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Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach

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Photo gallery for Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach

A beach with palm trees and a sailboat in the distance.
A poolside area with a glass table and chairs, a pool, and palm trees in the background.
A covered porch with a round table and wicker chairs, surrounded by lush greenery and a white picket fence.
A living room with a dining area, featuring wicker furniture, a glass table, and a ceiling fan.
A gated entrance with a small kiosk, a white fence, and a row of white buildings with balconies and palm trees.

Reviews

9.6 out of 10
Exceptional

Entire condo

2 bedrooms1 bathroomSleeps 6

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Key West, FL
  • Place, Florida Keys National Marine Sanctuary
    ‪5 min walk‬
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 min drive‬

Room options

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  • Pool
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The price is $147
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Total with taxes and fees
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About the neighborhood

Key West

Located in Old Town Key West, this condo is within a 10-minute walk of popular sights such as Duval Street and Ernest Hemingway Home and Museum. The condo includes a kitchen, a balcony, and a refrigerator.
View more Condo Rentals in Key WestOpens in a new window

What's nearby

  • Florida Keys Eco - Discovery Center - 3 min walk - 0.2 miles
  • Florida Keys National Marine Sanctuary - 5 min walk - 0.3 miles
  • Duval Street - 6 min walk - 0.4 miles
  • Ernest Hemingway Home and Museum - 8 min walk - 0.4 miles
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.4 miles

Getting around

  • Key West Intl. Airport (EYW) - 19 min drive

Restaurants

  • ‪Blue Heaven - ‬8 min walk
  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Moondog Cafe & Bakery - ‬8 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Bourbon Street Pub - ‬8 min walk

About this property

Entire place

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

Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach

This condo has been grandfathered in to allow for weekly rentals. One of only a few with City approval. This 2 bedroom, fully furnished condominium with brand new living room furniture and dining room table set is located in the Truman Annex, a gated community of private homes and condominiums. Located inside the Truman Annex is Truman's Little White House Museum, Eco-Discovery Center, Water Park for small children and Fort Zachary State Park. Freshly painted and upgraded with custom bedspreads, new key west style furniture, all flat screen televisions, comfortable outdoor furniture, queen bed with two twin beds that are easily converted to a king sleeper, a sofa sleeper, full kitchen, living room, washer/dryer and two private balconies one overlooking the swimming pool and the other facing the courtyard. Free assigned parking spot and Free Wi-fi. Steps from famous Duval Street, sunset celebration and all the downtown action one desires. High demand book early.
The condo is air-conditioned and features a kitchen and a balcony, and there's space to spread out with 2 bedrooms. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a washing machine, a coffee maker, and an ironing board.

Similar properties

Bar (on property)
Southwinds Motel
Old Town Key West
  • Pool
  • Breakfast included
  • Restaurant
  • Air conditioning
8.6 out of 10, Excellent, 1,381 reviews
$155 nightly
The price is $174
Sep 21 - Sep 22
Total with taxes and fees
Southwinds Motel

Property amenities

Ski

  • Close to skiing

Pool/Spa

  • Communal pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Car not required
  • Parking on site

Kitchen

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

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Towels provided

Entertainment

  • Books
  • DVD player
  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

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

Things to do

  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water skiing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • No carbon monoxide detector or gas appliances (host has indicated there are no carbon monoxide detectors or gas appliances on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in available

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

Check-out instructions

The host requires you complete the following before checking out:

Load the dishwasher

Strip any used beds and gather used towels

Remove personal items, remove leftover food and drinks, and take out the trash

Turn off the lights, lock the doors, and return the keys

Full detail check-out instructions are inside the owners manual.

Make sure you text me @ 305-797-5263 copy of both sets of keys.

The garbage and recycle cans are located next to your parking bay.

Failure to complete these may result in a negative review from the host.

Pets

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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 are no carbon monoxide detectors or gas appliances on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and 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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a fire extinguisher, a smoke detector, and a deadbolt lock.

Property is also known as

Early December Rent Five Days get Two Days Free-discount Applied

Early December Rent Five Days get Two Days Free-discount Applied

Frequently asked questions

What's there to do within easy reach of this condo?

This condo is situated in Old Town Key West within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum. You'll also find Florida Keys Beaches and Mallory Square less than a mile away.

Is this condo associated with a casino?

No, this condo is not connected to a casino.

Will I find an indoor pool at this condo?

No, there is no indoor pool at this condo.

Does this condo include breakfast service?

No, this condo doesn't offer breakfast.

Will this condo allow pets to stay for free?

No, pets aren't allowed at this condo.

How close is the airport from this condo?

The closest major airport to this condo is Key West Intl. Airport (EYW), which is 4.1 mi away (19 minutes by car).

Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 112 out of 141 reviews
Rating 8 - Good. 20 out of 141 reviews
Rating 6 - Okay. 7 out of 141 reviews
Rating 4 - Poor. 2 out of 141 reviews
Rating 2 - Terrible. 0 out of 141 reviews

9.4/10

Cleanliness

10/10

Amenities

9.4/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Jana G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great communication and help when needed!
Stayed 8 nights in May 2026
Verified review

10/10 Excellent

Gregory

Liked: Cleanliness, check-in, communication, listing accuracy
So very nice
Stayed 14 nights in Apr 2026
Verified review

8/10 Good

Rick L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The pool was nice. The location could not be beat. It was within walking distance to everything for tourists.
Stayed 8 nights in Dec 2025
Verified review

10/10 Excellent

David O.

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

Great Stay

Great location, close to the action on Duval St as well as the water front.
Stayed 9 nights in Oct 2024
Verified review

10/10 Excellent

Melissa P.

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

Great location and property!

Great location and property!
Stayed 7 nights in Aug 2022
Verified review

10/10 Excellent

Michele L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Roberta was wonderful I left something important behind and she mailed it to me the next day. The location is great. We LOVE the Annex. Would stay here again.
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

Kim R.

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

Great spot

Super location, easy check in, great spot for a week of vacation.
Stayed 7 nights in Feb 2022
Verified review

10/10 Excellent

Jamie W.

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

Great location

Love Key West and this is a fantastic location in the middle of everything, making all entertainment very walkable if you choose. Great pool and very friendly people.
Stayed 7 nights in Apr 2025
Verified review

10/10 Excellent

Amy B.

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

Great place

Love the location, couldn’t ask for a better place!
Stayed 7 nights in Oct 2023
Verified review

10/10 Excellent

Michael G.

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

Awesome stay at the Truman Annex

The stay at the Truman Annex was great. The location, facilities available and the staff are all commented for the nice appearance and wonderful environment.....
Stayed 8 nights in May 2024
Verified review

10/10 Excellent

Kenneth L.

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

Always great

Great stay, great unit and great location. Host was great as always
Stayed 12 nights in Apr 2025
Verified review

10/10 Excellent

Stacie K.

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

Excellent Location

Safe location, great for families! Steps from the community pool. Plus a really nice neighborhood walk to local attractions like the aquarium and museums.
Stayed 10 nights in Jun 2025
Verified review

10/10 Excellent

Verified traveler

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

Great location and comfortable stay

We had a great time at this property. It is conveniently located to Duval, Mallory Square, Fort Zachery, and the beach. Nice view of the pool from the balcony and overall comfortable stay.
Stayed 7 nights in Jul 2023
Verified review

10/10 Excellent

Donna G.

Perfect location and detailed information on places to eat and things to do!

The property is beautiful. Place is clean and very comfortable. Pool was awesome and location is excellent to everything!
Stayed 7 nights in Jan 2019
Verified review

10/10 Excellent

Dave C.

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

Great place to stay! Close to the pool!

It was a very nice place to stay! Truman Annex is close to all! Only a short walk to Duval St. I would strongly recommend staying in this condo!
Stayed 7 nights in Nov 2019
Verified review

10/10 Excellent

Bob C.

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

Quiet but Close

great location and close to all the activities we were interested in
Stayed 7 nights in Nov 2023
Verified review

10/10 Excellent

Jesica W.

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

Great Key West getaway

Loved the place and can’t beat the price. Excellent location, walking distance to almost everything and easy for kids. Loved the pool and the fun community at Truman Annex.
Stayed 10 nights in Jul 2023
Verified review

10/10 Excellent

Anne J.

Great location!! Our home away from home was perfect!! Thank you sooo much!

Excellent!! Clean and a fantastic location! Thanks for an amazing vacation
Stayed 7 nights in Dec 2018
Verified review

10/10 Excellent

Amy B.

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

Perfect Getaway

Great location right by the pool and walking distance to Duval Street. Will definitely book again.
Stayed 7 nights in Oct 2021
Verified review

10/10 Excellent

nicki m.

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

This is a great location, clean and efficient condo.

This is a great property. The host was informative and was easy to access. Great location and very clean.
Stayed 5 nights in Mar 2023
Verified review

10/10 Excellent

Thomas J.

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

Shipyard at Truman Annex

Awesome location, property as described in listing.
Stayed 7 nights in Apr 2023
Verified review

10/10 Excellent

Linda P.

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

Great location to duval

Property manager was helpful when needed. Great location.
Stayed 3 nights in Oct 2022
Verified review

10/10 Excellent

Michelle Sharon

Liked: Cleanliness, amenities, property conditions & facilities, communication
We had a wonderful time at the house…Very roomy and clean and the kitchen had everything we needed..We were also right next to the pool..Will definitely stay here on our next visit..Thanks for making our visit so enjoyable…
Stayed 7 nights in Oct 2022
Verified review

10/10 Excellent

Claudia B.

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

Comfortable in Great Location

Comfortable for the family. Great location near Duval St., Mallory Square, and all the attractions. Right next to the pool. Would definitely stay here again.
Stayed 6 nights in May 2022
Verified review

10/10 Excellent

Darlene D.

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

Great location

Well kept property with a great location to everything. Owner replied to my questions immediately.
Stayed 5 nights in Aug 2022

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