-maker, microwave oven, dishwasher, coffee-maker, and a toaster oven. Plates, glasses, silverware, utensils, a blender, pots, and pans are provided for guest use. brbr- Living Room: You will find a comfortable living area with a comfortable recliner, a love seat and matching 3 person couch which turns into a full sized sleeper sofa, great for the kids. Clean linen for the sleeper sofa is stored in the linen closet. There is a SmartTV and free WiFi so just connect, sit down and enjoy.brbr- Dining Area: The dining area comfortably fits 4 adults. brbr- Outdoor Dining Area: Enjoy the sea breeze and beautiful views as you have a meal in our outdoor terrace.brbr- Beach towels.brbrYou will have full access to the home, and one dedicated parking space underneath the home. After booking you will receive a link to the home`s site with tons of relevant information on the property, the community, and the area. br brVenture Out Resort charges a one-time resort fee upon entry of $125 (including tax), payable at the gate upon arrival. This payment is not to your host, it’s to Venture Out, and is the same amount regardless of the length of your stay. All guests must be registered prior to arrival. brbrWhen you arrive at Venture Out Resort, you will pay the fee at the Guard Gate and receive your access pass. This gives you full usage of the pool, Jacuzzi, marina, tennis courts, playground, and more. Cash or credit cards accepted for this fee. brbrFor boat trailer parking , extra parking, and other relevant details please see the `Other details to note` section.brbrOur on-site co-host Ruby is available in case you need assistance during your stay.brbrOur home is located in the Venture Out Resort, a gated association resort comprised of 659 individually owned properties and equipped with many amenities and security to make your stay both enjoyable and relaxing.brbrCudjoe Key is close to both Key West and Marathon in the section of the Florida Keys known as the Lower Keys. Bahia Honda state park which is home to one of the most beautiful beaches in the Florida Keys and is about 20 minutes north of us. brbrVenture Out is located on Kemp Channel, which is one of the most accessible boating channels to both the beautiful back country, as well as a quick, ten-minute ride to the open Atlantic, coral reefs, and world-famous Looe Key National Marine Sanctuary. brbrVenture Out has a one time Resort Fee of $125 which guests must pay directly to Venture Out prior to check-in, at the gate, and provides access to usage of all the amenities within Venture Out. brbrRules and regulations of the community must be followed for use of amenities and common grounds, and are enforced by Venture Out security. Approximately 70% of the lots at Venture Out are homes and 30% are RV lots.brbrFor more information please see the `other details to note` section in this listing.brbrGENERAL:brbrCheck in after 4pm on date of arrival and Check-out is 10am on departure date.brbrPlease note that maximum occupancy for this property is 5 people (no more than 4 adults). You will be asked to fill out a Renters Registration form at the time of booking, which will be provided to Venture Out Security, and is a requirement to access the Community. brbrMinimum rental age is 26. No pets are allowed. Smoking is not allowed inside the property. No inappropriate conduct or partying will be tolerated. Guests must follow the House and Community Rules.brbrViolation of rules are grounds for security to ask you to leave immediately without a refund. brbrPARKING:brbrOnly one car is permitted at each lot. Transportation vehicles must fit in the driveway or will have to be moved into overflow parking for a small nightly fee. Commercial vehicles are not allowed. brbrIf you have an extra car, boat trailer, or jet ski trailer you will need to park them in the Overflow parking lot and pay the appropriate nightly fee up to 14 days maximum pending availability. (The rates are $5 to $10 per night depending on size). brbrOverflow availability is first-come, first serve and in general is good, except for high season/some major holidays, however, there is NO GUARANTEE, implied or otherwise that Venture Out will provide Overflow parking so please plan accordingly. Backup options are available nearby:brbrOFF-SITE TRAILER PARKING FACILITIES (phone numbers available in the home site link you will receive after booking - VRBO does not allow listing phone numbers in the listing)brbrFirst Class Seafood:br22290 Overseas Hwy, Cudjoe Key, FL brbrKeys Rentals:brCudjoe Key, FL brbrAqua Boat Works: br24838 Overseas Hwy. Summerland Key, FL brbrLower Keys Tackle:br29770 Overseas Hwy. Big Pine Key, FLbrbrA1 Storage:br100 Industrial Rd. Big Pine Key, FLbrbrMile Marker 31 Storage: (Previously BLK Storage & Marine)br79 Industrial Rd. Big Pine Key, FLbrbrBig Pine Storage: (30 day +)br30677 Overseas Hwy. Big Pine Key, FLbrbrB&B Storage (3 month+):brUS1 & Spanish Main Drive. Cudjoe Key, FLbrbrCLEANING:brbrIf you need cleaning during your stay, please contact your co-host to arrange cleaning. Cleaning is subject to availability, coordinated and paid directly to the co-host Ruby.brbrIn case of cancellation, credit card fees, if applicable are non-refundable.brPlease note that maximum occupancy for this property is 5 people (no more than 4 adults). Parties are prohibited, and only registered guests are allowed in the property after 10pm, unless authorized exceptionally by the host, in writing. This is strictly enforced and non-compliance will be grounds for removal and reporting to Airbnb for removal from the Airbnb platform.brbrMinimum rental age is 26. The home has light colored furniture and is very well decorated so it is not ideal for families with energetic toddlers. No pets are allowed. Smoking is not allowed inside the property. No inappropriate conduct or partying will be tolerated. Violation of any of these rules are grounds for security to ask you to leave immediately without a refund. br brADDITIONAL CHARGES:brbrVenture Out Resort charges a one-time resort fee upon entry of $125 including tax (paid to Venture Out, not to the host), payable at the gate upon arrival. When you arrive at Venture Out Resort, you will pay the fee and to receive your parking pass. This gives you full usage of the pool, Jacuzzi, marina, tennis courts, playground, and more. Cash or check only is accepted for this fee. brbrYou will receive a Venture Out Resort Guest Registration Form that you will need to fill out and return to your host prior to your arrival to the resort, which will facilitate your access through the guard gate. You must read and accept the Venture out community rules, and follow those rules during your stay.brbrOnly one car is permitted at each lot. 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, boat trailer, or jet ski trailer you will need to park them in the overflow parking lot and pay the appropriate nightly fee up to 14 days maximum pending availability. (The rates are $5-$10 per night depending on size, subject to availability). brbrNO COMMERCIAL VEHICLES ALLOWED. THERE IS NO GUARANTEE, IMPLIED OR OTHERWISE, THAT VENTURE OUT WILL PROVIDE ANY OVERFLOW PARKING SPACES FOR ADDITIONAL UNIT BOAT TRAILERS OR VEHICLES. PLEASE PLAN ACCORDINGLY.
Bath 1

Bath

Sleep 5

Sleeps

Slider Thumb
Exceptional(20)

$364.74

/ Nightly
Private Vacation Home

WATERFRONT HOME 35' SEAWALL & DOCK 2 Bedroom 2 Bath Vacation Rental

Cudjoe Key, Florida, United States

Enjoy our little piece of paradise! Casa Del Sol is a cozy 820 square foot home that has everything you want for the perfect tropical vacation: Water views, a private 35-foot seawall equipped with boat bumpers, cleats and fish cleaning station. Direct open water access to the Gulf of Mexico or Atlantic Ocean. Kayaks and bicycles. Access to the wonderful amenities at Venture Out, a residential community with a heated 80-foot pool with Jacuzzi and Kiddie Pool, tennis courts, basketball court, bocce courts, swimming lagoon, marina and convenience market. Two double wide boat ramps with fuel on site. Recreation Center with billiards, darts, and ping pong, post office and a library. Nearby attractions include Snorkeling off Looe Key, Bahia Honda Beach and just a 25-minute drive to either Key West or Marathon Attractions!br**PLEASE NOTE: When you arrive at Venture Out, upon arrival at the gate you will be asked to pay a fee directly to Venture Out registration fee per reservation, regardless of the number of guests or vehicles . The fee is $125 and can be paid by either cash or credit card. brbr** Washer and Dryerbrbr** Central Heat and A/Cbrbr** Ceiling Fans Throughoutbrbr** Flat Screen Smart TVs in Living Room & Bedroomsbrbr** Fully-Equipped Kitchenbrbr** Basic stock of spicesbrbr** Starter supply of paper productsbrbr** Linens and Towels providedbrbr** Wireless high-speed Internet access and smart TVs throughout the housebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Seawall / Boat Dockage brbr**Swim Ladderbrbr**Cleatsbrbr**Fillet Stationbrbr**Boat Bumpersbrbr** Propane BBQ Grillbrbr** Patio Chairsbrbr** Community Pool Accessbrbr** Community Jacuzzi Spabrbr** Marina Store with Fuel onsitebrbr** Bait and Convenience Marketbrbr** Boat Wash Stationbrbr** Salt Water Swimming Lagoonbrbr** Post Officebrbr** Lighted Tennis, Basketball, and Bocce Courtsbrbr** Ping Pongbrbr** Off-Street Parking for 1 vehiclebrbr** This property will accommodate up to 6 adultsbrbr**Home is equipped with exterior RING camera system one at entrance second in the back of home facing canalbrbr
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb

$504.91

/ Nightly
Private Vacation Home

Beautiful High Rise w/Dock and Amenities in Gated Community

Cudjoe Key, Florida, United States

Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Our property has a 35 foot boat dock with easy access to Kemp Channel. Enjoy one of the most beautiful homes in the community with amazing views.brbrCommunity amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security community. All guests must be registered.brbrPLEASE NOTE THAT IN JUNE 2025 AT&T IS INSTALLING FIBER SO THERE MAY BE DIGGING OR STREET PAVING DURING YOUR STAY.brbrInside you will find a peaceful, tastefully decorated home with attention to detail, comfort and cleanliness. It contains all the basics for your comfort. br br- Bedrooms: Two bedrooms. The main bedroom is equipped with a queen sized bed, pillows, comfortable, clean, and professionally washed linen. Our second bedroom has a full sized futon.brbr- Bathroom: Two full bathrooms, each with an individual sink, shower and toilet. Clean, professionally washed towels are provided, as well as basic toiletries that should cover guests needs upon arrival. For longer stays, please plan accordingly.brbr- Laundry: Washer and dryer in the secondary bathroom.brbr- Kitchen: The kitchen is equipped with the basics: stove with electric countertop, refrigerator with ice-maker, microwave oven, dishwasher, coffee-maker, and a toaster oven. Plates, glasses, silverware, utensils, a blender, pots, and pans are provided for guest use. brbr- Living Room: You will find a comfortable living area with a 3 person couch which turns into a full sized sleeper sofa, and three individual sized sofa chairs. Clean linen for the sleeper sofa is stored in the linen closet. There is a SmartTV and free WiFi so just connect, sit down and enjoy.brbr- Dining Area: A granite countertop extension from the kitchen serves as dining area. There are three tall stools.brbr- Outdoor Area: Enjoy the sea breeze and beautiful views as you sit back and relax in our outdoor terrace.brbr- Beach towels.brbrYou will have full access to the home, and one dedicated parking space underneath the home. After booking you will receive a link to the home`s site with tons of relevant information on the property, the community, and the area. br brVenture Out Community charges a one-time fee upon entry of $125 (including tax), payable at the gate upon arrival. This payment is not to your host, it’s to Venture Out, and is the same amount regardless of the length of your stay. All guests must be registered prior to arrival. Cash or credit cards accepted for this fee. brbrFor boat trailer parking , extra parking, and other relevant details please see the `Other details to note` section.brbrOur on-site co-host Jessica is available in case you need assistance during your stay.brbrOur home is located in the Venture Out Community, a gated community association comprised of 659 individually owned properties and equipped with many amenities and security to make your stay both enjoyable and relaxing.brbrCudjoe Key is close to both Key West and Marathon in the section of the Florida Keys known as the Lower Keys. Bahia Honda state park which is home to one of the most beautiful beaches in the Florida Keys and is about 20 minutes north of us. brbrVenture Out is located on Kemp Channel, which is one of the most accessible boating channels to both the beautiful back country, as well as a quick, ten-minute ride to the open Atlantic, coral reefs, and world-famous Looe Key National Marine Sanctuary. brbrRules and regulations of the community must be followed for use of amenities and common grounds, and are enforced by Venture Out security. Approximately 70% of the lots at Venture Out are homes and 30% are RV lots.brbrFor more information please see the `other details to note` section in this listing.brbrGENERAL:brbrCheck in after 4pm on date of arrival and Check-out is 10am on departure date.brbrPlease note that maximum occupancy for this property is 5 people (no more than 4 adults). You will be asked to fill out a Renters Registration form at the time of booking, which will be provided to Venture Out Security, and is a requirement to access the Community. brbrMinimum rental age is 26. No pets are allowed. Smoking is not allowed inside the property. No inappropriate conduct or partying will be tolerated. Guests must follow the House and Community Rules.brbrViolation of rules are grounds for security to ask you to leave immediately without a refund. brbrPARKING:brbrOnly one car is permitted at each lot. Transportation vehicles must fit in the driveway or will have to be moved into overflow parking for a small nightly fee. Commercial vehicles are not allowed. brbrIf you have an extra car, boat trailer, or jet ski trailer you will need to park them in the Overflow parking lot and pay the appropriate nightly fee up to 14 days maximum pending availability. (The rates are $5 to $10 per night depending on size). brbrOverflow availability is first-come, first serve and in general is good, except for high season/some major holidays, however, there is NO GUARANTEE, implied or otherwise that Venture Out will provide Overflow parking so please plan accordingly. Backup options are available nearby:brbrOFF-SITE TRAILER PARKING FACILITIES (phone numbers available in the home site link you will receive after booking - Airbnb does not allow listing phone numbers in the listing)brbrFirst Class Seafood:br22290 Overseas Hwy, Cudjoe Key, FL brbrKeys Rentals:brCudjoe Key, FL brbrAqua Boat Works: br24838 Overseas Hwy. Summerland Key, FL brbrLower Keys Tackle:br29770 Overseas Hwy. Big Pine Key, FLbrbrA1 Storage:br100 Industrial Rd. Big Pine Key, FLbrbrMile Marker 31 Storage: (Previously BLK Storage & Marine)br79 Industrial Rd. Big Pine Key, FLbrbrBig Pine Storage: (30 day +)br30677 Overseas Hwy. Big Pine Key, FLbrbrB&B Storage (3 month+):brUS1 & Spanish Main Drive. Cudjoe Key, FLbrbrCLEANING:brbrIf you need cleaning during your stay, please contact your co-host to arrange cleaning. Cleaning is subject to availability, coordinated and paid directly to the co-host Jessica.brbrSERVICE ELEVATOR:brbrOur home is equipped with a service elevator, however this elevator is only available to guests with legitimate needs. To use the service elevator please reach out to your host for arrangements. A security deposit will be required prior to providing a key to the elevator.brbrIn case of cancellation, credit card fees, if applicable are non-refundable.brPlease note that maximum occupancy for this property is 5 people (no more than 4 adults). Parties are prohibited, and only registered guests are allowed in the property after 10pm, unless authorized exceptionally by the host, in writing. This is strictly enforced and non-compliance will be grounds for removal and reporting to Airbnb for removal from the Airbnb platform.brbrMinimum rental age is 26. The home has light colored furniture and is very well decorated so it is not ideal for families with energetic toddlers. No pets are allowed. Smoking is not allowed inside the property. No inappropriate conduct or partying will be tolerated. Violation of any of these rules are grounds for security to ask you to leave immediately without a refund. br brADDITIONAL CHARGES:brbrVenture Out Resort charges a one-time resort fee upon entry of $125 including tax (paid to Venture Out, not to the host), payable at the gate upon arrival. When you arrive at Venture Out Resort, you will pay the fee and to receive your parking pass. This gives you full usage of the pool, Jacuzzi, marina, tennis courts, playground, and more. Cash or check only is accepted for this fee. brbrYou will receive a Venture Out Resort Guest Registration Form that you will need to fill out and return to your host prior to your arrival to the resort, which will facilitate your access through the guard gate. You must read and accept the Venture out community rules, and follow those rules during your stay.brbrOnly one car is permitted at each lot. 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, boat trailer, or jet ski trailer you will need to park them in the overflow parking lot and pay the appropriate nightly fee up to 14 days maximum pending availability. (The rates are $5-$10 per night depending on size, subject to availability). brbrNO COMMERCIAL VEHICLES ALLOWED. THERE IS NO GUARANTEE, IMPLIED OR OTHERWISE, THAT VENTURE OUT WILL PROVIDE ANY OVERFLOW PARKING SPACES FOR ADDITIONAL UNIT BOAT TRAILERS OR VEHICLES. PLEASE PLAN ACCORDINGLY.
Bath 2

Bath

Sleep 5

Sleeps

Home Most popular vacation rentals in Cudjoe Key