Entire home

Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21

Photo gallery for Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21

A modern kitchen with white cabinetry, a central island with bar stools, and a wooden ceiling with exposed beams.
An attic room with a wooden ceiling, a golden statue, and a patterned mat on the floor.
A pool area with a hammock, palm trees, and a covered patio with outdoor furniture.
A covered porch with green chairs and a table, surrounded by lush tropical plants.
A wooden cabin bedroom with two beds, a ceiling fan, and a large window with curtains.

Reviews

9.0 out of 10
Wonderful

Highlights

  • 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.
  • Discover nearby landmarks
    Near Duval Street

Popular amenities

  • Balcony
  • Private pool
  • Barbecue grill
  • Air-conditioning
  • Refrigerator
  • Washing machine

Explore the area

View in a map
Key West, FL
  • Place, Key West Cemetery
    ‪6 min walk‬
  • Place, Duval Street
    ‪8 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪15 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪10 min drive‬

Rooms & beds

10 bedrooms (sleeps 21)

Bedroom 1

1 Single Murphy Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

1 King Bed

Bedroom 5

1 King Bed

Bedroom 6

1 King Bed

Bedroom 7

2 Double Beds

Bedroom 8

1 Double Bed

Bedroom 9

1 Queen Bed

Bedroom 10

1 King Bed

7 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Bathroom 5

Bathroom 6

Bathroom 7

Bathroom 8

Spaces

Porch or lanai
Kitchen
Balcony
Separate dining area
Garden
Dining area

Add dates for prices

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  • Pool
  • Kitchen
  • Washing machine
  • Dryer
9.6 out of 10, Exceptional, (8 reviews)
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About the area

Key West

Located in Key West, this holiday home is in the city centre. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Discover the area's water adventures with power boating and swimming nearby, or enjoy the great outdoors with ecotours.
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Map
Key West, FL

What's nearby

  • Key West Cemetery - 6 min walk - 0.6 km
  • Duval Street - 8 min walk - 0.7 km
  • Mallory Square - 13 min walk - 1.2 km
  • Harry S. Truman Little White House - 14 min walk - 1.2 km
  • Ernest Hemingway Home and Museum - 15 min walk - 1.3 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 13 min drive

Restaurants

  • ‪Kermit's Key West Key Lime Shoppe - ‬8 min walk
  • ‪Cuban Coffee Queen Waterfront - ‬5 min walk
  • ‪Schooner Wharf Bar - ‬7 min walk
  • ‪Half Shell Raw Bar - ‬5 min walk
  • ‪The Breakfast Club, Too - ‬9 min walk

Frequently asked questions

Does Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21 have a pool?

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

How much does it cost to stay at Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21?

As of 2 Nov 2026, prices found for a 1-night stay for 2 adults at Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21 on 9 Nov 2026 start from £5,961, 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 Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21 pet-friendly?

No, pets are not allowed at this property.

How much is parking at Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21?

On-site parking is available at the property.

What time is check-in at Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21?

Check-in begins at 4:00 PM.

What time is check-out at Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21?

Checkout is at 10:00 AM.

Where is Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21 located?

Located in Old Town Key West, this holiday home is within a 10-minute walk of The Kite House and Duval Street. Florida Keys Beaches and Mallory Square are also within 15 minutes.

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. 5 out of 8 reviews
Rating 8 - Good. 2 out of 8 reviews
Rating 6 - Okay. 1 out of 8 reviews
Rating 4 - Poor. 0 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

9.6/10

Cleanliness

10/10

Check-in

9.4/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A beautiful old home. We love homes with lots of character and charm. This is the perfect house for just that! The guest house was the perfect addition for our bigger kids to stay and have their own space. As a big family this property was perfect, right next to all the shops and restaurants and lots of space to hang out and relax indoor when needed.
Stayed 7 nights in Aug 2026
Response from VrboOwner on 28 Aug 2026
Thank you so much for your wonderful review, Thea! We’re thrilled to hear you and your family enjoyed the character and charm of the home, and the guest house gave your bigger kids the perfect space of their own. We’re especially happy you found the location convenient and you had enough space for everyone to relax and enjoy your time together. It was a pleasure hosting your family, and we look forward to welcoming you back to the island!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect get away for a 40th birthday trip. Place could not have been better
Stayed 4 nights in Aug 2025
Response from VrboOwner on 7 Jan 2026
Hello David,Thank you so much! We’re thrilled the place was perfect for your 40th birthday getaway. We’d love to welcome you back anytime for another special trip!
Verified review

10/10 Excellent

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

Wedding in Key West

We all wanted to stay together for a family wedding. It’s difficult to find a place to fit everyone. The home has a lot of historical charm, plenty of bedrooms and is convenient to downtown. Would definitely stay there again.
Stayed 4 nights in Nov 2024
Response from VrboOwner on 1 Dec 2024
Thank you Marianne! We're so glad to hear that the home had everything you needed to support your large family group. Congratulations on the wedding and we hope to see you again in the future. - VHKW
Verified review

10/10 Excellent

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

Amazing Experience

This beautiful property was perfect for a girls weekend! We were able to all meet in the mornings for coffee in the main house but still have privacy when needed! The location was perfect for walking to dinner and shopping. Look forward to staying here again for our next girls trip! Thank you!
Stayed 3 nights in Dec 2024
Response from VrboOwner on 18 Dec 2024
We're ecstatic to hear the Key West girls trip was a success and that you enjoyed all our home had to offer! Thank you for staying with and for taking the time to leave such a kind review. If you're ever back in the area we hope to host your group again! Best, VHKW
Verified review

8/10 Good

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

Fun Family getaway with 17 guests

We loved the property! The 3 houses (2 cottages and one large house) made it so we could have privacy and be super close with our large family group. Its super close to everything we wanted to do! Parking was 2 blocks away, so plan ahead, but its doable. The pool is smaller but deep, and the kids had a blast. The outdoor shower and bath tubs were really fun. The kitchen had two leaks, but the staff was quick to talk with and fix them, so they didn't affect our trip. We had a miscommunication about late check out that left a bad taste, but that was the only down side. Overall, we had a great time, and with 17 guests, we had plenty of space.
Stayed 8 nights in Jan 2024
Response from VrboOwner on 16 Jan 2024
Thank you for the nice review, Karen. We are glad that you and your family enjoyed your trip and we hope to have the opportunity to host you again in the future. VHKW
Verified review

6/10 Okay

Liked: Cleanliness, check-in, communication, location

Good…mostly

A beautiful property with awesome accommodations in a great location. We had a large family group stay here and had a good time overall. BUT, for paying as much as we did, the details were lacking. Over the course of the week, uncovered problems included: a shower door was missing parts and a doorknob had fallen off. The house iPad didn’t work, the WiFi didn’t work upstairs, a cabinet door was broken in the cottage, and the fridge water dispenser was very moldy. A fire alarm of some sort was beeping in the attic ALL DAY AND NIGHT and the cottage had no hot water whatsoever. Luckily one of our members has a background in property maintenance and with the great help of the management company, they talked us through fixing the hot water. I understand these things happen, but was told that these are a recurring set of complaints. Thus, the owner has failed to fix reported problems. This is what I had issue with. You could tell that problems had been neglected for some time now for this many to stack up. Nobody showed up to fix the issues, so I had to reset the water heater breaker multiple times a day for the remainder of the week to avoid cold showers for our family. So once again, a beautiful place. But for 20k, not nearly as kept as it should have been.
Stayed 7 nights in Mar 2024
Response from VrboOwner on 16 Jan 2025
Thank you so much for taking the time to leave a thorough, detailed review of your stay with us Jana. We truly appreciate your time and feedback as we are continuously trying to improve for future guests. It was an honor hosting you and we hope you had safe travels back home! Best, VHKW
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 4 nights in Jun 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Jan 2025
Response from VrboOwner on 20 Mar 2025
Thank you so much for staying with us and for taking the time to leave a review. It was a pleasure hosting you and we hope to have the chance to host you again sometime soon. Best, VHKW
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