Prime location, stunning views from 2 decks—walk or ride to explore the island!

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Entire home

Overview
Amenities
Policies
Location
Host

Exceptional

2 bedrooms1+ bathroomSleeps 474.3 sq m

Popular amenities

Dryer
Washer
Parking available
Kitchen
Barbecue grill

Explore the area

Key West, FL

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

1 bathroom, 1 half bathroom

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet

Spaces

Deck or patio

Porch or lanai

Kitchen

Balcony

Garden

Dining area

About this property

Walk everywhere from this little part of Paradise, you will never need a car. Located in beautiful Old Town, you are virtually 2 blocks from from Duval Street with shops, restaurants, and nightlife. Tastefully appointed with vintage rattan furniture and fully stocked with everything you will need in a newly redecorated kitchen with popular granite countertops. Bathrooms have been recently renovated with white vessel sinks which add to the contrast of vintage and contemporary decor. Walk out your back gate and you will enter the pool area with a heated pool that does not exceed 5 feet deep. The bedrooms each have queen size beds .We have free wifi as well. All cleaned and disinfected by our professional cleaning staff .

Sit outside to people watch from one of our 2 balconies or the friendly front porch where conversations ensue with the passerby's!!

Property manager

Kerry Higginbotham

Premier Host

Languages

English

Add dates for prices

Amenities

Pool

Kitchen

Washer

Dryer

Free WiFi

Air conditioning

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Pool
Hot tub
Kitchen
Washer

House Rules

Check in after 4:00 PM

Minimum age to rent: 23

Check out before 10:00 AM

Children

Children allowed: ages 3–17

Events

No events allowed

Pets

No pets allowed

Smoking

Smoking is not permitted

No smoking on property

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

On-site parties or group events are strictly prohibited

Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip

Host has indicated that there is a smoke detector on the property

Safety features at this property include a fire extinguisher and a deadlock

We should mention

A car is recommended for transport to and from this property

About the area

Key West

Located on the beach, this holiday home is in Old Town Key West, a neighbourhood in Key West. Fort Zachary Taylor Historic State Park and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. USCGC Ingham Maritime Museum and Florida Keys Eco - Discovery Center 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 hiking and cycling nearby.

Key West, FL

Getting around

Key West, FL (EYW-Key West Intl.) - 14 min drive

Restaurants

‪Margaritaville - ‬8 min walk
‪Blue Heaven - ‬9 min walk
‪Green Parrot Bar - ‬6 min walk
‪Willie T's - ‬7 min walk
‪Mangoes Restaurant & Island Cuisine - ‬7 min walk

Frequently asked questions

Does Prime location, stunning views from 2 decks—walk or ride to explore the island! have a pool?

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

Is Prime location, stunning views from 2 decks—walk or ride to explore the island! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Prime location, stunning views from 2 decks—walk or ride to explore the island!?

Check-in begins at 4:00 PM.

What time is check-out at Prime location, stunning views from 2 decks—walk or ride to explore the island!?

Checkout is at 10:00 AM.

Where is Prime location, stunning views from 2 decks—walk or ride to explore the island! located?

Nestled on the beach, this Old Town Key West holiday home is within a 10-minute walk of We Cycle Key West, Duval Street and Fort Zachary Taylor Historic State Park. Ernest Hemingway Home and Museum and Mallory Square are also within 15 minutes.

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.8/10

Cleanliness

10/10

Amenities

9.0/10

Property conditions & facilities

8.0/10

Eco-friendliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Patricia J.

27 Apr 2025

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

Paradise

We couldn’t have asked for a better place to stay. Within walking distance of Duval St, restaurants, bars, stores, attractions. All the amenities needed were provided. Quiet area with great porches for people watching. The kids loved spending time in the pool. Host was very responsive. 10/10 stay, I highly recommend this place.

Stayed 8 nights in Apr 2025

10/10 Excellent

Kathryn T.

21 Apr 2025

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

Beautiful townhouse with excellent location

Very convenient to both beach and Duval Street with pool directly behind townhouse . However still very quiet and private backyard

Stayed 11 nights in Apr 2025

10/10 Excellent

Arline G.

6 Apr 2025

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

Truman Annex

Bittersweet, because as 2026 they will no longer allow weekly rentals

Stayed 7 nights in Mar 2025

10/10 Excellent

Keith F.

15 Feb 2025

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

Keith’s

Beautiful place. Excellent location to every thing.

Stayed 14 nights in Feb 2025

10/10 Excellent

Marcie R.

25 Jan 2025

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

Perfect house. Perfect location.

I absolutely love this home. It’s close to everything but out of the way so you don’t hear people screaming late at night. Love Truman Annex and how adorable the neighborhood is. This rental has everything one could ever need including salt and pepper. Quiet deck out back. Socializing deck out front. Such a great home.

Stayed 7 nights in Jan 2025

10/10 Excellent

Tarrah Todd S.

24 Jan 2025

Stayed 7 nights in Dec 2024

10/10 Excellent

Patricia W.

11 Jan 2025

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

The perfect spot

Loved the location of this sweet little attached two story cottage. It is small and compact but had everything we needed.The community is just lovely, with an easy, scenic walk to everything we wanted to see. It's located in a cozy little block, and we did have vacationing neighbors that talked outside on their patio next to ours well in to the night. But it was still so enjoyable, we didn't mind. Any question we had was promptly answered by the owner. Parking was very convenient, and the pool was just outside our back gate. And even though we had a car, we walked everywhere, including the nearby small grocery store in the historic district. A truly lovely week.

Stayed 7 nights in Jan 2025

10/10 Excellent

Misty K.

2 Dec 2024

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

Stayed 8 nights in Nov 2024

10/10 Excellent

A j.

9 Aug 2024

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

Stayed 7 nights in Feb 2024

10/10 Excellent

LOIS E.

7 Aug 2024

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

Wonderful Property

Great Property - Great Owner

Stayed 9 nights in Jul 2024

10/10 Excellent

Tom D.

30 June 2024

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

Almost Haven

The property was fantastic and clean. As advertised it’s a short walk to Duval Street, Mallory Square and Ft Zachary Park. Nothing but sunshine for the whole week we were there.

Stayed 7 nights in Jun 2024

10/10 Excellent

Annalisa B.

7 May 2024

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

Key West Getaway

We loved everything about it! Perfect location with close proximity to the pool, a short walk to downtown, yet secluded and private.

Stayed 7 nights in Apr 2024

10/10 Excellent

Matthew T.

29 Apr 2024

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

Great property and location in a very quiet neighborhood

The description is completely accurate ... you really can walk or ride to anywhere. The property was very clean and well maintained. We really enjoyed our meals on the back deck. The pool was so close -- we only wish we had time to sit back and relax, but we were constantly on the go! It is hard to stay put, when all of Old Town is right the door. While the Truman Annex is conveniently located near any of the attractions or destinations you would want, it is just far enough that you do not get any street noise or disturbances. We previously stayed in a hotel in New Town, but we will be looking to rebook this property for our next KW adventure!

Stayed 7 nights in Apr 2024

10/10 Excellent

Stephanie D.

27 Mar 2024

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

Great getaway

Location was great, pool great, property manager was outstanding. Kerry communicated perfectly. She was always there to answer all questions. We had all the amenities we needed.

Stayed 7 nights in Mar 2024

10/10 Excellent

Chuck V.

21 Mar 2024

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

Truman Annex Rental (KW)

We had a great week (the weather was excellent), but the “house” also was a perfect fit - with the two bedrooms upstairs and combo living and dining area in an “open” plan. Perfect location to Duval Street but yet far enough so it was quiet at night.

Stayed 7 nights in Mar 2024

10/10 Excellent

Jim & Michelle B.

7 Mar 2024

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

Perfect!

Excellent location. Everything you could need for the perfect week long vacation. Pool was so warm and people watching from the balcony was a hoot!

Stayed 7 nights in Feb 2024

10/10 Excellent

Laurie W.

17 Feb 2024

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

First Keys trip

Perfect location, comfy beds, balconies off of each bedroom, pool immaculate and very close to the unit. Truman Annex was very nice and well-kept.

Stayed 7 nights in Feb 2024

10/10 Excellent

Frederick S.

11 Feb 2024

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

Truman Annex

Nice property and very convenient to the Key West parks and Duvall Street.

Stayed 14 nights in Jan 2024

10/10 Excellent

ralph e., Executive director of the seminar marketing Institute

27 Jan 2024

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

Already planning to book for next year

Looking forward to coming back next year. Definitely going to be a repeat customer which in my opinion speaks volumes about all of the qualities of the unit.

Stayed 14 nights in Jan 2024

10/10 Excellent

Deborah B.

17 Jan 2024

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

Wonderful week stay!

We stayed at this condo in January and had a wonderful time! The property was immaculate and had everything we needed for the week! Truman Annex is the perfect place to stay if you don’t want to rent a vehicle. Everything is within walking distance. We will definitely be planning another trip to Key West and hope to stay here again! I would definitely recommend it to friends and family!

Stayed 7 nights in Jan 2024

10/10 Excellent

Tarrah S.

4 Jan 2024

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

Loved it

Fantasic location & great property

Stayed 8 nights in Dec 2023

10/10 Excellent

Judith F., Norcross

8 June 2023

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

Everything you need!

The check in was so easy. The unit is located perfectly for walking around Key West. Pool is just outside your back gate and very well maintained. Bed is VERY firm - the only suggestion would be to add a cushie bed pad for comfort. Overall an excellent experience though. I will book again for sure! Thanks!

Stayed 7 nights in Jun 2023

10/10 Excellent

Elmer B.

12 May 2023

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

Location to town was perfect! So nice to have the pool right behind the townhome!

Loved it! Very considerate owners, thought of all the things needed for our stay!

Stayed 7 nights in May 2023

10/10 Excellent

Verified traveller

5 May 2023

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

Great condo in perfect location

Very well appointed condo . Everything we needed was provided. Perfect location within walking distance of everything. Had a great visit

Stayed 7 nights in Apr 2023

10/10 Excellent

Bobbie G., Chicago IL

21 Apr 2023

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

First timers

First time in Key West. Loved the town and loved it even more thanks to this rental. Perfect location, great little neighborhood close to the beach and to amazing food and good shopping. Couldn’t have been more comfortable. Thanks for making this vacation even better than we’d hoped!

Stayed 7 nights in Apr 2023

About the host

Hosted by Kerry Higginbotham

Bob and I got married in Key West in 2013 after vacationing here with my brother and sister-in-law (who live here) for years. We reside in the Dunedin-Clearwater area of Florida and come down as often as we can. I grew up in Deerfield Illinois a suburb of Chicago and Bob is a native St. Louisian, where we met and started dating 29 years ago. We love the active style of Key West and the attitude that presides there.

Why they chose this property

Key West has the unique style of" Live and let Live" that we treasure and wish to abide by. The friendly people, the "laid back" style of living, the perfect climate and the close beaches, make Key West the perfect place to go.

What makes this property unique

Travelling to Key West and bicycling through Truman Annex was a favorite pastime for us. The cute condos with their pastel colors and front porches just looked so inviting, and so"un-condo" like. When my brother and sister-in-law decided to move there, Truman Annex was their choice for a place to live. Six years later they called and said one was for sale close to them so we jumped on the opportunity.

Languages:

English

Premier Host

They consistently provide great experiences for their guests

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Prime location, stunning views from 2 decks—walk or ride to explore the island!

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Reviews

Popular amenities

Explore the area

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

Bedroom 2

1 bathroom, 1 half bathroom

Bathroom 1

Bathroom 2

Spaces

About this property