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Hands-Down Best Deal in Key West!

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Exterior - Hands-Down Best Deal in Key West! (Key West)
Terrace/patio - Hands-Down Best Deal in Key West! (Key West)
2 bedrooms, internet, bed sheets - Hands-Down Best Deal in Key West! (Key West)
TV, books, music library, video library - Hands-Down Best Deal in Key West! (Key West)
Property grounds - Hands-Down Best Deal in Key West! (Key West)
Step into 'The Writer's Retreat,' a two-bedroom condo where Ernest Hemingway and Jimmy Buffet memorabilia set the tone for a relaxing stay. Unwind in the luxurious Master Bedroom, or enjoy family time in the 1950’s themed kitchen equipped with imported European SMEG Fridge and Stainless Appliances.

Reviews

9.4 out of 10
Exceptional

Entire condo

2 bedrooms1 bathroomSleeps 665 sq m

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor Space

Add dates for prices

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

Hands-Down Best Deal in Key West!

City of Key West Business License # 28224

We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memorabilia welcome you into the abode our first guest affectionately called “The Writer's Retreat'.
This two bedroom, one bath condo with bleached grey hardwood flooring throughout is highlighted by a massive 65 inch Plasma TV loaded with thousands of movies at your fingertips. Relax on the designer furniture while enjoying the full collection of Hemingway's books or lose yourself in The Master Bedroom retreat which has been luxuriously decorated with 1000 thread count bedding on the Romantic Canopy Bed with French doors leading out to a spacious rear patio overlooking the pool.
The guest bedroom has two twin upgraded pillow top beds that can be converted to a King bed to accommodate a family or two couples. The King is stocked with a very thick down padding and luscious linens for maximum comfort. Enjoy the sounds of the keys or music of Buffet as the guest bedroom is decorated in tribute to crooner and the island lifestyle detailed in framed sheet music.
If staying in for the evening or fixing breakfast or lunch have fun in the 1950’s themed state of the art kitchen equipped with an imported European SMEG Fridge and Stainless Appliances. Likewise, the bathroom has been decorated in an art deco style typical of an earlier time in the Keys.
The front Family room area has features a queen sleeper sofa bed with a down pad and bedding for extra sleeping space. All pillows and bedding are down and of high quality in order to provide maximum comfort on your stay. Quite simply, we designed this home to fit in with the Keys lifestyle. It is bright, open and lends itself to a vibe which we hope catapults you to a great stay in our beloved Keys.

Please enjoy the slide show of our new wonderful home in Key West and we hope to accommodate your vacation needs.

TO VIEW OUR OTHER PROPERTIES VISIT
VRBO Listing #412277 & #497962 for Catalina Island
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VRBO Listing #592709 for San Clemente Beach
VRBO Listing #633858 for Park City Utah
VRBO listing #724909 for Garden District New Orleans
VRBO listing ID 815366 For Kiawah Island, Charleston South Carolina
VRBO Listing ID 901935 for Newport Beach

Please see contract for additional details.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Communal pool
  • Heated pool

Internet

  • Available in the condo: Internet access

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Books
  • Music library
  • TV with cable/satellite channels
  • Video library

Outdoor areas

  • Balcony
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Hardwood flooring in public areas
  • Smoking not allowed

Services and conveniences

  • Phone

Location highlights

  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • Near the marina
  • On the waterfront

Things to do

  • Heated pool
  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water tubing nearby
  • Whale watching nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Deadbolt lock

General

  • Garden
  • Unit size: 700 square feet

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Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 25

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

RENTAL AGREEMENT - A valid Driver's License and signed Short-Term Rental Agreement are due after booking confirmation.

Pets

Pets not allowed

Children and extra beds

Children are welcome
Note from host: two twin beds or can be converted to King

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 is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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

Property is also known as

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About the neighborhood

Located on the waterfront, this condo is in Old Town Key West, a neighborhood in Key West. 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. USCGC Ingham Maritime Museum and Mel Fisher Maritime Museum are also worth visiting. Be sure to check out the area's animals with activities such as game walks and birdwatching. Visit our Key West travel guide
View more Condo Rentals in Key West
Map
Key West, FL

What's nearby

  • Duval Street
    Duval Street
    5 min walk - 0.4 km
  • Ernest Hemingway Home and Museum
    Ernest Hemingway Home and Museum
    7 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park
    Fort Zachary Taylor Historic State Park
    8 min walk - 0.7 km
  • Mallory Square
    Mallory Square
    9 min walk - 0.8 km
  • Florida Keys National Marine Sanctuary
    5 min walk - 0.4 km

Getting around

  • Key West Intl. Airport (EYW)
    8 min drive

Restaurants

  • Green Parrot Bar
    6 min walk
  • Margaritaville
    6 min walk
  • Blue Heaven
    10 min walk
  • La Concha Bar
  • Jack Flats
    6 min walk

Frequently asked questions

Does Hands-Down Best Deal in Key West! have a pool?

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

Is Hands-Down Best Deal in Key West! 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 Hands-Down Best Deal in Key West!?

Check-in begins at 3:00 PM.

What time is check-out at Hands-Down Best Deal in Key West!?

Check-out is at 10:00 AM.

Where is Hands-Down Best Deal in Key West! located?

Located in Old Town Key West, this condo building is within a 10-minute walk of Jackson Square and Duval Street. Mallory Square and Ernest Hemingway Home and Museum are also within 15 minutes.

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Hands-Down Best Deal in Key West! Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 149 out of 210 reviews
Rating 8 - Good. 45 out of 210 reviews
Rating 6 - Okay. 14 out of 210 reviews
Rating 4 - Poor. 1 out of 210 reviews
Rating 2 - Terrible. 1 out of 210 reviews

9.2

Cleanliness

10

Location

2.0

Staff & service

6.8

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Michael M.

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

Great place to stay

Property is in a perfect location to all key west has to offer. Clean and modern condo, we will be back.
Stayed 2 nights in Nov 2024
Verified

8/10 Good

Kenneth M.

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

Key Condo

Very nice property in a great location, easy walk to bars, shops, beaches and the Port. Would recommend
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Ken B.

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

Perfect location

Condo was beautiful and located in the perfect location. Nice and quiet and a short walk to the fun busy town. Appreciate the stay and look forwarded to doing it again
Stayed 4 nights in Jan 2025
Verified

10/10 Excellent

Ryan O.

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

Excellent stay in Key West

Everything about the location and property was spot on. Would stay here again!
Stayed 4 nights in Dec 2023
Verified

10/10 Excellent

The Janet K.

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

Great location!

Excellent location, in walking distance of all the main attractions of historic Key West, yet very quiet, safe neighborhood.
Stayed 2 nights in Mar 2024
Verified

10/10 Excellent

Catherine N.

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

Nice place for a few relaxing days in Key West

Cozy place in a quiet condo very well located to visit Key West (old town, marina, southernmost point), enjoy the pool in a lovely garden, bars and restaurants and all the water activities nearby!
Stayed 2 nights in Mar 2024
Verified

10/10 Excellent

Christine B.

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

Birthday Getsway

We loved our stay! It was myself, my husband and my in laws.Clean, convenient and as advertised. We hope to return next year.
Stayed 5 nights in Mar 2025
Verified

10/10 Excellent

Melissa S.

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

Great location!

The Writer's Retreat was conveniently located near all of the Key West attractions we wanted to visit. Once we were checked in, we didn't need to move the car again until we left. The community pool was a great amenity and was located close to the unit. The apartment was the perfect size for our family of four.
Stayed 3 nights in Mar 2025
Verified

10/10 Excellent

Clayton C.

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

Perfect location

Perfect location for getting around! Nice quiet neighborhood/street and just a block away from the party. Make sure to rent bikes, best way to get around town.
Stayed 3 nights in Sep 2024
Verified

10/10 Excellent

Liz F.

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

Outstanding Location

This property is great! It’s located in a quiet area of a very active town. The property clean, safe easily accessible to Key West best shopping, restaurants and bars
Stayed 3 nights in Jun 2024
Verified

10/10 Excellent

Amy P.

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

Charming

Absolutely charming and a great location!
Stayed 2 nights in Jan 2024
Verified

10/10 Excellent

Mark E.

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

Wonderful stay

Completely enjoyed our stay. Great location, great place. Pictures and descriptions were very accurate. Condo was very cozy and comfy. Would highly recommend to anyone
Stayed 3 nights in Mar 2024
Verified

10/10 Excellent

Nina B.

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

Great little retreat.

Property as described. Very comfortable, nice amenities. The host was very responsive and accommodating, would recommend.
Stayed 5 nights in Sep 2024
Verified

10/10 Excellent

Deborah C.

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

Ladies Birthday Trip

My sister and niece and I came for a long weekend at Key West and had a great time! The location of the condo is so perfect- walkable to everywhere and the property is just as described. The pool was a great way to relax on the hot afternoons and all the bars and restaurants were so fun and convenient in the evenings .Would definitely recommend and stay here again.
Stayed 3 nights in Nov 2024
Verified

10/10 Excellent

Kristin L.

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

Perfect retreat.

My husband, 8 year old son and my father- in -law enjoyed a quick trip down to Key West. This was a perfect place to stay as everything we wanted to do was easily walkable. The pool was a welcome place to go to cool down mid day and the balcony was delightful for end of the evening drinks.
Stayed 2 nights in Apr 2024
Verified

10/10 Excellent

George W.

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

First Key West Visit

Writer's Retreat was a highlight. Conveniently located, quiet, clean and comfortable. Two porches a delight.
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Alan F.

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

Great getaway

Great place to stay, amenities were just right. Close to the pool. Quiet property to relax and unwind. Parking is limited so prepare.
Stayed 3 nights in Jul 2023
Verified

8/10 Good

Neil B.

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness

Great location

The property was in a great location to explore old town on foot. The complex and unit were comfortable. The unit could really use a deep clean and it would have been nice to have a workable freezer and ice machine. Otherwise the unit worked fine for our week stay.
Stayed 6 nights in Jan 2025
Verified

10/10 Excellent

Vicki C.

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

Great location

We love staying in the Shipyard and find it a fantastic location. This property was the best unit we’ve stayed in. Very clean and comfortable with awesome decor. One room is a little tight with the queen bed taking up most of the room but the bed and bedding were very comfortable so it was easy to forget. Highly recommended.
Stayed 4 nights in May 2024
Verified

10/10 Excellent

Elizabeth G.

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

Key West Adventure

Property was exactly as listed. It’s in a great location. We were within walking distance of any place we had planned to visit. Neighbors gave us some excellent restaurant recommendations. We had a wonderful time and can’t wait for a return visit!
Stayed 3 nights in Mar 2024
Verified

10/10 Excellent

Jeremy P.

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

Great location for KW getaway

First time to KW and the location is great and we comfortably walked everywhere. Condo owner was very responsive to questions. Comes with small kitchen and fridge for cooking but we did not use it because we were only there 4 days. Condo did accommodate our family of 6 but it was small and tight. Would be perfect for 4!Thank you for the opportunity the place was great.JP
Stayed 3 nights in Jan 2025
Verified

10/10 Excellent

Marlene P.

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

Great getaway in paradise

Our group of two couples couldn’t have asked for a better location, amenities, cleanliness, and ease of check in for our three night stay. While a small item, we were taken aback when we were told we had to provide our own toilet paper when the supply ran out.
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Sally R.

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

Our stay at Truman Annex

Great location in Key West. Easy to Uber or ride a bike around. The condo was very clean and the pool was nice. The beds were very comfortable. We had 4 adults stay there with one bathroom which was a little difficult. It was a little small for 4 adults. We really enjoyed sitting on both balconies, that did help with the space. Other than that it was a great choice in Key West!
Stayed 5 nights in Apr 2024
Verified

10/10 Excellent

Ashley W.

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

Lovely condo close to everything!

We had always wanted to stay at the Truman Annex and this was finally our chance! Our condo was just lovely and had basically everything we needed. There was comfortable bedding for all, two twins for our boys which was perfect. The kitchen was stocked with all that we needed and a full-size fridge, and W/D which was so so helpful as well. The bathroom was a tad tight for the 4 of us at times, but that would be the only "downside" I could see, and we made it work. Loved the Hemingway theme, check in/out was seamless and clear, no issues at all. We would stay here again for sure! Thank you for such a great stay!
Stayed 3 nights in Jul 2023
Verified

8/10 Good

Ben S.

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

Writers Retreat Winter 2024

Great location and tropical gardens and pool. 2 blocks to Duval and 1 block to the Parrot. The refrigerator should be replaced with a larger unit that can hold ice and frozen food if you are staying more than a few days. It worked fine but we could not really use the freezer. Management is aware of the issue as I have seen the same comments on several reviews. Overall a great stay. Tnanks Writers Retreat!
Stayed 28 nights in Feb 2024