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Cottage with swimming pool and dockage, just minutes to Key West!

Photo gallery for Cottage with swimming pool and dockage, just minutes to Key West!

A wooden dock extending into calm waters with clear skies.
A swimming pool with a curved edge, surrounded by a concrete deck. There are lounge chairs and a small green structure nearby.
A single-story house with a red exterior and white trim, number 3 on the side.
A room with a dining table, two chairs, a ceiling fan, a sofa, a small table with a lamp, and a framed picture on the wall.
A lakeside picnic area with a wooden table and benches, surrounded by lush greenery and a clear view of the water.

Reviews

9.0 out of 10
Wonderful

Highlights

  • Family fun awaits
    Top-rated for families.
  • Private garden
    A rare find — relax in the peaceful, private garden space.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Patio
  • Swimming pool
  • Dog-friendly
  • Barbecue
  • Air-conditioning
  • Refrigerator

Explore the area

View 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

1 bedroom (sleeps 2)

Bedroom 1

1 Queen Bed

1 bathroom

Bathroom 1

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Garden
Dining area

Add dates for prices

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About the area

Summerland Key

Located in Summerland Key, this cottage is near theme parks and by the ocean. 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. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with cycling and ecotours.
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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 Cottage with swimming pool and dockage, just minutes to Key West! have a pool?

Yes, this property has a pool.

Is Cottage with swimming pool and dockage, just minutes to Key West! pet-friendly?

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

How much is parking at Cottage with swimming pool and dockage, just minutes to Key West!?

On-site parking is available at the property.

What time is check-in at Cottage with swimming pool and dockage, just minutes to Key West!?

Check-in begins at 3:00 PM.

What time is check-out at Cottage with swimming pool and dockage, just minutes to Key West!?

Checkout is at 10:00 AM.

Where is Cottage with swimming pool and dockage, just minutes to Key West! located?

Situated by the ocean, 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

9.0

Wonderful

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. 111 out of 175 reviews
Rating 8 - Good. 46 out of 175 reviews
Rating 6 - Okay. 11 out of 175 reviews
Rating 4 - Poor. 2 out of 175 reviews
Rating 2 - Terrible. 5 out of 175 reviews

9.2/10

Cleanliness

7.0/10

Amenities

8.6/10

Property conditions & facilities

9.8/10

Check-in

9.4/10

Communication

9.6/10

Location

9.2/10

Listing accuracy

Reviews

Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy
The view from the docks was great. Convenient location to go to all the key islands. Very relaxing. Enjoyed our stay for sure.
Stayed 6 nights in Sep 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy
We had a nice stay at this property, which was clean and nicely presented. It is in a calm area by the water and has some good food options close by as well. We did use the pool on 2 days and it felt like a private pool just when we used it.
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location!
Stayed 3 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had everything I needed for my work trip. Perfect for families or solo trips.
Stayed 3 nights in Mar 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Quaint,clean cottage. Quite area, friendly neighbors. Close to alot of things with plenty within walking distance. Very dog friendly!
Stayed 7 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Communication
Location was perfect. Oceanfront dock had beautiful sunsets. Oceanfront pool lovely and warm with incredible view. Very friendly vibe and relaxed atmosphere.
Stayed 10 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for a Keys stay when you don’t want to be surrounded by Key West tourists.
Stayed 8 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, property conditions & facilities, communication
Everything was there that I needed. Very nice area for my dog.
Stayed 3 nights in Nov 2025
Verified review

10/10 Excellent

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

Another great stay....

Clean and comfortable.
Stayed 6 nights in Jun 2025
Verified review

10/10 Excellent

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

Wonderful oasis to feel at home!

Wonderful stay with great property and pool. Very well maintained!
Stayed 4 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Quiet area
Stayed 6 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean quaint charming little cottages.
Stayed 6 nights in Jun 2025
Verified review

10/10 Excellent

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

Cozy cottage with access to pool

We loved the location, right on the water with access to a pool and boat launch.
Stayed 6 nights in Jul 2024
Verified review

10/10 Excellent

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

Great getway to keys

Nice place and susan was an excellent hosts
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, property conditions & facilities, communication
Everything was perfect. The place was clean. Easy to find and get in and out. The cottage had everything we needed to make breakfast and dinner
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice
Stayed 5 nights in Nov 2025
Verified review

8/10 Good

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

Comfortable place to stay

The cottage was comfortable, and the bed was just right. We were in the Keys for a funeral, so not much running around.
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

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

Great place to stay. We brought a boat with us, tied it up 50 yards away.

Outstanding location for us. Our stay was quiet and relaxing. I
Stayed 3 nights in Apr 2025
Verified review

10/10 Excellent

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

Great get away

We have been staying at this property for over 20 years. It’s the perfect location for visiting all of the lower keys.
Stayed 7 nights in Mar 2025
Verified review

10/10 Excellent

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

Nice quite relaxing

We had a nice time at our stay. We stayed for 3 nights and it was close to key west and the docks were nice to fish off of. Place was clean and everything worked fine for us.
Stayed 3 nights in Mar 2025
Verified review

10/10 Excellent

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

It was great

Nice place
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

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

Had a great time

We will come back, was very relaxing
Stayed 6 nights in Jun 2020
Response from VrboOwner on 15 June 2020
Hey there, so glad you had a great time. means the world to me. O know it was great to your family, finally getting away. Thanks, Susan Rich
Verified review

10/10 Excellent

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

Another Wonderful Stay!

My third time staying at Cuddle Cottages. A great retreat. Relaxing, clean, and comfortable every time.
Stayed 6 nights in Jun 2023
Verified review

6/10 Okay

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cottage show signs of wear which comes with an older building. Bathroom is tight. No exit on one side of the bed due to smaller room. Latch on entry door was broken upon arrival but was remedied the next day. Screened porch was nice for relaxing after a day touring!
Stayed 4 nights in Feb 2026
Verified review

10/10 Excellent

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

Nice

Great location fair price and relaxing.
Stayed 8 nights in Feb 2023
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