Title: **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… - Latest Reviews, Deals & Photos 2025 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # \*\*CAREFREE ON CUDJOE @ THE BAY\*\* Waterfront Home & Pool + LAST KEY SERVICES… Vacation home in Summerland Key with private pool and kitchen ![A heated pool](https://images.trvl-media.com/lodging/90000000/89350000/89346900/89346801/ef86677b.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Smart TV](https://images.trvl-media.com/lodging/90000000/89350000/89346900/89346801/5004426f.jpg?impolicy=resizecrop&rw=297&ra=fit) ![A heated pool](https://images.trvl-media.com/lodging/90000000/89350000/89346900/89346801/5aaeabfe.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89350000/89346900/89346801/d870abbc.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89350000/89346900/89346801/d1753c16.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location Escape to CAREFREE ON CUDJOE, an expansive waterfront property that embodies the carefree spirit of the Florida Keys. Spend your days lounging in the heated pool, exploring nearby waters via kayak or boat docked outside, or strolling to local restaurants and entertainment options like Square Grouper for fresh seafood and live music. 10 Exceptional ### Entire home 3 bedrooms3 bathroomsSleeps 82227 sq ft ## Popular amenities - Parking available - Dryer - Hot tub - Washer - Pet-friendly - Pool ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### \*\*CAREFREE ON CUDJOE @ THE BAY\*\* Waterfront Home & Pool + LAST KEY SERVICES… FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! From the moment you arrive to this spectacular Florida Keys home, you will feel all your stresses and worries simply melt away. CAREFREE ON CUDJOE is an expansive waterfront property that evokes the easy-going nature of Keys living and provides an ideal setting for those looking to enjoy a ‘carefree’ vacation. There will certainly not be a shortage of fun to be had at CAREFREE ON CUDJOE; spend your days floating in the heated pool under the sun with beverage in hand or hop in your boat docked right outside to explore the beautiful waters of the Lower Keys. Included with your rental is Last Key Realty’s Five-Star Guest Services and Complimentary Concierge, known for providing memorable vacations. So leave the worries to us and prepare to experience the laidback lifestyle of the Florida Keys at CAREFREE ON CUDJOE. THE LOCATION… CAREFREE ON CUDJOE is located at Mile Marker 23 on Cudjoe Key. You'll be only a 30-minute drive or Uber ride from downtown Key West, and the commute is beautiful: sapphire blue waters on either side of the road. Best of all, you won't even have to go far to find restaurant and entertainment options within minutes of your front door. Take a leisurely stroll or bike ride to Keys' favorite, Square Grouper, for fresh seafood and live music. You’ll also be within a few minutes of Broil Small Island Steakhouse and Tonio’s Seafood Shack and Tiki Bar. THE PRIVATE POOL, BOAT LIFT & GROUNDS... CAREFREE ON CUDJOE has every coveted outdoor amenity one could ask for. Situated on an oversized corner lot, there is over 100 feet of boat dockage and the 14,000 lb lift allows for you to take your boat out of the water when needed. The floating dock is perfect for jet skis or smaller water crafts. There’s a convenient fish cleaning station next to the boat dock so you can clean your fresh catch before throwing it on the grill. Launch the tandem kayak right from your back yard to enjoy the abundance of marine life in this area. The heated pool gets plenty of sun all day long and there are multiple seating and lounging options in both the sun and shade. Gather the group under the covered patio for a poolside BBQ using the propane grill and outdoor dining table that seats 6. The grounds also include ample parking for multiple vehicles, an RV, boat trailer, and more. Guests can also use the snorkel gear and 2 sets of golf clubs on property. THE LIVING AREA... This elevated Keys home offers a homey, comfortable interior that complements the sunny, beachy exterior. The gorgeous ocean views can be appreciated from every angle of the living area. There are plenty of seating options for everyone in your group to gather in front of the large flat screen TV. The fully equipped gourmet kitchen includes stainless steel appliances and every tool you’ll need to prepare meals at home. The dining area inside has seating for 6 and the dining area on the screened in porch also has seating for 6. THE ACCOMMODATIONS... \*\* Master Suite - Located on the Second Floor with a King bed, a flat screen TV, a private balcony, and an en-suite bathroom with a walk-in shower and a soaker tub. \*\* Second Bedroom - Located on the First Floor with a Queen bed, a flat screen TV, a private balcony, and direct access to the hall bathroom with a shower and tub combo. \*\* Bonus Room – Located on the First Floor with a Twin trundle bed and access to the shared hall bathroom with a shower and tub combo. \*\* Guest House Suite - Located in the private Guest House with a Queen bed, a flat screen TV, and an en-suite bathroom with a walk-in shower. The guest house has a full kitchen, dining area, and living room with a Queen sleeper sofa. ALL LAST KEY VACATION HOMES INCLUDE: \*\* Washer & Dryer \*\* Central Heat and A/C \*\* Ceiling Fans \*\* Flat Screen Cable TVs in Living Room & All Bedrooms \*\* Fully Equipped Kitchen \*\* Basic stock of spices \*\* Starter supply of paper products \*\* Starter set of cleaning products \*\* Linens and Towels provided \*\* Wireless high-speed Internet access and HULU Live is included \*\* Full Time Concierge Service In addition, this fully stocked home also includes, but is not limited to the amenities on this list: \*\* Fully Fenced & Landscaped Private Yard \*\* Private Heated Pool \*\* Jacuzzi Spa \*\* Propane BBQ Grill \*\* 100’ Seawall and Floating Dock \*\* 14k lb Boat Lift \*\* Fish Cleaning Station \*\* Double Kayak w/ Paddles \*\* Snorkel Gear \*\* Bikes \*\* 2 Sets of Golf Clubs \*\* Outdoor TV \*\* Queen Sleeper Sofa \*\* Ample Off-Street Parking Other notes: \*\* All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month. \*\* Additional interim cleanings available \*\* This property will accommodate up to 8 adults \*\* Max of 2 Pets Allowed with Additional Fee of $200 per pet ## Property amenities ### Pool/Spa - Heated pool - Hot tub - Private pool ### Internet - Available in the house: Free WiFi ### Parking and transportation - Car recommended - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Ice maker - Microwave - Oven - Refrigerator - Spices - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 3 bedrooms - Bedsheets provided ### Bathroom - 3 bathrooms - Hair dryer - Towels provided ### Living spaces - Dining table - Living room ### Entertainment - Smart TV with cable/satellite channels ### Outdoor areas - Balcony - Barbecue grill - Firepit ### Laundry - Laundry facilities - Washing machine ### Work spaces - Desk - Desk chair ### Comfort - Air conditioning - Heating ### Pets - Pet friendly ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Concierge services - Iron/ironing board ### Location highlights - Near a health/beauty spa - Near a hospital - Near the marina - Near the sea ### Things to do - Heated pool - Tennis - Basketball nearby - Cycling nearby - Ecotours nearby - Fishing nearby - Golfing nearby - Jet skiing nearby - Motor boating nearby - Parasailing nearby - Sailing nearby - Scuba diving nearby - Snorkeling nearby - Swimming nearby - Water tubing nearby - Windsurfing nearby ### Safety features - Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector) - Smoke detector (host has indicated there is a smoke detector on the property) - First aid kit - Fire extinguisher ### General - Unit size: 2,227 square feet ## Similar properties ![Exterior](https://images.trvl-media.com/lodging/89000000/88520000/88512400/88512337/613f4d94.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### BLUE PEARL - 5 Bedroom/ 4 Bathroom Pool, Kayak, Bike, Canal Front w/ Boat Lift Cutthroat Harbor Estates - Pool - Kitchen - Washer - Dryer 9.4 Exceptional 3 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=88512337&PinnedHotelID=88512337&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87800000/87796200/87796180/w1920h1284x0y0-e0606bad.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Secluded Oceanfront property, Private pool, hot tub, boat ramp and dock Cutthroat Harbor Estates - Ocean view - Pool - Hot tub - Kitchen 10 Exceptional 5 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=87796180&PinnedHotelID=87796180&HadPinnedHotel=true®ionId=-1&adults=2) ![Pool](https://images.trvl-media.com/lodging/59000000/58110000/58100700/58100672/1572d490.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks! 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Cutthroat Harbor Estates - Ocean view - Pool - Hot tub - Kitchen 10 Exceptional 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=78327368&PinnedHotelID=78327368&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71740000/71734600/71734548/0286cd39.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot Upper Sugarloaf Key - Kitchen - Washer - Dryer - Pet-friendly 9.2 Wonderful 7 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=71734548&PinnedHotelID=71734548&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67440000/67437000/67436953/0ee9cdc5.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Key West Beach House with heated pool, tiki, and dock.♿︎ Bay Point - Ocean view - Pool - Kitchen - Washer 9.2 Wonderful 5 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=67436953&PinnedHotelID=67436953&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/84000000/83560000/83556000/83555970/e5a284d3.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West Cudjoe Key - Pool - Kitchen - Washer - Dryer 10 Exceptional 8 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=83555970&PinnedHotelID=83555970&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 4:00 PM Minimum check-in age: 25 ### Check-out Check-out before 10:00 AM ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions ### Pets Pets allowed Service animals are welcome, and are exempt from fees ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## Important information ### You need to know Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed Onsite parties or group events are strictly prohibited Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip Host has indicated there is a smoke detector on the property Safety features at this property include a fire extinguisher and a first aid kit This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ### We should mention A car is recommended for transportation to and from this property ### Property is also known as 208 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C24.65288%2C-81.47603&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=SdK_5vh6TU4gkL4CA_KlOJnTO6o=) Cudjoe Key, FL #### What's nearby - Upper Sugarloaf Key - 9 min drive - 7.3 km - Florida Keys Beaches - 12 min drive - 8.1 km - Sugarloaf Beach - 21 min drive - 18.4 km - Bahia Honda State Park - 39 min drive - 32.8 km - Boca Chica Nude Beach - 41 min drive - 31.5 km #### Getting around - Key West Intl. Airport (EYW) - 32 min drive #### Restaurants - ‪Boondock's Grille & Drafthouse - ‬9 min drive - ‪Kiki's Sandbar - ‬11 min drive - ‪5 Brothers Two - ‬9 min drive - ‪Morning Joint - ‬17 min walk - ‪Broil - ‬5 min drive ## Frequently asked questions ### Does **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… have a pool? > Yes, this property has a pool. Pool types include heated pools. ### Is **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… pet-friendly? > Yes, pets are allowed at this property. ### What time is check-in at **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…? > Check-in begins at 4:00 PM. ### What time is check-out at **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…? > Check-out is at 10:00 AM. ### Where is **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… located? > Located in Cutthroat Harbor Estates, this vacation home is within a 10-minute walk of Venture Out Keys, Venture Key, and Out Key. Florida Keys Beaches is 2.4 mi (3.9 km) away. ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. 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