Vacation Rentals By Owner In Cudjoe Key, FL

$322.82

Saltwater Serenity #392 - Ocean Views on Cudjoe Key

Cudjoe Key, Florida, United States

Welcome to Saltwater Serenity #392, your perfect getaway in the heart of the beautiful Florida Keys.brNestled on a serene interior large corner lot, this high-rise home offers stunning privacy surrounded by lush, vibrant vegetation and ocean views. Saltwater Serenity is designed for relaxation and fun, making it the ideal spot for your next vacation. Step inside and you'll find an open floor plan that seamlessly connects the kitchen, dining room, and living room, creating a spacious and inviting atmosphere. The modern kitchen is fully equipped, ready for you to whip up delicious meals. There is a Hamilton Beach Flex-Brew 12-cup drip Coffee Maker at this home for you to enjoy your favorite brew.brThe living space is comfortably furnished, providing the perfect setting for cozy evenings or lively gatherings.brThis home boasts two well-appointed bedrooms and two pristine bathrooms, ensuring a comfortable stay for all guests.brThe Primary Bedroom has a Queen size bed and an ensuite bathroom for privacy and convenience. brThe Guest Bedroom has a comfortable Queen size bed. This charming home comfortably accommodates up to 4 guests. The covered porch, with its ample seating, is a true highlight. Overlooking the ocean, it's the perfect spot to enjoy your morning coffee, watch the sunrise, or simply relax with a good book while taking in the breathtaking views!brThere is a downstairs patio with comfortable seating featuring a gas grill to cook up your fresh catch and a dedicated area for family gatherings, making it easy to enjoy al fresco dining and create lasting memories with loved ones. There are also 4 bicycles for your use during your stay to explore the islands.brStaying connected is a breeze with high-speed Wi-Fi provided here. There is a washer and dryer for your convenience meaning you can pack light and keep your wardrobe fresh throughout your stay.brWhether you're seeking a peaceful retreat or a base for adventure, Saltwater Serenity is the perfect choice for your Florida Keys rental. Come and experience the charm and beauty of this exceptional property, and make memories that will last a lifetime.brSorry, no pets allowed at this home.brA 4-seater electric golf cart is available for an additional fee: $50 per day, $250 per week, or $750 per month. Perfect for cruising around Venture Out and exploring the community with ease. Please contact the rental manager to add this to your reservation.brVenture Out is a golf cart friendly, private gated community that boasts a plethora of amenities to elevate your stay to the next level. Indulge in resort-style amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball and bocce courts.brAdventure beyond the gates for a bite to eat at some of Florida Keys favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki's Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away!brWhether you're a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the waters edge, our Florida Keys getaway promises an unforgettable vacation experience. Book your stay now and discover the ultimate blend of luxury, convenience, and coastal charm at our oceanfront retreat in Venture Out on Cudjoe Key.brLocated inside Venture Out on Cudjoe Key. A separate Registration Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. This fee must be paid with cash or credit card (4% credit card fee will apply). Parking for 1 vehicle per Unit. This vehicle must fit on the driveway and not extend out to the road. The driveway measurements are 24'L x 13'W. If your vehicle does not fit when you arrive, you will need to see the guard gate for an additional parking pass for the overflow lot which costs $5/day. Extra parking permit may be available at the Guard Station for an additional nightly fee for a maximum of 14 days depending on availability. Must follow all the Rules and Regulations during your stay.brMain guest must be 25 years of age or older and will need to email a copy of your drivers license to the Rental Manager after booking has been accepted. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance. There is a 4% credit card processing fee. brSocial Media -br@bluescaperealestatebrYouTube Videos @bluescapevacationsbrBook your stay today and experience the beauty of waterfront living!

2

Bed

2

Bath

4

Sleeps

$318.04

/ Nightly

Private Vacation Home

Casa del Mare #42 - Oceanfront, Gated Community!

Cudjoe Key, Florida, United States

Beautiful Florida Keys Home located in a Gated Community with Lots of Amenities!brWelcome to Casa del Mare #42 - Your perfect getaway! This beautiful 2-bedroom, 2-bath home offers everything you need for a relaxing and enjoyable Florida Keys vacation. Open living room to the fully equipped kitchen and dining area.brKey Features:br*Open Kitchen Dining: The fully equipped kitchen opens to a welcoming dining area that comfortably seats up to 4, perfect for family meals or entertaining friends. There is a Kenmore drip drip Coffee Maker at this home for you to enjoy your favorite brew.br*Spacious Bedrooms: Two cozy bedrooms designed for comfort, ensuring restful nights after your adventures.brThere is a Queen size bed in the primary bedroom and an ensuite full bathroom for privacy equipped with a stand up shower.brThe Guest bedroom has a full size bed and the full guest bathroom is located just steps away in the hallway for your guests convenience. There is also an attached balcony for your guests to use in the morning to enjoy the views and a cup of coffee or sit out there at night to do a little stargazing.brThere is also a pull out sleeper sofa bed in the living room for additional sleeping accommodations.br*Outdoor Oasis: Enjoy the expansive covered patio downstairs with plenty of seating. A BBQ grill is here for you to cook up your fresh catches too.br*Laundry Facilities: A washer and dryer are available within the home, so you can pack light and keep your clothes fresh throughout your stay.brWhether you are here for a weekend getaway or an extended vacation, our waterfront retreat promises a unique blend of relaxation and adventure. Explore the local attractions, enjoy the water activities, or simply kick back and enjoy the stunning views from your patio.brThis home has a 4 person maximum occupancy. 4 guests allowed plus 1 child.brSorry, no pets allowed at this home.brVenture Out is a golf cart friendly, private gated community that boasts a plethora of amenities to elevate your stay to the next level. Indulge in resort-style amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball and bocce courts.brAdventure beyond the gates for a bite to eat at some of Florida Keys favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki's Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away!brWhether you're a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the waters edge, our Florida Keys getaway promises an unforgettable vacation experience. Book your stay now and discover the ultimate blend of luxury, convenience, and coastal charm at our oceanfront retreat in Venture Out on Cudjoe Key.brLocated inside Venture Out on Cudjoe Key. A separate Registration Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. This fee must be paid with cash or credit card (4% credit card fee will apply). Parking for 1 vehicle per Unit. This vehicle must fit on the driveway and not extend out to the road. The driveway measurements are 25'L x 10'W x 8'6H. If your vehicle does not fit when you arrive, you will need to see the guard gate for an additional parking pass for the overflow lot which costs $5/day. Extra parking permit may be available at the Guard Station for an additional nightly fee for a maximum of 14 days depending on availability. Must follow all the Rules and Regulations during your stay.brMain guest must be 25 years of age or older and will need to email a copy of your drivers license to the Rental Manager after booking has been accepted. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance. There is a 4% credit card processing fee. brSocial Media -br@bluescaperealestatebrYouTube Videos @bluescapevacations

Bed

Bath

Sleeps

$341.45

/ Nightly

Private Vacation Home

Spectacular 4 bedroom 2 bath pool home with great boating

Cudjoe Key, Florida, United States

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

3

Bed

1

Bath

6

Sleeps

$817.26

/ Nightly

Private Vacation Home

Stunning 4 bedroom 3.5 bath Open Water home with great boating

Cudjoe Key, Florida, United States

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

4

Bed

3

Bath

8

Sleeps

$280.84

/ Nightly

Private Vacation Home

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

Cudjoe Key, Florida, United States

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

Bed

Bath

Sleeps

$462.32

/ Nightly

Private Vacation Home

Salty Kisses in Cudjoe Key

Cudjoe Key, Florida, United States

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

2

Bath

4

Sleeps

Exceptional(4)

$475.21

/ Nightly

Private Vacation Home

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

Cudjoe Key, Florida, United States

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

Bed

Bath

Sleeps

$308.94

/ Nightly

Private Vacation Home

Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

Cudjoe Key, Florida, United States

Escape to Island Breeze #412, a charming 2-bedroom, 2-bath canal-front home in the Florida Keys, designed for boaters, adventurers, and anyone who loves the laid-back island lifestyle.brStep outside to your private 35' concrete seawall, complete with dock posts, cleats, a swim ladder, and a fish-cleaning table. With room to comfortably accommodate up to a 32' boat, you'll enjoy quick and easy access to open water - perfect for fishing, diving, or a day trip to nearby sandbars.brAfter a day on the water, unwind on the spacious covered porch overlooking the canal. With seating for six, an electric grill, and a bar cart, it's the perfect place for outdoor dining and sunset cocktails. For more fun, take out the included kayaks (2-person and 1-person) or explore the community by bicycle - four are provided. A golf cart is also available for rent to make getting around even easier. Please contact Cudjoe Custom Carts to inquire about the rental.brInside, the open living room features a comfy sofa that converts to a sleeper for additional guests, along with cable TV for evening relaxation. The primary bedroom offers a queen bed, while the guest bedroom has a sleeper sofa that opens into another queen bed, providing flexible accommodations for family and friends.brThere is a Keurig and Black and Decker 12 cup drip coffee maker at this home for you to enjoy your favorite brew.brIsland Breeze is also pet-friendly! One dog is welcome with a non-refundable $250 pet fee, so you don't have to leave your four-legged friend behind.brWhether you're boating, biking, kayaking, or simply enjoying the breeze off the canal, this home is your perfect Keys getaway.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. Adventure beyond the gates for a bite to eat at some of Florida Keys favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki's Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away! 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. Located 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 16'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. 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. Social Media - @bluescaperealestate YouTube Videos @bluescapevacations Book your stay today and experience the beauty of waterfront living!

Bed

Bath

Sleeps

$311.57

/ Nightly

Private Vacation Home

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Cudjoe Key, Florida, United States

Welcome to your Florida Keys retreat!brUnit #359 is an inviting 2-bedroom, 2-bath canal-front home is designed for both relaxation and adventure, offering modern comforts and an unbeatable location.brStep inside to find two bedrooms furnished with queen beds, plus a queen sleeper sofa in the living room - ideal for hosting family and friends. Each bedroom has its own mini-split AC for personalized comfort, while the living room and primary bedroom are equipped with TVs and Rokus so you can easily stream your favorite shows. A spacious dining table for six makes gathering for meals or planning your next day on the water effortless.brThere is a Keurig and 12 cup drip coffee maker at this home for you to enjoy your favorite brew.brOutdoors is where this home truly shines. A 35-foot concrete seawall accommodates boats up to 32 feet, complete with new dock posts, cleats, and a ladder for easy access. From the dock, enjoy peaceful ocean views and a straight shot out to open water - perfect for boaters, anglers, and water lovers. After a day on the water, fire up the propane grill - conveniently stored in a large air-spring lid dock box - and savor your fresh catch at the canal-side concrete picnic table.brWhether you're here to relax by the water, explore the world-class fishing and boating of the Lower Keys, or simply enjoy the tranquil setting, this home combines comfort, convenience, and true Florida Keys charm.brPet lovers are welcome too! This pet-friendly home allows up to 2 dogs with approval and a non-refundable pet fee of $250 per pet.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. Adventure 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! Whether 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. Located 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 16'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. 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 or you may pay with an e-check with no additional charges. TO PAY VIA CREDIT CARD WITH A 4% CREDIT CARD PROCESSING FEE. Social Media - @bluescaperealestate YouTube Videos @bluescapevacations Book your stay today and experience the beauty of waterfront living!

Bed

Bath

Sleeps

$435.45

/ Nightly

Private Vacation Home

Cudjoe Key Sportsman's Retreat

Cudjoe Key, Florida, United States

Discover the beauty of Cudjoe Key from this 3-bedroom, fully furnished, over 1800 sq ft house. This gorgeous property features 1 king bed and 2 queen beds, perfect for a peaceful getaway. With amenities like AC, heated and cooled pool, outdoor shower, kayak's, bait freezer, grill, ice machine and more. 85 feet of dock space with a 7500 lb. boat lift and fish cleaning station. Mature landscape makes it very private.

3

Bed

2

Bath

8

Sleeps

$162.37

/ Nightly

Caravan Park/Campsite

RV Lot 442 Venture Out, Canal Front, 35ftx69ft

Cudjoe Key, Florida, United States

Welcome to RV Lot 442 in the exclusive gated community of Venture Out, located in stunning Cudjoe Key, Florida! This spacious 69ft x 35ft canal-front RV lot is your gateway to some of the best fishing the Florida Keys has to offer, with direct access to both the Atlantic Ocean and the Bay. The lot features prime canal frontage with cleats and a fish cleaning station, 30 and 50 amp hookups, water/sewer hookups & a picnic table. Enjoy community amenities including a swimming pool, Jacuzzi, marina, marina store, boat ramp, tennis courts, and playgrounds. Nearby attractions include great restaurants such as Square Grouper Bar & Grill, Toni's Tiki Bar & Seafood Shack, Boondocks Draft House & Miniature Golf, Broil, and The Bent Prop. Additionally, the vibrant nightlife and daily attractions of Key West are just a short 20-minute drive away. Book your stay at RV Lot 442 and immerse yourself in the beauty and adventure of the Florida Keys. Whether you're here for the fishing, the amenities, or the local attractions, this spot has it all for an unforgettable vacation!brbrRV SITE ONLY - NO RV FOR RENT.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 upon arrival. Additionally, parking is provided for one vehicle per unit, with the possibility of obtaining an extra parking permit at the Guard Station for an additional nightly fee, subject to availability and a maximum stay of 14 days. It is essential to adhere to all the community's Rules and Regulations during your stay to ensure a harmonious experience for all residents and guests. To comply with county and state regulations, proper taxes are collected regardless of the booking platform used. 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 and Venture Out. Venture Out Regulations allow for up to 2 dogs per lot, providing the perfect opportunity to bring your furry companions along for the adventure. Check-in time is at 4pm, and check-out time is at 10am unless alternative arrangements have been made with the Rental Manager prior to arrival. To safeguard both guests and the property owner, a refundable $150 Security Deposit is required at the time of booking. A 4% credit card processing fee will be applied if paying with a credit card. Immerse yourself in the laid-back charm of Cudjoe Key and make the most of your vacation by securing this inviting RV Lot. The main guest of the reservation will be required to submit a copy of your driver's license to rental manager for our records. 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.

1

Bed

1

Bath

6

Sleeps

$263.33

/ Nightly

Private Vacation Home

Fabulous Florida Keys!

Cudjoe Key, Florida, United States

VO118brTropically Decorated 2Bd/2Ba Stilt HomebrLovely Covered Porch with Water ViewbrYou won't be disappointed in the beautiful decorated 2 Bedroom/2 Bath stilt home with a canal view. Relax on the covered deck with privacy palms. Lovely tropical decor with a spacious living room and dining area. Sleeping accommodations include a Queen size bed in the Master bedroom with its own private bath and flat screen television. A full size bed in the guest bedroom with a small balcony. Living room offers a queen size sleeper sofa. Amenities include a flat screen TV with DVD and expanded cable, updated appliances, glass top stove, dishwasher, plenty of counter space, stackable Washer/Dryer, covered parking, central A/C, ceiling fans, gas grill and FREE WIRELESS INTERNET.brSECURITY DEPOSIT REQUIRED, NO SMOKING, NO PETS,br7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL,brOVERFLOW PARKING ADDITIONAL FEE 14 DAYS MAX,brVO REGISTRATION FEE $125.00 DUE UPON ARRIVAL CASH OR CHECK ONLY.

Bed

Bath

Sleeps

$830.09

/ Nightly

Villa

Beachfront • Heated Pool • Hot Tub • Oceanview

Cudjoe Key, Florida, United States

Welcome to Colson Cudjoe Key 916 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay.brbrWelcome to your slice of paradise in Cudjoe Key! This two-story Oceanview villa combines tropical serenity with modern comfort, perfect for families, couples, or friends. Enjoy a private heated pool and spa, spacious living areas, and breathtaking Atlantic views from the master suite.brbrWhether you’re exploring Key West or relaxing under the sun, every moment here feels like pure vacation bliss.brbr⭐ HIGHLIGHTS ⭐br✔️️4 Bedrooms: 1x King Bed, 2x Queen Bed, 1x Bunk ✔️️Bed, 1x Queen Size Sofa Bedbr✔️️2 Full Bathroomsbr✔️️Fully Equipped Kitchenbr✔️️Spacious Living Area br✔️️Private Outdoor Pool and Hot Tubbr✔️️Free Wi-Fi br✔️️On-site Washer and Dryerbr✔️️BBQ Grillbr✔️️Free driveway and in building parking spotsbr✔️️Pets are welcome!br✔️️Maximum Capacity: 10brbr⭐ BEDROOMS ⭐brSleep peacefully in tastefully furnished bedrooms, each thoughtfully designed for comfort and style. Wake up to ocean breezes, natural light, and plush bedding — your perfect home away from home.brbr✔️️Extra pillows and blankets upon request and availabilitybrbr✔️️ Master Bedroom: King bed br✔️️ ensuite bathroom br✔️️Ceiling fan brbr✔️️ Bedroom 2: Kids Room With Bunk Bedbr✔️️AC unitbrbr✔️️ Bedroom 3: Queen bedbr✔️️Ceiling fan br✔️️AC unitbrbr✔️️Bedroom 4: Queen bedbr✔️️Ceiling fan br✔️️AC unitbrbr✔️️ Additional sleeping arrangement: Queen Size Sofa Bedbrbr⭐ BATHROOMS ⭐brBright, clean, and thoughtfully designed, our bathrooms offer everything you need for a refreshing start or a relaxing end to your day. Step into sparkling spaces stocked with plush towels, complimentary toiletries, and all the little comforts that make you feel right at home. Whether you prefer a quick rinse or a long soak, you’ll find everything you need to unwind and rejuvenate.brbr✔️️ Fresh towels and linens br✔️️ Complimentary toiletriesbr✔️️ Hair dryerbrbr✔️️ Bathroom 1: Full Bathroom - Master bedroom br✔️️ Double vanitybr✔️️ Bathtub brbr✔️️Bathroom 2: Full Bathroom brbr⭐ KITCHEN and DINING ⭐brCook and dine together in a fully stocked kitchen featuring everything you need to prepare family meals or tropical cocktails.brbr✔️️ High-end appliancesbr✔️ Refrigerator, Stove, Oven, Microwavebr✔️ Coffee Maker + Coffee Grounds and Pods providedbr✔️ Toaster, Blender, Air Fryer, Rice Maker, Mixerbr✔️ Dishwasher and Cleaning Suppliesbr✔️️ Spicesbr✔️ Plates, Bowls, Glasses, Wine Glasses, Utensilsbr✔️ Pots, Pans, Baking Trays, Mixing Bowls, Knife Setbr✔️️ Stocked with basic supplies: paper towels, cleaning supplies, trash bags, etc.br✔️ Spacious Dining Table for 6brbr⭐ LIVING ROOM ⭐brGather and unwind in the open-concept living area — the perfect place to connect, laugh, or simply relax.brbr✔️️ Comfortable sofa seatingbr✔️️ Smart TV (Cable)br✔️️ Bright windows with pool and garden viewsbrbr⭐ OUTDOOR SPACE ⭐brStep outside to your private paradise where relaxation meets tropical charm. Whether you’re sipping morning coffee by the pool, enjoying a family BBQ, or watching the sun dip below the horizon, this outdoor oasis invites you to slow down and soak in the island vibe.brbr✔️️Private Heated Pool and Hot Tub (Electric and Heat Pump System)br✔️️BBQ Grillbr✔️️Outdoor seating area and dining tablebr✔️️Outdoor Showerbr✔️️Sun loungers for soaking up the Florida sunbrbrPlease keep the pool gate closed to prevent iguanas and wildlife from entering.brbr⭐ LAUNDRY AREA ⭐brOur convenient laundry area makes keeping up with chores effortless. Equipped with essential appliances, it's designed to handle your laundry needs efficiently and seamlessly.brbr✔️️ Washer and dryerbr✔️️ Laundry detergentbr✔️️ Iron and Iron BoardbrbrDon’t miss out on this fantastic vacation home! Book now to experience the best of Cudjoe Key and the Florida Keys with all the comforts of a home away from home.brbr✨ Book Today and Let Us Take Care Of You In Cudjoe Key, Florida! ✨brbr✔️️ We use Charge Automation to provide a secure guest portal, which can be shared with your group and adds an extra layer of verification to prevent fraudulent bookings. You'll receive this link after your booking is confirmed.brbr✔️️ We hold a security deposit during your stay, which will be fully refunded after check-out, provided there are no damages to the property.brbr✔️️ Please take a moment to read our House Rules in the House Rules section.brbr✔️️This property comfortably accommodates up to 10 guests.brbr✔️️ This property may have regular maintenance (e.g., lawn, pool, pest control) during your stay. If you'd prefer no service during your visit, just let us know in advance.brbr✔️️ Long-term stays allowed — maximum 28 days.brbr✔️️ We’d like to set your expectations that the (heated pool/hot tub) temperature will be determined by the weather temperature, as this is a contributing factor if the heater reaches its limit and is unable to overcome the weather.br br✔️️ Pool and Spa Use Notice - Use of the pool, spa, and related facilities is entirely at the guest’s own risk. The property owners, management, and staff assume no liability for any injuries, accidents, or damages that may occur. This includes, but is not limited to, incidents arising from slips, falls, equipment malfunction, or other unforeseen circumstances. Guests are required to supervise children at all times and to follow all safety instructions provided. Your safety and comfort matter to us — please enjoy the pool and spa responsibly.brbr✔️️ We offer options for early check-in and late check-out, subject to availability and fees.brbr✔️️To make your stay as comfortable as possible, we perform weekly pest control to keep no-see-ums, mosquitoes, and other insects to a minimum. Florida’s warm, tropical environment can occasionally attract pests, but rest assured, we do everything we can to ensure your stay is enjoyable and relaxing. We’re thrilled to host you and can’t wait for you to create wonderful memories here!brbr✔️️ Unregistered guests are not allowed.br✔️️ Max # of pets: 2; Pet Fee Applies $100 per pet; Pets must be registered and approved by the host. Please ensure they are well-behaved and that no shedding, waste, or damage is left behind. Guests are responsible for any additional cleaning or repair costs caused by pets.br✔️️ No smoking within the property’s premises. Smoking is only permitted outdoors. Please use the provided ashtrays and dispose of cigarette butts properly.br✔️️ No parties, events, or large gatherings allowed.br✔️️There may be NO loud music/sustained noises at any time throughout the day. And at night,brmusic etc. should not be audible by neighbors AT ALL.br✔️️ Quiet hours are from 9:00 PM to 8:00 AM.br✔️️ Respect the neighbors. Do not park on their property or cause any disturbance.br✔️️ Treat the villa as you would your own home. Keep it clean, handle furniture and appliances with care, and promptly clean any spills to prevent stains or damage.br✔️️ Please park only on the concrete area in front of the house. Parking underneath the house is not allowed, as the surface is not designed for vehicle tires and may cause stains or damage. A $100 fee will apply for any violations.br✔️️ Do not flush anything other than toilet paper to avoid plumbing issues.br✔️️ Follow the guidebook instructions. Guests will be held responsible for any issues that arise from not adhering to these instructions.br✔️️ Adhere to check-in (after 5:00 PM) and check-out (by 10:00 AM) times. Early check-in or late check-out is subject to approval.br✔️️ All furniture, appliances, and items should be returned to their original place before departure. Missing or damaged items may result in additional charges.br✔️️ A Rental Agreement, Photo ID, and Security Deposit may be required upon check-in.br✔️️ We reserve the right to charge additional fees if any policy is violated.brbrHousekeeping and Cleanlinessbr ✔️ No shoes inside the house.br ✔️ Clean spills immediately to prevent damage.br ✔️ Load and run the dishwasher before checkout.br ✔️ Place used towels in the bathroom hamper.brbrTrash Disposalbr ✔️ Take trash out on Monday and Thursday evenings.br ✔️ Place bags outside the gate, under the coconut trees on the left.br✔️Note: $100 will be deducted from your deposit, if you forget to take garbage bins out prior to your checkout.brbrPool and Outdoor Areasbr✔️ Keep the pool gate closed to prevent iguanas or other animals from entering.br✔️ All pool users must shower before entering the pool or spa. br✔️ Guests under 18 years must be accompanied by a parent or guardian at all times.br✔️ Use of the pool and spa is at your own risk.br✔️ No alcohol is permitted in the pool or on the pool deck.br✔️ No glass or metal containers are allowed in or around the pool and spa areas. Only non-alcoholic beverages in plastic containers are permitted.br✔️ Report all accidents to the Property Manager immediately.br✔️ Notify the Property Manager of any maintenance or repair needs.br✔️ Diving is strictly prohibited — serious injury may occur.br✔️ Guests with open wounds or infectious diseases are not permitted in the pool or spa.br✔️ No running, rough play, or horseplay on wet deck areas.br✔️ For health and safety reasons, pregnant women and children under 5 should not use the spa.br✔️ All minors under 18 must be closely supervised by an adult when using the pool or spa.br✔️ Pool and spa users must be...

Bed

Bath

Sleeps

$331.95

/ Nightly

Private Vacation Home

Relax, Unwind & Reconnect at This Waterfront Getaway

Cudjoe Key, Florida, United States

Welcome to your ideal Keys getaway!brThis beautifully renovated stilt home offers year-round comfort and direct waterfront access, perfect for those looking to relax, explore, or do a little of both.brbrStep outside to your own private outdoor retreat. brFire up the gas grill for a fresh-catch cookout, dine comfortably in the shade, or sway the afternoon away in the hammocks. Launch your boat right from the private dock and cruise through the turquoise waters to discover the breathtaking sandbars of the Lower Keys and Key West. As the sun sets, gather around the wood-burning firepit and unwind beneath a sky full of stars.brbrInside, you'll find an airy open layout, a thoughtfully curated ocean-theme decor, and a sleek, modern kitchen with stainless steel appliances. The main living area is perfect for movie nights, while a cozy sitting room offers a quiet retreat for reading or relaxing.brbrWhether you're here for adventure or peace and quiet, this home delivers a perfect blend of style, comfort, and waterfront living.brbrBook your stay today — the Keys are calling.

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Bath

Sleeps

$357.91

/ Nightly

Private Vacation Home

3-bedroom waterfront house in fabulous Cudjoe Key

Cudjoe Key, Florida, United States

Discover the beauty of Cudjoe Key from this marvelous 3-bedroom house. The bedrooms feature a king bed, queen bed, murphy bed, and bunk bed, ensuring a lovely stay for all guests. With amenities like a hair dryer, AC, iron, and heating, your comfort is guaranteed. We'll be available to answer any questions while you stay at our place.

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Bath

Sleeps

$385.81

/ Nightly

Private Vacation Home

Relax at Keys Time – 2BR Waterfront Rental and Boat Dock

Cudjoe Key, Florida, United States

Keys Time #437 – Canalfront 2BR Vacation Rental in Cudjoe Key | Pet-Friendly, Boat Dock & MorebrWelcome to Keys Time, your relaxing Florida Keys escape located in the sought-after Venture Out community on Cudjoe Key. This beautifully furnished 2-bedroom, 2-bath canalfront home offers the perfect setting for guests looking to unwind, explore, and enjoy the laid-back island lifestyle.brDesigned for comfort and convenience, Keys Time comfortably accommodates up to 6 guests. The primary bedroom features a king-size bed and private en suite bathroom. The guest bedroom includes a full-size bed and generous closet space, while a sleeper sofa in the living room offers additional sleeping accommodations.brThis home is ideal for boaters and water lovers, offering a 21-foot concrete dock with space for boats up to 17 feet. A fish cleaning station, swim ladder, and dock post make your boating and fishing days effortless. There is a gas BBQ grill outside to cook up your fresh catch!brTake in serene canal views from your covered patio, and if you're lucky, spot a manatee swimming by. Inside, enjoy central A/C, a fully equipped kitchen, and smart TVs in the living room and bedroom to keep you comfortable and connected throughout your stay.brThere is a combo Hamilton Beach drip and single serve coffee maker at this home for you to enjoy your favorite brew.brKeys Time is pet-friendly, welcoming up to two well-behaved dogs with a non-refundable pet fee of $250 per pet. Please notify the rental manager at the time of booking if you're bringing your furry companions.brLocated within Venture Out, a gated, golf cart-friendly community, you'll have access to a wide range of amenities. These include an 80-foot heated pool, saltwater lagoon, Jacuzzi, tennis courts, basketball and bocce courts, a marina with fuel, bait shop, post office, convenience store, boat ramp, and wash-down station—all just steps from your door.brExplore local dining favorites like Square Grouper, The Morning Joint, Mangrove Mama's, Boondocks Mini Golf & Draft House, Kiki's Sandbar, and The Bent Prop—all within a 10-minute drive. Or take a short, scenic drive just 20 miles south to enjoy the energy, dining, and attractions of Key West.brWhether you're here to fish, dive, kayak, boat, or simply soak in the Keys lifestyle, Keys Time delivers the ideal blend of coastal charm, convenience, and island comfort. Book your stay today and discover why Venture Out is one of the Florida Keys' most loved vacation destinations.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 20'L x 9.5'W. If your vehicle does not fit when you arrive, you will need to see the guard gate for an additional parking pass for the overflow lot which costs $5/day. Extra parking permit may be available at the Guard Station for an additional nightly fee for a maximum of 14 days depending on availability. Must follow all the Rules and Regulations during your stay.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!

2

Bed

2

Bath

6

Sleeps

$189.8

/ Nightly

Private Vacation Home

Pelican Perch – 3BR Canal Front Home with Dockage, Pet-Friendly, Quick Access to Atlantic & Gulf!

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 brbrPelican Perch – Waterfront Escape with Quick Access to the Atlantic & Gulf! brbr brbrWelcome to Pelican Perch, a 3-bedroom canal front home on beautiful Cudjoe Key, offering the perfect blend of relaxation and adventure. With 60 feet of seawall, you’ll have ample space for your boat, and quick access to Kemp Channel makes getting to the Atlantic or Gulf a breeze. Unwind on the spacious decks or enjoy the tropical breeze from the screened porch, an ideal spot for morning coffee or evening cocktails. Inside, you'll find a comfortable, well-equipped home designed for a laid-back island lifestyle. Pet-friendly, so your furry friends can join the fun! Conveniently located just 30 minutes from Key West or Marathon, Pelican Perch is the perfect home base for exploring the Lower Keys. Whether you're boating, fishing, diving, or simply soaking up the sun, this waterfront retreat has everything you need for an unforgettable stay! brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1 (1st Floor): Full Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 2 (1st Floor): Full Bed brbr brbrBedroom 3 (1st Floor): Two Twin Beds brbr brbrLiving Room (2nd Floor): Sofa, Loveseat, 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- 60' of Seawall (35' available for dockage, ~6' depth at seawall) brbr brbr- Fish Cleaning Station brbr brbr- Bait Freezer brbr brbr- Outdoor Seating brbr brbr- Propane BBQ Grill brbr brbr- Exterior Elevator does not work brbr brbr- Parking for a maximum of 4 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 one friendly and well-behaved dog 100 LBS or less or up to two friendly and well-behaved dogs or cats 30 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.

Bed

Bath

Sleeps

$300.36

/ Nightly

Private Vacation Home

Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key

Cudjoe Key, Florida, United States

Welcome to your Little Piece of Paradise #233 here at the gated community of Venture Out! brThis cozy, canal front, 1-bedroom, 1-bath room home PLUS bonus Guest room offers everything you need for a relaxing and enjoyable Florida Keys vacation.brKey Features:brOutdoor Oasis: Enjoy the expansive 35' concrete seawall that can accommodate up to a 32' boat - ideal for fishing, sunbathing, or simply enjoying the gentle ocean breeze. Take a dip in the canal as there is a swim ladder attached to the dock for your use. A table and 4 chairs is set up on the dock to sit back, relax and watch the boaters return from their daily adventures on the ocean. Additional outdoor chairs are available as well.brThere is a grill outside ready for you to cook up your fresh catch, along with a convenient fish cleaning station to prepare it right on site.brThe equipped kitchen opens to a welcoming dining area that comfortably seats up to 6, perfect for family meals or entertaining friends. For those who may need to work on the road, there is a desk and chair set up in the dining area. There is a drip coffee maker at this home for you to enjoy your favorite brew.brThere are Smart TVs in the Living Room and Primary Bedroom. A Roku TV is located in the Guest bonus room.brThe Primary bedroom has a Queen size bed.brThe bonus guest bedroom has a Queen size bed and is adjacent to the living room and the Primary bedroom. Please note that this bedroom has a curtain for the entryway from the living room. brThere is also a pull-out sleeper sofa in the living room for additional sleeping accommodations. brThe full bathroom has a standup shower.brA washer and dryer are available within the home, so you can pack light and keep your clothes fresh throughout your stay.brThere is a bait freezer/refrigerator located in the kitchen to keep your supplies fresh!brThis is a pet friendly home that allows up to 2 dogs with a $250 pet fee per pet. Rental manager must be notified at time of booking.brWhether you are here for a weekend getaway or an extended vacation, our waterfront retreat promises a unique blend of relaxation and adventure. Explore the local attractions, enjoy the water activities, or simply kick back and enjoy the stunning views from your patio.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' 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 15'6 L x 10'W. If your vehicle does not fit when you arrive, you will need to see the guard gate for an additional parking pass for the overflow lot which costs $5/day. Extra parking permit may be available at the Guard Station for an additional nightly fee for a maximum of 14 days depending on availability. Must follow all the Rules and Regulations during your stay.brMain guest must be 25 years of age or older and will need to email a copy of your drivers license to the Rental Manager after booking has been accepted. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance. There is a 4% credit card processing fee. brSocial Media -br@bluescaperealestatebrYouTube Videos @bluescapevacationsbrBook your stay today and experience the beauty of waterfront living!

Bed

Bath

Sleeps

$433.13

/ Nightly

Private Vacation Home

Open Water Retreat with 58' Seawall, Kayaks, Paddleboards, Bikes & Panoramic Ocean Views

Cudjoe Key, Florida, United States

Welcome to Palm Paradise #477, a true Florida Keys escape located directly on the open ocean. This waterfront retreat features an expansive 58-foot seawall that can accommodate up to a 56' boat, complete with mooring whips, dock posts, cleats, a fish cleaning station, swim ladder, and outdoor shower—perfect for boaters, anglers, and water lovers alike. After a day on the water, rinse off, then fire up the propane grill and enjoy outdoor dining for six while taking in endless views of the Atlantic.brGuests have full use of 4 bicycles, fishing poles, 2 paddleboards, 2 single kayaks, bait buckets, lobster traps, a bait freezer, and an ice machine, making it easy to turn every day into an adventure.brInside, this bright and comfortable home offers 2 bedrooms and 2 full baths. The master bedroom features a plush queen bed, while the guest bedroom offers two twin beds—perfect for families or friends. The spacious living and dining area is lined with large windows, showcasing panoramic ocean views. Dine inside at the table for six or relax in the living room with a large smart TV, where you can sign in to your favorite streaming platforms.brThere is a Hamilton Beach 12-cup Drip coffee maker at this home for you to enjoy your favorite brew. brWhether you're fishing, boating, kayaking, or simply relaxing with a cocktail at sunset, Palm Paradise provides everything you need for the ultimate Keys getaway.brPlease note: No pets are permitted.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 11' L X 10' W X 6.5' 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

Bath

Sleeps

$266.94

/ Nightly

Private Vacation Home

Aqua Vista

Cudjoe Key, Florida, United States

Bright, colorful and tropical this freshly remodeled home is located within easy walking distance to convenience store and swimming pool /spa and ocean swimming are! You are close to everything!! Cook inside in easy access kitchen with large counter space. VO REGISTRATION FEE $125.00 DUE UPON ARRIVAL. Overflow parking for boat trailers and extra vehicle is available on a first come first serve bases and is not guaranteed ($10 per day).

2

Bed

1

Bath

4

Sleeps

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