58,368 properties available

Located in Cudjoe Key, Florida, United States. 20 MINUTES TO KEY WEST , BOATERS PARADISE COMPLETELY RENOVATED TOP TO BOTTOM , 2 BEDROOM , 35' DOCK WITH ALL NEW PAVERS AND 13' UMBRELLA , FISH CLEANING TABLE , HOSE AND ELECTRIC AT DOCK. COMMUNITY STORE , GIANT NEW RAM, ICE, BAIT, AND GROCERY. COMMUNITY POOL AND HOT TUB. DOG FRIENDLY. GATED COMMUNITY WITH FULL TIME GUARDS. ****PLEASE NOTE THERE IS A $113 REGISTRATION FEE IMPLEMENTED BY THE ASSOCIATION AND COLLECTED AT THE GATE.

Located in Cudjoe Key, Florida, United States. WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification Come vacation in this cozy two bedroom with one bath home. The home has been recently renovated. Just added a non touch sink and a UV light air sanitizing purification system . Which is proven to kill mold and air borne bacteria and viruses including the flu . Your health is our biggest concern . Perfect location on a canal with dockage for up to 35 ft boat right outside the back steps with a cleaning station. . .Located on last street in Venture Out towards the entrance of the canal for more privacy & easy access. Comfortably sleeps five adults. Your dogs are also welcome. Located at MM 23 in Venture Out. *Venture Out Resort does charge a one time entrance fee upon arrival at the security gate. This allows you unlimited access to the boat ramp & other amenities on the property. Fee is $125.00 tax included .

Located in Cudjoe Key, Florida, United States. Waterfront home with numerous amenities on popular Cudjoe Key! 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 coffee pot and Keurig 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 BBQ grill, fish cleaning station, and swim ladder. Seawall can accommodate a boat up to35'! This privately owned community offers amazing amenities that

Located in Cudjoe Key, Florida, United States. Waterfront Home 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.

Located in Cudjoe Key, Florida, United States. Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes This Chic style home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. Our home is fourth from the waters 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. The property also features it owns little sandy beach perfect for sunbathing. Breathtaking southwest views of the blue-green ocean can be seen from the balcony off of each bedroom. Your boat, up to 24 feet, can be kept at the dock for your entire stay in the calm waters . Looe Key and American Shoal Reef can be seen from the house where you’ll find the most beautiful snorkeling and diving reefs in the keys, along with the excellent fishing. Fish or kayak right off the end of the dock or you can venture out to experience the hi

Located in Cudjoe Key, Florida, United States. Ocean Front - Private 56' Dock VO095Spectacular Oceanfront Panoramic Views56' Seawall Boaters Paradise!$150 additional discount given at booking for stays between March 15, 2024 and May 1, 2024. Enjoy breathtaking panoramic ocean views from this beautiful stilt 2 Bd/2 Ba vacation home located on a quiet col-de-sac in a secure gated community. Features a sprawling 56' full length concrete seawall! Perfect for boaters who need deep water and quick access to the ocean or gulf. Dock amenities include heavy duty dock posts, cleats, swim ladder, fish cleaning table, outdoor shower, water hose and electric. (ELEVATOR IS CURRENTLY OUT OF ORDER) The main living area is surrounded by windows and sliding glass doors, designed to capture the best of views, from the sparkling turquoise blue Atlantic Ocean, color changing sunrise skies, to romantic moonlit starry nights. Living room features a large 55' flat screen television with DVD player, leather sofa and 2 comfortable chairs with ottomans

Located in Cudjoe Key, Florida, United States. Location, location, location briefly describes this small piece of Paradise. Located on a private and quiet open water lot, this charming cottage offers a wonderful view even to those people who do not want to go outside. While sitting inside or lazing out on a lounger, the tranquility and beauty of the tropics are yours. Fabulous open water from 35 foot seawall with dock posts, cleats and fish cleaning table, and swim ladder. Cook your catch on the outdoor grill or eat inside still enjoying the relaxing ocean view from the bright great room facing the canal. Kitchen has beautiful wood cabinets and breakfast bar. The Master bedroom has large mirrored closet, built-in drawers. The comfy guest bedroom has a full closet, bureau and twin beds. Both rooms are equipped with cable TV.40” flat-screen TV placed for convenient viewing from living and dining area. New tile flooring throughout this home, Washer/ Dryer, Central Air provided for comfort and relaxation.Venture Out Resort is a quiet

Located in Cudjoe Key, Florida, United States. Tropical Getaway in Paradise. 3 Nite Minimum Stay! **7 day minimum for Lobster Fest, July 22-Aug. 13. **This bright, freshly decorated, modern 2 bedroom, 1 bathroom has everything you need for your Florida Keys Getaway. Wood floors throughout, A/Cs in every room, and wireless internet. The full kitchen has a stacked washer dryer, microwave, coffee maker, slow cooker, toaster, blender and more. With a Brand New Queen Bed in bedroom one, a twin and twin trundle in bedroom two and a full size futon in the living area, you can sleep up to six. Outdoor furniture, gas grill and bait freezer are also available outside. The unit is also located just two lots from the nearest bath house for when an extra shower, bathroom or washer and dryer is needed. No cable TV but free WiFi. Just 25 minutes to Key West and 30 minutes to Marathon. The property is a dry lot but you can launch your boat each day at the boat ramp within the park. Boating access is second to none with quick access to the Atlantic

Located in Cudjoe Key, Florida, United States. Cozy Venture Out Cottage MANDATORY $125 FEE NOT INCLUDED, PAID TO VENTURE OUT COMMUNITY UPON ARRIVAL. One bedroom home with all that you need. Located in Venture Out which has many amenities including marina and boat ramps.

Located in Cudjoe Key, Florida, United States. Riley's Retreat - Venture Out 107 Riley's Retreat 2Bd/2Ba 35' DockageOpen Water Views, Free WiFiThis sparkling clean 2Bd/2Ba vacation rental is located on a 60' wide canal overlooking look down views of the wide L-shaped canal with open water views from the dock and porch and dining room. Perfect boating property, features 35' concrete seawall, dock posts, fish cleaning table, cleats and swim ladder. Interior features laminate wood flooring, central air conditioning, stack washer and dryer, microwave, dishwasher with kitchen and dining open to the living room. The master bedroom features a queen size bed with full bathroom. The guest bedroom features a queen size bed with access to the hallway full bathroom. For additional sleeping, there is a pull out sofa sleeper in the living room. This home is beautifully decorated with Tommy Bahama furnishings and is open and bright with high ceilings throughout. Additional amenities include FREE WIFI, ceiling fans, gas grill, 2 bicycles

Located in Cudjoe Key, Florida, United States. Waterfront Relaxation and Barefoot Sunsets Pack your bags and bring your boat! This home is located on the canal with easy access to the Gulf and Atlantic. It is equipped with everything you need for a relaxing resort-like feel with the privacy of a home away from home.The home features a 1488sqft spacious two-bedroom two-bathroom split open floor plan that comfortably sleeps four people. The Master Bedroom has a king bed, two dressers, large walk-in closet, and en-suite bathroom with shower. The Second Bedroom has a bunk bed with two full beds, a pull-out twin, and large walk-in closet. The hall bathroom has a tub/shower combo. The office has a desk, a reading chair, and plenty of books to read. The kitchen is properly equipped with a toaster, coffee maker, french press, coffee grinder, dishwasher, utensils, etc for all your cooking needs. The living room and master bedroom have a Smart TV (No Cable TV) for you to log into your own personal streaming services (Netflix, Amazon, Hulu,

Located in Cudjoe Key, Florida, United States. Crystal Clear Water Getaway! Welcome to Venture Out on Cudjoe Key! This gated resort community located in the beautiful keys offers your perfect getaway in paradise. This 2 bedroom, 1 bath sleeps 6 comfortably.Just a short drive to Key West, just 20 minutes away, this is the ideal spot for all vacationers. This 800 sq. ft. property offers 2 bedrooms, master bedroom w/ a queen bed. 2nd bedroom offers twin bunk bed setup. Sleeper sofa(queen) also provided to sleep another 2. Best of all, avoid the community laundromat, there is a washer/dryer located in the property!!! Super convenient!!!Fully stocked with all the linens needed for your stay. WIFI connection is supplied. Flat screen tvs plus DVD player. The outside sitting area is a great setup to hangout in comfort! BBQ grill provided for those family cookouts! Convenient store located in community!!Immaculate shape and well appointed. Our goal is to make your visit to paradise the best we possibly can!NO SMOKING AND NO PETS

Located in Cudjoe Key, Florida, United States. LATITUDE ADJUSTMENT Need a “LATITUDE ADJUSTMENT”? Our spotless 2 BR, 2 BA stilt home on a 60’ wide canal in VO at MM23, on Cudjoe Key awaits your arrival. Sleeps 6 with a queen bed in the master, queen bed in the 2nd bedroom, and a queen sleeper sofa in the living room. There are smart TVs in both bedrooms and the living room. Stunning canal views in two directions from the covered patio, with a view of the ocean to the northeast. The gated community of Venture Out offers a short drive to Key West (23 mi.) & many activities without leaving the park, such as a heated pool, kiddie pool, hot tub, salt water swimming, playground, bocce, tennis, & pickle ball courts, pool table, and ping pong. We have 4 adult bikes for your use. Nearby you have Bahia Honda State Park or tour the Civil War fort at Ft. Zachery Taylor Park in Key West. There’s amazing snorkeling on Looe Key. You may take a tour from just a couple of islands away. Park your boat at your front door. Our 35’ seawall i

Located in Cudjoe Key, Florida, United States. "WEEKLY RENTAL" Florida Keys Pool & Waterfront Vacation Rental (108) SEA ESCAPEThis two story home with breathtaking full views of the crystalline Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community with only 10 other homes. Just steps from the house is the stunning oceanfront heated swimming pool and charming Tiki hut, or enjoy the gorgeous tropical landscape and Keys breezes from your own private hammock and manicured space. Ocean sunrise and sunsets can be viewed from every room and from two decks. WiFi-enabled, this immaculate home boasts two master suites, both with a master king bed; both have a private bathroom with private full bath, and access to the second floor balcony. Downstairs you’ll find a third full bath with a shower, a 40'' HDTV, a full sleeper sofa, dining table for six, a breakfast bar, a second balcony with lush foliage and views of the Atlantic Ocean, washer/dryer, and a fully equipped gourmet stainless steel kitchen. The ground floor

Located in Cudjoe Key, Florida, United States. Tropical Island Paradise W / Open Water Views! Please see our other property if you do not see your dates available! Property # 2092236https://www.vrbo.com/2092236?adultsCount=2&arrival=2020-10-27&departure=2020-10-31&unitId=2656769Sparkling 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

Located in Cudjoe Key, Florida, United States. Mile Marker Mahi - Venture Out #465 Mile Marker Mahi 2Bd/2Ba35' Boat Dockage Open Water ViewsA sun seeker's haven, and a fisherman's paradise, this quaint ocean cottage is in a great location in the gated Venture Out Community of Cudjoe Key with quick and easy access to open water (both Gulf and Ocean sides). We're on a wide, deep water canal with a 35' dock, an open water seascape, and panoramic views of the sunrise and sunset. The house is a charming and relaxing space. The kitchen comes fully stocked. There are flat screen TVs throughout with access to YouTube TV and high speed Xfinity WiFi. There are two queen beds as well as a double pull-out sleeper sofa, fitting up to 6 guests (it will be a tight squeeze with more than 4 people, but it is doable). On the dock, you'll find a fishing rod holder, a guest dock box for your fishing/boating supplies, a bait freezer, and a cleaning station. Two Adirondack chairs are the perfect location to catch some rays. There are also four bikes for

Located in Cudjoe Key, Florida, United States. Salty Breeze - Canal Front Venture Out Home on Cudjoe Key Welcome to Salty Breeze, where you can embrace a slower pace and savor the Island Life. This beautifully appointed 2-bedroom, 2-bathroom canal front residence is situated in a secure gated condominium community, providing a wide range of amenities for an opulent vacation stay. Situated in the exclusive Venture Out community, guests have access to a heated pool, a tranquil hot tub, tennis and basketball courts, pickleball, a playground, a convenient on-site store, a marina lounge, a boat ramp, tiki huts, and a swimming area directly in the ocean. Located just 23 miles north of Key West and 32 miles south of Marathon, this unit boasts an ideal location for various occasions. This property can comfortably accommodate up to six adults, and a Queen sofa bed is provided for extra guests for added convenience. Its prime location allows for easy and swift boating access to both the Atlantic and Gulf sides. Featuring a 35' concrete dock,

Located in Cudjoe Key, Florida, United States. Pelican's Roost, Waterfront comfort at Venture Out About this spacePelicans Roost is a waterfront home on the Atlantic side of Cudjoe Key with a 17’ dock. Only 20 miles from historic Key West. Explore the lower keys from this great central location. Big Pine is only 8 miles away, Bahia Honda state park only 16 miles. Also plenty of family friendly activities within the Venture Out Resort like a hot tub, pool, tennis courts, pickle ball, basket ball, a private beach with tikis for beautiful ocean viewing and a community store. A perfect home for your adventureThe spaceComfortable 2 bedroom 2 bathroom, the master bedroom has a comfortable king. The second bedroom has two twins that can convert to a king.Guest accessGuests have access to the entire home along with all of the amenities inside of Venture Out. A key code will be sent along with instructions before arrival. Venture Out requires a resort fee to stay at the resort that is paid upon arrival.Other things to noteThere is a resort

Located in Cudjoe Key, Florida, United States. **TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!TURTLE COVE VIEWS is a cozy waterfront cottage that provides a picturesque Florida Keys vacation setting. Take in the expansive open water views from inside the home through the large windows or from your covered porch, with outdoor dining. The private 35-foot boat slip offers easy access to the beautiful waters of the Florida Keys and the home comes with kayaks and a paddleboard for guest use. TURTLE COVE VIEWS is located at Venture Out, a residential community with a heated 80-foot pool with large Jacuzzi and Kiddie Pool, tennis courts, basketball court, bocce courts, swimming lagoon, marina and convenience market with fuel on site and two double wide boat ramps, Recreation Center with billiards, darts, and ping pong, post office and a library. Venture Out enjoys 24 Hour Patrolled Security.TURTLE COVE

Located in Cudjoe Key, Florida, United States. Judy's place at Venture Out Judy's Place is located in the Venture Out Resort. A quiet little secret escape just 20 miles from Key West. Judy's Place is a 2 bedroom and 1 bathroom mobile home that has all the comforts of home. Offering a spacious living room, kitchen area, large master bedroom and guest room with ample closet space. The space continues outside with outside dining area, BBQ and sitting area. This is the perfect hideaway for a vacation of rest & relaxation. The Venture Out Resort has numerous offerings that makes this your perfect Key's hideaway. Bring your boat and take advantage of the private launch ramps for the resort guests. Soak up the sun poolside in the large community pool or relax in the jacuzzi. The resort also offers tennis courts, playground and much more. Bring your family for a true authentic Key's experience. Venture Out will soon become a MUST STAY for all of your future stays. ADDITIONAL CHARGES:When you arrive at Venture Out Resort, you will go to th

Located in Cudjoe Key, Florida, United States. RV Lot 621 Venture Out This beautiful, lush newly landscaped RV Lot located in Venture Out with it's own picnic table on property for your outdoor dining is placed within walking distance to all the wonderful amenities the Community has to offer. This 35' by 70' lot with a 10' by 30' concrete pad for parking with enough space to park an oversized RV. Hook up for water and sewer, 50 amp plug-in. This RV Lot is situated directly across from a common area over looking the ocean which is the perfect place to watch the sunrise with your cup of coffee. Venture Out is a community on Cudjoe Key surrounded by the Atlantic Ocean providing an 80' community pool, tennis courts, recreation center, convenient store with boat fueling station, boat ramp, laundry mats, and more. A Registration/Check-In Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. Parking for 1 vehicle per Unit. Extra parking permit may be available at the Guard Station for an additional nightly fee

Located in Cudjoe Key, Florida, United States. OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS! ***NEVER RENTED BEFORE!!Be one of the first to stay in our newly renovated home! With a 35' Seawall for docking your boat or water toys, this can be your 2 bedroom 2 bath waterfront getaway in Cudjoe Key!! Ocean views from every room in the house. 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*2 Full Bath* WiFi* * TV * A/C & heat *Fully equipped kitchen*Dishwasher*Stove & self clean oven* Refrigerator/freezer with ice maker*Microwave* Blender* Toaster oven* Service for 12* All eating utensils, bake & cookware*Keurig & 12 cup coffee maker* New King, queen & queen sofa sleeper*Brand New Amenities including propane grill, 4 Bikes & 2 two-person Kayaks **COMMUNITY AMENITIES: Olympic size heated Pool, kiddie pool, HotTub, Marina, Boat Ramp, fuel docks, fish filet station, boat wash down station, Children's playgroun

Located in Cudjoe Key, Florida, United States. Come stay and play in the Florida Keys! This colorful, tropical vacation home has two bedrooms, one bath, with new 2022 central air conditioning, and is located in a gated community . The living room is nicely decorated, has a 42" flat screen Smart TV, and 4 recliners for your relaxation.  There is a desk and chair, with lighting, for working or studying remotely, and free WI-FI. The living room has two overhead ceiling fans with lights, the same as the second bedroom does. In addition to three overhead units, there are two stand alone fans as well. Dining area is conveniently located in the kitchen. The kitchen has a glass top dining table and 4 chairs, plus another two folding chairs in the utility room if needed. There's a side by side water and ice dispensing refrigerator, lots of cabinets, counter space, full size stove/oven, microwave and a dishwasher, plus plenty of small appliances like an air fryer, crock pots, blender, and mixer. There's also another 42" wall mounted s

Located in Cudjoe Key, Florida, United States. Nice home on Atlantic side of Cudjoe Key! 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)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. TV 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.There are 3 beds and a sleeper sofa in the Livingroom to accommodate 8 guests. There is an outdoor shower by the picnic table and an another restroom in the garage.To help prevent the sprea