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Charming cottages, dockage, pool, just minutes to Key West

Photo gallery for Charming cottages, dockage, pool, just minutes to Key West

An aerial view of a residential area with multiple houses, a swimming pool, and a small dock with boats.
A single-story house with a blue exterior, a white door, and a small window.
A bedroom with a bed, a dresser, a chair, a lamp, a ceiling fan, and a window with blinds.
A bedroom with two single beds, a small bedside table, and a window with blinds.
A bedroom with a bed, a desk, a chair, a lamp, and a door.

Reviews

8.6 out of 10
Excellent

Highlights

  • Dive into relaxation
    Unwind in the top-rated pool, your perfect spot for relaxation.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Swimming pool
  • Dog-friendly
  • Barbecue grill
  • Air-conditioning
  • Refrigerator
  • Washing machine

Explore the area

View in a map
Cudjoe Key, FL
  • Place, Upper Sugarloaf Key
    ‪3 min drive‬
  • Place, Upper Sugarloaf Sound
    ‪4 min drive‬
  • Place, Florida Keys Beaches
    ‪8 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪34 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Kitchen
Dining area

Add dates for prices

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About the area

Summerland Key

Summerland Key is home to this cottage. Florida Keys Beaches and Coupon Bight Aquatic Preserve reflect the area's natural beauty and area attractions include Blue Hole and Wilhelmina Harvey Park. Big Munson Island and Looe Key National Marine Sanctuary are also worth visiting.
View more Cottages in Summerland KeyOpens in a new window
Map
Cudjoe Key, FL

What's nearby

  • Upper Sugarloaf Key - 3 min drive - 3.3 km
  • Upper Sugarloaf Sound - 4 min drive - 4.6 km
  • Lower Sugarloaf Sound - 7 min drive - 8.2 km
  • Florida Keys Beaches - 8 min drive - 8.6 km
  • Great White Heron National Wildlife Refuge - 10 min drive - 8.0 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 27 min drive

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Morning Joint - ‬2 min drive
  • ‪Looe Key Tiki Bar & Restaurant - ‬9 min drive
  • ‪Tonio's Seafood Shack & Tiki Bar - ‬6 min drive
  • ‪Square Grouper Bar and Grill - ‬2 min drive

Frequently asked questions

Does Charming cottages, dockage, pool, just minutes to Key West have a pool?

Yes, this property has a pool.

Is Charming cottages, dockage, pool, just minutes to Key West pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much is parking at Charming cottages, dockage, pool, just minutes to Key West?

On-site parking is available at the property.

What time is check-in at Charming cottages, dockage, pool, just minutes to Key West?

Check-in begins at 3:00 PM.

What time is check-out at Charming cottages, dockage, pool, just minutes to Key West?

Checkout is at 10:00 AM.

Where is Charming cottages, dockage, pool, just minutes to Key West located?

Situated in Summerland Key, this cottage is within 3 miles (5 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound and Venture Key. Venture Out Keys and Out Key are also within 3 miles (5 km).

Reviews

8.6

Excellent

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 75 out of 134 reviews
Rating 8 - Good. 33 out of 134 reviews
Rating 6 - Okay. 16 out of 134 reviews
Rating 4 - Poor. 8 out of 134 reviews
Rating 2 - Terrible. 2 out of 134 reviews

8.4/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

9.6/10

Check-in

9.4/10

Communication

9.2/10

Location

8.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lots of places to stay on the property. You really need a boat to get the most for your money or at least a canoe or something. The dack is just too nice. Lots of parking for cars and boats. Plenty of places to eat nearby.
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Good location, comfortable cabin.!
Stayed 4 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location within walking distance from the way. Places to fish and swim at the pool and good value for the location.
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was really nice. Bed was a little firm for my liking but thats just me. Place was great.
Stayed 3 nights in Jan 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication
Value for money: Fair This is a unit in a 3-unit divided house, not a cottage as described. It was clean, comfortable, quiet, and a good size, located a convenient drive to Key West. We enjoyed our stay.
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and neat. All the kitchen utensils you need. Pool and docks fantastic. Top shelf
Stayed 7 nights in Mar 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy
Great location. Nothing fancy, but a good value. Dock and waterfront access. The pool was lovely, but not heated. Very quiet other than road noise. This unit #6 was the only one without a screened in porch. That would have been a nice addition. Overall a good value.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches.
Stayed 6 nights in Apr 2025
Verified review

8/10 Good

Liked: Cleanliness
Everything close by. The AC barely wirking. The couldn't get access to the wifi.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

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

Relaxing stay

Our unit was clean and comfortable, it was nice to have the use of the shore areas, pool, and laundry. We had a great stay.
Stayed 4 nights in Feb 2023
Verified review

10/10 Excellent

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

Perfect for family.

We enjoyed are stay. The customer service was great. The area was quiet and had access to the water for a boat.
Stayed 4 nights in Mar 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Jennifer was very nice and accommodating.
Stayed 4 nights in Jul 2025
Verified review

8/10 Good

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

Convenient to key west .

Nice to be able to bring our dogs.
Stayed 4 nights in Apr 2023
Verified review

10/10 Excellent

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

We really enjoyed ourselves!

The place was lovely. Enjoyed the keys!
Stayed 3 nights in Jan 2023
Verified review

10/10 Excellent

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

Quaint Cottage

Nice Location, has a dock, pool and allows Dogs.
Stayed 4 nights in Jul 2023
Verified review

8/10 Good

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

Good Value

Great value. Really enjoyed the location. The apartment could use some attention to detail but overall was a great experience.
Stayed 6 nights in Apr 2025
Verified review

10/10 Excellent

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

Great location

Cudjoe Key is centrally located. There are a lot of activities close by, but the location itself is quite and peaceful.
Stayed 7 nights in Dec 2022
Verified review

10/10 Excellent

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

Charming cottage

Lovely cottage with an old Florida charm. Shade trees, swimming pool, dock, beautiful water view. Would definitely stay here again.
Stayed 3 nights in Feb 2023
Verified review

10/10 Excellent

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

Peaceful

Enjoyed the serenity of your place
Stayed 6 nights in Feb 2025
Verified review

10/10 Excellent

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

Great Location

We have stayed at this property multiple times. It is a super convenient location. We bring our boat and it's only a short ride out to either the Gulf or Ocean.
Stayed 7 nights in Mar 2023
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy
host answered our question. Did not know w& d was coin washer and dryer
Stayed 4 nights in Nov 2025
Verified review

10/10 Excellent

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

Good place

Couldn’t beat the price
Stayed 3 nights in Mar 2024
Verified review

10/10 Excellent

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

Cudjoe Cottages

We absolutely love staying here at this location! It’s a nice/safe location with so many things to access while you stay. The house is clean and perfect whether you stay there all day or are just there to sleep. We always look forward to coming back!
Stayed 5 nights in Jun 2023
Verified review

10/10 Excellent

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

Realtor

Great quite location but close enough to Key West to go to dinner or the day
Stayed 2 nights in Mar 2024
Verified review

10/10 Excellent

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

Perfect

30 minutes from Key West. No problems finding the place. No traffic.
Stayed 3 nights in Mar 2025
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