Entire home

Contra House - Private Pool & Steps to Duval Street

Photo gallery for Contra House - Private Pool & Steps to Duval Street

Private Pool
Private Pool
Building Overview
Front House - Patio
Front House - Patio - Alt View

Reviews

9.6 out of 10
Exceptional
4 bedrooms4 bathroomsSleeps 12226.8 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space

Explore the area

View map
Naval Air Station Key West, FL
  • Place, Duval Street
    ‪2 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪5 min walk‬
  • Place, Southernmost Point
    ‪12 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪13 min drive‬

Rooms & beds

4 bedrooms (sleeps 12)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

1 Queen Bed

Living Room 1

1 Double Sofa Bed

Living Room 2

1 Double Sofa Bed

4 bathrooms

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Office
Balcony
Garden
Dining area

About this property

Contra House - Private Pool & Steps to Duval Street

Summary:

This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. Just one block from Duval Street in a highly sought-after location, Contra House is a must-see and must-stay in downtown Key West. With an amazing pool, Contra House is comprised of two one-of-a-kind homes, each with two bedrooms and two bathrooms.



The Space:

The galley kitchen in the front house has all of your essentials along with a wine cooler!



The back house has a state-of-the-art, open concept living area that is bright and airy as the back sliding doors open up the private pool area. The gourmet kitchen includes a wine cooler and spacious countertops for all of your backyard barbecuing and delicious dinners!



Splitting the two homes is a heated in-ground pool with seating. Along with the pool you can find a grill and plenty of backyard entertaining space.



The bed layout is as follows:

Front House sleeps up to 6 guests:

Bedroom 1: Queen (on first floor with shared bathroom access)

Bedroom 2: King (on second floor with en-suite bathroom)

Extra Sleeping: queen pull out couch in living room



Back House sleeps up to 6 guests:

Bedroom 1: King (with en-suite bathroom)

Bedroom 2: King (with shared bathroom access)

Extra Sleeping: Queen pullout couch in living room



Guest Access:

Our contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to check-in to enter the unit.



The Neighborhood:

On the southern end of town, in one of the most desirable locations, the Contra House is just 1 block from Duval Street. It's easily less than a mile from the beach and walking distance to locals' favorite restaurants such as Banana Cafe, Blue Heaven Lolas Bistro and Old Town Tavern.



Getting Around:

Parking Information: Two off-street parking spots are included with your stay. If you need additional parking, there are spots along Simonton Street. The other spaces are for neighboring properties.

We can provide you with recommendations for parking additional vehicles upon request!



There are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance.



Other Things to Note:

​​- Contra House features a private washer/dryer in both the front & back house.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

Events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
• Damages to the property or additional cleaning due to excessive mess are subject to charges.

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
Parties and events are allowed on site
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the area

Key West

Located by the sea, this holiday home is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. The Kite House and Key West Butterfly and Nature Conservatory are also worth visiting. Fishing offers a great chance to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
Map
Naval Air Station Key West, FL

What's nearby

  • Duval Street - 2 min walk - 0.2 km
  • Ernest Hemingway Home and Museum - 5 min walk - 0.4 km
  • Key West Lighthouse and Keeper's Quarters Museum - 5 min walk - 0.4 km
  • South Beach - 11 min walk - 0.9 km
  • Southernmost Point - 12 min walk - 1.1 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 10 min drive

Restaurants

  • ‪Bourbon Street Pub - ‬4 min walk
  • ‪801 Bourbon Bar - ‬3 min walk
  • ‪Mangoes Restaurant - ‬3 min walk
  • ‪Old Town Tavern - ‬5 min walk
  • ‪Kaya Island Eats - ‬3 min walk

Frequently asked questions

Does Contra House - Private Pool & Steps to Duval Street have a pool?

Yes, this property has a pool.

How much does it cost to stay at Contra House - Private Pool & Steps to Duval Street?

As of 10 April 2026, prices found for a 1-night stay for 2 adults at Contra House - Private Pool & Steps to Duval Street on 27 June 2026 start from NZ$2,977, 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 Contra House - Private Pool & Steps to Duval Street pet-friendly?

No, pets are not allowed at this property.

How much is parking at Contra House - Private Pool & Steps to Duval Street?

On-site parking is available at the property.

What time is check-in at Contra House - Private Pool & Steps to Duval Street?

Check-in begins at 4:00 PM.

What time is check-out at Contra House - Private Pool & Steps to Duval Street?

Checkout is at 10:00 AM.

Where is Contra House - Private Pool & Steps to Duval Street located?

Located in Old Town Key West, this holiday home is within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum. Florida Keys Beaches and South Beach are also within 15 minutes.

Reviews

9.6

Exceptional

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. 22 out of 26 reviews
Rating 8 - Good. 2 out of 26 reviews
Rating 6 - Okay. 2 out of 26 reviews
Rating 4 - Poor. 0 out of 26 reviews
Rating 2 - Terrible. 0 out of 26 reviews

9.6/10

Cleanliness

8.0/10

Amenities

8.0/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

James P.

Liked: Cleanliness, check-in, communication, listing accuracy
Great location!!
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Cina P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house and close to everything.
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

tracy m.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This place was amazing!! The only downside was the Jacuzzi was almost empty
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

John Martin B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing house and location! The hot tub and pool were heated to the perfect temps. We had an absolute blast! If anything, the pictures do not do the house and yard justice. There are lots of indoor/outdoor places to relax and gather and the bedrooms/bathrooms are very spacious.
Stayed 3 nights in Feb 2026
Verified

6/10 Okay

Tom H.

Liked: Location
Disliked: Listing accuracy
Experience was disappointing. Location was as promised. Host did respond following multiple requests.
Stayed 5 nights in Mar 2026
Verified

10/10 Excellent

Travis L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Property inside was nice. Lights outside need to be fixed and there needs to be better pool furniture
Stayed 7 nights in Dec 2025
Response from VrboOwner on 9 February 2026
Hi Travis, we took care of the things noted. Hope you enjoyed your stay overall! Kind regards, Brightwild
Verified

10/10 Excellent

Pamela

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

Exceptional Location

It is a beautiful compound. Clean and spacious. The center grounds with the pool are lovely! Nicely situated near Duvall St. I have recommended this property to friends.
Stayed 3 nights in Jan 2025
Verified

10/10 Excellent

James P.

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

Great location

The house is a great location.
Stayed 2 nights in Mar 2024
Response from VrboOwner on 18 April 2024
Hi James, thanks for the review!
Verified

10/10 Excellent

Doug L.

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

Extended Weekend - First time in Key West

Attended a wedding in Marathon and decided to explore Key West with some old friends for the weekend! House was close to everything but far enough away to still be quiet and safe!
Stayed 2 nights in Mar 2025
Response from VrboOwner on 20 August 2025
Thank you for your wonderful review! We’re thrilled to hear that you enjoyed your first visit to Key West and found the house both conveniently located and peaceful. It’s great that you were able to explore the area with friends while feeling safe and comfortable. We look forward to welcoming you back for another memorable stay!
Verified

10/10 Excellent

Kurt F.

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

Key West

Great house. 2nd time staying. Will stay there again
Stayed 4 nights in Jan 2025
Response from VrboOwner on 28 January 2025
Thank you for your loyal support and great review! We’re so happy to hear that you enjoyed your second stay with us. We can’t wait to welcome you back for a third time!
Verified

10/10 Excellent

Eric C.

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

Great location

Fantastic property
Stayed 2 nights in Mar 2023
Response from VrboOwner on 13 September 2023
We love this property! So happy you got to enjoy it Eric! We hope to host you again! Sara Brightwild
Verified

10/10 Excellent

Spencer C.

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

Boys Trip

This place was amazing! Location location location. We had a big group, all slept comfortably, and can't wait to go back again
Stayed 2 nights in Jan 2025
Response from VrboOwner on 22 February 2025
Thank you so much Spencer! We're thrilled to hear your group was comfortable and that you loved the location. We'd be happy to host you again anytime—can't wait to welcome you back!
Verified

10/10 Excellent

Charles "Chris" A.

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

Nice place

Nice place in a good part of town
Stayed 3 nights in Jun 2024
Response from VrboOwner on 20 August 2024
Hi Charles, thanks for the review! I'm glad you enjoyed your experience with us! We hope to host you again soon:)
Verified

10/10 Excellent

Mike F.

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

Business trip

Location is fantastic….the pictures don’t do the property justice….walking distance to everything and host was fantastic and extremely responsive….
Stayed 4 nights in Feb 2025
Response from VrboOwner on 23 February 2025
We’re so happy you loved the location and found the property even better than expected! Thank you for your kind words about our team—we truly appreciate it. Hope to host you again soon!
Verified

10/10 Excellent

Sean M.

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

Great house

Best location and property
Stayed 2 nights in Dec 2022
Response from VrboOwner on 13 September 2023
Thanks so much for the awesome review Sean! Our team appreciates hosting great guests such as yourself.
Verified

10/10 Excellent

Alejandro S.

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

Perfect Stay

Fantastic accommodations and customer service made my 25th birthday trip with friends unforgettable! Thank you BrightWild team!!
Stayed 2 nights in Aug 2023
Response from VrboOwner on 7 October 2023
Thank you for your positive feedback! We appreciate your kind words and communication with us! Come back again anytime!
Verified

10/10 Excellent

Dale K.

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

LOVED IT

Great property Super Secluded for being in Key West
Stayed 4 nights in Dec 2022
Response from VrboOwner on 13 September 2023
Thank you so much for the great review Dale! I am so pleased to hear that you enjoyed your stay with us and I hope we get the chance to host you again in the future! Cheers!
Verified

10/10 Excellent

Mark Q.

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

Mark Quayle

Amazing home. Perfect spot for everything and very quiet.
Stayed 3 nights in Mar 2024
Verified

10/10 Excellent

Christopher K.

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

A wonderful modern villa in a great location

my 9 friends and I loved staying at this property over the weekend. The location couldn't be better with a very short walk to Duval street and a central location on the island. The home fit us easily with large beds and spacious rooms. The check in process was easy and the host was very kind, responsive and easy to communicate with. All around great property I would recommend to anyone.
Stayed 2 nights in Oct 2023
Response from VrboOwner on 15 November 2023
Thank you for your review! We are happy to hear you enjoyed our location! You’re welcome back anytime!
Verified

10/10 Excellent

pAEcd0Lr3O2ECPWffSl2fK29sG1pXlAFYrxOI2htvZ/iKlCiUceUtAAAAcDBuBgkqhkiG9w0BBwagYTBfAgEAMFoGCSqGSIb3DQE y.

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

Amazing

Our host was the best, we rent thru VRBO all the time and we could not have asked for a better experience. It was like arriving at our own key west vaca home. The location is perfect, the house was immaculate and price is reasonable. We will stay here every time we go down south! Thank you for everything,
Stayed 3 nights in Nov 2022
Response from VrboOwner on 13 September 2023
Fernanda, thank you so much for the kind review! I'm so happy to hear that you enjoyed your stay with us for your daughters 16th birthday. All of our hosts love hosting such awesome guests and we hope to host you again in the future. Cheers! One of One, Hannah
Verified

10/10 Excellent

Hunter H.

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

July 2023

A+ Old Town location, cool house, great A/C, pool was clean, host was super responsive and the house is all yours.
Stayed 4 nights in Jul 2023
Response from VrboOwner on 13 September 2023
Thank you for your review! We are happy you enjoyed our location! You're welcome back anytime! Isa Brightwild
Verified

10/10 Excellent

Shannon S.

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

Vacay 2022

Beautiful, Roomy, and Clean. Loved the communication that was given! They go above and beyond to help in any way possible. I truly appreciate the hospitality that was given by everyone!
Stayed 4 nights in Nov 2022
Response from VrboOwner on 13 September 2023
Shannon, it was so nice to meet you! Thank you so much for your review. We are so happy you enjoyed your stay. We hope to host you again! Best, Sara, One of One Stays
Verified

8/10 Good

Traci

Liked: Cleanliness, amenities, property conditions & facilities, communication
The pool area needed ALOT of attention!!! It was a hot mess and the patio chairs need replaced or freshened up .
Stayed 4 nights in Feb 2024
Verified

6/10 Okay

Dawn A.

Liked: Check-in, communication, location
Disliked: Listing accuracy

Weekend stay

The photos online showed a hot tub, but it is not. They told us it wasn’t advertised as a hot tub but the photos made us believe it was a hot tub. Also the kitchen had several leaks, lots of water everyday in the kitchen. We called and they came and cleaned it but it continued to leak, we believe it was coming from the ice machine. No kitchen towels, no rugs by the doors and it was raining so not only did the floor get wet but muddy as well. The sink in the master bathroom barely ran and there was no hot water. We were disappointed in the quality of the home. Also suggest you leave more than 1 extra garbage bag. We had a good time but would not rent this home again
Stayed 3 nights in Jan 2023
Response from VrboOwner on 13 September 2023
Thank you for the insightful review Dawn! The dipping pool is not a hot tub and is never advertised as a hot tub, so there are no photos online of a hot tub. It is clearly described as a dipping pool. We apologize that the few mats we had in the homes were not enough rugs for your stay, but I am happy that we were able to purchase them and deliver them to the home for you during your stay! Typically, our guests just remove their shoes at the door so the floors throughout the home don't get dirty. The hot water was coming in at 98 degrees upon our maintenance team checking. Our team thought an extra trash bag in each kitchen would have been enough for your 3 day stay, but we were happy to deliver you more when you asked. I am happy to hear that you had a good time however!
Verified

10/10 Excellent

Bridgett S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Mar 2025
Response from VrboOwner on 20 August 2025
Thank you so much for your perfect 10/10 review! We’re thrilled to hear that you had such a positive experience and truly enjoyed your stay with us. Providing a comfortable and memorable stay is always our goal, and it’s wonderful to know we met your expectations. We sincerely appreciate your feedback and look forward to welcoming you back for another excellent stay in the future!

About the host

Hosted by Brightwild

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Premier Host

They consistently provide great experiences for their guests
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