Entire home

Captains Quarters is a charming canal front Keys house in delightful Islamorada

Photo gallery for Captains Quarters is a charming canal front Keys house in delightful Islamorada

A spacious living room with a large sofa, a television, and a ceiling fan. There are large windows providing natural light and a view of greenery outside.
An aerial view of a coastal resort with clear turquoise waters, a sandy beach lined with palm trees, and a mix of residential and commercial buildings.
A two-story house with a covered porch and a small outdoor seating area.
A two-story house with a covered porch, a palm tree, and a view of the water.
A sandy beach area with palm trees, a water body, and a wooden fence.

Reviews

10 out of 10
Exceptional

Highlights

  • Cook, dine, and unwind
    Top-rated for its fully equipped kitchen, perfect for every meal.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Sunset Drive Beach

Popular amenities

  • Dog-friendly
  • Barbecue grill
  • Air conditioning
  • Refrigerator
  • Washer
  • Non smoking

Explore the area

View in a map
Islamorada, FL
  • Place, Sunset Drive Beach
    ‪11 min walk‬
  • Place, Anne's Beach
    ‪2 min drive‬
  • Place, Robbie’s of Islamorada
    ‪5 min drive‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪35 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed and 2 Twin Beds

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Kitchen
Separate dining area

Add dates for prices

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About the neighborhood

Islamorada

Matecumbe, a neighborhood in Islamorada, is home to this vacation home. Keys History & Discovery Center and History of Diving Museum are cultural highlights, and some of the area's activities can be experienced at Robbie’s of Islamorada and Bud n' Mary's Dive Center. Ready for a night out? Consider Lorelei Restaurant & Cabana Bar and Hog Heaven.
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Map
Islamorada, FL

What's nearby

  • Sunset Drive Beach - 11 min walk - 0.9 km
  • Anne's Beach - 2 min drive - 3.0 km
  • Robbie’s of Islamorada - 5 min drive - 5.7 km
  • Bud n' Mary's Dive Center - 9 min drive - 10.6 km
  • Florida Keys Brewing Co. - 11 min drive - 13.9 km

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon) - 30 min drive

Restaurants

  • ‪Hungry Tarpon Restaurant - ‬6 min drive
  • ‪Habanos Oceanfront Dining - ‬3 min drive
  • ‪Lazy Days Restaurant - ‬8 min drive
  • ‪Papa Joe’s Waterfront - ‬8 min drive
  • ‪Tiki Bar at Amara Cay Resort - ‬8 min drive

Frequently asked questions

Is Captains Quarters is a charming canal front Keys house in delightful Islamorada pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 50 lbs per pet.

What time is check-in at Captains Quarters is a charming canal front Keys house in delightful Islamorada?

Check-in begins at 4:00 PM.

What time is check-out at Captains Quarters is a charming canal front Keys house in delightful Islamorada?

Check-out is at 11:00 AM.

Where is Captains Quarters is a charming canal front Keys house in delightful Islamorada located?

Located in Matecumbe, this vacation home is 0.4 mi (0.7 km) from Sunset Drive Beach and 1.3 mi (2.1 km) from Anne's Beach. Robbie’s of Islamorada and Indian Key Historic State Park are also within 6 mi (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great communication with host. Location provided everything we were looking for.
Stayed 30 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Captain's Quarters is a lovely property located in an upscale neighborhood. If you're a boater this one is for you! Large dock frontage and water hoses thru out. The house is charming, cleaned well and has all the kitchen amenities you'll need. The AC was almost too cold! The outdoor space is huge and easy to park a trailer on the side of the home. Ivette was a wonderful host and promptly replied to any request! Hope to rent this one again in the future!
Stayed 28 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, listing accuracy
Stayed 29 nights in Jul 2026
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