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

Outdoor pool, a heated pool
Fridge, microwave, oven, stovetop
Beach nearby, beach towels
Outdoor dining
Smart TV

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
    ‪8 min drive‬
  • Place, Florida Keys Beaches
    ‪9 min drive‬
  • Place, Upper Sugarloaf Sound
    ‪9 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪44 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 - 8 min drive - 3.9 miles
  • Florida Keys Beaches - 9 min drive - 3.6 miles
  • Upper Sugarloaf Sound - 9 min drive - 4.7 miles
  • Lower Sugarloaf Sound - 13 min drive - 7.1 miles
  • Sugarloaf Beach - 20 min drive - 10.8 miles

Getting around

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

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬7 min drive
  • ‪Kiki's Sandbar - ‬10 min drive
  • ‪Morning Joint - ‬7 min walk
  • ‪Broil - ‬3 min drive
  • ‪5 Brothers Two - ‬7 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

Terrace/patio
Island Comfort at Cudjoe Key
  • Kitchen
  • Washer
  • Air conditioning
  • Parking available
Island Comfort at Cudjoe Key

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

  • 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 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. 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

10/10 Excellent

CHARLES W.

Liked: Cleanliness
Very nice location and home.
Stayed 28 nights in Aug 2025

10/10 Excellent

Barbara R.

Liked: Cleanliness

Beautiful home

Beautiful home, great location
Stayed 30 nights in Mar 2022