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**CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service...

Photo gallery for **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service...

A pool with a hot tub, lounge chairs, and umbrellas, surrounded by palm trees and a view of the sea.
A beachfront property with a swimming pool, multiple houses, and palm trees.
A poolside area with lounge chairs and umbrellas, overlooking a beach and sunset.
A swimming pool with a curved edge, surrounded by a sandy beach and palm trees.
A spacious living room with a large window, a flat-screen TV, and a view of the beach.

Reviews

8.8 out of 10
Excellent

Highlights

  • Bring your furry friends
    Top-rated for creating memorable stays with your pets.
  • Firepit available
    One of the few properties with a dedicated outdoor firepit.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Balcony
  • Hot tub on site
  • Private pool
  • Barbecue grill
  • Air conditioning
  • Pet-friendly

Explore the area

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

Rooms & beds

3 bedrooms (sleeps 9)

Bonus Room

1 Twin Bed

Guest House

2 Queen Beds and 2 Double Sofa Beds

Master Suite

1 King Bed

Second Bedroom

1 Queen Bed

3 bathrooms

Bathroom 2

Guest House Bathroom

Master Bathroom

Spaces

Kitchen
Balcony

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About the neighborhood

Summerland Key

Located by the sea, this vacation home is in Cutthroat Harbor Estates, a neighborhood in Summerland Key. 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.
View more Vacation Homes in Summerland KeyOpens in a new window
Map
Cudjoe Key, FL

What's nearby

  • Upper Sugarloaf Key - 7 min drive - 7.6 km
  • Florida Keys Beaches - 8 min drive - 7.7 km
  • Upper Sugarloaf Sound - 8 min drive - 8.9 km
  • Boondocks Grille & Draft House - 11 min drive - 12.0 km
  • Lower Sugarloaf Sound - 12 min drive - 12.5 km

Getting around

  • Key West Intl. Airport (EYW) - 32 min drive

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Morning Joint - ‬17 min walk
  • ‪Kiki's Sandbar - ‬11 min drive
  • ‪Looe Key Tiki Bar & Restaurant - ‬9 min drive
  • ‪Tonio's Seafood Shack & Tiki Bar - ‬6 min drive

Frequently asked questions

Does **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service... have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service...?

As of Oct 24, 2026, prices found for a 1-night stay for 2 adults at **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service... on Sep 14, 2027 start from $444, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service... pet-friendly?

Yes, pets are allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service...?

Check-in begins at 4:00 PM.

What time is check-out at **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service...?

Check-out is at 10:00 AM.

Where is **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service... located?

Located in Cutthroat Harbor Estates, this vacation home is 0.4 mi (0.7 km) from Venture Out Keys and 2.4 mi (3.9 km) from Florida Keys Beaches. Venture Key and Out Key are also within 10 minutes.

Reviews

8.8

Excellent

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 2 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 1 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

8.8/10

Cleanliness

10/10

Check-in

8.0/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Comforts of. Home.

1st I would like to say Nadia went above and beyond to make our trip.. Outstanding. It was peaceful it was comfortable it was everything it said it was and we loved it
Stayed 29 nights in Mar 2023
Verified review

10/10 Excellent

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

Perfect Waterfront Getaway in the Keys – Dog-Friendly with Top-Notch Amenities!

We had an incredible month-long stay at this beautiful home in the Florida Keys! The house was spotless, well-equipped, and perfectly located right on the water. Having access to the boat lift made our time on the water even more enjoyable and convenient.The pool was a great bonus, and the outdoor space—including a nice screened-in porch that kept the bugs away—was perfect for relaxing after a day out boating or exploring. The incredible sunsets each evening were a highlight, and it was such a treat to be able to walk right out the door and go paddleboarding anytime we wanted.One of the best parts was that they allow dogs, so our pup Finn had a great time too!The management team was top-notch—very responsive and attentive, with a concierge service that went above and beyond by delivering packages and checking in to ensure we had everything we needed.Everything about this property made our stay easy, comfortable, memorable, and a short drive to Key West. We would absolutely stay here again and highly recommend it to anyone looking for a great spot in the Keys!
Stayed 31 nights in Apr 2025
Verified review

6/10 Okay

Liked: Check-in, location, listing accuracy
Disliked: Communication
The property was fantastic. Beautiful sunsets and an awesome swimming pool. The cottage was nice. The main house was OK. I wouldn’t say it was commiserate with the cost however. The furniture was a mish mash of stuff from what I would call garage sale level. There were stains on all the upholstery and the carpet. The pool was 65 degrees when I checked in. I was told the pool temperature was set to 90 degrees and the hot tub was set to 104. I had to manually go in and adjust the temperature so we could use them. The master bath is plumbed backwards so hot is cold and cold is hot. I had to call the property manager to figure this out. There were people constantly coming and going without us being notified. This was beyond the maintenance people that were scheduled to be there. The cleaning people never showed up for the mid stay cleaning. I had gotten up early and tidied the house and left for the day so as not to be in their way.they were supposed to be there at 10 AM. I returned after 3 PM and no one had come to clean. It was a big inconvenience. The house smells musty and the cottage has an over powering perfume smell that even after leaving all the doors and windows open for an afternoon could not be cleared. Not sure what they are trying to cover up. The home should be furnished like a 3m house not a college frat house. The outdoor furniture was dirty and stained as well. The chairs for the table on the balcony don’t go with the table so they are the wrong height.
Stayed 27 nights in Feb 2026
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