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

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A swimming pool with lounge chairs, palm trees, and a view of the ocean.
An aerial view of a residential area with multiple houses, a swimming pool, and a small dock with boats.
A marina with two boats docked, a picnic table, and a view of the water and trees.
A living room with a sofa set, a chair, a lamp, and a small table.
A bedroom with a bed, a desk, a chair, a lamp, and a door.

Reviews

8.6 out of 10
Excellent

Entire home

2 bedrooms1 bathroom73 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi

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

Room options

About the area

Summerland Key

At this cottage you'll be 3 km (1.9 mi) from Upper Sugarloaf Key and 3.7 km (2.3 mi) from Upper Sugarloaf Sound. .Accommodation features a washing machine, free WiFi and a Smart TV. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A coffee/tea maker and a hairdryer are also available.
View more Cottages in Summerland KeyOpens in a new window

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

  • ‪Morning Joint - ‬2 min drive
  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Tonio's Seafood Shack & Tiki Bar - ‬6 min drive
  • ‪Square Grouper Bar and Grill - ‬2 min drive
  • ‪5 Brothers Two - ‬8 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.

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

Cottage #6 - Only 20 miles from Key West, but a world away from the hustle and bustle. Come experience a truly relaxing Keys experience. Our fully equipped cottages mean all you need is your swimming costume and sun cream! Anglers will find easy access to crystal clear waters using our small boat launch and convenient dock and sea wall. Runners and cyclists will find easy access to the Florida Keys Overseas Heritage Trail - 75 miles of paved trail tracing the original route of the Flagler Railway. When you're ready for tourist activities make the short drive to Key West and visit the Aquarium or hop on the Conch Tour Train. Big Pine offers nature enthusiasts the Blue Hole with Key Deer lots of wildlife.

Similar properties

A waterfront building with a flat roof, large windows, and a balcony.
Sugar Loaf Lodge
Summerland Key
  • Pool
  • Parking included
  • Free Wi-Fi
  • Restaurant
4.1 out of 5, Very good, 1,001 reviews
The price is NZ$198
includes taxes & fees
30 Nov - 1 Dec
Sugar Loaf Lodge

Property amenities

Pool/Spa

  • Communal pool

Internet

  • Available in the cottage: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shower
  • Towels provided

Entertainment

  • Smart TV

Outdoor areas

  • Barbecue grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No lift (single-level property)
  • Smoke-free property

Safety features

  • No carbon monoxide detector or gas appliances (host has indicated there are no carbon monoxide detectors or gas appliances on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Unit size: 785 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in and check-out are available

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

Rules

Rates are subject to change until reservation is confirmed. Occupancy limits strictly enforced. This unit accommodates a maximum of 4 guests.
ONLY registered guests permitted to use Cudjoe Cottage amenities to include pool, boat launch, kayaks, seawall and dock.

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 2 pets
    • Service animals are exempt from fees.

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
On-site parties or group events are strictly prohibited
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
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. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher and a smoke detector in all accommodation.

Frequently asked questions

Are there any beaches close to Charming cottages, dockage, pool, just minutes to Key West?

The closest beach to Charming cottages, dockage, pool, just minutes to Key West is Florida Keys Beaches (8.3 km).

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

Charming cottages, dockage, pool, just minutes to Key West has a pool and a communal pool.

Is there a free airport shuttle available at Charming cottages, dockage, pool, just minutes to Key West?

No, Charming cottages, dockage, pool, just minutes to Key West does not offer an airport shuttle service.

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

Check-in begins at 3:00 PM. Check-out time is 10:00 AM.

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

Reviews

8.6

Excellent

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

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

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, 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

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

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

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

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

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

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

Good place

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

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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