10/10 Excellent
CHARLES W.
Sep 2, 2025
Liked: Cleanliness
CHARLES W.
Stayed 28 nights in Aug 2025
Entire home
Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock
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Photo gallery for Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock
Reviews
1010 out of 10
Exceptional
Entire home
3 bedrooms2 bathroomsSleeps 81817 sq ft
Popular amenities
- Ocean view
- Pool
- Kitchen
- Washer
- Dryer
- Free WiFi
Explore the area
Cudjoe Key, FL
- Florida Keys BeachesPlace, Florida Keys Beaches5 min drive
- Upper Sugarloaf KeyPlace, Upper Sugarloaf Key6 min drive
- Upper Sugarloaf SoundPlace, Upper Sugarloaf Sound7 min drive
- Key West, FL (EYW-Key West Intl.)Airport, Key West, FL (EYW-Key West Intl.)36 min drive
Room options
About the neighborhood
Summerland Key
This vacation home is located within a mile (2 km) of Venture Out Keys and Venture Key. The vacation home includes a private pool, a kitchen, and a balcony.
What's nearby
- Florida Keys Beaches - 5 min drive - 3.8 miles
- Upper Sugarloaf Key - 6 min drive - 3.9 miles
- Upper Sugarloaf Sound - 7 min drive - 4.7 miles
- Lower Sugarloaf Sound - 10 min drive - 6.9 miles
- National Key Deer Refuge Visitor Center - 15 min drive - 10.5 miles
Getting around
- Key West Intl. Airport (EYW) - 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!
The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a balcony. There's space to spread out with 3 bedrooms and a dining area. Guests can enjoy a Smart TV and stay connected with free WiFi. The bathroom offers a jetted tub and hair dryers. Other standard amenities include a private pool, a washing machine, and a coffee maker.
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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 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
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
- This property doesn't allow pets
Children and extra beds
Children allowed: ages 0-17
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 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
- Check-in: 4:00 PM
- Check-out: 10:00 AM
- Minimum check-in age: 28
We should mention
Details about charges, deposits, or other important information:
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
- Charges for extra guests may apply and vary depending on the property's policy.
- A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
- Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
- Onsite 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
What is there to do close to this vacation home?
This vacation home is located in Summerland Key, a short 19-minute walk from Venture Out Keys and also 19 minutes on foot from Venture Key. You'll also find Florida Keys Beaches and Upper Sugarloaf Key within a short drive.
Is there parking available at Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock?
Yes, there is a garage.
Is this vacation home adjacent to a casino?
No, this vacation home is not connected to a casino.
Is there an indoor pool at this vacation home?
No, this vacation home doesn't have an indoor pool; however, there is an outdoor pool.
What do couples enjoy most about Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock?
This historic vacation home offers many amenities for couples such as a private pool, a private pool in some house, as well as an outdoor pool.
Does Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock have a hot tub?
No, but all house at this vacation home have jetted bathtubs.
Does this vacation home offer breakfast?
No, this vacation home doesn't offer breakfast.
Does this vacation home allow pets to stay for free?
No, pets aren't allowed at this vacation home.
Does Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock have connecting rooms available?
No, this vacation home doesn't feature connecting guestrooms.
How close is the airport from this vacation home?
The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 20.9 mi away (30 minutes by car). Another top airport is Marathon, FL (MTH-Florida Keys Marathon), which is located 28.8 mi away (41-minute drive).
Are there rooms with balconies at Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock?
Yes, every house at Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock comes with a balcony and some offer ocean views.
Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers 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.
Apr 11, 2022
Liked: Cleanliness
Beautiful home
Beautiful home, great location
Barbara R.
Stayed 30 nights in Mar 2022