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

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Coffee/tea maker, fridge, microwave, oven
A bedroom with a bed, a desk, a chair, a lamp, and a door.
A marina with boats docked and a picnic table on the dock.
An aerial view of a residential area with multiple houses, a swimming pool, and a small dock with boats.
A swimming pool with lounge chairs, palm trees, and a view of the ocean.

Reviews

8.6 out of 10
Excellent

Entire home

2 bedrooms1 bathroom785 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

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

Room options

Similar properties

Karaoke room
Looe Key Reef Resort
Summerland Key
  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
3.8 out of 5, Good, 1,001 reviews
$128 nightly
The price is $144
Aug 12 - Aug 13
Total with taxes and fees
Looe Key Reef Resort

About the neighborhood

Summerland Key

With a stay at this cottage in Summerland Key, you'll be within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key. .This cottage is 2.2 mi (3.6 km) from Upper Sugarloaf Sound and 2.5 mi (4.1 km) from Venture Key.
View more Cottages in Summerland KeyOpens in a new window

What's nearby

  • Upper Sugarloaf Key - 3 min drive - 2.1 miles
  • Upper Sugarloaf Sound - 4 min drive - 2.9 miles
  • Lower Sugarloaf Sound - 7 min drive - 5.1 miles
  • Florida Keys Beaches - 8 min drive - 5.4 miles
  • Great White Heron National Wildlife Refuge - 10 min drive - 5.0 miles

Getting around

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

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Morning Joint - ‬2 min drive
  • ‪The Bent Prop - ‬19 min walk
  • ‪Looe Key Tiki Bar & Restaurant - ‬9 min drive
  • ‪Square Grouper Bar and Grill - ‬2 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 swimsuit and sunscreen! 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 Railroad. 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.
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and an oven. Complimentary wireless internet access keeps you connected, and a Smart television is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.
Guests will find features like internet access and onsite parking.

Property amenities

Pool/Spa

  • Communal pool

Internet

  • Available in the cottage: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • 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 elevator (single-level property)
  • Smoking not allowed

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 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 allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets

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
Onsite parties or group events are strictly prohibited
Host has indicated there are no carbon monoxide detectors or gas appliances on the property
Host has indicated 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

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

Reviews

8.6

Excellent

Rating 10 - Excellent. 72 out of 130 reviews
Rating 8 - Good. 32 out of 130 reviews
Rating 6 - Okay. 16 out of 130 reviews
Rating 4 - Poor. 8 out of 130 reviews
Rating 2 - Terrible. 2 out of 130 reviews

8.4/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

David C.

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

10/10 Excellent

Ashby P.

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

8/10 Good

Laura

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

Verified traveler

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

joe S.

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

David

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

Martin

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

ANJANA

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

10/10 Excellent

Sheila G.

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

Randy G.

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

Adrian S.

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

6/10 Okay

Kelsey I.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Susan was great to work with. This place is functional, but lacking in routine maintenance and some cleaning. Grease stuck on cabinets near stove area, fan and heating vents had lots of dust. The master bedroom had whit tape on ceiling to cover up some needed repair, drywall chipped near couch, no drywall repair job for ripped out toilet paper and hand towel holder. Areas around the ground could be improved as well.
Stayed 3 nights in Feb 2026
Verified review

8/10 Good

Robin D.

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

8/10 Good

PJ H.

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

8/10 Good

Debbie M.

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

Chris H.

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

Jerie F.

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

6/10 Okay

Ty A.

Liked: Cleanliness, check-in, communication, location
Property was in disrepair. Holes in walls / not repaired when items removed in bathroom. No microwave, just an old stove for heating up food.
Stayed 8 nights in Nov 2025
Verified review

10/10 Excellent

Tommy K.

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

Jennifer C.

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

Terry M.

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

S

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
Verified review

10/10 Excellent

Michael W.

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

Jennifer C.

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

CINDY L.

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