Title: **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… Reviews, Deals & Photos 2026 - Expedia.co.uk [See all properties](http://www.expedia.co.uk/Hotel-Search?regionId=&selected=89346801&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # \*\*CAREFREE ON CUDJOE @ THE BAY\*\* Waterfront Home & Pool + LAST KEY SERVICES… ## Photo gallery for \*\*CAREFREE ON CUDJOE @ THE BAY\*\* Waterfront Home & Pool + LAST KEY SERVICES… ![Outdoor dining - **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… (Cudjoe Key)](https://images.trvl-media.com/lodging/90000000/89350000/89346900/89346801/d870abbc.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Fridge, microwave, oven, stovetop - **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… (Cudjoe Key)](https://images.trvl-media.com/lodging/90000000/89350000/89346900/89346801/426319bb.jpg?impolicy=resizecrop&rw=297&ra=fit) ![A heated pool - **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… (Cudjoe Key)](https://images.trvl-media.com/lodging/90000000/89350000/89346900/89346801/1488fd87.jpg?impolicy=resizecrop&rw=297&ra=fit) ![A heated pool - **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… (Cudjoe Key)](https://images.trvl-media.com/lodging/90000000/89350000/89346900/89346801/ef86677b.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV - **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… (Cudjoe Key)](https://images.trvl-media.com/lodging/90000000/89350000/89346900/89346801/3810d57b.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies 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. ## Reviews 10 Exceptional ### Entire home 3 bedrooms3 bathroomsSleeps 82227 sq ft ## Popular amenities - Ocean view - Pool - Hot tub - Kitchen - Washing machine - Dryer ## 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 transport - Car recommended - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Hob - Ice maker - Microwave - Oven - Refrigerator - Spices - 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 ### Pets - Pet friendly ### Suitability/Accessibility - Smoke-free property ### 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 - Snorkelling 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 ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118800000/118790500/118790414/7a6957b6.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Serenity Now Seaside Escape - Brand New Build! 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The provision of housing is linked to their trade, business or profession. 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 On-site 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 that 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 If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal. ### We should mention A car is recommended for transport to and from this property ### Property is also known as 208 ## About the area Located by the sea, this holiday home is in Cutthroat Harbor Estates, a neighbourhood in Summerland Key. Florida Keys Beaches and Coupon Bight Aquatic Preserve reflect the area's natural beauty and area attractions include Blue Hole and Wilhelmina Harvey Park. Big Munson Island and Looe Key National Marine Sanctuary are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with ecotours and cycling. [Visit our Summerland Key travel guide](https://www.expedia.co.uk/Summerland-Key.dx6177802) [View more Holiday homes in Summerland Key](https://www.expedia.co.uk/Summerland-Key-Private-Holiday-Homes.d6177802-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ![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 - ![Beach and Pier at Sunset, Florida, USA](https://images.trvl-media.com/place/553248635976496782/1bfe637a-381c-425d-ba50-7340e2c8b6bb.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Florida Keys Beaches 11 min drive \- 4.4 miles - ![Lower Sugarloaf Sound](https://images.trvl-media.com/place/1187/b42a0b6b-5eb4-455f-a9d2-51a80c178105.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Lower Sugarloaf Sound 14 min drive \- 7.8 miles - ![Stopped by the sea on a ride down the Overseas Highway from Miami to Key West. The bike is a KZ750 lent to me by the guy living in the condo next door. #TheKeys #florida #beach #kawasaki ](https://images.trvl-media.com/place/553248635983994028/1d746f78-98d9-4591-8682-e70514df330b.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Sugarloaf Beach 21 min drive \- 11.4 miles - Upper Sugarloaf Key 9 min drive \- 4.5 miles - Upper Sugarloaf Sound 10 min drive \- 5.3 miles ### Getting around - Key West, FL (EYW-Key West Intl.) 32 min drive ### Restaurants - Boondock's Grille & Drafthouse 9 min drive - Kiki's Sandbar 11 min drive - Morning Joint 17 min walk - Broil 5 min drive - 5 Brothers Two 9 min drive ## Frequently asked questions ### Does **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… have a pool? ### Is **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… pet-friendly? ### How much is parking at **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…? ### What time is check-in at **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…? ### What time is check-out at **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…? ### Where is **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## \*\*CAREFREE ON CUDJOE @ THE BAY\*\* Waterfront Home & Pool + LAST KEY SERVICES… Reviews ## Reviews ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. [More information](https://www.expedia.co.uk/lp/b/content-guidelines) 10 - Excellent 2 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 10 Location ## Reviews ### 10/10 Excellent #### Kim S. 22 May 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect Waterfront Getaway in the Keys – Dog-Friendly with Top-Notch Amenities! We had an incredible month-long stay at this beautiful home in the Florida Keys! The house was spotless, well-equipped, and perfectly located right on the water. Having access to the boat lift made our time on the water even more enjoyable and convenient.The pool was a great bonus, and the outdoor space—including a nice screened-in porch that kept the bugs away—was perfect for relaxing after a day out boating or exploring. The incredible sunsets each evening were a highlight, and it was such a treat to be able to walk right out the door and go paddleboarding anytime we wanted.One of the best parts was that they allow dogs, so our pup Finn had a great time too!The management team was top-notch—very responsive and attentive, with a concierge service that went above and beyond by delivering packages and checking in to ensure we had everything we needed.Everything about this property made our stay easy, comfortable, memorable, and a short drive to Key West. We would absolutely stay here again and highly recommend it to anyone looking for a great spot in the Keys! ![](https://a.travel-assets.com/ugc/hotel-reviews/47d061f7-3a3d-4ed5-a77b-8b1ba9f0aa57-1747915638956.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/10aaed1d-c532-43ca-b8c9-6e5c0c46e2f6-1747915651422.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/a80f7a8b-3549-43d0-8ae5-2895492c3492-1747915651005.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/723f104d-f14d-44e9-8cf9-8eb6e37c1d51-1747915651342.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ##### Kim S. Stayed 31 nights in Apr 2025 ### 10/10 Excellent #### Michael W. 25 Apr 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Comforts of. Home. 1st I would like to say Nadia went above and beyond to make our trip.. Outstanding. It was peaceful it was comfortable it was everything it said it was and we loved it ##### Michael W. Stayed 29 nights in Mar 2023 ---