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Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock

Waterfront holiday home with private pool and kitchen

Photo gallery for Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock

Pool
Pool
Property grounds
Private kitchen
Living area

Reviews

10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 81817 sq ft

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Air conditioning
  • Pool
  • Kitchen

Explore the area

View in a map
Cudjoe Key, FL
  • Place, Venture Out Keys
  • Place, Upper Sugarloaf Key
    ‪6 min drive‬
  • Place, Florida Keys Beaches
    ‪8 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪37 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Guest Bedroom

1 Queen Bed

Guest Bedroom

2 Double Beds

Master Bedroom

1 King Bed

2 bathrooms

Guest Bathroom

Toilet · Shower only

Master Bathroom

Toilet · Shower only · Jetted bathtub

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Outdoor play area
Dining area

About this property

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!

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 28
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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

About the area

Summerland Key

Located in Summerland Key, this holiday home is in a rural area and on the waterfront. Coupon Bight Aquatic Preserve and Bahia Honda State Park reflect the area's natural beauty and area attractions include Blue Hole and Big Munson Island. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Cudjoe Key, FL

What's nearby

  • Upper Sugarloaf Key - 6 min drive - 6.6 km
  • Florida Keys Beaches - 8 min drive - 7.1 km
  • National Key Deer Refuge Visitor Center - 16 min drive - 16.9 km
  • Sugarloaf Beach - 20 min drive - 17.7 km
  • Bahia Honda State Park - 28 min drive - 32.1 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 30 min drive

Restaurants

  • ‪Kiki's Sandbar - ‬10 min drive
  • ‪Boondock's Grille & Drafthouse - ‬7 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?

Checkout is at 10:00 AM.

Where is Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock located?

Situated on the waterfront, this holiday home is within 1 mile (2 km) of Venture Out Keys, Venture Key and Out Key. Upper Sugarloaf Key and Crab Key are also within 6 miles (10 km).

Reviews

10

Exceptional

9.0/10

Cleanliness

9.0/10

Check-in

9.0/10

Communication

9.0/10

Location

9.0/10

Listing accuracy
Rating 10 - Excellent. 2 out of 2 reviews
Rating 8 - Good. 0 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

Reviews

10/10 Excellent

CHARLES W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice location and home.
Stayed 28 nights in Aug 2025

10/10 Excellent

Barbara R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home

Beautiful home, great location
Stayed 30 nights in Mar 2022

About the host

Hosted by Conch Collection

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Languages:

English

Premier Host

They consistently provide great experiences for their guests