Entire home

Old Town Retreat near Upper Duval St

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A spacious living area with a large sectional sofa, a coffee table, and wicker furniture.
A bedroom with a four-poster bed, a ceiling fan, and a nightstand with a lamp.
A covered outdoor area with a pool, a dining table, and a seating area.
A kitchen with white cabinets, a granite countertop, a stainless steel sink, a Keurig coffee maker, and a microwave.
A modern kitchen with granite countertops, wooden stools, and a large island.

Reviews

10 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Onsite parking available
    Convenient and secure onsite parking, a rare amenity in the area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Duval Street

Popular amenities

  • Balcony or patio
  • Private pool
  • Kitchenette
  • Barbecue grill
  • Air conditioning
  • Off-street parking available

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪1 min walk‬
  • Place, South Beach
    ‪3 min walk‬
  • Place, Southernmost Point
    ‪5 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪9 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 2

1 King Bed

Bedroom 3 Cottage Suite First Floor

1 King Bed

Bedroom 4 Cottage Suite Second Floor

1 Queen Bed

Main Bedroom

1 King Bed

4 bathrooms

Bath 2

Bath 3 Ensuite

Bath 4 Ensuite

Main Bath Ensuite

Spaces

Deck or patio
Porch or lanai
Kitchen
Kitchenette
Balcony

Add dates for prices

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About the neighborhood

Key West

Located by the sea, this vacation home is in Old Town Key West, a neighborhood in Key West. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Key West Butterfly and Nature Conservatory and Florida Keys Eco - Discovery Center are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking/biking trails and cycling.
View more Vacation Homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Duval Street - 1 min walk - 0.0 km
  • South Beach - 3 min walk - 0.3 km
  • Key West Butterfly and Nature Conservatory - 3 min walk - 0.3 km
  • Ernest Hemingway Home and Museum - 4 min walk - 0.4 km
  • Southernmost Point - 5 min walk - 0.4 km

Getting around

  • Key West Intl. Airport (EYW) - 9 min drive

Restaurants

  • ‪Circle K - ‬2 min walk
  • ‪Cuban Coffee Queen (Duval) - ‬1 min walk
  • ‪Southernmost Point Bar in the USA - ‬3 min walk
  • ‪Southernmost Beach Café - ‬3 min walk
  • ‪Banana Cafe - ‬1 min walk

Frequently asked questions

Does Old Town Retreat near Upper Duval St have a pool?

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

How much does it cost to stay at Old Town Retreat near Upper Duval St?

As of Nov 3, 2026, prices found for a 1-night stay for 2 adults at Old Town Retreat near Upper Duval St on Nov 14, 2026 start from $1,351, 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 Retreat near Upper Duval St pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Old Town Retreat near Upper Duval St?

Check-in begins at 4:00 PM.

What time is check-out at Old Town Retreat near Upper Duval St?

Check-out is at 10:00 AM.

Where is Old Town Retreat near Upper Duval St located?

Located in Old Town Key West, this vacation home is steps from City Zoo Gallery and Duval Street. Florida Keys Beaches and South Beach are also within 5 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 78 out of 86 reviews
Rating 8 - Good. 8 out of 86 reviews
Rating 6 - Okay. 0 out of 86 reviews
Rating 4 - Poor. 0 out of 86 reviews
Rating 2 - Terrible. 0 out of 86 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing location!
Stayed 4 nights in Sep 2026
Response from VrboOwner on Sep 29, 2026
Thank you so much for the kind words! We're thrilled you enjoyed the location, it's truly one of the best features of the property. We'd love to welcome you back anytime. Thanks for staying with us!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect house for a small group! The space was very clean and comfortable. Management was very attentive and prompt. Would recommend this vrbo!
Stayed 4 nights in Oct 2026
Response from VrboOwner on Oct 6, 2026
Thank you so much for the wonderful review! We're thrilled you had a great stay and that your group enjoyed the space. Your kind words about our cleanliness and responsiveness truly mean the world to us. We'd love to welcome you back anytime, and we really appreciate you recommending us to others. Thanks for being such a pleasure to work with!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Really great space and location for our extended family. Easy to walk to all the must do/see in Key West. The pool was a perfect afternoon break!!
Stayed 4 nights in Jun 2026
Response from VrboOwner on Jul 10, 2026
Thank you so much for the wonderful review! We're thrilled you and your family had such a fantastic stay. The location really is perfect for exploring everything Key West has to offer, and we're so glad the pool provided a nice retreat during your visit. We'd absolutely love to welcome you back next time you're in town!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Accommodations were excellent . Perfect location.
Stayed 6 nights in Apr 2026
Response from VrboOwner on May 2, 2026
We're thrilled you enjoyed your stay Salvatore! Being in such a perfect location makes exploring the island so much easier, and we're glad the accommodations were everything you needed for a great trip. Thank you for staying with us!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing property! The host was very responsive and we loved the setup with the two separate buildings and outdoor patio/pool in the middle. It gave everyone space if they wanted to unwind alone with enough shared space for all 7 of us to hangout together.
Stayed 6 nights in Jun 2026
Response from VrboOwner on Jun 17, 2026
We are so glad to here that you enjoyed your stay with us Megan! Casa Caribe is such a perfect layout for big groups so I'm glad to hear it worked so well for your trip. We hope to see you again sometime soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home was very clean, pool was great, bathrooms were little tight, location was excellent!!
Stayed 5 nights in Mar 2026
Response from VrboOwner on Mar 23, 2026
Thank you for the wonderful review! We are so glad you enjoyed the pool and our excellent location, it really is the best way to experience Key West. We appreciate the feedback on the bathrooms; while our historic cottage layout is cozy, we strive to make every inch as comfortable as possible. We’re thrilled you had a clean and relaxing stay and would love to host you again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved the house! Perfect for our group!!
Stayed 3 nights in Mar 2026
Response from VrboOwner on Mar 25, 2026
We are so happy to hear the house was perfect for your group! We love hosting larger families and groups, and we're thrilled you found the space and layout to be just what you needed for a great Key West getaway. We’d love to welcome you all back again soon!
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
The main house was excellent. The pool was very nice, but we had to dodge some falling palm leaves. One of the lights fell out of the ceiling while we were staying there. The upstairs in the cottage was very hot and humid, despite using the air conditioner and dehumidifier. There were bugs in the upstairs room of the cottage as well. Beds were very firm. Overall it was in a great location with a great outdoor space.
Stayed 6 nights in May 2026
Response from VrboOwner on Jun 4, 2026
We love hearing that you enjoyed the main house and our great outdoor space! Thank you for staying with us and for the helpful heads-up about the cottage upstairs and the light. You're welcome back to our island retreat anytime!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location. Plenty of things to do in walking distance!
Stayed 4 nights in Nov 2025
Response from VrboOwner on Nov 16, 2025
Hello Emily, thank you for the 5star review! We're glad you enjoyed the location and all the nearby activities. We’d love to host you again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A very comfortable and well designed unit right off Duval street in the heart of Key West.Lovely little pool. 2 of the bed/room bathroom units are in an adjacent building which would provide a bit of privacy if traveling in a group.Highly recommend
Stayed 6 nights in Feb 2026
Response from VrboOwner on Mar 7, 2026
Thank you for the fantastic review! We are so glad you enjoyed the 'comfort meets design' vibe of the home. You hit on one of our favorite features, the layout with the adjacent building units is absolutely perfect for providing that extra layer of privacy while still keeping everyone together in the heart of Old Town. We’re also happy you enjoyed the pool, it’s our favorite little oasis just steps from the Duval action. Thank you for the high recommendation, and we can’t wait to host your group again!
Verified review

10/10 Excellent

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

Super location and wonderful place!

Roomy enough for everyone to be comfortable and the location was fantastic! Hope to come back!!
Stayed 5 nights in Dec 2022
Response from VrboOwner on Dec 21, 2022
Thank you for your Five Star review of Casa Caribe Key West. We are so glad that you enjoyed the house and its fantastic, convenient old town location. We hope to welcome you back soon!
Verified review

10/10 Excellent

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

Great place

Beautiful place. It has 4 bedrooms and 4 bathrooms, so perfect for our group of 4 couples. Feet away from Duval Street. It is a perfect place to stay.
Stayed 7 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We very much enjoyed our time at this lovely property! The entire house was clean, a pool service came to maintain the pool during our stay and there were many suggestions for restaurants for kid friendly stops! We loved the outdoor space. We were also steps away from Duval. Overall, so happy with the stay, the home and our host!
Stayed 5 nights in Sep 2025
Response from VrboOwner on Sep 27, 2025
Thank you so much for your wonderful 5 star review! We’re thrilled you enjoyed the home, pool, and location. We’re so glad you loved the outdoor area and had a great family stay. We’d be delighted to host you again anytime!
Verified review

10/10 Excellent

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

Key West

Great property in a terrific location. Comfortable and convenient base for visiting Key West and Dry Tortugas. We had a great time and would stay again.
Stayed 6 nights in Oct 2023
Response from VrboOwner on Oct 22, 2023
We are happy to hear that our condo met your needs and that you will stay with us again!
Verified review

10/10 Excellent

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

Great Location

We thoroughly enjoyed our stay. The house is great and super comfortable. The pool and patio are delightful. The location is great - close enough to walk to everything but away from all the hustle and bustle.
Stayed 3 nights in Mar 2023
Response from VrboOwner on Mar 18, 2023
Thank you for your Five Star review of Casa Caribe Key West. We are delighted that you enjoyed the house, pool and the convenient location. We look forward to welcoming you back again soon!
Verified review

10/10 Excellent

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

Great for 4 couples

We loved having two houses and the central private pool area.
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

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

Casa Caribe

Property was very clean and management was accommodating.
Stayed 7 nights in Aug 2024
Verified review

8/10 Good

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

Great Place

We had a group of 8 people and there was plenty of room for everyone. Great location 1/2 block from Duval at the quiet end.
Stayed 5 nights in Dec 2023
Verified review

10/10 Excellent

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

Key West Getaway

Property was in a perfect location! We loved every minute of our stay ! Plenty of room and extremely clean!! Wonderful experience!!
Stayed 4 nights in Aug 2023
Response from VrboOwner on Aug 22, 2023
Thank you for your Five Star review of Casa Caribe Key West. We are delighted that you enjoyed the house and its perfect location. We look forward to welcoming you back for another wonderful experience!
Verified review

10/10 Excellent

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

Key West Get Together

Great location. Nice bedrooms with plenty of bathrooms. Pool was perfect. No complaints. And Key West was a blast!
Stayed 5 nights in Jan 2025
Response from VrboOwner on Jan 15, 2025
Thank you for your kind words! We're so glad you enjoyed the location, bedrooms, and pool. We're happy to hear you had a blast in Key West and hope to host you again soon!
Verified review

10/10 Excellent

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

High School Graduation Get Away

The property is beautiful and was perfect for our family. My daughters loved the house and we enjoyed our first trip to Key West!
Stayed 7 nights in Jun 2022
Response from VrboOwner on Jun 27, 2022
Thank you for your Five Star review of Casa Caribe! We are so glad that you loved the house and your first trip to Key West. We hope to welcome you back soon!
Verified review

10/10 Excellent

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

Stay

Great location and setup
Stayed 3 nights in Mar 2024
Verified review

10/10 Excellent

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

Great Spot

Great location. Great house. Comfortable beds. The property managers were awesome to deal with. Highly recommend this house!
Stayed 5 nights in May 2023
Response from VrboOwner on May 16, 2023
Thank you for your Five Star review of Casa Caribe Key West. We are so glad that you enjoyed the house, its great location and your interactions with our team. We greatly appreciate your recommendation and look forward to welcome you back again soon!
Verified review

10/10 Excellent

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

Second time here.

Everything was great again & hoping to stay again in the future.
Stayed 5 nights in Jan 2025
Response from VrboOwner on Jan 12, 2025
Thank you for the wonderful feedback! We're so glad everything was great again, and we’d love to have you stay with us in the future!
Verified review

10/10 Excellent

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

Great location!

Great location, nice outdoor “hangout” area. Perfect for 4 couples because each couple had their own bathroom. Only feedback I would give is add a memory foam to the beds (just a tad hard). Had a wonderful vacation!
Stayed 6 nights in Sep 2023
Response from VrboOwner on Oct 8, 2023
Thank you for your Five Star review of Casa Caribe Key West. We are delighted that you enjoyed the house and its great location. We appreciate your feedback and we look forward to welcoming you back for another wonderful vacation!
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