HEMINGWAY'S HIDEOUT ~ Historic Old Town Cottage with Pool!

Photo gallery for HEMINGWAY'S HIDEOUT ~ Historic Old Town Cottage with Pool!

A modern kitchen with white cabinetry, a central island, and a built-in refrigerator.
A poolside area with a table and chairs, a washing machine, and lush tropical plants.
A modern kitchen with a large island, white cabinetry, and a view of a pool.
A white house with a green roof, a white picket fence, and a gravel driveway.
A backyard with a swimming pool, a barbecue area, and outdoor seating.

Reviews

9.2 out of 10
Wonderful

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • 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
    Close to Duval Street

Popular amenities

  • Patio
  • Private pool
  • Waterpark access
  • Barbecue grill
  • Air-conditioning
  • Pet-friendly

Explore the area

View in a map
Key West, FL
  • Place, Ernest Hemingway Home and Museum
    ‪12 min walk‬
  • Place, South Beach
    ‪12 min walk‬
  • Place, Southernmost Point
    ‪14 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪8 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Garden

Add dates for prices

Similar properties

private pool with waterfall feature
MONTHLY RENTAL, 1 block to Duval, POOL, personal resort, 3/3, pets OK
Bahama Village
  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
10.0 out of 10, Exceptional, (21 reviews)
MONTHLY RENTAL, 1 block to Duval, POOL, personal resort, 3/3, pets OK

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. Key West Butterfly and Nature Conservatory and The Kite House are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby.
View more Holiday homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Duval Street - 9 min walk - 0.8 km
  • Clarence S. Higgs Memorial Beach Park - 11 min walk - 0.9 km
  • Ernest Hemingway Home and Museum - 12 min walk - 1.0 km
  • South Beach - 12 min walk - 1.1 km
  • Southernmost Point - 14 min walk - 1.2 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 8 min drive

Restaurants

  • ‪Circle K - ‬10 min walk
  • ‪Sandy's Café - ‬5 min walk
  • ‪El Siboney Restaurant - ‬2 min walk
  • ‪Tipsy Rooster - ‬10 min walk
  • ‪Better Than Sex - ‬8 min walk

Frequently asked questions

Is HEMINGWAY'S HIDEOUT ~ Historic Old Town Cottage with Pool! pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at HEMINGWAY'S HIDEOUT ~ Historic Old Town Cottage with Pool!?

Check-in begins at 4:00 PM.

What time is check-out at HEMINGWAY'S HIDEOUT ~ Historic Old Town Cottage with Pool!?

Checkout is at 10:00 AM.

Where is HEMINGWAY'S HIDEOUT ~ Historic Old Town Cottage with Pool! located?

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

Reviews

9.2

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. 9 out of 12 reviews
Rating 8 - Good. 2 out of 12 reviews
Rating 6 - Okay. 0 out of 12 reviews
Rating 4 - Poor. 1 out of 12 reviews
Rating 2 - Terrible. 0 out of 12 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

9.6/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Great place to stay

Property is close to everything one needs: grocery, dining, beaches, and bars. Property managers, Whitney and Shana, were very attentive and responsive.
Stayed 30 nights in Dec 2024
From a partner site

10/10 Excellent

Great vacation rental

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Adorable little house
Response from VrboOwner on 5 Mar 2024
Thank you for this short & sweet five star review Susan, we hope to have the pleasure to host you again next time you visit the island.
Verified review

10/10 Excellent

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

Just Another Day in Paradise!!

I can't say enough about this property. My daughter and I stayed just about 3 months and it was absolutely wonderful! When we had to leave, I left a little piece of me there. I will miss Hemingway's Hideout!! You will not regret staying in this amazing little home.
Stayed 83 nights in Aug 2019
Response from VrboOwner on 21 Mar 2020
Dear Lorie, Thank you for your wonderful review. We are so happy you loved this home and hope to see you back again. Best Regards, Wendy Zintsmaster and Team
From a partner site

10/10 Excellent

Wonderful month!!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This cottage was small but very comfortable. From the outdoors to well appointed bedrooms and kitchen. The days by the private pool were delightful as we knew it was very windy on beach. Santiago and nine one five were two favorite resturants. Bicycles were a plus but walked easily as well.
Response from VrboOwner on 3 Apr 2025
We are delighted to read your wonderful review Linda. We hope to host you again soon and welcome you back to Key West.
From a partner site

8/10 Good

February Stay in Key West

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was more than happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: In general, we enjoyed our stay at this property (our 4th monthly rental in KW). Pluses: (1) property management - Whitney was very responsive; (2) location - we like this area of KW; (3) bikes (although they need lights for riding at night); (4) great back deck with vegetation and shaded places to relax. Not so good: (1) for half our stay the pool was too dirty to use; (2) limited, not-so-comfortable seating in the living/kitchen area; (3) appliances are old and there is no kitchen vent over the stove.
Response from VrboOwner on 7 Mar 2023
Thank you for your feedback on your recent stay Ava. We are so glad that you enjoyed your time spent at this home. We appreciate your feedback about the seating + applicances that we will relay back to the owners for consideration. As for the pool, it gets professionally cleaned weekly but the lush vegetations finds its way into the pool really quickly on a windy day and most of our guests use the provided skimmer to get the leaves out before swimming. We hope you understand we cannot provide pool cleaning every day like a resort would. Thank you again and please reach out to us for your next Key West vacation!
From a partner site

10/10 Excellent

Wonderful place,great customer service

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The property lived up to it’s online description and then some. Very comfortable, nicely furnished, and very nice well equipped. Having two bikes included was a much appreciated added feature. The rental agency’s customer service was five star outstanding. Whitney, our manager, responded to every question or concern we had immediately, and made sure it was resolved. We would not hesitate to return.
Response from VrboOwner on 22 May 2022
Thank you for your fantastic review Ken. It was a pleasure hosting you and we hope to welcome you again next time you visit the island!
From a partner site

10/10 Excellent

Key West Feb.2022

Rating Details: The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: From end to start it was a pleasure to work with this company.The house is small but perfect for two people, great location in a quiet and quaint neighborhood. Pool was lovely, kitchen had everything you needed and beds were comfortable. Having the bikes was an extra bonus. We absolutely loved it and will be back!
Stayed 28 nights in Feb 2022
Response from VrboOwner on 5 Mar 2022
Thank you for your wonderful review Bjorn. We enjoyed hosting you and look forward to welcoming you back in Key West again soon!
Verified review

10/10 Excellent

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

Great month in Key West

We loved this house and would love to rent it again. We spent most of our time poolside. Whitney was very helpful and responded quickly to any questions we had. Location is great and neighborhood was quiet.
Stayed 30 nights in Oct 2021
Response from VrboOwner on 19 Nov 2021
Thank you for taking the time you review your stay John, we are glad you enjoyed the property and hope to welcome you again in the future!
Verified review

8/10 Good

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

Cozy House but needs work

We stayed in the house for the month of July. The location is good. You have easy access to the major roads and the street is quiet. The management company is very attentive. Upon entering we were a bit disappointed with the overall state of the house for the money we paid. The walls need to be repainted, the closet situation in the first bedroom looks like the door fell off so they just put up a cheap curtain, there is a huge gap in the doorframe of the front door of the home, the mirrors were hung upside down. It felt like there was not much attention to detail. The rooms were cozy enough but it is a space better suited for 2 or 3 people. The outside pool is lovely but there is quite a bit of mold in the corners and the last renters that commented about the trash being around the back yard are correct. I think the deck and awning were brand new as they are in great shape but the outside furniture needs to be replaced (particularly the lounge chairs). The beds were comfortable and we were provided plenty of linens. I will say there was a grill and the use of two bikes which we didn’t know before we got there and were a great addition to our stay. The kitchen is packed with everything you can need as far as equipment. Again, it’s just they little things and when you are paying nearly $7k for a month, it feels like they add up. Again, it’s a solid rental but it can be made so much better with a bit of upkeep.
Stayed 28 nights in Jul 2021
Response from VrboOwner on 16 Nov 2021
Thank you for taking the time to review your stay. The window that you mentioned has been fixed. The home's furniture is in good condition and appears just as marketed in the description and photos on the listing. We are unaware of the trash you mentioned as the entire underside of the home was previously cleaned prior to your visit. The pool is serviced and cleaned weekly as you mentioned and bikes are marketed with the home and mentioned in the guest manual. We appreciate your feedback and hope your stay was otherwise very enjoyable!
From a partner site

4/10 Poor

Disappointed

Rating Details: The property manager was very helpful. The vacation rental was clean. I was more than happy with the location. I was very dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: First, Melanie and the crew that support this house are among the best we’ve experienced. The house is another matter. It is extremely small and uncomfortable for a monthly rental. There is ONE piece of furniture to sit on (an uncomfortable couch) and four very uncomfortable stools around an island. The bedrooms are ok, but the social/living space on this house is one small room that includes the kitchen. And the pool area has the only table and chairs, so you eat outside or around the small island. The pool is ok, but the deck is a big mess. They said it was scheduled to be replaced and is long overdue. The owner stores junk and old deck furniture along and under the house. If you have pets they can get under the house and pool deck (not clean). Few of the doors close properly. The pictures on the rental site are old and out of date and do not reflect the current condition of the property. Bottom line, it fell way short of our expectation considering the price to rent it.
Response from VrboOwner on 12 May 2022
Thank you for your feedback! We are so sorry for your disappointment of this rental. In regards to the furnishings, each item was thought out diligently by the owner in order to create a comfortable space for guests given the square footage the home of which is advertised, so we are sorry if you were dissatisfied. There is a beautiful awning now that creates a wonderful environment for dining on the back deck which is being improved as we speak. The photos are are only about a year old, but since the owner is currently making some small adjustments in the home, new photos will be taken in the month of November. We hope your time here was otherwise very enjoyable!
From a partner site

10/10 Excellent

Best. Stay. Ever. (even in a pandemic)

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This house is beautiful. It is absolutely charming inside and out. The neighborhood is quiet, but a quick walk to everything. The backyard is absolutely spectacular. The moment we walked in the door on our first day we all had the same reaction - it's even better than the pictures. It truly came to feel like home and we were so, so sad to leave it. I would go back in a heartbeat and would absolutely recommend this property to anyone who's looking to stay in - and fall in love with - Key West. Things not to miss: El Siboney cuban food right around the corner. A walk up and down Duval street. Take the (provided free of charge!) bicycles down to Mallory Square and hit Simonton pier to watch the sunset. Sit on the porch with your coffee or take in sunrise over the pool and palm trees in the backyard. The only thing I wouldn't recommend is leaving!
Response from VrboOwner on 26 May 2022
Wow, thank you for your beautiful review on this incredible home. We enjoyed hosting you in Paradise and hope to see you back again soon!
From a partner site

10/10 Excellent

Just Another Day In Paradise

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This was the perfect place for our 3-month stay. They thought of everything that you would need (except the first-aid kit). We absolutely loved it. In our short-long stay it became part of us. We were sad to leave, but I will always remember Hemingway's Hideout and the new love I have for Key Wes. It was a complete pleasure to have the opportunity to stay in this fantastic home.
Stayed 83 nights in Aug 2019
Response from VrboOwner on 25 Apr 2020
Dear Lorie, Thank you for your wonderful review! We are so happy to hear how much you loved this home. We enjoyed hosting you and hope to have you back again soon. Best Regards, Wendy Zintsmaster and Team
Tell us how we can improve our siteShare feedback