Vacation Rentals By Owner In Cudjoe Key, FL

$311.57

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Cudjoe Key, Florida, United States

Canal Front 2BR/2BA in Venture Out with Ocean Views, 35' Seawall, Golf Cart Option & Pet-Friendly Island LivingbrWelcome to Island Time #110, a beautifully positioned canal-front retreat located inside the private, gated community of Venture Out on Cudjoe Key in the Lower Florida Keys. Situated at the end of a peaceful canal with breathtaking blue water views, this 2-bedroom, 2-bath home offers the perfect blend of boating, relaxation, and laid-back island charm.brWake up to stunning sunrises, enjoy your coffee while pelicans glide overhead, and settle into the true Florida Keys lifestyle.brThe SpacebrIsland Time #110 comfortably accommodates up to 6 guests and is thoughtfully designed for families, couples, anglers, and boating enthusiasts looking for a relaxing waterfront escape.brThe spacious living room offers comfortable seating and includes a queen-size pull-out sleeper sofa, providing additional sleeping accommodations when needed. Large windows bring in natural light and showcase the beautiful canal and ocean views that make this home so special.brThe fully equipped kitchen provides everything needed for preparing meals during your stay and includes both a Keurig single-cup coffee maker and a Mr. Coffee drip coffee maker so guests can enjoy their preferred morning brew.brCentral A/C, Wi-Fi, and an in-home washer and dryer are provided for added comfort and convenience throughout your stay.brBedrooms & Sleeping ArrangementsbrPrimary Bedroom: King-size bed and private ensuite bathroom with stand-up showerbrGuest Bedroom: Twin-over-queen bunk bedbrLiving Room: Queen-size sleeper sofabrMaximum Occupancy: 6 GuestsbrBathroomsbrPrimary Bathroom: Ensuite full bathroom with stand-up showerbrGuest Bathroom: Full bathroom with stand-up showerbrOutdoor Living & Waterfront ViewsbrIsland Time #110 is all about enjoying the outdoors and taking in the beautiful waterfront setting. The backyard offers stunning open blue water views at the end of the canal, creating the perfect spot for morning coffee, sunset cocktails, or simply relaxing and enjoying the ocean breeze.brBoaters and anglers will love the private 35' seawall, which can accommodate boats up to approximately 30 feet. The property also features a dedicated fish cleaning station, making it easy to prepare your catch after a day on the water.brAdditional outdoor amenities include:br2 bicycles for exploring Venture Out and nearby local spotsbrOptional golf cart rental available for an additional fee:br$40/day - $200/week - $550/monthbrGuests interested in reserving the golf cart should notify the rental manager prior to arrivalbrCommunity Amenities at Venture OutbrVenture Out is one of the most amenity-rich waterfront communities in the Lower Florida Keys and offers guests access to:br80' heated saltwater swimming pool, hot tub, kiddie pool, and saltwater swimming lagoonbrMarina store with fuel, bait, and convenience itemsbrBoat ramp and boat wash-down stationbrLighted tennis courts, pickleball, basketball, bocce courts, and playgroundbrPost office and oceanfront common areasbrGated security and electric golf cart-friendly streets throughout the communitybrLocationbrConveniently located on Cudjoe Key, Island Time #110 places you close to many of the Lower Keys' favorite restaurants, bars, and attractions including Square Grouper, Morning Joint, The Bent Prop, Mangrove Mama's, Kiki's Sandbar, and Boondocks Draft House & Miniature Golf.brThe property is also located near world-class boating, fishing, snorkeling, diving, and the famous Looe Key Reef.brFor additional nightlife, shopping, dining, and entertainment, Key West is only about 25 minutes away.brPet-Friendly DetailsbrThis property is pet-friendly for up to 2 dogs with 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' long x 10' wide and vehicles must fit fully within the driveway without extending into the roadwaybrOverflow parking may be available through Venture Out for an additional fee depending on availabilitybrQuiet hours: 10:00 PM to 6:00 AMbrStarter supplies provided: A starter supply of essentials is included to get you started. These supplies are generally enough for a 1-night staybrWi-Fi provided throughout the homebrPrimary 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 boating the backcountry, fishing the flats, enjoying sunset cruises, or simply relaxing beside the water, Island Time #110 delivers the perfect Florida Keys vacation experience with unbeatable waterfront views and true island-style living.

2

Bed

2

Bath

6

Sleeps

$504.28

/ Nightly

Private Vacation Home

Luxurious Oceanfront Home on Beach, Pool, Dock, Kayaks, Bikes, Amazing Views!

Cudjoe Key, Florida, United States

This luxurious Cudjoe Key vacation rental home, located directly on a sandy beach overlooking the crystalline Atlantic Ocean, is part of Sunrise Beach Resort, an exclusive gated community with only 10 other homes. In addition to high end furnishings in the living area, it features two tastefully decorated master suites, each with a full private marble bathroom. You can soak up the sun on the beach, on the pool deck, or enjoy the shade under the tiki hut by the sparkling, heated/cooled swimming pool located directly beside the house, also overlooking the ocean. Lounge in your private hammock or enjoy a drink in the double swing underneath our home which overlooks the beach. Or, you can soak in the gorgeous tropical landscaping and cool breezes on the comfortable, luxurious furniture located on the home’s deep shaded lanai, which includes a flat screen TV adjacent to the beach. Breathtaking views of the blue green ocean, Cudjoe Bay, and the sunrise and sunset can be seen from every room and from the two decks accessible from both bedrooms, the dining room and the living room. brbrIf you are looking for a lower keys short or long term rental, Cudjoe Key has a reputation as the best place to stay on the water in the keys. Your boat, up to 25 feet, can be kept for free at the stationary or floating docks in the calm waters directly behind our house, while your boat trailer can be stored close by, at no cost to you. Or you can rent a boat and have it delivered to the dock behind our home. Looe Key and American Shoal Reef can be seen from the house where you’ll find the most beautiful snorkeling and diving reef in the keys, along with the best fishing. Their off-the-beaten path location guarantees a thriving ecosystem. You can fish right off the end of the dock or kayak in the crystal clear, calm waters in Cudjoe Bay directly behind our house (kayaks are included). Venture out to experience the history and action in Key West located only 20 miles away, or explore dozens of nearby islands and a trove of nature preserves by land or sea. Ours is the perfect Cudjoe Key vacation house rental located near Big Pine Key, Summerland Key, Sugarloaf Key and Key West, Fl. brbrIn the immediate area you’ll find several good restaurants. For example, you can take your boat or catch a free ferry to Little Palm Island where you can enjoy lunch or dinner at a top ranked best restaurant in the world. Several other excellent restaurants in the keys are located on or close to Cudjoe Key. A gym/wellness center and Cudjoe Garden’s Marina, a full service marina, are located one mile away. Fishing, snorkel, dive or sightseeing trips can be arranged through Nothing Better Boat Rentals on Cudjoe Key, and they can either captain a rental boat for you or have one delivered to our docks. The only 18 hole miniature golf course in the keys is located five miles away. Pack a lunch and spend the day at Bahai Honda State Park, voted the #1 beach in the U.S., which is only a 20 minute drive away. The Dolphin Research Center, which offers dolphin encounters, is another area attraction. brbrWe provide bikes, kayaks, a corn hole game, beach chairs, a beach umbrella, beach toys and towels, bocce ball, and a cooler for your enjoyment. We are always adding extra toys and oftentimes have a clear see-through kayak and stand up paddle boards available as well. Relax on our hammock or on our swing overlooking the beach. Four bikes are available for you to enjoy a leisurely bike ride down the scenic tree lined bike path, accessible directly across the street from Sunrise Beach, which traverses Cudjoe Key and continues all the way to Key West. Cudjoe Bay is the perfect calm place to kayak and enjoy the clear water. Our home has something for those who want to relax and enjoy the views off the beaten path, and as well as for those who wish to explore all the keys have to offer!brbrThis casually elegant home provides:br* High ceilings with crown moldingbr* Gourmet kitchen with stainless appliances, granite countertopsbr* Keurig for individual pods or full pots of hot beverages br* Kitchen stocked with a blender, spices and staplesbr* Private full marble bathrooms in each bedroom, plus a full marble bathroom next to the living roombr* Shampoo, conditioner, and body wash provided in all 3 bathroomsbr* Jacuzzi tub in one master bathroom, walk in showers in the other two bathrooms.br* Plantation shutters in bedrooms and bathrooms.br* 4 flat screen HD TV’s br* SMART TV with DVRbr* Wi Fi Internet br* Private hammock br* Large selection of books, including local guides, and gamesbr* Luxurious decor and furnishingsbr* Covered parking for 2 vehicles br* Large walk in closets with round windowsbr* Pack 'N Play Crib, baby linens and bedrailsbr* Gas grill br* Bikes (4), with helmetsbr* Beach chairs, umbrella, cooler, corn hole, bocce ball, beach toys br* Fishing poles, tackle box, snorkeling finsbr* Kayaks (2 singles, 1 double), with life vests, and paddlesbr* Flat screen TV overlooks the luxurious outdoor furniture on the shaded lanai underneath the house overlooking the beachbr* Private swing overlooking beach br* Pool, beach, and dock are shared with only 10 other homes in our small gated community. brbrThis is the perfect vacation home for families or couples looking for relaxing ambiance in an opulent tropical hideaway and for those who want it all – beach, pool, boat dock, and stunning views in order to experience the 'real' Florida keys. brbrbrbrbrbrbrbrbrbrbrKeywords: Oceanfront, Beachfront, Gated Community, Boat Dockage, Heated Pool, Kayaks, Bikes, Cudjoe Key Cottages, Fishing, Corn Hole, Hammock, Snorkeling, Views

Bed

Bath

Sleeps

$331.88

/ Nightly

Private Vacation Home

Tropical Island Paradise W / Open Water Views!

Cudjoe Key, Florida, United States

Please see our other property if you do not see your dates available! Property # 2092236brhttps://www.vrbo.com/2092236 adultsCount=2&arrival=2020-10-27&departure=2020-10-31&unitId=2656769brbrSparkling clean and beautifully remodeled 2Bd/2Ba vacation home that features OPEN WATER views with great boating access to the ocean or gulf! This home is fully furnished will all the amenities for an over the top vacation experience. This waterfront paradise features a 35' concrete seawall with cleats, dock posts, fish table and BBQ grill to cook your catch! Main living room offers high ceilings with awesome views of the water and leads to a spacious covered porch overlooking the water. This home is designer decorated with lovely accents and decor throughout. Kitchen features clean and white kitchen cabinets with full line of appliances and granite countertops. Living room features lots of comfortable seating with queen sleeper sofa, love seat and 2 comfortable chairs with a large flat screen television with full expanded cable and you will enjoy splendid water views. Master bedroom features a king size bed with lots of closet storage and full size private bathroom. Guest bedroom features a queen bed with closet storage and access to the hallway full bathroom. Additional amenities include central air conditioning, heat, dishwasher, microwave, washer, dryer, tile floor, BBQ grill, fish table, expanded cable, ceiling fans, patio furniture and covered porch. You'll set your mind at ease when you stay at this beautiful home in the Florida Keys!br7 day minimum during lobster season. No Smoking, No Pets. There is a resort usage fee of $125 payable upon arrival at entrance at security gate to Venture Out.brbrRental agreement is agreed upon at booking and pre-registration form of guests must be completed prior to stay or when checking in at the security gate.brbrThe community will be limiting overflow parking lot spaces (which is at a nightly fee to guest). They will only be able to accommodate for one spot for an extra car or boat trailer if available; do know there's a driveway at the home to park a car, this is only in regards to extra cars or boat trailers.brIf no spots are available guest will need to find a spot outside of the park. We understand this is a great inconvenience so we have negotiated a spot for a trailer at a nearby marina at a rate of $20 a day, if interested please let us know so we notify the marina. Thank you

Bed

Bath

Sleeps

$400.0

/ Nightly

Private Vacation Home

Beach house in the Keys - VO074

Cudjoe Key, Florida, United States

VO074brCanal Front Open Water 35' Seawall brStilt 2Bd/2Ba Covered Porch brSimply elegant describes this 2 Bedroom / 2 Bath canal front stilt home only 3 lots from open water! This home features a 35' concrete seawall with access to the Gulf and Ocean! Dock amenities include dock posts, cleats and fish cleaning table. The upper porch as comfortable lounging furniture overlooking the water. Interior features tile flooring, living room flat screen TV, full line of appliances, washer, dryer, ceiling fans and central A/C. Sleeping accommodations include a King size bed in the Master bedroom and a private bathroom, Guest bedroom as 2 twin beds that can be pushed together as a king. Master bedroom with sliding glass door provides access to a balcony, flat screen TV and private full bath. Downstairs features outdoor shower, access to storage room and covered parking. Additional amenities include in home FREE WIFI, basic cable, gas grill, bait freezer an assortment of bicycles.br SECURITY DEPOSIT REQUIRED, NO SMOKING, NO PETS,br7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL,brOVERFLOW PARKING S NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.brVO REGISTRATION FEE -**EFF 7-1-23 new fee is $125**DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE.

2

Bed

2

Bath

4

Sleeps

$431.25

/ Nightly

Private Vacation Home

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Cudjoe Key, Florida, United States

You're in the tropics... listen to the waves, rest, relax or fish, kayak and snorkel, if you wish to lose a few pounds. Three bedroom, two bath home, with direct ocean access, boat parking at the back door. Sunrise view, ocean breezes. Fully furnished, linens, cable/internet. This home is on a compound, we also have several one bedroom units as well as 2 bedroom. The perfect spot for large groups! Square Grouper restaurant and bar in the is down the street. Lower Keys Shuttle to Key West just steps from the home. Come and stay with us, you're sure to have a wonderful vacation.

Bed

Bath

Sleeps

$338.43

/ Nightly

Private Vacation Home

Bimini Breeze - VO 313

Cudjoe Key, Florida, United States

Bimini Breeze - VO 313brWalk to Pool and Marina!brCentrally Located Charming 2Bd/1BabrThis home is located on a quiet circle yet centrally located within walking distance to the pool, marina, store, tennis and more! Turn key furnished midrise 2Bd/1Ba, central air conditioning, tile floor, washer, dryer and very well maintained. New remodeled kitchen and dining room area. Located next to a common ground for peaceful enjoyment. brOVERFLOW PARKING IS 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

Bed

Bath

Sleeps

$607.43

/ Nightly

Private Vacation Home

Gorgeous Newer Oceanfront Home! Private heated pool, dock and great views!

Cudjoe Key, Florida, United States

Our oceanfront oasis with a private heated saltwater pool, private dock for a boat up to 30`, kayaks and bikes! brbrOur 4 bed, 3 bath home has 2 king master suites, queen room, and a bunk room. brbrKitchen is stocked with essentials: laundry & dishwasher soap, paper towels, and toilet paper. Keurig or a traditional coffee pot. Free high-speed WiFi to keep you connected.brbrLounge poolside, fish off the dock, or explore nearby reefs. Tucked on a quiet street in Cudjoe Key, just 30 mins to Key West.br2 cars permitted. Private dock space for a 30` boat.

1

Bed

3

Bath

8

Sleeps

$426.8

/ Nightly

Mobile Home

Canalfront Keys Home - Dock for 35' Boat, Large Porch, Big Yard & Quick Access to Open Water

Cudjoe Key, Florida, United States

BIG BOATS WELCOME! Waterfront 2BR in Venture Out with 70' Dock, Gated Community, Pool & World-Class FishingbrWelcome to Bimini Breeze #333, a spacious 2-bedroom, 1.5 bath canal-front getaway located in the heart of Venture Out. This home sits on a rare double lot, giving guests an oversized yard and back porch perfect for relaxing after a day on the water. 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 SpacebrInside, the living room is spacious and overlooks the canal with lots of windows to capture the sunshine and views. There is a 55'' Roku Smart TV for movie nights. A dining area is set near the living room that seats 4 and also overlooks the canal. The kitchen is just around the corner and has built-in bar seating for 2, stainless steel appliances, stove top, built-in microwave and dishwasher making it easy to enjoy meals at home. Although there is no traditional oven in the kitchen, the home includes a toaster oven, microwave and a propane grill out on the patio to cook up your fresh catch of the day! For 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 central air conditioning and ceiling fans are located throughout. There is a dedicated workspace with a desk and chair for remote work or school while you enjoy the island lifestyle. This home is steps to the on-site store, two boat ramps, and the community pool - an unbeatable location for convenience and fun. Whether you're boating, snorkeling, fishing, or simply soaking in the peace of the Keys, Bimini Breeze offers the comfort and coastal charm you're looking for.brBedrooms & Sleeping ArrangementsbrPrimary bedroom: Queen-size bed, Roku TVbrGuest Bedroom: Queen-size bedbrLiving area: Sleeper Futon bedbrMaximum occupancy: 6 guestsbrBathroombrThe home features one full bathroom in the Primary bedroom that has a walk-in shower, sink and toilet. There is also a guest half bathroom located just off the main living area. brWaterfront Living, Boating & FishingbrBimini Breeze #333 is a true boater and angler-friendly dream, featuring a 70' concrete dock that can accommodate boats up to approximately 35 feet even with the owners boat stored on the davits, with easy access to open water via a short and peaceful canal ride. There is also a bait freezer to store all of your supplies safely. Step outside to the large screened-in back porch with seating for up to eight - a perfect spot for morning coffee, evening cocktails, grilling, games, and fresh-caught dinners. The oversized yard provides plenty of room to relax, unwind, and enjoy the salty breeze. 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 will enjoy calm canal views and effortless days on the water. After 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 daysbrThis is a pet friendly home. 1 dog allowed with a $250 paid pet fee. Rental manager must be notified at the time of booking. brGolf 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 23'Lx11'W. Overflow parking may be available for an additional fee.brCommunity 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 payments.brWhether you're here for world-class Atlantic and Gulf backcountry fishing, boating adventures, or relaxed evenings by the water, Bimini Breeze #333 offers a comfortable, well-equipped home base for your Florida Keys vacation.

Bed

Bath

Sleeps

$258.55

/ Nightly

Cottage

Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

Cudjoe Key, Florida, United States

1Bd/1Ba Highrise UnitbrbrLocated in a gated community, just 20 miles from Key West, this cottage is the perfect place if you are looking to lay back, relax, and re-energize after a day of adventures and activities during your time in paradise. If you are looking for peace and quiet in a safe environment, this is the place for you.brbrThis cozy chalet has all the comforts of a home. It offers a bright and comfortable living room, 2 TVs with access to log into applications, Wi-fi, washer and dryer, kitchen equipped with everything you need to prepare your meals at home, a cozy master bedroom with ample closet space and a sofa bed for an extra guest in the living room. brbrEnjoy the breeze from the keys on the spacious porch equipped with a dining area and comfortable chairs and end the day in the private patio surrounded by a beautiful and well-kept garden with comfortable chairs to rest and an additional dining room where you can enjoy a delicious barbecue.brbrOur home is located in the Venture Out, on Kemp Channel, which is one of the most accessible boating channels to both the beautiful back country, as well as a quick, ten-minute ride to the open Atlantic, coral reefs, and world-famous Looe Key National Marine Sanctuary.brbrBeautiful open water views abound! Easy access to great fishing, catching lobsters, boating, scuba diving and snorkeling. Amenities include a marina with store, boat ramps, swimming pool, spa, tennis courts, and much more, in a gated 24-hour security resort. Cudjoe Key is close to both Key West and Marathon in the section of the Florida Keys known as the Lower Keys. This provides easy access to events such as the offshore powerboat races, sailing regattas, fishing tournaments, Fantasy Fest, Star Party, and many more. The Lower Keys include well-known destinations such as Big Pine Key, Summerland, and Sugarloaf.brbrCheck in after 4pm on date of arrival and Check-out is 10am on departure date.brbrPlease note that maximum occupancy for this property is 3 people. There is a queen bed in the bedroom and a sleeper sofa in the living room which can accommodate an extra guest if necessary. brbrNo pets are allowed. No smoking is allowed inside the property and no smoking is allowed on the terrace. No inappropriate conduct or partying will be tolerated. brbrThe property is monitored by security guards. Violation of any of these rules are grounds for security to ask you to leave immediately without a refund.brbrbrADDITIONAL CHARGES:brbrVenture Out charges a one-time resort fee upon entry of ($125.00), payable at the gate upon arrival. When you arrive at Venture Out , you will go to the Venture Out Office (or the Guard Gate if it is after hours) to pay the fee and to receive your parking pass. Credit Card or Cash only are accepted for this fee. brbrOnly one car is permitted at each lot. Transportation vehicles must fit in the driveway or will have to be moved into overflow parking for a small nightly fee. If you have an extra car you will need to park in the overflow parking lot and pay the appropriate nightly fee up to 14 days maximum pending availability. brbrThere is no jet ski trailer parking available. Boat trailer parking may be available, subject to availability and for a fee. The rates are $5-$10 per night depending on size. brbrNO COMMERCIAL VEHICLES ALLOWED. THERE IS NO GUARANTEE, IMPLIED OR OTHERWISE, THAT VENTURE OUT WILL PROVIDE ANY OVERFLOW PARKING SPACES FOR ADDITIONAL UNIT BOAT TRAILERS OR VEHICLES. PLEASE PLAN ACCORDINGLY.brbrIF YOU ARRIVE WITH MORE THAN THE MAXIMUM ALLOWED IN THE RENTAL UNIT, YOU WILL NOT BE PERMITTED INTO THE PARK AND NO REFUND WILL BE ISSUED.brbrCOVID-19-Related Information:brbr- Additional cleaning measures are being enforced at all units so NO EARLY CHECK INS or OUTS will be accommodated so we can have the maximum amount set to sanitize each unit properly for the safety of our guests. CHECK IN TIMES are 4 PM and OUT 10 AM please make your travel accommodations accordingly or book a day earlier / later if arriving early or departing late.brbr- No baggage holding will be allowedbrbr- All additional back up supplies and additional bedding will be removed from each unit to avoid cross contamination.brbrAMENITIES:br brEssentialsbrInternetbrLinens providedbrTowels providedbrAir conditioningbr brKitchenbrMicrowavebrRefrigeratorbrDishes & UtensilsbrCoffee MakerbrKitchenbrStovebrToasterbrOvenbrGrillbr brPool & SpabrCommunal PoolbrCommunal Spa (for adults only)br brEntertainmentbrTelevisionbr brLaundrybrWashing MachinebrClothes Dryerbr brSuitability:brMinimum Age limit for RentersbrbrOccupancy:br3 person maximum capacity - ENFORCED

Bed

Bath

Sleeps

$299.66

/ Nightly

Cottage

Charming cottages, dockage, pool, just minutes to Key West

Cudjoe Key, Florida, United States

Cottage #6 - Only 20 miles from Key West, but a world away from the hustle and bustle. Come experience a truly relaxing Keys experience. Our fully equipped cottages mean all you need is your swimsuit and sunscreen! Anglers will find easy access to crystal clear waters using our small boat launch and convenient dock and sea wall. Runners and cyclists will find easy access to the Florida Keys Overseas Heritage Trail - 75 miles of paved trail tracing the original route of the Flagler Railroad. When you're ready for tourist activities make the short drive to Key West and visit the Aquarium or hop on the Conch Tour Train. Big Pine offers nature enthusiasts the Blue Hole with Key Deer lots of wildlife.

Bed

Bath

Sleeps

$351.75

/ Nightly

Private Vacation Home

Tarpon Alley - Venture Out 509

Cudjoe Key, Florida, United States

Tarpon Alley - VO509brCanal Front35' DockagebrbrCasually elegant, beautifully decorated, and fully stocked for your convenience and enjoyment, this 35-foot canal-front 2-Bedroom 2-Bath home comfortably sleeps six. Interior includes all tile flooring, transom windows, two queen beds, double sleeper sofa, 3 flat-screen TVs, internet/cable, and full line of appliances including washer, dryer, coffee maker, air fryer, Insta pot, crock pot, and George Foreman grill. Dock amenities include posts, cleats and fish table with running water. Downstairs includes covered parking, full size gas grill, outdoor shower, bicycles, inside storage space, bait freezer, and outdoor seating with tables upstairs and downstairs. Conveniently located just minutes from the on-property marina, pool, convenience store and recreation center.brNo Pets / No SmokingbrbrSECURITY DEPOSIT REQUIRED, 7 DAY MINIMUM LOBSTER SEASON,brFREE WI-FI IN THE REC HALL,brOVERFLOW PARKING IS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.brVO REGISTRATION FEE $125.00**DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE.br****VEHICLE MAY NOT HANG INTO STREET-brGUEST MUST VERIFY PRIOR TO RESERVING****

2

Bed

2

Bath

6

Sleeps

$394.76

/ Nightly

Private Vacation Home

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Cudjoe Key, Florida, United States

House A - You're in the tropics... listen to the waves, rest, relax or fish, kayak and snorkel, if you wish to lose a few pounds. Three bedroom, two bath home, with direct ocean access, boat parking at the back door. Sunrise view, ocean breezes. Fully furnished, linens, cable/internet. This home is on a compound, we also have several one bedroom units as well as 2 bedroom. The perfect spot for weddings, reunions, or large groups! Broil Restaurant is just across the street, Square Grouper restaurant and bar in the is down the street. Shuttle to Key West just steps from the home. Come and stay with us, you're sure to have a wonderful vacation.

Bed

Bath

Sleeps

$647.98

/ Nightly

Private Vacation Home

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Cudjoe Key, Florida, United States

Oceanfront Island Escape | 2BR/2BA Home in Venture Out with 35' Seawall & Sunrise ViewsbrWelcome to your tropical escape here at Casa Tartaruga #56 in Venture Out on Cudjoe Key — a brand new 2-bedroom, 2-bath oceanfront gem with uninterrupted turquoise water views and all the charm of island living.brPerched directly on the Atlantic Ocean with a 35' seawall perfect for boats up to 32', this vibrant coastal retreat offers the best of Keys life—whether you're boating, grilling, or simply swaying in a rocking chair at sunrise. Sip your morning coffee on the oceanfront balcony, where manatees drift past the canal and egrets and pelicans glide overhead, adding to the tranquil rhythm of the island.brInside, this home is a breezy blend of comfort and coastal elegance. The open-concept living area is flooded with natural light from oversized windows and sliding glass doors that frame the endless sea. The fully equipped kitchen features stainless steel appliances, a kitchen island, a Hamilton Duo - Drip and Single Cup Coffee Maker for you to enjoy your favorite brew, and fridge with ice maker & water dispenser—everything you need to whip up fresh-caught seafood feasts.brThe primary suite boasts a plush king bed, ensuite bathroom with tiled glass shower, and its own TV for cozy evenings. The guest bedroom features two twin beds that convert to a king, its own private balcony, and another full bathroom is just steps away with a stand-up shower. The living room has a queen pull-out sleeper sofa for additional sleeping accommodations.brOutside, unwind on the lower level with an outdoor dining table for six, a Weber grill, comfortable lounge seating, and a fish cleaning station ready for your daily catch.brWhether you're here to explore the reefs, fish from your backyard, or simply soak up the sun with a salty breeze in your hair, this home is the perfect base for your next Florida Keys getaway.brHighlights:br*Direct oceanfront with unobstructed water viewsbr*35' seawall with dock posts – bring your boat!br*Sunrise-facing open balcony with double rocking chairbr*Manatees & seabird sightingsbr*2BR/2BA (King + Twins that convert to King)br*Fully equipped kitchen with island & coastal décor throughoutbr*TVs in both bedrooms + ceiling fans in each roombr*Downstairs living space with grill, sofa, & dining table for 6brSoak in the sun. Savor the sea. Stay awhile in your own slice of oceanfront paradise.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 is a pet friendly home. Up to 2 dogs allowed with a paid pet fee of $250 per pet. Rental Manager must be notified at time of booking.brThis home has a ring camera at the front door. A 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.brWelcome to Venture Out on Cudjoe Key – A Private, Gated Coastal CommunitybrExperience the charm of Venture Out, a golf cart-friendly, oceanfront neighborhood in the Lower Keys offering one of the most amenity-rich settings in the Florida Keys. Whether you're seeking adventure or relaxation, this private community has something for everyone:br*Full-Service onsite ship store with Fuel, Bait & Convenience Storebr*Boat Wash-Down Stationbr*Olympic-Style Heated 80' Pool + Jacuzzibr*Kiddie Pool & Saltwater Swimming Lagoonbr*Lighted Tennis Courts, Pickleball Courts, Bocce, & Basketball Courtsbr*Onsite Post Office & Market for Daily EssentialsbrHungry You're just minutes away from local favorites like Square Grouper, The Bent Prop, Morning Joint, Mangrove Mama's, Kiki's Sandbar, and Boondocks Draft House with Mini Golf — all within a 10-minute drive. If you're craving the buzz of Duval Street, Key West is just 20 minutes away.brWhether you're an avid boater, a fishing enthusiast, or simply ready to unwind by the water, your oceanfront stay in Venture Out promises the perfect blend of comfort, convenience, and coastal living.brNeed-to-Know Information Before You Book:brCommunity Registration Fee: A $125 fee (subject to change) is required by the Venture Out HOA. This must be paid at the guard gate upon arrival (cash or credit card; 4% credit card fee applies).brParking: 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 91/2'W x 12'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.brOccupancy Limit: Strictly limited to 6 guests total, including infants and children.brMinimum Age Requirement: The primary guest must be 25 years or older and must email a copy of their valid driver's license to the rental manager within 24 hours of booking acceptance.brRental Agreement: Must be signed and returned within 24 hours of booking confirmation.brPayment Details: A 4% fee applies to credit card payments. brCommunity Rules: Guests are required to follow all Neighborhood Association rules and regulations. Violations may result in fines or immediate removal from the property without refund.brNo Smoking allowed in the home.

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$532.58

/ Nightly

Private Vacation Home

Blue Palms w/boat dock and saltwater pool.

Cudjoe Key, Florida, United States

This 3 bedroom/2 bath oceanfront home with amazing views on Cudjoe Key private heated salt water swimming pool, shaded hang out area, ping pong table, corn hole game. The pier, gazebo, kayaks and kayak launch area is shared with one other home, Latitudes. You can dock your 24' boat at the pier. The water is shallow getting out to the channel with about a 2' draft.brbrYour property manager lives nearby and is available if you have any requests during your staybrbrQuite/peaceful neighborhoodbrbrYou will be provided with check in instructions prior to your arrivalbrbrThis 3 bedroom/2 bath oceanfront home with amazing views on Cudjoe Key has a large, heated swimming pool with shaded hang out area, ping pong table and corn hole game. 1 Double and 2 single kayaks provided. This home has a boat Foch that is shared with The Latitudes home Ultimate location only 20 minutes from Key West and 20 minutes to Bahia Honda State Park. This is a vacation experience you will remember.br*Master Bedroom: 1 King bedbr•King Bedroom: 1 King bed br•Queen Bedroom: 1 Queen bed br•Living Room: Queen sleeper sofa, Flat screen Smart TVbr•Kitchen: Fully stocked with blender, toaster, coffee maker, microwave oven. Full supply of; dishes, bowls, silverware, stemware, drinking glasses, pots, pans and utensils. br•Linens: All sheets, towels and beach towels provided. Iron and ironing board. br•Supplies: Dish soap, dishwasher soap, dish sponge, some large trash bags, bar soap and liquid hand soap in bathrooms, propane for grill, one full roll of paper towels, one extra full roll of toilet paper per bath. We do not supply laundry soap. br•Outdoor Features: Propane BBQ, Hammock br•Boat Dockage: Tall pier for boats up to 24'. The dock is shared with Latitudes home guests. br•Parking: Contract is for 2 cars and 1 boat trailer. Please let us know if you need additional parking. br•Central A/C: Not to be set below 70 degrees. br•Other: Washer/Dryer, ice maker in refrigerator, wireless internet, Smart TV's br•Location: 20 minutes from Key West, 15 minutes from Bahia Honda State Park. br•Pool: 10X30, heated Salt water poolbr Square Footage of House: 1456 sq ftbrbrCancellation: If you cancel your reservation in writing 90 days or more before your arrival, you will receive a full refund, less a cancellation fee of $25.00 and Administrative fee. If you cancel less than 90 days before arrival, your payment and any prepaid rent will be refunded only if we are able to procure another rental for that same period. If no rental is procured, you will lose your payment and any prepaid rent, not to exceed the amount of your rental. If you cancel within 30 days of your arrival, there will be no refund. If the Florida Keys are closed for weather related or other emergencies for your arrival date, you will be given the opportunity to re-schedule your reservation or receive a refund. brbrbrNon-Refundable Damage Deposit Waiver: Instead of charging a security deposit, Host charges a non-refundable $74 damage waiver fee that covers up to $3000 for damage to real or personal property of the vacation rental property as a result of your acts or omissions.brbrBus service available. It is recommended that you rent a carbrbrThis is a pet friendly home. A pet fee and approval of your pet is required.brPrior to your stay we require you to complete a pre-arrival form and sign and agree to our rental conditions.

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$274.15

/ Nightly

Private Vacation Home

Coastal Oasis, Canal front

Cudjoe Key, Florida, United States

COASTAL OASIS is just for you. This three-bedroom two-bath canal-front home offers a comfortable base for your Keys adventures. The living room, dining room, and kitchen are all found in a large open area adjacent to the large screened porch. The kitchen is fully equipped. Amenities include a washer/dryer, TV, central A/C, dishwasher, and barbecue grill. For sleeping, there is a Queen in 2 bedrooms and 2 full beds in the 3rd one. For the boaters and fishermen, there is a concrete dock on the canal. Access to the Atlantic, coral reefs, Gulf Stream, Gulf, and backcountry is easy. Located nearby are restaurants, groceries, fuel and bait, convenience stores, banks, post offices, and more. Within an easy drive, there is much more to be found, Key West with all it offers, dining, shopping, history, and the like, is 23 miles to the south. Big Pine Key with its natural attractions is 7 miles north. Just a bit further north is the world-class beach at Bahia Honda State Park. The Miami airport is a three-hour drive. This is a nonsmoking home. THIS HOME IS A 28 DAY RENTAL PER MONROE COUNTY CODE. This home is a 28 day rental per Monroe county code.br

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$487.3

/ Nightly

Private Vacation Home

Oceanfront Dream Home - VO048

Cudjoe Key, Florida, United States

Oceanfront Dream Home - VO048br2Bd/2Ba OCEANFRONT 45' SEAWALL! br This BEAUTIFUL 2Bd/2Ba OCEANFRONT with endless ocean views features a 45' SEAWALL! Wake up to beautiful sunrises and the Atlantic Ocean every morning. heavy duty padded dock posts, cleats and extension swim ladder with over 4' controlling depth at the seawall, so a larger boat is welcome. A bright and spacious living area features oversized windows to bring the outdoors. The dining room offers seating for 4, kitchen features a full line of appliances with white kitchen custom cabinets and Corian countertops. A large island countertop makes the perfect place to serve or entertain your family and friends. The living room leads to a covered porch overlooking the ocean. This welcoming property features 2 queen bedrooms, perfect for guests to unwind after a day of exploring. With amenities like WiFi, a washing machine, and AC, your stay will be nothing short of enjoyable. Make your holiday one for the books with a stay at our place.SECURITY DEPOSIT REQUIRED, NO SMOKING,br7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL,brOVERFLOW PARKING IS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.brVO REGISTRATION FEE $125**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****

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$638.79

/ Nightly

Private Vacation Home

Tropical Paradise - Ocean front with swim spa

Cudjoe Key, Florida, United States

Oceanfront home with private pool, boat dock, kayaks, and private beach brbrTropical Paradise has been a popular and romantic vacation rental getaway since 2003. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24' boat allowed) screened in porch for dining There are 2 king bedrooms, 3rd bedroom has a queen with trundle 2 1/2 bath. This home has an open floor plan and recently remodeled kitchen.brbrOur offices are located about 6 miles from this home. we are available 24 seven for any issues you may have. we respect our guest space and will let you know if we need to be on property for any reasonbrbrbrbrQuiet residential neighborhoodbrbrEntire homebrbrYou will be provided with check in instructions prior to your arrivalbrbrThis adorable home has 3 bedrooms and 2 1/2 baths. A screened in porch with walkout to the dipping pool.brThe pool deck is fully fenced for safety and for your pet. Banana trees and coconut trees give this home that Tropical VibebrbrUber, Lyft and Taxis area available as well as Public Bus transportation. It is recommended that you have a carbrbrThis is a pet friendly home. A pet fee and approval of your pet is required.brPrior to your stay we require you to complete a pre-arrival form and sign and agree to our rental conditions.

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$485.99

/ Nightly

Private Vacation Home

Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape

Cudjoe Key, Florida, United States

Wastin' Away Again #468 is your perfect Florida Keys escape - a beautifully appointed 2 bedroom, 2 bathroom waterfront retreat with open water views, a 35' seawall, and everything you need for a relaxed island stay. Designed with comfort and functionality in mind, this home blends coastal charm with modern conveniences, making it ideal for boaters, anglers, remote workers, and families alike.brStep outside and enjoy true Keys living. The 35' seawall accommodates boats up to 32', and the private fish-cleaning station makes prepping your fresh catch easy after a day on the water. Fire up the Charbroil propane grill or gather around the outdoor dining area with seating for six to enjoy sunsets, ocean breezes, and laid-back evenings.brInside, the bright open-concept living space features central A/C, high-speed WiFi, and comfortable seating centered around a 50'' Smart TV - perfect for relaxing after a day exploring the Keys. The fully equipped kitchen includes stainless steel appliances, plenty of cookware, and a Hamilton Beach FlexBrew 14-cup coffee maker so you can enjoy your favorite brew each morning. The dining area offers a table with four chairs plus two additional seats at the kitchen bar.brBoth bedrooms feature king beds for a restful night's sleep. The primary suite includes a 32'' Smart TV and a private ensuite bathroom with a walk-in shower. The guest bedroom also offers a 32'' smart tv. The guest bathroom is located in the hall and features a convenient shower/tub combination.brNeed extra sleeping space The living room sofa pulls out to a full-size bed for additional guests. An in-unit washer and dryer adds convenience for longer stays, and the open water views create the perfect backdrop for your Florida Keys getaway.brWhether you're here for boating, fishing, or simply unwinding by the water, Wastin' Away Again #468 delivers the classic island lifestyle with the comforts of home.No pets are allowed at this home. There is one security camera underneath the house facing the canal. Venture 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, saltwater swimming lagoon, post office, and lighted tennis, basketball, and bocce courts. Adventure beyond the gates for a bite to eat at some of the Florida Keys' favorite restaurants such as Square Grouper, The Morning Joint, The Bent Prop, Mangrove Mama's, Kiki's Sandbar, or Boondocks Draft House and Miniature Golf—each just a short 10-minute drive away. Or head a little further south to Key West for even more island 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, this Florida Keys getaway promises an unforgettable vacation experience. 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 applies). Parking for 1 vehicle per unit. The vehicle must fit on the driveway and not extend out to the road. The driveway measurements are 18'Lx8;10''Wx7'2''H. If your vehicle does not fit when you arrive, please see the guard gate for an additional parking pass for the overflow lot, which costs $5 per day. Extra parking permits may be available for a maximum of 14 days depending on availability. Guests must follow all Venture Out rules and regulations during their stay. The main guest must be 25 years of age or older and will need to email a copy of their driver's 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. Follow us on social media: YouTube: @bluescapevacations Book your stay today and experience the beauty of waterfront living in the Florida Keys!

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$293.78

/ Nightly

Cottage

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

Cudjoe Key, Florida, United States

Cottage #12 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound with 2 swimming pools. Spacious cottage offers a full kitchen, screened patio, two queen bedrooms. This cottages is only steps away from our pool. The pool, dock and seawall are all available to our guests. A coin laundry is also available on site. Whether you come to the Florida Keys to escape the winters, or enjoy the calm waters and great fishing and diving of the summers, you will find Cudjoe Oceanside Cottage to be your Home Away From Home.

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$257.14

/ Nightly

Mobile Home

Waterfront home with numerous amenities on popular Cudjoe Key!

Cudjoe Key, Florida, United States

Crystal Clear Canal front home with open water view! Home is located in a desirable community called Venture Out. Fully furnished, and beautifully decorated with popular Key West colors! Spacious and bright rooms are waiting for you! 3 Beds Cable TV throughout! Master bedroom features a queen bed, full bath, TV, and storage. Guest bedroom includes two twin beds, TV, storage and stackable washer and dryer. Living has lots of windows, sliding glass doors that lead to the porch, TV, 5 electric recliners in recliner, loveseat and couch. Kitchen is nicely equipped and includes a Keurig coffee maker, microwave and toaster. Home has ramp in front of property, and steps in back. Porch offers beautiful views with a small seating area. Out back is seating area seawall dock has grill, fish cleaning station, and swim ladder. Seawall can accommodate a boat up to35'! This privately owned community offers amazing amenities that include: a guarded and patrolled gate 24/7, Recreation Hall, Pavillion, heated pool, Jacuzzi, Fishing, Diving, Tennis and Basketball courts, bocce ball, pickleball, mini golf, Volleyball, Horse shoes, Shuffleboard and playground! Security cameras are located near the pool, jacuzzi and throughout the common areas of the property. Community events like yoga, pancake breakfasts on Saturday, pool aerobics, church bingo and more! One parking space for the home. Overflow parking is available for one other vehicle OR trailer. For convenience, be sure to visit the Venture Out Ships Store for those last minute necessities! There, you will also find two boat ramps and gas! Venture Out charges a one time registration fee of $125.00 for security and amenities of the community. It is due upon arrival and collected at the guard gate. You will be given a parking pass that needs to be displayed in your vehicle. Cash or credit card only. Book your much needed and well deserved stay, today!

2

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1

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4

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