See all properties
Entire home

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

Summerland Key vacation home with private pool

Choose dates to view prices

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

A swimming pool with a curved edge, a covered seating area with chairs, and a balcony with railings.
A covered outdoor dining area with a table and chairs, a ceiling fan, and a view of the ocean.
A pebbled beach with three Adirondack chairs in green, orange, and gray.
Smart TV
A spacious kitchen with wooden cabinets, a large island, and a view to the outside.

Reviews

10 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

View in a map
Cudjoe Key, FL
  • Place, Upper Sugarloaf Key
    ‪5 min drive‬
  • Place, Florida Keys Beaches
    ‪5 min drive‬
  • Place, Upper Sugarloaf Sound
    ‪6 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪36 min drive‬

Room options

About the neighborhood

Summerland Key

Seaside stay .You'll find Venture Out Keys and Venture Key within 2 miles (3 km) of this vacation home. Also, Out Key is within 2 miles (3 km) and Florida Keys Beaches is within 6 miles (10 km).
View more Vacation Homes in Summerland KeyOpens in a new window

What's nearby

  • Upper Sugarloaf Key - 5 min drive - 3.9 miles
  • Florida Keys Beaches - 5 min drive - 3.6 miles
  • Upper Sugarloaf Sound - 6 min drive - 4.7 miles
  • Lower Sugarloaf Sound - 9 min drive - 6.9 miles
  • Big Pine Key Flea Market - 13 min drive - 10.3 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
  • ‪Looe Key Tiki Bar & Restaurant - ‬7 min drive
  • ‪The Bent Prop - ‬5 min drive

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!

Similar properties

Outdoor pool
Sugarloaf Key RV Resort & Cottages
Summerland Key
  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
4.7 out of 5, Exceptional, 21 reviews
Sugarloaf Key RV Resort & Cottages

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
  • 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

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
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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. 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

How close is Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock to the airport?

This vacation home is 20.9 mi (30-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock to the beach?

This vacation home is 3.6 mi (7-min drive) from Florida Keys Beaches and 10.6 mi (20-min drive) from Sugarloaf Beach. Don't forget your sunscreen!

Does Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock?

No, there is no casino at this vacation home.

What time is check-in at Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock?

Check-in begins at 4:00 PM.

Is there free parking at Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock?

Free parking is not available at this vacation home.

Does Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock have a pool?

This vacation home features an outdoor pool.

Does Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock have a spa?

There are no spa services available at this vacation home.

How close is Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock to downtown Summerland Key?

This vacation home is 1.8 mi away from Summerland Key.

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

Reviews

10

Exceptional

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

9.0/10

Cleanliness

Reviews

Verified

10/10 Excellent

CHARLES W.

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

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

Explore More Ways to Travel with Travelocity