10/10 Excellent
CHARLES W.
2 Sept 2025
Liked: Cleanliness
CHARLES W.
Stayed 28 nights in Aug 2025
Entire home
Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock
Photo gallery for Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock
Reviews
1010 out of 10
Exceptional
Entire home
3 bedrooms2 bathroomsSleeps 8169 sq m
Popular amenities
- Ocean view
- Pool
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
Explore the area
Cudjoe Key, FL
- Upper Sugarloaf KeyPlace, Upper Sugarloaf Key5 min drive
- Florida Keys BeachesPlace, Florida Keys Beaches5 min drive
- Upper Sugarloaf SoundPlace, Upper Sugarloaf Sound6 min drive
- Key West, FL (EYW-Key West Intl.)Airport, Key West, FL (EYW-Key West Intl.)38 min drive
Room options
About the area
Summerland Key
At this holiday home you'll be within a 20-minute stroll of Venture Out Keys and Venture Key. Highlights at this holiday home include a kitchen, a private pool and a washing machine. .Home features free WiFi, 2 bathrooms and a balcony. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. In-room jetted baths, a living room and a dining area are also available. .This smoke-free holiday home offers an outdoor pool and barbecues. Plus you'll find laundry facilities. .With a stay at this Summerland Key holiday home, you'll be 5.8 km (3.6 mi) from Florida Keys Beaches.
What's nearby
- Upper Sugarloaf Key - 5 min drive - 6.2 km
- Florida Keys Beaches - 5 min drive - 5.7 km
- Upper Sugarloaf Sound - 6 min drive - 7.5 km
- Lower Sugarloaf Sound - 9 min drive - 11.1 km
- National Key Deer Refuge Visitor Center - 14 min drive - 17.2 km
Getting around
- Key West, FL (EYW-Key West Intl.) - 30 min drive
Restaurants
- Boondock's Grille & Drafthouse - 7 min drive
- Morning Joint - 7 min walk
- Kiki's Sandbar - 10 min drive
- Mangrove Mama's - 5 min drive
- Square Grouper Bar and Grill - 11 min walk
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!
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!
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Property amenities
Beach
- Beach nearby
- Beach towels
Pool/Spa
- Heated pool
- Outdoor pool
- Private pool
Internet
- Available in the house: Free WiFi
Parking and transport
- Onsite parking options include a garage
Kitchen
- Blender
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dishwasher
- Hob
- Ice maker
- Kitchen island
- Lobster/crab pot
- Microwave
- Oven
- Refrigerator
- 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
- Smoke-free property
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
- Snorkelling 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
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age - 28
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
Information provided by the property may be translated using automated translation tools
Pets
- No pets allowed
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
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 not indicated whether there is a smoke detector on the property
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited.
Property is also known as
Captains Quarters - Cudjoe Key - Pool- Up to 45' Boat Cudjoe Key
Frequently asked questions
Are there any beaches close to Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock?
The closest beach to Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock is Florida Keys Beaches (9.9 km).
Does Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock have a pool?
Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock has a heated pool and a pool.
What luxury perks are available at Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock?
This property features a heated pool, as well as a private pool and a jetted bath.
Is there a private hot tub at Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock?
No, but there is Jetted Baths and a private pool.
Is there a free airport shuttle available at Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock?
No, Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock does not offer an airport shuttle service.
What time are check-in & check-out at Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock?
Check-in begins at 4:00 PM. Check-out time is 10:00 AM.
Are pets allowed at Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock?
No, pets are not allowed.
Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock Reviews
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.
Rating 10 - Excellent. 2 out of 2 reviews
10 - Excellent
2
Rating 8 - Good. 0 out of 2 reviews
8 - Good
0
Rating 6 - Okay. 0 out of 2 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 2 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 2 reviews
2 - Terrible
0
9.0/10
Cleanliness
Reviews
10/10 Excellent
Barbara R.
11 Apr 2022
Liked: Cleanliness
Beautiful home
Beautiful home, great location
Barbara R.
Stayed 30 nights in Mar 2022