Vacation Home Rentals By Owner In Cudjoe Key, FL

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!

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

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$435.45

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.

Cudjoe Key Sportsman's Retreat

Cudjoe Key, Florida, United States

3

Bed

Bath

8

Sleeps

$263.33

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.

Fabulous Florida Keys!

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$331.95

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.

Relax, Unwind & Reconnect at This Waterfront Getaway

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$357.91

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.

3-bedroom waterfront house in fabulous Cudjoe Key

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$385.81

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!

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

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$189.8

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.

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

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$300.36

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!

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

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$433.13

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!

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

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$266.94

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).

Aqua Vista

Cudjoe Key, Florida, United States

Bed

Bath

4

Sleeps

$582.75

Oceanfront 2BR/2BA in Venture Out with 70' Seawall, Pet-Friendly, Pool, Stunning Views & Island ComfortbrWelcome to Ocean Blue #225, a beautifully positioned 2-bedroom, 2-bath open-water retreat located inside the private, gated community of Venture Out on Cudjoe Key. With sweeping ocean views, a spacious layout, and a 70' concrete seawall, this pet-friendly home is the perfect escape for boaters, families, couples, and anyone craving laid-back Florida Keys living.brThe SpacebrOcean Blue #225 offers a bright, comfortable interior designed for easy island living. Large windows and outdoor seating areas allow you to take in the beautiful open-water views, while the central A/C keeps the home cool after a day in the sun.brThe well-equipped kitchen features plenty of space to prepare meals, complete with a center island for prep and a Black & Decker 12-cup drip coffee maker to start your mornings right. A washer and dryer are also provided for added convenience during your stay.brThe living room is the perfect place to relax and unwind, featuring comfortable seating, a queen sleeper sofa, and a smart TV for movie nights or lazy afternoons.brBedrooms & Sleeping ArrangementsbrPrimary Bedroom: Queen-size bed, smart TV, and private ensuite full bathroom with walk-in showerbrGuest Bedroom: Queen-size bed and smart TVbrLiving Room: Queen-size sleeper sofabrMaximum Occupancy: 6 guestsbrBathroomsbrPrimary Bathroom: Ensuite full bathroom with walk-in showerbrGuest Bathroom: Full bath with tub/shower combinationbrOutdoor Living & Open Water ViewsbrOcean Blue #225 is perfectly situated on open water, offering beautiful sunrise views and the relaxing sounds of the ocean right from your backyard. Enjoy your morning coffee or evening cocktail from the outdoor seating area while taking in the breeze and waterfront scenery.brThe home also features a propane grill on the front porch, making it easy to cook your fresh catch or enjoy dinner at home after a day exploring the Keys.brBoating & Seawall InformationbrThis property features an impressive 70' concrete seawall that can accommodate boats up to approximately 45 feet once repairs are complete.brImportant: The seawall is currently undergoing repairs and is expected to be completed by July 2026. Boating access and dockage will not be available until construction is finished. Guests booking prior to completion should be aware that no boat use or dock access will be possible during this time.brCommunity Amenities at Venture OutbrVenture Out is one of the most sought-after waterfront communities in the Lower Florida Keys and offers guests access to:br80' heated saltwater swimming pool, hot tub, kiddie pool, and saltwater swimming lagoonbrBoat ramp and wash-down stationbrMarina store with fuel, bait, and convenience itemsbrTennis courts, pickleball, bocce, basketball, and playgroundbrOceanfront common areas with thatched umbrellas and lounge areasbrGated security and electric golf cart-friendly streets throughout the communitybrLocationbrLocated on Cudjoe Key, Ocean Blue #225 places you just minutes from excellent local restaurants, bars, and attractions including Square Grouper, Broil, Mangrove Mama's, Kiki's Sandbar, Boondocks Draft House, and the world-famous Looe Key Reef for snorkeling and diving.brYou're also just a short drive from Key West for shopping, dining, and nightlife, while still enjoying the quieter, more peaceful side of the Lower Keys.brPet-Friendly DetailsbrUp to 2 pets are welcome with prior approval and a paid pet fee of $250 per pet. Guests must notify the rental manager at the time of booking if bringing pets.brGood to KnowbrVenture Out registration fee: $125 (subject to change), paid directly to the community at arrival (cash or credit card; processing fees may apply)brParking: 1 vehicle only. Driveway measures approximately 19'1” long x 11'8” wide and must fit entirely within the driveway without street overhangbrQuiet hours: 10:00 PM to 6:00 AMbrStarter supplies provided: A starter supply of essentials is included to get you started. These supplies are plenty for a 1 night stay.brPrimary guest must be 25 years of age or olderbrPayment & Booking RequirementsbrSigned rental agreement and government-issued ID are required after booking. Please reply to the email you receive from us after signing your rental agreement with a photo of your ID.brA 4% credit card processing fee applies to credit card payments.brWhether you're here to soak in open-water views, relax poolside, fish the flats, or simply enjoy the laid-back beauty of the Florida Keys, Ocean Blue #225 offers the perfect island getaway.

Ocean Blue #265 | Open-Water Views, Pet-Friendly 2BR Retreat in Venture Out

Cudjoe Key, Florida, United States

3

Bed

Bath

Sleeps

$427.5

This Home has some of the absolute best views of the Ocean; sitting on your deck watching nature at its best. Our 53ft sea wall perfect for fishing or docking your boat. Underwater Lights Make this an Awesome Place to fish from your deck. brEasy access to either the Atlantic or the gulf; some of the best fishing or lobstering spots located in all of the Keys. Plus, one of the most beautiful Light Houses located just a short Boat ride to an awesome light house with great snorkeling opportunities.brAlso, some of best food located just around the corner (Square Grouper and Broil) are Great places to eat and just a short 19-mile drive to downtown Key West.brbr****THERE WILL BE A RESORT CHARGE TO BE COLLECTED AT THE MAIN ENTERENCE WHEN YOU CHECK IN WITH THE GUARD**** $125.00- This gives access to all the amenities including the clubhouse with games and pool area.

KING's POINT Open Water views and a great resort for family and Fishing.

Cudjoe Key, Florida, United States

Bed

Bath

8

Sleeps

$459.88

Waterfront Modern Home w/ Dock, Ocean Access + Golf Cart | Fishing Paradise | Resort AmenitiesbrbrStay at this beautifully furnished, modern 2BR/ 2 Bath home in the Florida Keys, located in the private, gated community of Venture Out. Clean, well-stocked, and designed for comfort, this home includes a golf cart for easy access around the resort.brbrPerfect for Boaters & Anglers:brbr• Direct ocean access—ideal for serious fishingbr• Private concrete dock with water & electric, fits up to a 29' boatbr• Fish cleaning station on-sitebr• Off-site trailer parking includedbr• World-class fishing nearby: sailfish, mahi (dolphin), marlin, grouper, snapper, tarpon & morebrbrbrWater Adventures:brbr• Easy access to Looe Key Reef for snorkeling & divingbr• Nearby charters for diving, snorkeling, and fishingbr• Snorkel gear provided for guest usebrbrbrResort-Style Amenities:brbr• Private sandy beachbr• Heated pool + kiddie poolbr• Tennis, pickleball, basketball & bocce courtsbr• Marina with gas, boat ramps, wash-down stations & air pumpsbrbrbrExtras Included:brbr• bicyclesbr• golf cartbr• paddleboard & kayakbrbr brbrNearby Attractions:brbr• Key West festivals like Fantasy Fest, Goombay & Hemingway Daysbr• Marathon’s Turtle Hospital & Dolphin Research Center (swim with dolphins)brbrbrImportant Info:brbr• $125 resort registration fee per stay (paid directly to Venture Out at check-in; not an owner fee)br• Security camera located under the house facing the dock (visible above the lockbox)brbrbrbrbrWhy Guests Love This Home:br✔ Direct ocean access + private dockbr✔ Ideal for fishing & boatingbr✔ Golf cart + water gear includedbr✔ Family-friendly resort amenitiesbr✔ Prime Florida Keys locationbrbrBook now and experience the ultimate Florida Keys getaway—perfect for relaxation, adventure, and unforgettable days on the water.

Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$533.46

Welcome to Cudjoe Gardens Sanctuary – Your Perfect Keys Getaway!brbrLocated in the heart of Cudjoe Key, this beautifully appointed 3-bedroom, 2-bathroom home offers everything you need for a relaxing and adventure-filled vacation.brbrSPACIOUS AND COMFORTABLE LIVING! With nearly 1,800 square feet of living space, the home comfortably accommodates families or groups looking to unwind in paradise. You'll enjoy:br- A fully equipped kitchenbr- Bright, open-concept living areasbr- Cozy, coastal décor throughoutbrbrBOATERS DREAM! Bring your boat (up to 42') and dock along the private bulkhead with deep water access to the Atlantic. Just moments away, Cudjoe Gardens Marina offers convenient fuel and boating supplies.br- Room for boat, trailer, RV & 3 vehiclesbr- Garage access includedbr- Easy ocean access – no bridges or boat liftsbrbrOUTDOOR OASIS! Relax and recharge in your own tropical retreat:br- Large heated/chilled pool*br- Spacious sun deck & shaded outdoor seating areabr- Fully fenced yard – great for privacy and peace of mindbr- Located right on a canalbrbrPERFECT LOCATION! Cudjoe Gardens is a guest favorite for a reason! Just a short drive to:brbr- Key West – vibrant nightlife, dining & historybr- Marathon – family attractions & beachesbrbrLocal fishing hotspots – ideal for anglers of all levelsbrbrWhether you're here to fish, relax by the pool, or explore the Keys, Cudjoe Gardens Sanctuary is your home base for the perfect island escape!brbr*Pool heating/chilling available – inquire for details.brbrbrbrHOUSE FULL DETAILS AND AMENITIES…brWelcome to your canal-front retreat!brThis spacious 3-bedroom, 2-bath home boasts an open floor plan filled with natural light, creating a bright and inviting atmosphere. The seamless flow between the living room, dining area, and kitchen makes everyday living and entertaining effortless.brbrThe thoughtfully designed split-bedroom layout offers privacy and comfort, with the primary suite situated on one side of the home and two guest bedrooms on the opposite side—perfect for hosting visitors or long-term guests.brbrTastefully decorated and fully outfitted with user-friendly amenities, this home is ready for you to relax and enjoy the waterfront lifestyle.brbrPROPERTY OVERVIEWbrThis single-level, stair-free home offers the perfect getaway with spacious indoor comfort and a stunning outdoor oasis. Located in a quiet, well-kept residential neighborhood—ideal for extended stays!brbrSLEEPING ARRANGEMENTSbrPrimary Suite: King BedbrGuest Bedroom 1: Queen BedbrGuest Bedroom 2: Bunk Bed (Full on bottom, Twin on top)brbrBATHROOMSbrPrimary Ensuite: Full bath with shower & separate bathtubbrGuest Bathroom: Full bath with shower/tub combobrbrbrOUTDOOR LIVINGbrPrivate Pool with spa and waterfallbrCovered sitting area, multiple sun loungers, and all-day sunbrBoat access: Accommodates 1 boat up to 42' along the bulkhead (note: lifts not available)brbrPARKINGbrSpace for up to 3 cars, 1 boat, and 1 boat trailerbrRV Parking with hookups available for an additional $30/day (must be arranged in advance)brIncludes blackwater hookupbrRV space does not increase max guest count (6 total guests max)brbrPETSbrNo pets allowed—no exceptionsbrbrPOOL HEATING AND COOLINGbrOptional pool heating or chilling available at $20/daybrbrBOOKING & RENTAL RESTRICTIONSbrMinimum stay: 28 daysbrStart date must be the 1st of the monthbrSplit months not allowed unless pre-approved by managementbrBookings not adhering to these rules will be cancelledbrbrCANCELLATION POLICYbr100% refund if canceled 60+ days before check-inbrbrLOCAL MANAGEMENT & CONCIERGEbrEnjoy peace of mind with direct access to a local property manager during your stay for assistance or local recommendations.

CUDJOE GARDENS SANCTUARY- 3 BED/ 2 BATH- POOL, SPA, RV HOOK UP, BRING YOUR BOAT

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$293.6

Waterfront 1BR Cottage in Venture Out with a 35' Dock, Kayaks, Pool, World-Class Fishing & Boating AccessbrWelcome to Pelican's Paradise #507, a beautifully renovated 1-bedroom, 1-bath waterfront cottage located inside the private, gated community of Venture Out on Cudjoe Key. This inviting retreat is ideal for couples, boaters, and anglers looking to enjoy the Florida Keys with direct water access, excellent amenities, and easy island living.brThe SpacebrThis thoughtfully updated home offers an open-concept living area filled with natural light and coastal charm. The modern kitchen features granite countertops, bar-top seating, and a dining area for four, making it easy to enjoy meals at home. Coffee lovers are well covered with a Keurig, French press, and Cuisinart drip coffee maker.brFor added convenience, high-speed Wi-Fi is available throughout the home, and a washing machine and dryer are provided for use during your stay, making longer visits and boating days easy and comfortable. The home is cooled by two mini-split air conditioning systems, allowing for efficient, customizable comfort.brThe living room features a smart TV and provides a comfortable space to relax after a day on the water.brBedrooms & Sleeping ArrangementsbrPrimary bedroom: Queen-size bed and smart TVbrLiving area: Queen-size Murphy bed with privacy screenbrAdditional sleeping: Air mattress availablebrMaximum occupancy: 6 guestsbrBathroombrThe home features one full bathroom with a tub/shower combination, offering a practical and comfortable setup for both quick rinses after a day on the water and relaxed evenings in.brWaterfront Living, Boating & FishingbrPelican's Paradise is a true boater and angler-friendly getaway, featuring a 35' concrete dock that can accommodate boats up to approximately 32 feet, with easy access to open water via a peaceful canal. Conveniently located near Looe Key, one of the most famous reef systems in the Florida Keys, offering world-class snorkeling, diving, and vibrant marine life in crystal-clear waters just a short boat ride away. Picnic Island is a nearby local sandbar popular with locals and visitors. A beautiful place to hang out after a day of fishing.brGuests enjoy world-class fishing opportunities, with convenient access to both:brThe Atlantic Ocean, ideal for offshore and reef fishingbrThe Gulf backcountry, known for exceptional flats and inshore fishingbrThe private dock includes a fish cleaning station, and Venture Out also offers a boat ramp and wash-down station, making it easy to head out early and return with a smooth end-of-day setup.brGuests may also enjoy:brTwo single sit-on-top kayaksbrOne two-person Hobie Cat kayakbrCalm canal views and effortless days on the waterbrAfter a day outdoors, unwind with the propane gas grill, perfect for preparing your fresh catch or an easy island-style dinner.brCommunity Amenities at Venture OutbrVenture Out is one of the most amenity-rich communities in the Lower Florida Keys, offering:brMarina store with fuel, bait, and convenience itemsbrBoat ramp and wash-down stationbrBeautiful stretch of island along the oceanfront with many thatched roof umbrellas and loungers to take in the clean ocean breezes and relaxbrMassive 80' heated saltwater swimming pool, hot tub, kiddie pool, and saltwater swimming lagoonbrTennis courts, basketball, bocce, and pickleballbrOn-site marina store/market and post officebrElectric Golf cart-friendly streets throughout the communitybrLocationbrYou're just minutes from popular local favorites including Square Grouper, Morning Joint, The Bent Prop, Broil, Mangrove Mama's, Kiki's Sandbar, and Boondocks Draft House with mini golf, all within a 10-minute drive. Key West is only 20 minutes away, offering additional dining, nightlife, and iconic attractions. brGood to KnowbrMinimum stay: 3 nights (7-night minimum during Lobster Mini Season)brStarter supplies provided: A starter supply of toilet paper and paper towels is provided and typically lasts 1–2 daysbrNo pets permitted due to allergies. Hypoallergenic dogs may be considered with prior approval and a $250 pet feebrGolf cart rentals available: $50 per day, subject to availabilitybrVenture Out registration fee: $125 (subject to change), paid directly to the community at arrival (cash or credit card; processing fees apply)brParking: 1 vehicle per unit. Driveway size is 16'L x 12'W. Overflow parking may be available for an additional feebrCommunity rules: Guests must follow all Venture Out rules and regulations, including quiet hours from 10:00 PM to 6:00 AMbrAge requirement: Primary guest must be 25 years of age or olderbrPayment & Booking RequirementsbrSigned rental agreement and government-issued ID required after booking. Please reply to the email you receive from us after signing your Rental Agreement with a photo of your ID.brA 4% credit card processing fee applies to credit card paymentsbrWhether you're here for world-class Atlantic and Gulf backcountry fishing, boating adventures, or relaxed evenings by the water, Pelican's Paradise #507 offers a comfortable, well-equipped home base for your Florida Keys vacation.

Waterfront 1BR in Venture Out with 35' Dock, Kayaks, Pool & World-Class Fishing

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$437.39

brbrbrLike new pool home, built in 2022. 3 bedroom, 2 bath home, canal front property. Private 37’ dock with fish cleaning station, on 28’ wide end of canal. Predominant winds keep canal clean. Short distance to Atlantic side access. Enjoy the constant sea breeze being one lot off Cudjoe Bay. Quiet walking and biking community. Relax by the pool and sit in the shade under the tikis. Close to Key West, restaurants and area attractions. Master bedroom has king size bed, on suite and walk in closet. One bedroom has two twin beds, and other bedroom has king size bed. Black out curtains in all bedrooms. All bedrooms have large screen tvs. House has large laundry room with washing machine and dryer. Kitchen has frig, microwave, dishwasher, and oven. Rental comes with everything needed for your cooking need's. Plates, cups, silverware are all in kitchen. Grill located on upper deck.

Awesome water front keys home 3bedroom, 2 bath. 20 miles from Key West!

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$633.5

House B - This lovely 3 bedroom 2 full bath home is located on the Atlantic Ocean. There is always a gentle breeze on the deck facing the ocean with a sunrise view. Comfortably sleeping six guest with dockage available.This property has a sunrise view, grassy yard for grilling. The kids and pets can swim and play all day. Boating, fishing and ocean snorkeling from the property. There also is a pool. All linens and dishes are provided along with washer and dryer.

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$244.16

Welcome to Coconut Cottage #653, your charming oasis nestled within the exclusive gated community of Venture Out in Cudjoe Key, FL.brThis cozy vacation rental home offers the perfect retreat for couples or small families seeking relaxation and adventure in the Florida Keys. Step inside to discover a thoughtfully designed space featuring one bedroom and one bathroom, providing comfort and convenience during your stay.brSink into the plush queen bed after a day of exploration, or utilize the two full-sized pullout couches for additional sleeping arrangements. The heart of Coconut Cottage lies in its inviting backyard seating area, complete with a BBQ grill, where you can savor al fresco meals under the swaying palm trees. With free Wi-Fi, you can stay connected while unwinding in this tranquil setting.brPrimary Bedroom: Queen BedbrOther sleeping arrangements: Two full-size sleeper sofas in the Living RoombrHome is equipped with a washer and dryer in the home so you can pack light.brStocked kitchen to cook up some fresh meals and a dining table with seating for 4. There is a Mr. Coffee Drip Coffee Maker at this home for you to enjoy your favorite brew.brThis home is close to all of the amenities at Venture Out.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.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 19'L x 12'W. If your vehicle does not fit when you arrive, you will need to see the guard gate for an additional parking pass for the overflow lot which costs $5/day. Extra parking permit may be available at the Guard Station for an additional nightly fee for a maximum of 14 days depending on availability. Must follow all the Rules and Regulations during your stay.brMain guest must be 25 years of age or older and will need to email a copy of your drivers license to the Rental Manager after booking has been accepted. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance. There is a 4% credit card processing fee.brSocial Media -br@bluescaperealestatebrYouTube Videos @bluescapevacationsbrBook your stay today and experience the beauty of waterfront living!

Coconut Cottage #653 - Oceanfront Community

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$390.0

VO259brFINS HideawaybrCanal Front Home 35' DockagebrBeautiful bay views at this canal front home located only 120' from the main channel. This boaters paradise has a 35' seawall at the intersection of 2 canals for spacious docking and swimming. Conveniences include cleats, fenders, docking whips, a new fillet table, an outdoor shower, and market umbrellas available to set up on the dock posts. Relax on the outdoor covered deck with your morning coffee and in the evening grill your catch while watching the shrimp, snapper and tarpon swimming around the underwater green light. Extra toys stored under the deck: 4 kayaks, SUP, rafts and noodles. Also included: Fast ATT WIFI, Amazon Fire TVs, newly renovated kitchen with blender/smoothie maker, rice cooker, electric skillet, crock pot, coffee maker, knife sharpener, and a bait freezer. The spacious living room has a queen size fold out sofa and a futon. The master bedroom with en suite bathroom has a queen size bed. The guest room has a single over double bunk bed. Washer and dryer are included. Pet friendly must comply with Venture Out Pet Rules & Regulations. brSECURITY DEPOSIT REQUIRED, NO SMOKING,br7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL,brOVERFLOW PARKINGIS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.brVO REGISTRATION 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- GUEST MUST VERIFY PRIOR TO RESERVING****

Fin's Hideaway - Venture Out #259

Cudjoe Key, Florida, United States

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Bath