58,368 properties available

Located in Cudjoe Key, Florida, United States. Casa Del Mar in Venture Out Unit 253 VO253Open Water Views 35' DockageSparkling Clean 2Bd/1Ba Vacation Home!THIS IS ONE OF THE NICEST UNITS IN ALL OF VENTURE OUT!!! THE HOME HAS BEEN COMPLETELY RENOVATED TOP TO BOTTOM IN MARCH OF 2018 INCLUDING BUT NOT LIMITED TO THE FOLLOWING - NEW ROOF, NEW AC AND DUCT WORK, NEW HOT WATER TANK, NEW SIDING AND SKIRTING, NEW TINTED WINDOWS AND DOORS, NEW INTERIOR WALL PANELING, NEW OUTLETS AND SWITCHES, NEW FANS AND LIGHT FIXTURES, NEW FURNISHINGS, NEW FLOORING, NEW CABINETS, NEW QUARTZ COUNTER TOPS AND SO MUCH MORE!!!This is Oceanside Waterfront 2 bedroom with 1 full bathroom (with room to add a second) home located in Venture Out's private gated community offering ocean views from your private back yard and lanai, living room and kitchen, this rental comes with everything you need to live, kick back and relax in the Florida Keys.Located on Kemp Channel, one of the most accessible boating channels to both the beautiful back country as well as a quick

Located in Cudjoe Key, Florida, United States. Canal front home @ Venture Out Resort in the Florida Keys! 3 Nite Minimum Stay! **7 day minimum for Lobster Fest, July 22-Aug. 13. **SUPER beautiful canal front home with open water views from your spacious covered open-air porch. Located in the Gated Community of Venture Out. 19 minutes to Key West.This 2 bedroom , 2 full bath, upscale stilt home includes a covered deck for outdoor dining and entertaining with water views. 35' custom-tiled concrete seawall for docking your boat or water toys and a brand new fish table with water spigot. Downstairs features access to a secure storage room, 2 bikes, 2 large kayaks, bait freezer and outdoor sitting area and gas grill with beautiful canal views. Beautiful kitchen with stainless appliances, Corian countertops and lots of cabinets for all your storage needs. Full sized stacked washer and dryer. Open floor plan w/dedicated dining area, large living room, tile floors, recessed lighting throughout. Spacious master-suite with both guest and m

Located in Cudjoe Key, Florida, United States. A slice of paradise Wanna go on vacation but feel Cozy as if your home? 🦎 We got the place for you! 2 bedroom,1 bathroom with living room,dining room and kitchenette in a secure gated community of Venture Out.Fully furnished,Colorful & great island vibe. This is a Florida lovers Paradise.This dry lot home can sleep 6. The house is fully furnished with a colorful island vibe. 2 modern bedrooms and 1 full bathroom.There is a queen bed in the bottom floor bedroom,along with AC & a flat screen TV. One full pull out couch in the living room with a flat screen TV and AC unit. As you make your way through the kitchenette there is a single bed in its own part of the hallway before the bathroom. The back bedroom has a Full bed with a AC unit. 3 AC units. (All beds are New and replaced on 1/18/21 ) (New bikes- Two 3/17/22)(Newly painted bedrooms and living room 1/4/23)(Two new AC units 4/19/23) The decoration in all the rooms give you that feel of paradise.The kitchenette has a 4 person sit

Located in Cudjoe Key, Florida, United States. Keys Time - Unit 437 Venture Out 2Bed/2Bath Canal Front Home Welcome to Keys Time!! Slow it down. Unwind. Enjoy the Island Life!This Beautifully furnished 2 bedroom 2 bath canal front home awaits your arrival. In a gated condominium community, Keys Time offers all the amenities one may want for their Dream Vacation. Including a Community Pool and Spa, Tennis Courts, Recreational Hall, Community Store, Ocean View access at the Community's Tiki Huts, and more. Being only 22 miles North of the famous Key West and 32 miles South of Marathon, this unit is perfectly located for any occasion. Accommodations to sleep up to 6 adults comfortably. Excellent location for quick and easy boating access to both Atlantic and Gulf Side. This property has a 21 foot concrete dock which will accommodate a boat up to 17’ maximum. There is a fish cleaning station, swimming ladder, and dock post. Enjoy biking the paved community or kayaking out to Kemp Channel. The possibilities are endless when you are on

Located in Cudjoe Key, Florida, United States. Island Therapy Beautiful 2BD/2BA vacation home features open water views and a full size 35' seawall for docking a boat. Amenities include central air conditioning, new tile floor, new furnishing and decorations throughout, wireless internet, flat screen television, washer, dryer, dishwasher, microwave and covered porch. Master bedroom has a queen bed with lots of closet storage, flat screen television and private full bathroom. Guest bedroom has a queen bed with full length closet storage, private full bathroom entrance. Living room features a queen sleeper sofa with flat screen television and access to covered porch. Beautiful open water views and quick access to the ocean or gulf from this property. 7 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.Please e-mail with any questionsRental agreement is agreed upon once you book and pre-registration form of guests must be complet

Located in Cudjoe Key, Florida, United States. RV Lot Venture Out, 35x69' Accommodates Large/Oversized RVs Welcome to this remarkable and generously spacious RV Lot nestled within the beautiful community of Venture Out on Cudjoe Key. This meticulously maintained 35' by 69' lot offers a concrete pad for parking, providing ample space for an oversized RV. Equipped with water and sewer hookups, as well as a 50 amp plug-in, this lot ensures a comfortable and convenient stay for all guests.Venture Out is an idyllic community overlooking the ocean, boasting an 80-foot communal pool, tennis courts, a recreation center, a convenient store with a boat fueling station, boat ramp, basketball court, laundry facilities, and more. Within walking distance, you'll have access to a plethora of wonderful amenities to enhance your vacation experience.Please note that a Registration/Check-In Fee of $125 (subject to change) will be charged by Venture Out upon arrival. Additionally, parking is provided for one vehicle per unit, with the possibility of o

Located in Cudjoe Key, Florida, United States. Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities. 1Bd/1Ba Highrise UnitLocated 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.This 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. Enjoy 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 wh

Located in Cudjoe Key, Florida, United States. Cozy and modern island living, Cudjoe Key Unit #617Bright, modern, 2bed, 2bath, midrise home. Across from canal and common area. Open floor plan, hardwood, central a/c with fans in every room. Cable TV, wifi, smart TV with Netflix, YouTube, and much more. Full kitchen, dishwasher, microwave, full range top, stacked washer/ dryer. Queen bed in master bedroom with full bath. 2 twin beds in second bedroom. A pullout sofa offering a queen bed. 2 kayaks, 1 SUP board, 4 bikes, outdoor seating with table. Gas grill.Located in Venture Out resort community; gated, fully staffed, with security, 2 ramp marina, grocery, gas, pool, hot tub, tennis courts.Best of all: open ocean access for boaters to both ocean side and gulf waters. 20 minutes to Key West, and Marathon. Close to it all, but away from everything!!Nightly, weekly, or monthly rentals allowed.Boat/ trailer storage on site, at marina. Nightly storage fee of $10.00 collected by venture out. There is a $125.00 registration

Located in Summerland Key, Florida, United States. Keys House - Venture Out Lot 220 VO220Keys Home w/ 40' Dockage 2Bd/2Ba This beautiful home on stilts overlooks the open water with amazing views from dusk to dawn. Features in the home include two furnished bedrooms with two full bathrooms, well appointed with all the amenities one could ask for while on vacation! The main living room has french glass doors and large picture windows allowing the outdoors in and leads to a porch overlooking the water. The kitchen features lots of cabinets , countertop space and an island with seating for preparation of your favorite meals with stainless steel appliances such as microwave, dishwasher, range, oven and refrigerator with ice and water at the door, and full attention to small appliances and cookware. The master bedroom features a queen bed, flat screen TV, double closets, ceiling fan and private full size bathroom. The guest bedrooms features a queen bed, a flat screen TV, ceiling fan, closet, and access to hallway full size bathroom.

Located in Cudjoe Key, Florida, United States. WATERFRONT HOME 35' SEAWALL & DOCK 2 Bedroom 2 Bath Vacation Rental Enjoy our little piece of paradise! Casa Del Sol is a cozy 820 square foot home that has everything you want for the perfect tropical vacation: Water views, a private 35-foot seawall equipped with boat bumpers, cleats and fish cleaning station. Direct open water access to the Gulf of Mexico or Atlantic Ocean. Access to the wonderful amenities at Venture Out, a residential community with a heated 80-foot pool with Jacuzzi and Kiddie Pool, tennis courts, basketball court, bocce courts, swimming lagoon, marina and convenience market. Two double wide boat ramps with fuel on site. Recreation Center with billiards, darts, and ping pong, post office and a library. Nearby attractions include Snorkeling off Looe Key, Bahia Honda Beach and just a 25-minute drive to either Key West or Marathon Attractions!**PLEASE NOTE: When you arrive at Venture Out, upon arrival at the gate you will be asked to pay a fee directly to Venture Ou

Located in Cudjoe Key, Florida, United States. BIG BLUE waits for you in the sunny Keys Our vacation home in the Lower Keys awaits your arrival! We live here during the winter so our home is available spring - fall. The gated, community of Venture Out has all of the amenities that you could want for a sunny getaway. Lounge by, and swim in the heated pool or salt water canal. Play pool, ping pong, tennis or pickle ball with family and friends. Gather together a group for a game of bocce. Forgot a "good read"? No worries - we have a well-stocked library. There's a playground as well as a kiddie pool for the little ones in the family. Four adult bikes are provided, with miles of bike paths along the Overseas Hwy. It's an easy bike to Mangrove Mamas for bloodies and brunch or to The Square Grouper for a delicious meal & nightly entertainment. Venture Out is located at MM 23 so if the hubbub, nightlife, and shopping of Key West is your pleasure, you will not have far to drive. Our house is maintained, not as a rental, but as our home,

Located in Cudjoe Key, Florida, United States. Latitude Adjustment in Cudjoe Key Nestled in a serene location in the Florida Keys, this Oceanfront house offers breathtaking open water views that promise a tranquil and delightful stay for all guests. The 54' seawall is perfect for docking your boat!This 2 bedroom, 2 bathroom vacation home is equipped with everything you need to unwind and relax!Step outside onto the spacious deck and you’ll understand why it is a truly special destination. With unobstructed views of the blue water, it’s the perfect spot for sipping your morning coffee, enjoying an al fresco meal or simply sitting back with a good book as the water sparkles under the sun.You are 19 miles away from the vibrant Key West. We've got your convenience covered with amenities like Wi-Fi, Streaming TV, four new Bicycles, and more to ensure a hassle-free stay. This property is centrally located within walking distance to the community activities and amenities; Oceanfront Saltwater Heated Pool, Jacuzzi, Pickleball Courts, Baske

Located in Cudjoe Key, Florida, United States. Oceanside home, dock,kayaks,bikes,pool,fishing,109 This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. I also rent units 111 and 107 on VRBO 4441714 and 342851) in case you need more than one home. We are 80 feet the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on one of two balconies, dock or poolside, where you can soak up the sun steps from the house. Breathtaking southwest views of the blue-green ocean and sunsets can be seen from either balcony. PLEASE NOTE: Beginning in 2023 the cleaning fee is to be left for housekeeping upon departure. Current amount is $225. This is in addition to the price you pay via this site.Your boat, up to 25 feet, can be kept at the dock for your entire stay in the calm waters directly behind the house. I pay for you to store your trailer off-site at Cudjoe Gardens Marina where

Located in Cudjoe Key, Florida, United States. Canal-front home w/dock, resort-style amenities, patio, & high-speed WiFi Dock HolidayOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'*We offer a 15% discount on seven (7) days or more!*We offer a 40% discount on 30 days or more!Experience waterfront living at its finest at this family and snowbird-friendly coastal gem! This home offers unlimited access inside out and access to incredible shared amenities, including a heated 80-foot pool (located on the ocean), hot tub, tennis and basketball courts, kiddie pool, saltwater swimming lagoon, and a rec center with Ping-Pong and pool tables and plenty of books during their stay.This coastal-themed home boasts an inviting living area with comfortable furniture (a sofa and a loveseat) and a large flatscreen TV with cable. The full kitchen features full-size appliances, including a French-door fridge, stove, oven, microwave, dishwasher, and even a Keurig co

Located in Cudjoe Key, Florida, United States. Sirena Key Cottage in Venture Out VO365Sirena Key Cottage​​​​​​​ 35' SeawallIt's a wonderful time to enjoy Paradise! Quick ocean side access to gulf and ocean, near Looe Key Reef. Main living room overlooking water with two sliders off open porch to bring the outdoors in. Master suite with queen size bed with full bathroom and lots of closet storage and stack washer/dryer. Guest bedroom full bed and bathroom with stand up shower. Amenities include central air conditioning, ceiling fans, tile floor, outdoor patio furniture. Unit includes 2 bikes, kayaks and a Golf Cart available for a fee per day. Waiver must be signed at office. Please advise prior to booking if you will be bringing a boat or if you plan on renting one while you are staying in the unit.We are located in a spotlessly clean gated community with 24 hr. security, marina, ship store, boat ramps, picnic garden, heated pool, hot tub, tennis, basketball, playground, pickle ball, bocce ball and tennis, pavilion and clu

Located in Cudjoe Key, Florida, United States. Venture Out- Million Dollar Island Resort Oceanfront Home, Pool Access/50 Ft Dock Fresh & Fabulous best describes this island listing . This fantastic Ocean home is in a Island resort community that is one the most unique places in the world. The stylish 2 Bedrooms, King or 2 Twins & living area will make your stay in Paradise one to remember. Deep water dock so in minutes you can visit tropical islands by boat or kayak . Enjoy the two Pools/ Resort amenities or just BBQ & fish off your dock. Resort 1 time fee $125

Located in Cudjoe Key, Florida, United States. Luxury Rv lot with access to all the Resorts amenities! This beautifully landscaped and well maintained RV Lot measuring 70 x 35 feet is nestled within the community of Venture Out on Cudjoe Key at mile marker 23. Venture Out is a private, gated community overlooking the Atlantic ocean, boasting an 80-foot communal pool, hot tub, tennis, pickleball, bocce & basketball courts, childrens playground, a recreation center, a convenience store with a boat fueling station, boat ramp and washout area, laundry facilities, 24 hour security and more. You'll have access to a plethora of wonderful amenities to enhance your vacation experience. With water and sewer hookups, as well as 50 or 30 amp service, an outdoor dining table for 6 and picnic table, this lot is designed to accommodate your every need. Conveniently located within a short walking distance of the community's amenities, this lot offers easy access to all that Venture Out has to offer.Please note that a Registration/Check-In Fee of

Located in Cudjoe Key, Florida, United States. Oceanfront Venture Out Home on Cudjoe Key Escape to paradise in Slow M'Ocean at this stunning ocean front home located in the private, gated community of Venture Out located on Cudjoe Key, FL. This 2 bedroom, 2 bath home is the ideal location with dazzling views of the ocean and nearby islands. Boasting a prime boating location with a 35-foot concrete dock, this waterfront retreat offers unparalleled access to both the Atlantic Ocean and the Gulf of Mexico, each just a five minute boat ride away. This charming home features two cozy bedrooms complete with ensuite bathrooms, perfect for accommodating up to four guests comfortably. Wake up to breathtaking views of the sunrise over the shimmering waters, or unwind on the spacious deck while soaking in the salty breeze. Downstairs is complete with a bait freezer for your fishing trips while a BBQ grill awaits your fresh catch upon your return. Indulge in resort-style amenities, including a Marina store with fuel onsite, bait and convenienc

Located in Summerland Key, Florida, United States. 44ft Seawall at Sportsman's Paradise 44ft Seawall at Sportsman's ParadiseTrue Island Paradise. Brand New in the rental program, this 2020 Stilted 2Bd/2Ba is located on a wide 60' sparkling canal with immediate ocean access in just seconds! 1 king bed and 1 queen bed plus a queen pull out sofa. Mini split air conditioners allow you to set your temperature in each room. The most perfect sportsman's retreat, with everything you will need, with oversized seawall to accommodate PLUS SIZE BOAT! Features a newly poured sprawling 44' concrete dock, equipped with dock posts, mooring whips, fish cleaning table, cleats and swim ladder. 20 and 30 amp receptacles at dock. Use of the downstairs locking enclosure, the 350# per day commercial ice maker and large chest freezer is available for guests. Being an oversized lot, there is more room to enjoy the outdoors, with a spacious side yard garden oasis, surrounded by tropical oversized planters to add privacy, while at night, lounge around and v

Located in Cudjoe Key, Florida, United States. Sea Breeze Cottage - Venture Out Unit 066 Sea Breeze CottageVO066 2Bd/2Ba South End of Park Walk to Ocean!This delightful 2 bedroom, 2 bathroom cottage sleeps 4 in comfort. New smart Tv's, phone/device charging stations along with cable tv and Wi-Fi. New Queen bed in the master and new bedding and pillows. The guest bedroom has twin beds with new bedding and pillows. Pet friendly..2 pets allowed, under 25 lbs. Short driveway...large trucks/SUVs may not fit. Verify vehicle length before booking.VO REGISTRATION FEE of $125.00- DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE.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. Cash or CC only is accepted for this fee.OVERFLOW PARKING IS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.

Located in Cudjoe Key, Florida, United States. Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds! *ALL NEW AND A PERFECT LOCATION! * NEVER RENTED BEFORE!*35' Seawall *Magnificent newly renovated 2 bedroom 1 bath waterfront home in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 19 minutes to Key West. Our home is in the gated community of Venture Out. *Sleeps 6 guests*1 Full Bath with shower/ tub combination* WiFi* *45" TV * A/C & heat *Fully equipped kitchen*Dishwasher*Stove & self clean oven* Refrigerator/freezer with ice maker*Microware* Blender* Toaster oven* Service for 12* All eating utensils, bake & cookware*Keurig & 12 cup coffee maker* New carpeting throughout* New King, queen & queen sofa sleeper*Brand New Amenities including propane grill, 4 Bikes & 2 two-person Kayaks **COMMUNITY AMMENITIES: Olympic size heated Pool, kiddie pool, HotTub, children's playground, Marina, Boat Ramp, fuel docks, fish filet station, boat wash down station, Convenience Store, Recreation hall with darts

Located in Cudjoe Key, Florida, United States. RV Lot 69Venture Out ,Lot Dimensions:35x69' Welcome to your slice of paradise on this 35ft x 69ft RV Lot in the breathtaking Florida Keys! Nestled in the vibrant community of Venture Out, this waterfront community offers the perfect escape for your next vacation. With water and sewer hookups, as well as 50 or 30 amp service, this lot is designed to accommodate your every need. Conveniently located within walking distance of the community's amenities, this lot offers easy access to all that Venture Out has to offer including an 80' community pool, tennis courts, a recreation center, a convenient store with boat fueling station, a boat ramp, and laundry facilities.LOT FOR RENT ONLY- NO RV FOR RENT​​​​​​​ **No cable or WIFI service is provided at this site** Please note that a Registration/Check-In Fee of $125 (subject to change) will be charged by Venture Out Security upon arrival. Additionally, parking is available for only one vehicle per unit, and extra parking permits may be obtained

Located in Cudjoe Key, Florida, United States. Venture Out 1 bed/1 bath Cottage on Cudjoe Key Welcome to Coconut Cottage, your charming oasis nestled within the exclusive gated community of Venture Out in Cudjoe Key, FL. This cozy vacation rental home offers the perfect retreat for couples or small families seeking relaxation and adventure in the Florida Keys. Step inside to discover a thoughtfully designed space featuring one bedroom and one bathroom, providing comfort and convenience during your stay. Sink into the plush queen bed after a day of exploration, or utilize the two full-sized pullout couches for additional sleeping arrangements. The heart of Coconut Cottage lies in its inviting backyard seating area, complete with a BBQ grill, where you can savor al fresco meals under the swaying palm trees. With free Wi-Fi, you can stay connected while unwinding in this tranquil setting. Venture Out community offers an array of amenities for your enjoyment, including an oceanfront communal heated pool and jacuzzi, tennis courts, play

Located in Cudjoe Key, Florida, United States. Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West 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.Winter, work or just typical life got you stressed and wore out. Well come rejuvenate at Lobster Nirvana! Welcome 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