Vacation Rentals By Owner In Cudjoe Key, FL

Escape to this inviting 2-bedroom, 2-bath canalfront vacation rental in the Florida Keys, perfectly designed for boaters, anglers, and guests seeking effortless access to the water. Situated on a 35-foot seawall that comfortably accommodates boats up to 32 feet, this home offers open-water views directly from the dock and is just seconds from open water—ideal for quick runs to fishing grounds, sandbars, or sunset cruises.brThe private dock is fully equipped with a swim ladder, fish-cleaning station, dock box, and outdoor dining table for four, creating the perfect setup for waterfront meals and relaxing evenings by the canal. A propane grill makes outdoor cooking easy, while two bicycles are provided for guests to explore the neighborhood and enjoy the island lifestyle.brInside, the home features a bright and comfortable living space with a 42-inch smart TV, high-speed Wi-Fi, and a sleeper sofa for additional guests. The dining table seats six, with extra seating available at the kitchen bar for casual meals or morning coffee. The kitchen is equipped with a Keurig coffee machine and everything needed for preparing meals at home.brBoth bedrooms feature queen beds, offering comfortable and restful accommodations for all guests. The primary bedroom includes a 32-inch smart TV, while the second bedroom provides a quiet retreat after a day on the water. A washer and dryer are conveniently located in the unit, making longer stays easy and stress-free.brWith open-water views, quick boating access, and thoughtful amenities throughout, Riley's Retreat #107 is an ideal home base for a laid-back island getaway focused on boating, fishing, and waterfront living. This home is dog friendly with a $250 non-refundable fee of $250 per dog. br 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 amazing amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball and bocce courts. Adventure beyond the gates for a bite to eat at some of Florida Keys favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki's Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away! Whether you're a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the waters edge, our Florida Keys getaway promises an unforgettable vacation experience. Book your stay now and discover the ultimate blend of luxury, convenience, and coastal charm at our oceanfront retreat in Venture Out on Cudjoe Key. Located inside Venture Out on Cudjoe Key. A separate Registration Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. This fee must be paid with cash or credit card (4% credit card fee will apply). Parking for 1 vehicle per Unit. This vehicle must fit on the driveway and not extend out to the road. The driveway measurements are 20'L X 11.5'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. 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.brSocial Media - @bluescaperealestate YouTube Videos @bluescapevacations Book your stay today and experience the beauty of waterfront living!

Mobile Home

Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open Water

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$223.45

This home would be the perfect vacation spot for a small family or a group of friends. There are plenty of fun restaurants, tiki bars and even the southern most point of the United States, within a short drive from our home. Bring your own kayaks or motor boat for some fun in the water (this home has a sea wall that you can dock at, but you must bring your own bumpers and mooring)brbrThere are 3 beds and a sleeper sofa in the Livingroom to accommodate 6 guests. There is an outdoor shower by the picnic table and an another restroom in the garage.brbrNo Parties or eventsbrNeighbors value the serenity of a quiet neighborhood. Please follow all Parking, pet restrictions and property boundaries as well as monitor occupancy and noise levels to ensure consistency.br **Do not set the temps below 70 degrees. This will cause the ac to freeze up as they will not be able to cycle on and off. In Florida weather all ac’s can only cool so far with doors constantly being open and closed.**br• Smoking is strictly prohibited inside the home including vaping of any kind and the use of medical marijuana. If smoking outside, please dispose of butts in appropriate containers and do not litter gardens or the yards.br• Garbage and recycling Day is Monday and Thursday. Please place garbage containers curbside on Wednesday night.br• The Sewage System of our home will be damaged if products other than toilet paper are flushed. The following are a few examples of items that cannot be flushed: diapers, bones, sanitary products, coffee grounds, band aids and dental floss.brTV is Wi-Fi streaming only using apps such as Netflix. Please bring your log in information for those apps as you will need them. There is no cable. It is a Roku device which does have the Roku channel for some free tv.br Quiet time is from 9 pm until 7am. Visitors who remain in the home after 9 pm will be considered extra guests and you will be charged as such. Visitors are any persons not listed in the reservation. br• We allow up to 2 pets for an additional fee of $150.00. You can add a third animal for another $50 fee. Our homes will only accommodate up to 3 pets, per reservation. If pets are brought in without our knowledge then a $500 daily fee will be applied or result in immediate eviction with no refunds for remainder of your stay. Please keep pets on leash and please clean up after your pet and dispose of pet waste properly.br• The Barbeque grill has propane. Please clean and turn off tank after each use. br• Please wear shoes at all times when walking on shells in side yard as they are sharp and can cut your feet.br• Please note that Lawn maintenance will be done between the hrs of 7am and Sunset dependent on weather any day of the week. brDisclaimer: there is a security camera at the top of the stairs and the back porch ceiling which are also the porch lights and will be running during your entire stay and result in a fee or immediate eviction if turned off.br To help prevent the spread of Covid-19, we have enhanced our cleaning procedures by blocking off 24 hours before and after a guest has stayed in the home. br PLEASE NOTE: we cannot offer refunds for issues related to insects or weather conditions including but not limited to no wifi, power outages or issues out of our control. Our property is located in a natural environment where insects and changing weather are part of the experience. We appreciate your understanding and hope you enjoy your stay. br No Electric vehicle charging. Please google and use nearest chargers.br**** Owner or manager may stop by ANYTIME to verify number of guests Or maintain Property****brbr• Check out is 10am.

Nice home on Atlantic side of Cudjoe Key!

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$135.0

RV RESORT SPOT. BIG Rig Friendly br discount per month when booking 1ST to the 1ST of the month br RV RESORT SITE DISCOUNT PER MONTHLY rental /CAMPSITE/ SPOT / LOT IN Venture Out Cudjoe Key Florida. Bring your RV. Bring your Boat. this is a 35x70 ft. DRY RV-SITE Lot. This memorable place is anything but ordinary. THIS INCREDIBLE LOCATION IN VENTURE OUT RESORT.!!BRING YOUR PERSONAL(NO COMMERCIAL RENTAL RVs )20FT.min TRAVEL TRAILER OR YOUR 45FT BIGRIG!! Walk to marine/food store, saltwater swimming area, walk to pool, game room, tennis,pickle ball and basketball courts. WALK to EVERYTHING. MM23 23 miles from KEY WEST. Near Bahia Honda State Park. Water, electric 50/30 amp and sewer are included low avg/night plus taxes and 1 time $125 resort use of amenities fees paid at arrival. 2 pets allowed. Everything is included, Walk to all resort amenities. HEATED and COOLED pool, jacuzzi, activity room, boat ramp, and BOAT STORAGE IF AVAILABLE ON A FIRST COME FIRST SERVE BASIS, tennis courts 180 DEGREE TROPICAL OCEAN VIEWS.

Mobile Home

RV resort site/rvsite/spot/lot Cudjoe Florida mm23 Key West MONTHLY DISCOUNT

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$170.46

Welcome to your slice of paradise in the Florida Keys. This exceptional open-water RV lot is located in the desirable gated community of Venture Out on Cudjoe Key and offers everything you need for the ultimate waterfront experience. Positioned directly on the Atlantic, the lot features a split seawall measuring 41 feet and 12 feet respectively, for a total of 53 feet of deep water dockage. The concrete dock is equipped with dock posts, cleats, and a swim ladder, making it easy to tie off your boat or take a refreshing dip in the clear waters. A spacious double-size concrete pad and driveway provide ample room for your RV and vehicle, with full hookups including water, sewer, and 110, 30, and 50 amp electric service. You'll enjoy sweeping views of the Atlantic Ocean right from your site – perfect for sunrises, stargazing, or docking your boat after a day on the water.brbrEnjoy extras like a picnic table for outdoor dining, and custom stairs with a railing designed for seamless RV access. Lot dimensions are approximately 12'x41'x67'x20'x74'. Please note: Maximum placement of RV and vehicle must be at least 10 feet from the water, and vehicles may not overhang into the street. This listing is for the RV lot only—there is no RV on site.brbrSituated in Venture Out, guests have access to a range of community amenities including a heated pool and jacuzzi, tennis and pickleball courts, playgrounds, a community boat ramp, and an on-site convenience store. Some amenities may be temporarily unavailable due to ongoing electrical upgrades, so please contact us in advance for the latest updates.brbrNearby, you'll find great dining and entertainment, including local favorites such as Square Grouper, My New Joint Cocktail Lounge, Morning Joint Coffee, the Bent Prop, Tonio's Seafood Shack and Tiki Bar, and Boondock's Mini Golf and Draft House. Whether you're seeking a quiet waterfront escape or easy access to adventure in the Lower Keys, this lot offers the perfect balance of relaxation and recreation.brbrVenture Out charges a $125 registration/check-in fee upon arrival, which is subject to change. Parking is included for one vehicle per lot, with the possibility of purchasing an additional parking permit for a nightly fee based on availability. Guests must be at least 25 years old to book, and overnight occupancy is limited to six people who must be registered with both the Rental Manager and Venture Out. Up to two dogs are allowed per lot. Check-in time is 4:00 PM, and check-out is at 10:00 AM unless prior arrangements are made with the Rental Manager. A refundable $150 security deposit is required at the time of booking. A 4% credit card processing fee applies.brbrThe primary guest must submit a copy of their driver's license and sign a rental agreement within 24 hours of booking. All reservations are subject to final approval by the local Rental Manager.

Caravan Park/Campsite

Oversized RV Lot with 41'+12' Seawall, Deep Water Access, and Stunning Open Water Views

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$149.14

**THIS IS FOR AN RV LOT ONLY - THIS RENTAL DOES NOT INCLUDE AN RV - JUST THE LOT SITE**brbrWelcome to your own private oasis nestled in the stunning Florida Keys! This exceptional 70' x 35' canal front RV lot offers a picturesque setting for your dream RV getaway. Bordering a charming canal, this property provides stunning canal views with just a short distance away, along with direct access to some of the most sought-after waterways in the Keys. You can bring your boat and dock it conveniently at the 35' seawall, ensuring easy access for your water adventures in Cudjoe Key. With water and sewer connections included, along with the choice of 110, 50, or 30 amp service, this lot is tailored to meet all your needs. Located in Venture Out, just a few canals away from the pool, amenities, store, and marina, everything you need is close at hand, allowing you to relax and enjoy your time away without traveling far.brbrNearby attractions include great restaurants such as Square Grouper Bar & Grill, Toni's Tiki Bar & Seafood Shack, Boondocks Draft House & Miniature Golf, Broil, and The Bent Prop. Additionally, the vibrant nightlife and daily attractions of Key West are just a short 20-minute drive away. Book your stay at RV Lot 442 and immerse yourself in the beauty and adventure of the Florida Keys. Whether you're here for the fishing, the amenities, or the local attractions, this spot has it all for an unforgettable vacation! RV SITE ONLY - NO RV FOR RENT. **No cable or WIFI service is provided at this site**brPlease note that a Registration/Check-In Fee of $125 (subject to change) will be charged by Venture Out upon arrival. Additionally, parking is provided for one vehicle per unit, with the possibility of obtaining an extra parking permit at the Guard Station for an additional nightly fee, subject to availability and a maximum stay of 14 days. It is essential to adhere to all the community's Rules and Regulations during your stay to ensure a harmonious experience for all residents and guests. To comply with county and state regulations, proper taxes are collected regardless of the booking platform used. Renters must be 25 years or older, and overnight occupancy is limited to a maximum of 6 people, all of whom must be registered with the Rental Manager and Venture Out. Venture Out Regulations allow for up to 2 dogs per lot, providing the perfect opportunity to bring your furry companions along for the adventure.brCheck-in time is at 4pm, and check-out time is at 10am unless alternative arrangements have been made with the Rental Manager prior to arrival. To safeguard both guests and the property owner, a refundable $150 Security Deposit is required at the time of booking. A 4% credit card processing fee will be applied if paying with a credit card. Immerse yourself in the laid-back charm of Cudjoe Key and make the most of your vacation by securing this inviting RV Lot. The main guest of the reservation will be required to submit a copy of your driver's license to rental manager for our records. The Rental Agreement is required to be signed within 24 hours from time of booking. All reservations are subject to final approval from the local Rental Manager.

Caravan Park/Campsite

RV Lot 498 in Venture Out at Cudjoe Key

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$386.52

Welcome to Reel Life, a beautiful Cudjoe Gardens oasis! Located on the ocean side of Cudjoe Key, this home has everything you need to enjoy a true Florida Keys vacation! It features an in-ground heated pool, a large Tiki hut/bar for hanging out by the pool, an expansive dock to accommodate your boat, a sandy beach area overlooking the canal, a screened lanai and a top of the line outdoor kitchen...and it's all located on a deep, wide, clear, flow-through canal with no bridges to the open ocean! It's truly an outdoor oasis and a boater's dream! Spend the afternoon out on the boat and/or exploring the canals with your snorkel gear then cook up your fresh catch and hang pool-side for the evening! Cudjoe Marina is right around the corner with a ramp and fuel and you are only 30 minutes to Key West or 15 minutes to Big Pine for all your shopping and conveniences.brbrThe home itself is ground-level and is super spacious with an open floor plan, 3 bedrooms that sleeps 6 adults, a bonus room with bunks for kids, 2 bathrooms, a large updated kitchen, separate dining and plenty of essentials. It's clean, comfortable and fully equipped with everything you need to enjoy your vacation!brbrCome stay at your very own tropical paradise!brbr*For a complete viewing of this home, check out the posted video*brbr***PETS ALLOWED BY APPROVAL ONLY***brbrPLEASE NOTE: This is a monthly rental. During season (Winter and Summer), we only rent full months at a time, ie. all of January, all of February, all of March. We do not split months, ie. Jan 15 - Feb 15.brbrbrNOTE: All images used are for illustrative purposes only. Individual features such as bed sizes/configuration, bedding, décor, appliances, colors, extra amenities, etc. may vary since these are private homes and owners redecorate often. Please also note that pictures are taken in different light conditions and computer screens have different individual settings that moderate colors. Please read the written description and ask questions if you have any specific needs and/or concerns. All furnishings and décor are subject to change at any time.

JUNE & JULY SPECIAL! 3 Bedroom/2 Bath Canal Home w/ Private Pool in Cudjoe Key

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$334.57

Relax! Swim! Boat! Bike! Kayak! Hike! Pickle Ball, yes even that. Just a short distance to Key West with quick and easy access to the Gulf or open water, a perfect location for family chill days, fishing & boating. Spacious living areas with 3 oversized bedrooms and 2 full bathrooms. Store your boat on site or tie up to the dock. Beautiful pool, tiki hut, bikes, kayaks, pickle ball court, grill, fruit trees and even a hiking trail across the street to keep everyone happy and entertained.brbrWinter, work or just typical life got you stressed and wore out. Well come rejuvenate at Lobster Nirvana! brWelcome to our dream! A large lot with grass in the Keys Yes and totally fenced to sprawl out with the privacy your looking for. The first eye catcher is the refreshing pool the kids will actually have room to play in and the tiki bar right there so you can relax poolside. 150' dock so you have plenty of room to tie up a boat or two. Dock has a step down area with a ladder for easy in and out, also has a fish cleaning station. Throughout the yard there are several fruit trees, star fruit, mangos, and avocados. There are several patios and decks to hang out on. Sit out back and look over the canal or out front and watch the sunrise or sit in the screened in deck, sip coffee while you gaze at the canal (my favorite morning spot).brUpstairs you have an open kitchen, dining and living room. All of the bedrooms are spacious, one has a king size bed and workspace in case you need to take care of some business. All of the bedrooms are spacious. One has a king size bed and a workspace in case you need to get some work done. The other has a queen bed. The master bedroom is huge and has a king bed with on suite. Everything you need to relax and recharge. All this with some interesting lobster house history, if you stay you'll learn the insights of the past for the Lobster Nirvana

Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West

Cudjoe Key, Florida, United States

3

Bed

Bath

8

Sleeps

$368.54

Welcome to Gecko House! This canal-front 2 bedroom, 2 bath house is located in a great boating area with easy access to the ocean. It has a beautiful pool area under the house with seating for cocktail hour and a deck for viewing the sunrise while you sip your morning coffee.brbrThis home has a two bedrooms, one with a King size bed with an en-suite bathroom with a full size tub and shower. The second bedroom has a Queen bed. The second bathroom has a walk-in shower. There is a loft with a futon.brbrThe living room has lots of comfy seating to relax and watch the flat screen TV.brbrOutside under the house is a table with 4 chairs and a swing to relax in the shade while sipping your favorite cocktail. In the morning, you can sit on the deck upstairs drinking your coffee while watching the sun rise.brbrThere are two kayaks for your use and of course a concrete dock for your boat.brbrEnjoy all the unlimited water activities like swimming, fishing, and diving the Keys has to offer. Discover an assortment of Florida Keys wildlife. Big Pine Key is located a few miles up where you’ll find a shopping plaza hosting Winn-Dixie, Artists in Paradise, Beall’s Outlet, Radio Shack and branch of the Monroe County Library with Wi-Fi internet access.brbrTake a trip down to Key West for the daily sunset celebration or a romantic sunset cruise. Or visit one of the many venues offering the finest in live entertainment and great food. Be sure to take a stroll up and down Duval Street and visit the art galleries, shops, and more! Take the family for a sunset cruise or go snorkeling, kayaking, or whatever water sport the beautiful Florida Keys has to offer.brbr***PETS ALLOWED BY APPROVAL ONLY***brbrNOTE: All images used are for illustrative purposes only. Individual features such as bed sizes/configuration, bedding, décor, appliances, colors, extra amenities, etc. may vary since these are private homes and owners redecorate often. Please also note that pictures are taken in different light conditions and computer screens have different individual settings that moderate colors. Please read the written description and ask questions if you have any specific needs and/or concerns. All furnishings and décor are subject to change at any time.

2 Bedroom Canal Home in Cudjoe Key, FL w/ Private Pool & Extra Loft Space

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$132.19

Enjoy stunning open water views from RV Lot #378, a well-maintained dry RV lot located in a prime Florida Keys setting. While this lot does not include a dock or direct boat access, it offers beautiful water views and a peaceful island atmosphere that makes it a perfect home base for your Keys getaway.brThe total lot dimensions measure approximately 23' x 59' x 35' x 69', providing ample space for most RVs. Full hookups are available, including water, sewer, and 50/30-amp electric service. Mature palm trees provide natural shade, creating a comfortable outdoor space throughout the day.brA concrete driveway and paved patio area offer convenient parking and outdoor living space, complete with a picnic table that seats four—ideal for outdoor meals, morning coffee, or relaxing after a day of exploring the Keys.brRV Lot #378 is an RV site only. No RV is provided. This is a dry lot with no dock or boat slip. No WiFi or cable service is provided, allowing guests to truly unplug and enjoy the laid-back Florida Keys lifestyle.brGuests enjoy close proximity to open water views, community amenities, and easy access to boating, fishing, dining, and all that the Florida Keys have to offer.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 all of the amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball and bocce courts. Adventure beyond the gates for a bite to eat at some of Florida Keys favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki's Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away! Whether you're a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the waters edge, our Florida Keys getaway promises an unforgettable vacation experience. Book your stay now and discover the ultimate blend of luxury, convenience, and coastal charm at our oceanfront retreat in Venture Out on Cudjoe Key. Located inside Venture Out on Cudjoe Key. A separate Registration Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. This fee must be paid with cash or credit card (4% credit card fee will apply). Parking for 1 vehicle per property. This vehicle and your RV must fit on the driveway and not extend out to the road. 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. Social Media - @bluescaperealestate YouTube Videos @bluescapevacations Book your stay today and experience the beauty of waterfront living!

Caravan Park/Campsite

Stunning water views RV lot with full hookups paved patio

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$306.56

You found it!! Bring your boat! Charming cottage located in Venture Out, resort style community located on Cudjoe Key, just 20 miles from Key West. Remodeled cottage, Two bedroom, two bath, sleeps 4 (2 queen beds, there is also a sleep sofa), well equipped kitchen. Screened porch that overlooks the wide canal, 35' concrete bulkhead, with easy access to the Atlantic Ocean or Gulf. Amenities include heated 80' swimming pool, hot tub, tennis courts, full service marina and community convenience store. Wonderful restaurants nearby, post office, gourmet grocery, liquor store. There is a $125.00 fee that is due at check in payable to Venture Out for use of the amenities. Parking for one car, one golf cart and one motorcycle, additional vehicles will park in overflow parking. If you are bringing a boat, we have trailer storage for you just down the street. Please let me know.

Cottage

Waterfront Home

Cudjoe Key, Florida, United States

Bed

Bath

4

Sleeps

$268.84

Island Cottage Retreat in Venture Out - Pet-Friendly 2BR, Lots of Amenities & Private PatiobrWelcome to Island Home in Paradise #624, a charming 2-bedroom, 1-bath vacation retreat located inside the private, gated community of Venture Out on Cudjoe Key in the beautiful Lower Florida Keys. Tucked away on a peaceful lot with tropical landscaping and multiple outdoor living spaces, this cozy island getaway is perfect for couples, small families, remote workers, or anyone looking to relax and experience true Keys living.brThe SpacebrIsland Home in Paradise #624 offers a comfortable and inviting layout designed for easy vacation living. Inside, you'll find a bright living area with comfortable seating, smart coastal décor, and a dedicated desk workspace for guests needing to work remotely during their stay.brThe fully equipped kitchen makes it easy to prepare meals at home and includes everything needed for cooking and dining in. Enjoy your morning coffee with the Black & Decker 12-cup drip coffee maker before heading out for a day on the water.brCentral A/C and Wi-Fi are provided throughout the home for added comfort and convenience.brBedrooms & Sleeping ArrangementsbrPrimary Bedroom: Queen-size bed with cozy bedding and ample storagebrGuest Bedroom: Queen-size bed with comfortable furnishingsbrMaximum Occupancy: 4 GuestsbrBathroombrFull bathroom with walk-in showerbrOutdoor LivingbrOne of the highlights of this home is the private outdoor space. Guests can enjoy two separate patios designed for relaxing and entertaining.brThe rear patio offers a peaceful and secluded setting surrounded by tropical landscaping, perfect for morning coffee, reading, or unwinding after a day exploring the Keys.brThe front patio is tucked beside lush palms and includes outdoor seating and a barbecue grill, creating the ideal space for outdoor dining and enjoying warm island evenings.brPet-Friendly DetailsbrThis property is pet-friendly for up to 1 dog with a maximum weight of 25 pounds. A paid pet fee of $250 applies. Guests must notify the rental manager at the time of booking if bringing a pet.brCommunity Amenities at Venture OutbrVenture Out is one of the most popular waterfront communities in the Lower Florida Keys and offers guests access to outstanding amenities including: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 community common areasbrGated security and electric golf cart-friendly streets throughout the communitybrLocationbrConveniently located on Cudjoe Key, you'll be just minutes from some of the Lower Keys' favorite restaurants and attractions including Square Grouper, The Bent Prop, Morning Joint, Mangrove Mama's, Kiki's Sandbar, and Boondocks Draft House & Miniature Golf.brThe home is also located near the world-famous Looe Key Reef, known for exceptional snorkeling, diving, and fishing opportunities.brFor additional dining, nightlife, shopping, and entertainment, Key West is only about 25 minutes away.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. The driveway measures approximately 18' long x 13' wide and vehicles must fit fully within the driveway without extending into the roadwaybrOverflow parking may be available through Venture Out for an additional daily 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 spending your days boating, fishing, snorkeling, relaxing poolside, or simply soaking in the laid-back atmosphere of the Florida Keys, Island Home in Paradise #624 offers the perfect tropical escape in one of the Keys' most amenity-rich waterfront communities.

Island Home in Paradise #624 - OCEANFRONT Community!

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$318.43

Get ready to relax in this spacious and serene 2-bedroom waterfront resort villa in Cudjoe Key. brOur exquisitely designed, private villa in the beautiful Venture Out resort offers an unparalleled escape for solitude seeking. discerning travelers. Enjoy breathtaking views, spacious outdoor living areas, and a list of resort ammenities unrivaled in the Florida Keys. Perfect for relaxation and rejuvenation. brNestled off the main streets. on a serene cul de sac/ surrounded by lush vegetation and water views. A community park is located directly out the back door. Which offers vast outdoor space with picnic tables, a huge pensilula for fishing and beautiful water views.brbr You will find a open floor plan which seamlessly connects the kitchen, dinning room and living area creating a spacious and inviting atmosphere. The 52 inch t.v. offers roku and fast wifi. Staying connected will be a breeze.brThis property features a queen bed in the master which overlooks the butterfly garden and water views. Second bedroom offers a full bed with a 45 inch smart t.v. and ample privacy, and a queen sofa bed in the living area, perfect for a small group of 6 guests. brbr The modern kitchen is fully equipped with a new gas stove, microwave, and dishwasher and refrigerator, 3 different coffee makers, blender and instapot are just a few of the amenities. brbr The bathroom features a full size shower with body wash, shampoo and conditioner and a hairdryer for your convenience. brbrYou'll have plenty of space to kick back and enjoy your vacation. It's easy to see why you'll be able to unwind at our place. Included with the rental is a golf cart, and 2 bicycles to use on property during your visit.brbrVenture out community offers many amenities including Heated Pool, Hot Tub, Basketball Courts, Tennis Courts, Marina, Boat Ramp, Private Convenience Store, Children's Pool, Bath Houses, Laundry Facilities, Fish Cleaning Station, Horseshoes, Children's Play Area, Bocce Ball, 24 Hour Gated Security, Salt Water Swimming Area, Recreation Hall and Pickle Ball Court.brbrThe resort collects it's own $125 fee at the gate when you check in. This fee is per stay this is separate from the villa rental fee and covers the resort amenities. They have a small charge for credit cards, cash is also accepted. We offer parking for one vehicle at the villa. For any additional vehicles or boat trailers venture out offers overflow parking for a small fee per night first come bases.brbrWhen booking we will need an email address to send a renters registration form and Venture out rules package. This is a gated community so check in with the guard you will be given a car pass for your stay, along with a map of the resort. I will send you a code to lock box for keys.

Hotel Resort

July Discount. Waterfront, Dock ,Kayak, Paddleboard,golf cart, bikes,

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$460.67

Come and see the beautiful sunsets in the Florida Keys. This fully furnished 3 bedroom, 2 bath home on Cudjoe Bay with a pool/hot tub has it all. It includes all utilities, cable, wifi, laundry. Private covered parking for 4 vehicles. MBR has a King and full bath. Second bedroom has a Queen and an attached bath. Third bedroom has Queen sleeper. Living Room has a Full size sleeper. Also includes dedicated office space and a screened in porch. Bring your kayak or your small boat or fish from the dock. Plenty of parking for an RV.brbr28 day rental is required in Monroe County.brbrThe pool and outdoor bar are a potentially shared space.

Waterfront Keys Sunset Spectacular

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$686.28

Oceanfront with stunning open water views and deep water access! Oceanview Serenity offers stunning Atlantic views, and a private seawall for your boat. Kayaks, paddle boards, and more. This renovated 2BR cottage sleeps 4 with one King and one Queen size bedrooms, and one with an ensuite bathroom. Both bedrooms are equipped with JW Marriott mattresses for your ultimate comfort and relaxation. ALL new appliances! Enjoy resort amenities like a pool, hot tub, tennis, pickle ball, and marina store. Just 30 minutes from Duval Street, Key West. $125 resort fee due at check-in (per stay). One (1) parking spot. brbrWe can't wait to host you at this beautiful oceanfront cottage!brbrThe spacebrOceanview Serenity – True Oceanfront Cottage with open water views!brWake Up to Endless Atlantic Views – Just 30 Minutes from Key West!brbrAbout this spacebrUnlike canal-front properties, Oceanview Serenity sits directly on the Atlantic Ocean, offering stunning, uninterrupted water views and a true seaside experience. Located in the secure, amenity-rich Venture Out Resort, this recently renovated 2-bedroom cottage includes a private seawall, perfect for boating enthusiasts. Enjoy complimentary kayak/paddle boards and many board games, and more! Relax knowing you're only 30 minutes from the heart of Old Town Key West and the world famous Duval Street!brbrThe SpacebrWatch the sun rise over the ocean from your living room in this beautifully updated cottage with an open floor plan and expansive ocean views. Perfect for families or groups, the home comfortably sleeps up to 4 guests.brbrStep outside and launch your kayak or paddle board directly from the seawall. Explore the nearby Venture and Out Keys or lounge in the ocean with provided floats and life jackets.brbrAdditional Amenities Include:brbr* Washer & dryer in the unit (plus coin laundry nearby)br* Access to resort amenities: pool, hot tub, tennis & pickleball courts, playground, picnic areas, boat ramp, and marina store with fuel, groceries, and tacklebr* 24/7 gated security for peace of mindbrbr**Please Note**brUpon arrival, Venture Out Resort collects a *one-time* mandatory $125 resort fee (per stay, not per night), which includes full access to all resort amenities and a parking permit. Overflow parking is available for boats, trailers, or additional vehicles for a nightly fee.brbr**Guest Access**brGuests have full private access to the entire cottage, private seawall, and all the resort amenities.

Oceanfront w/stunning open water views and private seawall! 30 mins to Key West!

Cudjoe Key, Florida, United States

Bed

Bath

4

Sleeps

$149.41

Spectacular Sunsets & Bay View | Waterfront Lounge Area | 2 Kayaks brbrPlanning a long-term stay in the Florida Keys Book this 2-bedroom, 2-bath Cudjoe Key vacation rental! Enjoy slow mornings with coffee on the spacious deck, then take the provided kayaks out for a spin or beachcomb at Bahia Honda State Park. Later, gather around the fire pit and savor the sunset. No matter who you’re traveling with, this home offers the perfect base for a memorable month in the Sunshine State!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Living Room: 1 queen sleeper sofabr- Additional Sleeping: 1 queen air mattressbrbrOUTDOOR LIVINGbr- Bay & sunset viewsbr- Deck w/ seating & Smart TVbr- Gravel patio, wood-burning fire pit, gas grillbr- 2 kayaksbr- Private dock, canal accessbrbrINDOOR LIVINGbr- 3 Smart TVsbr- Dining table, dry barbrbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Dishware/flatware, children’s dinnerware, cooking basicsbr- Keurig coffee maker (starter pods provided)br- Blender, ice makerbr- Microwave, toaster, toaster ovenbrbrGENERALbr- Free WiFibr- Central A/C, ceiling fansbr- Central/electric heatingbr- Linens/towels, iron/boardbr- Washer/dryer (detergent provided)br- Trash bags, paper towelsbr- Hair dryer, complimentary toiletriesbrbrFAQbr- Pet fee (paid pre-trip)br- 4 exterior security cameras (facing out)brbrACCESSIBILITYbr- Single-story home, exterior stairs requiredbrbrPARKINGbr- Carport (2 vehicles)br- Gravel driveway (2 vehicles)brbr-- THE LOCATION --brbr- Walk to grocery store, coffee shop & restaurantbr- Near kayaking areas, boat rentals & fishing chartersbr- 11 miles to Sugarloaf Beach & 14 miles to Bahia Honda State Parkbr- 19 miles to Key West Tropical Forest & Botanical Gardenbr- 22 miles to Key West: Smathers Beach, parks, shops, galleries, cafes, bars, restaurantsbr- 21 miles to Key West International Airport & 138 miles to Miami International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking or vaping of any kind, including marijuanabr- Pet friendly w/ $90 fee (+ fees & taxes; dogs only, 1 max)br- No events, parties, or large gatheringsbr- Per Florida guidelines, guests must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This property sleeps 4 guests in 2 beds, with room for 6 total by using the queen air mattressbr- This single-story home requires exterior stairs to enterbr- Your safety matters. This property features 4 exterior security cameras: 1 camera is on the side facing the homeowner’s boat, 1 camera is in the carport facing the front yard and street, 1 camera is at the top of the entry stairs facing the staircase and side yard, and 1 camera is on the back facing the backyard and dock area. These cameras are outward facing and do not look into any interior spaces. They record sound and video when activated by motion

Canal-Front Gem w/ Peekaboo Views in Cudjoe Key!

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$316.65

Canal front home in a gated resort community. There is a $125 resort fee and parking for one vehicle at the property. There is limitted additional first come first serve vehicle or trailer parking at $5 per night vehicle, $10 per night trailer. These fees are separate from VRBO. The property has a large screened in porch. Two bedrooms one king with private bath. One Queen with full bath in the hall. Sleeps 4 comfortably + a queen sleeper sofa if needed in the living room. We need to update pictures of the interior It's freshly painted and new washer and dryer. we will up date soon. Freshly updated deck furniture, bait freezer on porch Docking post and fish cleaning table on a spacious deck and 64' seawall. Direct access to the Atlantic and Gulf. Pamper yourself and your boat. Community amenities including boat ramp ,marina with pressurewasher to clean your boat, pool, hot tub, tennis and pickle ball, Bochy ball, shuffle board, Saturday morning, pancake breakfast in the winter

Sun Bake @ Sponge Cake, 64' Sea Wall,

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$310.65

Enjoy our little peace of paradise! Come and make memories at this laid back and family-friendly waterfront home. Located in a gated community, just 20 miles from Key West, this cottage is the perfect place if you want to relax and re-energize after a day of adventures and activities during your time in the Florida Keys!brbrVO 453 - Island Oasis brOpen Water Views 17' SeawallbrEnjoy expansive open water views from this beautiful midrise, a 2bd/1.5Ba vacation home in a highly desired 24 hour gated community. This home features a 17' seawall overlooking a 60' wide canal and Atlantic Ocean, great for launching your kayaks, paddleboards or small boat. Enjoy stunning sunrises and peaceful evenings right from your porch!brbrBoth bedrooms feature a queen sized bed and flat screen tv. The smaller bedroom is attached to a half bath. The main bathroom has a standup shower and plenty of counter space. The kitchen is fully equipped, including a coffee maker, filters, sugar and tea.brbrAdditional amenities include: Central air conditioning, ceiling fans, WIFI, streaming cable, family games, iron, dishwasher, queen size blowup mattress for the surprise extra guest/s, BBQ Grill and BBQ utensils.brbrWe are located in a spotlessly clean gated community with 24 hour security, marina, ship store, boat ramps, picnic garden, heated pool, hot tub, basketball, playground, pickle ball, bocce ball and tennis, pavilion and club house for activities, over 4 miles of paved streets.brSECURITY DEPOSIT REQUIRED, NO SMOKING,br7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL, brOVERFLOW PARKING ADDITIONAL FEE 14 DAYS MAXbr*** IMPORTANT *** WHEN ENTERING, THERE IS A ONE TIME AMENITIES FEE OF $125.00 - DUE UPON ARRIVAL. THIS FEE IS PAID DIRECTLY TO VENTURE OUT AND GOES TOWARDS ALL OF THE GREAT AMENITIES THIS RESORT HAS TO OFFER.

Cottage

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$792.71

This tropical 6 bedroom 4 bath oceanfront home has a private heated salt water pool and huge outdoor living space. There is beach access, shared dock space and outdoor gazebo to watch sunsets. There is a 3rd story balcony that offers spectacular views of the sunrise and sunset. Bring up to a 24' boat or paddle out on one of the shared kayaks onsite. Fully equipped kitchen, linens, beach towels, a propane BBQ grill and 2 washer/dryers.brThis home is priced based on the number of guests. brbrYour property manager lives nearby and is available if you have any requests during your staybrbrOcean front private location!brbrYou will be provided check in instructions prior to your arrival.brbrbrbr• Master Bedroom: 1 King bedbr• King Bedroom: 1 King bed br• King Bedroom: 1 King bedbr• King Bedroom: 1 King bed br• Queen Bedroom: 1 Queen bed br• Queen Bedroom: 1 Queen sleeper Sofabr• Living Room: Queen sleeper sofa, Flat screen TV, br• 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. br• Outdoor Features: Propane BBQ,br• Boat Dockage: Tall pier for boats up to 24. The dock is shared with the Latitudes Home guests. The water is shallow, about a 2' draft getting out to the channel.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 TVsbr• Games: Corn Hole Gamebr• The dock, gazebo, kayaks and kayak launch area are shared with Latitudes Home guests. There are a couple kayaks for your use. You may rent additional kayaks locally.br• Location: 20 minutes from Key West, 15 minutes from Bahia Honda State Park. br• Pool: heated salt water pool. This is a private pool - not sharedbrbrbrCudjoe Key is the perfect get away spot...removed from the hassle but close enough to enjoy Key West or Bahia Honda State Park in about 20 minutes!brbrUber, 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.brbrThis home is priced based on the number of guests. The base rate is for up to 6 guests. Additional guests fee is $25 per night per person.brbrbrOur Cancellation policy is:brCancellation: 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 to visitors because of the COVID-19 pandemic for your arrival date, you will be offered the opportunity to reschedule your reservation or receive a refund. brbrNon-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.

Latitudes - Ocean front with salt water pool.

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$318.38

Welcome to Casa Kiwi #472, your perfect getaway in the heart of the beautiful Florida Keys.brNestled on a serene interior large corner lot, this high-rise home offers stunning privacy surrounded by lush, vibrant vegetation and ocean views. Casa Kiwi is designed for relaxation and fun, making it the ideal spot for your next vacation. Step inside and you'll find an open floor plan that seamlessly connects the kitchen, dining room, and living room, creating a spacious and inviting atmosphere. The modern kitchen is fully equipped, ready for you to whip up delicious meals. The living space is comfortably furnished, providing the perfect setting for cozy evenings or lively gatherings.brThere is a 3 night minimum stay required at this home.brDISCOUNTS AVAILABLE - 10% off the nightly rate for stays of 7 nights or more. 22% off the nightly rate for stays of 30 days or more.brCasa Kiwi boasts two well-appointed bedrooms and two pristine bathrooms, ensuring a comfortable stay for all guests.brThe Primary Bedroom has a King size bed and an ensuite bathroom for privacy and convenience. brThe Guest Bedroom has a comfortable Queen size bed. This charming home comfortably accommodates up to 6 (4 Adults & 2 Children) guests. The covered porch, with its ample seating, is a true highlight. Overlooking the ocean, it's the perfect spot to enjoy your morning coffee, watch the sunrise, or simply relax with a good book while taking in the breathtaking views.brFor those who love outdoor activities, Casa Kiwi offers 4 bikes, perfect for exploring the scenic surroundings. The property also features a gas grill to cook up your fresh catch and a dedicated area for family gatherings, making it easy to enjoy al fresco dining and create lasting memories with loved ones.brStaying connected is a breeze with high-speed Wi-Fi provided here. There is a washer and dryer for your convenience meaning you can pack light and keep your wardrobe fresh throughout your stay.brThere is a Mr. Coffee drip and KCup Single Coffee Maker at this home for you to enjoy your favorite brew.brWhether you're seeking a peaceful retreat or a base for adventure, Casa Kiwi is the perfect choice for your Florida Keys rental. Come and experience the charm and beauty of this exceptional property, and make memories that will last a lifetime.brVenture Out is a golf cart friendly, private gated community that boasts a plethora of amenities to elevate your stay to the next level. Indulge in resort-style amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball and bocce courts.brAdventure beyond the gates for a bite to eat at some of Florida Keys favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki's Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away!brWhether you're a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the waters edge, our Florida Keys getaway promises an unforgettable vacation experience. Book your stay now and discover the ultimate blend of luxury, convenience, and coastal charm at our oceanfront retreat in Venture Out on Cudjoe Key.brSorry, no pets allowed at this home.brLocated inside Venture Out on Cudjoe Key. A separate Registration Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. This fee must be paid with cash or credit card (4% credit card fee will apply). Parking for 1 vehicle per Unit. This vehicle must fit on the driveway and not extend out to the road. The driveway measurements are 25'L x 10'W. If your vehicle does not fit when you arrive, you will need to see the guard gate for an additional parking pass for the overflow lot which costs $5/day. Extra parking permit may be available at the Guard Station for an additional nightly fee for a maximum of 14 days depending on availability. Must follow all the Rules and Regulations during your stay.brMain guest must be 25 years of age or older and will need to email a copy of your drivers license to the Rental Manager after booking has been accepted. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance. There is a 4% credit card processing fee. brSocial Media -br@bluescaperealestatebrYouTube Videos @bluescapevacations

Ocean View High-Rise in Venture Out | Pool, Boat Ramp & close to Key West

Cudjoe Key, Florida, United States

Bed

Bath