Title: Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock - 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 # Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock Waterfront vacation home with private pool and kitchen ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/70000000/69550000/69549700/69549655/b0f6acce.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/70000000/69550000/69549700/69549655/cefcd11e.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69550000/69549700/69549655/8f9ba482.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Marina](https://images.trvl-media.com/lodging/70000000/69550000/69549700/69549655/3c706aff.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69550000/69549700/69549655/9e6b2e6d.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location Located in Cudjoe Bay, Captain's Quarters is a beautifully decorated waterfront estate that checks all the boxes. Enjoy an unobstructed view of the bay from its spacious living space with open floor plan, beautiful balcony with outdoor seating, large pool and fire pit. 10 Exceptional ### Entire home 3 bedrooms2 bathroomsSleeps 81817 sq ft ## Popular amenities - Parking available - Dryer - Washer - Pool - Kitchen - Barbecue grill ## 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. ### Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock Welcome to Captain’s Quarters — Your Waterfront Escape on Beautiful Cudjoe Bay Discover the perfect blend of comfort, luxury, and stunning natural beauty at Captain’s Quarters, a breathtaking waterfront estate nestled in the heart of “Fisherman’s Paradise.” This beautifully decorated home offers everything you need for an unforgettable getaway. Key Features: 3 Bedrooms | 2 Bathrooms Unobstructed panoramic views of Cudjoe Bay Spacious second-floor open-plan living area Large pool with comfortable seating Inviting fire pit with ample chairs Private boat dock accommodating vessels up to 45’ Step inside and experience a thoughtfully designed interior: Living Room: Relax on plush couches while enjoying water views through French doors, or catch your favorite shows on the large flat-screen TV. Kitchen: Prepare meals effortlessly in the spacious kitchen featuring a breakfast bar with seating. Dining Room: Host formal dinners for up to 8 guests in the elegant dining space. Master Suite: Retreat to the master bedroom with a king bed, dedicated work area, flat-screen TV, walk-in closet, and a luxurious en-suite bathroom complete with a his & hers vanity, jacuzzi tub, and shower. Guest Bedrooms: A cozy queen bedroom and a family-friendly bunk room with full-over-full beds and flat-screen TV provide comfortable accommodations for all. Additional Amenities: Guest bathroom with shower, laundry area with washer & dryer, and a storage space under the house including a bait refrigerator. Outdoor Living: Enjoy breathtaking views from the upstairs patio seating area overlooking the bay. Take a refreshing dip in the large pool or gather around the fire pit for evenings under the stars. Please Note: Guests do not have access to the garage or boat lift. Pet Policy: One dog under 50 lbs is allowed with pre-approval, subject to a $20/day fee. Pet occupancy reduces total guest count by one. Pool Heating: Available as an optional add-on ($20/day) from November 15 to May 15, arranged prior to check-in. Pool heat is not included in rental rates. Captain’s Quarters is more than just a vacation rental—it’s your next favorite destination. Experience the charm and serenity of Cudjoe Bay in style and comfort. We look forward to welcoming you! ## Property amenities ### Beach - Beach nearby - Beach towels ### Pool/Spa - Heated pool - Outdoor pool - Private pool ### Internet - Available in the house: Free WiFi ### Parking and transportation - Onsite parking options include a garage ### Kitchen - Blender - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Ice maker - Kitchen island - Lobster/crab pot - Microwave - Oven - Refrigerator - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 3 bedrooms - Bedsheets provided ### Bathroom - 2 bathrooms - Hair dryer - Jetted bathtub - Shower - Towels provided ### Living spaces - Dining table - Living room - Separate dining area ### Entertainment - Smart TV ### Outdoor areas - Balcony - Barbecue grill - Firepit - Outdoor furniture ### Laundry - Laundry facilities - Washing machine ### Work spaces - Desk - Desk chair ### Comfort - Air conditioning - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Iron/ironing board ### Location highlights - In a rural location - Near a health/beauty spa - Near a hospital - Near the marina - Near the ocean - On the waterfront ### Things to do - Boat - Heated pool - Kayak - Water sports equipment - Birdwatching nearby - Cycling nearby - Ecotours nearby - Golfing nearby - Jet skiing nearby - Kayaking nearby - Motor boating nearby - Parasailing nearby - Sailing nearby - Scuba diving nearby - Snorkeling nearby - Swimming nearby - Wildlife walks 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 not reported (host has not indicated whether there is a smoke detector on the property) ### General - Unit size: 1,817 square feet ## Similar properties ![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=2025-11-24&endDate=2025-11-25&selected=71734548&PinnedHotelID=71734548&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67640000/67635800/67635740/774f0228.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Amazing waterfront home with private beach, dock, pool, WiFi & outdoor kitchen Cutthroat Harbor Estates - Ocean view - Pool - Kitchen - Air conditioning 10 Exceptional 5 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=67635740&PinnedHotelID=67635740&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/46000000/45610000/45605300/45605298/1d3f0732.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Night jasmine oceanfront vacation house Cutthroat Harbor Estates - Pool - Hot tub - Kitchen - Washer 10 Exceptional 25 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=45605298&PinnedHotelID=45605298&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78600000/78593100/78593015/c695f624.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### REEL ESCAPE - 4 Bedroom / 2 Bathroom w/ Pool, Boat Dock & Sleeps 8! 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You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ### Property is also known as Captains Quarters - Cudjoe Key - Pool- Up to 45' Boat Cudjoe Key ## 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%7C24.66133%2C-81.47332&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=UrpvwY3G2NPgTsewUhC0L-7obzM=) Cudjoe Key, FL #### What's nearby - Upper Sugarloaf Key - 8 min drive - 6.2 km - Florida Keys Beaches - 9 min drive - 6.7 km - Sugarloaf Beach - 20 min drive - 17.4 km - National Key Deer Refuge Visitor Center - 22 min drive - 16.5 km - Bahia Honda State Park - 37 min drive - 31.4 km #### Getting around - Key West Intl. Airport (EYW) - 30 min drive #### Restaurants - ‪Boondock's Grille & Drafthouse - ‬7 min drive - ‪Kiki's Sandbar - ‬10 min drive - ‪5 Brothers Two - ‬7 min drive - ‪Morning Joint - ‬7 min walk - ‪Broil - ‬3 min drive ## Frequently asked questions ### Does Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock have a pool? > Yes, this property has an outdoor pool. Pool types include heated pools. ### Is Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock pet-friendly? > No, pets are not allowed at this property. ### What time is check-in at Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock? > Check-in begins at 4:00 PM. ### What time is check-out at Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock? > Check-out is at 10:00 AM. ### Where is Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock located? > Situated on the waterfront, this vacation home is within 1 mi (2 km) of Venture Out Keys, Venture Key, and Out Key. Upper Sugarloaf Key and Florida Keys Beaches are also within 6 mi (10 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock Reviews 10 ### 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.ca/lp/b/content-guidelines) ### 9.0 Cleanliness ### 9.0 Location 10 - Excellent 2 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10/10 Excellent #### CHARLES W. Sep 2, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Very nice location and home. ##### CHARLES W. Stayed 28 nights in Aug 2025 ### 10/10 Excellent #### Barbara R. Apr 11, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Beautiful home Beautiful home, great location ##### Barbara R. 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