See all properties
Entire condo

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

Condo near Duval Street in Key West

Choose dates to view prices

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

Beach
Outdoor dining
Pool
Smart TV, DVD player, books
Property grounds

Reviews

9.6 out of 10
Exceptional

Entire condo

2 bedrooms1 bathroomSleeps 6

Popular amenities

  • 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, Fort Zachary Taylor Historic State Park
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪15 min drive‬

Room options

You may also like

Ad
2 outdoor pools, open 7:00 AM to 10:00 PM, cabanas (surcharge)

Blue Flamingo Resort Key West

New Town
  • Pool
  • Hot tub
  • Pet friendly
  • Free WiFi
4.2 out of 5, Very Good, 2,311 reviews
$184 nightly
The price is $207
May 31 - Jun 1
Total with taxes and fees
Blue Flamingo Resort Key West

About the neighborhood

Key West

Old Town Key West stay.Within a 10-minute walk of this Old Town Key West condo, you'll find Duval Street and Ernest Hemingway Home and Museum. Florida Keys Beaches and Mallory Square are also within half a mile (1 km).
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

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Moondog Cafe & Bakery - ‬8 min walk
  • ‪Rams Head Southernmost - ‬7 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.

Similar properties

Bar (on property)
Southwinds Motel
Old Town Key West
  • Pool
  • Breakfast included
  • Restaurant
  • Air conditioning
4.3 out of 5, Excellent, 1,338 reviews
$158 nightly
The price is $178
Jun 29 - Jun 30
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

Living spaces

  • Living room

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

Minimum check-in age: 27

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

  • No pets allowed

Children and extra beds

  • Children are welcome.

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.

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

How close is Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach to the airport?

This condo is 4.1 mi (19-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach have an airport shuttle?

Airport shuttle services are not available at this condo.

How close is Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach to the beach?

This condo is a short 12-minute walk from Florida Keys Beaches and 0.8 mi (8-min drive) from South Beach. Don't forget your sunscreen!

Does Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach offer free breakfast?

This condo does not offer free breakfast.

Is there a casino at Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach?

No, there is no casino at this condo.

What time is check-in at Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach?

Check-in begins at 4:00 PM.

Is there free parking at Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach?

Free parking is not available at this condo.

Does Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach have a pool?

Yes, there's a pool.

Does Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach have a spa?

There are no spa services available at this condo.

How close is Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach to downtown Key West?

This condo is 0.2 mi away from Key West.

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

Reviews

9.6

Exceptional

Rating 10 - Excellent. 107 out of 135 reviews
Rating 8 - Good. 19 out of 135 reviews
Rating 6 - Okay. 7 out of 135 reviews
Rating 4 - Poor. 2 out of 135 reviews
Rating 2 - Terrible. 0 out of 135 reviews

9.4/10

Cleanliness

10/10

Amenities

9.4/10

Property conditions & facilities

Reviews

10/10 Excellent

Genna B.

Liked: Cleanliness
Our family had an amazing vacation at this Truman Annex property! The grounds were beautiful and we were close to everything. We loved sitting on the back porch with the palm trees swaying overhead. My kids loved the pool area and we found the other residents/ visitors to be very friendly. We would come back to this property in a heartbeat! This is also the third time we have rented a property managed by Roberta Mira. We have always found her to be very kind, organized, and a great communicator.
Stayed 10 nights in Mar 2026

8/10 Good

Rick L., Grand Rapids, Mi

Liked: Cleanliness
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

10/10 Excellent

Will H.

Stayed 7 nights in Dec 2025

10/10 Excellent

Michele L.

Liked: Cleanliness
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

8/10 Good

Jeffrey Y.

Liked: Cleanliness
Stayed 7 nights in Jul 2025

10/10 Excellent

Stacie K.

Liked: Cleanliness

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

10/10 Excellent

Elizabeth M., ROCHESTER

Liked: Cleanliness
Just as advertized !
Stayed 7 nights in May 2025

10/10 Excellent

Joey C.

Liked: Cleanliness

Our Favorite Place

This property was a wonderful stay. The beds were comfy, the showers were refreshing, the air conditioning was cold. Perfect place to come "home" to after a hot day out on the water. A dip in the pool was greatly enjoyed after getting used to the initial chill of the water, a little colder than previous years, but tolerable. We look forward to more visits to this complex in the coming years!
Stayed 7 nights in May 2025

10/10 Excellent

Kenneth L., Midwest

Liked: Cleanliness

Always great

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

8/10 Good

Anne Marie B.

Liked: Cleanliness

Angled Narrow Rise/Run Stairs

Several recommendations were sent to property manager - some regarding cleanliness others repairs, fixes. We were without air on holiday when temperature and humidity was high. Air fixed next day. Requested partial refund but have received no response. I sent photos of all issues some of which handyman and others couldn’t find. Do not recommend for older people due to stairs.
Stayed 7 nights in Apr 2025

10/10 Excellent

Jamie W.

Liked: Cleanliness

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

10/10 Excellent

Missy C.

Liked: Cleanliness

Perfect location

This property checked every box. The place was clean, and just the right size. Everything we needed for a two week stay was there from beach towels, linens, pans, dishes, even hand soap and dish soap was provided. The few questions I had were answered immediately. The location is absolutely perfect. Within walking distance to everything. The pool was cleaned daily and the grounds were immaculate. I highly recommend this place.
Stayed 14 nights in Mar 2025

10/10 Excellent

Carol W.

Stayed 7 nights in Nov 2024

10/10 Excellent

Sue D.

Liked: Cleanliness

Perfect location and host

Roberta was wonderful to work with. Extremely responsive. The unit was spectacularly clean. We could not have asked for a better location.
Stayed 7 nights in Oct 2024

10/10 Excellent

David O.

Liked: Cleanliness

Great Stay

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

10/10 Excellent

Linda M.

Liked: Cleanliness

Close to everything

We had an amazing time at this condo. The place had everything we needed. Having two balconies and one that overlooked the pool was a plus. We walked everywhere, this condo was right in the middle of town. You just needed to decide everyday go right or left. Take a Sunset cruise!!! Visit Hemingway house and Butterfly Exhibit. Oh yeah and Irish Kevin’s on Duvall St. Thank you Roberta.
Stayed 7 nights in Oct 2024

10/10 Excellent

Carolynn M.

Liked: Cleanliness

Great location… nice property

We had a great stay… loved being overlooking the pool as it was quiet and pretty. Lots of Key West chickens about and nice to hear the national anthem at 8 am every morning from the nearby military base. Many good restaurants within walking distance and the parking for a car/golf cart was really handy. The unit is cute and clean. Everything you need is available. Loved the two porches although they were being painted for much of our stay. The unit could do with a spot of paint but overall it was wonderful.
Stayed 9 nights in Sep 2024

10/10 Excellent

Brian K.

Liked: Cleanliness

Amazing Week

This was a great vacation and this unit/location was amazing!!! Literally walk to everything and in the complex the pool was just outside the door, 2 balconies so you could always find shade and relax
Stayed 7 nights in Aug 2024

10/10 Excellent

Lin L.

Liked: Cleanliness
Stayed 7 nights in May 2024

10/10 Excellent

Michael L.

Liked: Cleanliness
Stayed 4 nights in Apr 2024

10/10 Excellent

Stacey C.

Liked: Cleanliness

Excellent Location

You can't beat this location. It is quiet, safe, and within walking distance from nearly everything you want to do in Key West. We saw a manatee at the waterfront right next to the complex the second night we were there. We also spent several days at Fort Zachary Taylor State Park, which is walking distance from the property if you don't have a lot of items to carry. This is a great spot for families. Despite the heat, we also spent a lot of time reading on the balcony overlooking the pool. The pool is clean and very quiet during this time of year. There were several points during our 10 day trip when we had the pool to ourselves. The complex property is immaculate and everyone was very friendly. Property manager was responsive and helpful.
Stayed 10 nights in Jul 2024

6/10 Okay

Sheila S.

Liked: Cleanliness

Kind of small and very steep steps

I wasn't really thrilled with this particular property. There were a lot of rules for the pool, the interior stairs were narrow and steep, the condo itself was kind of small. However, and huge however, Roberta, the property manager is amazing and will make everything right for you. She quickly put us somewhere larger and nicer when the tv and internet were not working correctly and the new place was AMAZING! We will definitely be back with Roberta again, she is awesome and caring.
Stayed 5 nights in Jul 2024

10/10 Excellent

Jonathan M.

Liked: Cleanliness

Walking distance to Duval

Property is exactly as described. Easy check in/out. Walking distance to Duval.
Stayed 7 nights in Jun 2024

10/10 Excellent

Michael G.

Liked: Cleanliness

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

4/10 Poor

Susan B., Camberley, United Kingdom

Disliked: Cleanliness

Tatty and tired property with a lot wrong with it

The Truman complex is lovely, great location and very well maintained. But the property is very tired (as per other reviews) and needs a major overhaul to bring it up to a reasonable standard. The experience was pretty awful. From getting the dates on our booking messed up (and host was no help to get this resolved - had to escalate through to Directors at VRBO to get help), through to broken floor tiles in every room, fridge door held on by sticky tape, dirty and discoloured kitchen sink, dangerous looking electrics, wall tile hanging off the wall in the bathroom, dirty bottom bed sheet in the master bedroom, sofa bed that you cannot sleep on as the mattress is so bad and the springs make it totally impossible to sleep on. Made the host aware of all these issues and she did nothing.
Stayed 4 nights in Apr 2024