5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval. in Key West

See all properties

Entire home

Choose dates to view prices

Where to?

Dates

May 2025

June 2025

Overview
Amenities
Policies
Location
Host

Exceptional

Entire home

4 bedrooms1 bathroomSleeps 81800 sq ft

Popular amenities

Dryer
Hot Tub
Washer
Parking available
Kitchen

Explore the area

Key West, FL

Duval Street
‪8 min walk‬
Ernest Hemingway Home and Museum
‪10 min walk‬
Mallory Square
‪12 min walk‬
Key West, FL (EYW-Key West Intl.)
‪14 min drive‬

Room options

About the neighborhood

Key West

Located in Old Town Key West, this vacation home is within a 10-minute walk of popular sights such as Duval Street and Fort Zachary Taylor Historic State Park. The vacation home includes a private pool, a kitchen, and a patio.

View more Vacation Homes in Key West

What's nearby

Duval Street - 8 min walk - 0.5 miles
Fort Zachary Taylor Historic State Park - 9 min walk - 0.5 miles
Ernest Hemingway Home and Museum - 10 min walk - 0.6 miles
Mallory Square - 12 min walk - 0.7 miles
Southernmost Point - 17 min walk - 0.9 miles

Getting around

Key West Intl. Airport (EYW) - 14 min drive

Restaurants

‪Margaritaville - ‬8 min walk
‪Blue Heaven - ‬9 min walk
‪Green Parrot Bar - ‬7 min walk
‪Willie T's - ‬7 min walk
‪Mattheessen's - ‬9 min walk

About this property

Entire place

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

5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval.

Our calendar is updated in real time and our rates are accurately displayed. You can book instantly without waiting for owner approval. Flexible cancellation policy. We try to beat rates of all of the other houses in Truman Annex.

Millionaires Row – Welcome to Island Living. Cozy, but upscale.

Truman Annex is the most exclusive private residential community in Old Town Key West, located just off the main drag of Duval Street. Quiet streets lined with palms and beautiful Old Florida Homes. The entrance has a 24 hour staffed guard gate.

Unplug and recharge in wonderful Key West, stop and smell the flowers and the salt air. You will be located only 1 block from mile ZERO.

Truman Annex is adjacent to the newly constructed Truman Waterfront Park complete with a family friendly playground and splash pad, and the Amphitheater where you can enjoy lots of live concerts and events.

If you want sand between your toes instead of the private pool, the beautiful beach at Fort Zachary Taylor Park is just at the end of the street. Enjoy a tour of the fort, snorkeling, fishing, or just sunning and watch the yachts go by.

You will have every luxury and convenience you might want. Large flat screen TV in the living room and flat screens also in other parts of the property. Complimentary, secure Wi-Fi service. Our home is meticulously maintained and immaculate.

First floor is an open floor plan overlooking the private cocktail pool. There is dining space for 10. There is also a first floor bedroom with twin beds and a computer desk.

Upstairs you will find the Owner’s bedroom which is spacious with vaulted ceilings, a king size bed, ample closet and storage area, flat screen TV, and ensuite bath.

There is also a third bedroom upstairs, which is split from the Main bedroom, with a queen bed and flat screen TV. Another bath is adjacent.

The unique guest cottage is complete with vaulted ceilings, queen bed, flat screen TV, full bath, microwave, coffee maker, and refrigerator. It has its own private entrance.

The pool is surrounded by tropical plants and mood lighting.

When you are ready to venture out, walk over to Mallory Square where there is free entertainment every single night before sunset. Great viewing area for Key West’s famous sunsets that set into the ocean. Also within walking distance is The Aquarium, Little White House, The Key West Lighthouse, the Hemingway house, the Audubon House, and Mel Fisher’s Maritime Museum.

You will also be in walking distance to boutique shopping and many art galleries. Be sure to check out the gourmet restaurants and live music venues everywhere.

Nearby there is parasailing, snorkeling trips, fishing charters, and wonderful sunset cruises.

The vacation home is air-conditioned and features a kitchen and a patio, and there's space to spread out with 4 bedrooms. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a private pool, a washing machine, and a sofa bed.

Property manager

Penny Feeser

Languages

English

Similar properties

Ocean view
Pool
Kitchen
Washer

Property amenities

Beach

Beach towels

Pool/Spa

Heated pool
Hot tub
Outdoor pool
Private pool

Internet

Available in the house: Free WiFi

Parking and transportation

Car not required
Onsite parking options include a garage

Kitchen

Blender
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Kitchen island
Microwave
Oven
Refrigerator
Spices
Stovetop
Toaster

Dining

Dining table

Bedrooms

4 bedrooms
Bedsheets provided
Sofa bed

Bathroom

0.5 bathroom
Bathtub or shower
Hair dryer
Shower
Soap
Towels provided

Living spaces

Dining table
Living room

Entertainment

DVD player
Smart TV with cable/satellite channels
Stereo

Outdoor areas

Barbecue grill
Fenced yard
Garden
Outdoor furniture
Patio

Laundry

Laundry facilities
Washing machine

Work spaces

Desk
Desk chair

Comfort

Air conditioning
Heating

Pets

No pets allowed

Suitability/Accessibility

Area rugs in public areas
Hardwood flooring in public areas
Tile flooring in public areas
Smoke-free property

Services and conveniences

Iron/ironing board

Location highlights

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

Things to do

Heated pool
Optional golf privileges
Water park
Birdwatching nearby
Cycling nearby
Fishing nearby
Golfing nearby
Jet skiing nearby
Kayaking nearby
Motor boating nearby
Parasailing nearby
Sailing nearby
Scuba diving nearby
Snorkeling nearby
Swimming 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)
Fire extinguisher
Deadbolt lock

General

Garden
Unit size: 1,800 square feet

Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in available

Minimum check-in age: 21

Check-out

Check-out before 10:00 AM

Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

This property doesn't allow pets

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 fire extinguisher and a deadbolt lock

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
Minimum check-in age: 21

We should mention

Details about charges, deposits, or other important information:

This property is managed by a private host, not a professional engaged in trade or business.
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 carbon monoxide detector, a fire extinguisher, a smoke detector, and a deadbolt lock.

Property is also known as

Pool Home Reduced!!!

Truman Annex Pool Home + Cottage = Fun

NEW TO Market 5 Star Property 4/3 1/2 Pool Wifi Renovated

Frequently asked questions

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

This vacation home is situated in Old Town Key West within a 10-minute walk of Duval Street, Fort Zachary Taylor Historic State Park, and Ernest Hemingway Home and Museum. You'll also find Mallory Square and Florida Keys Beaches less than a mile away.

Will I be able to park at this vacation home?

Yes, there is a garage.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, this vacation home doesn't have an indoor pool; however, there are an outdoor pool and a hot tub.

What will couples enjoy most about a stay at 5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval.?

This historic vacation home offers many amenities for couples such as a private pool, private pools in some accommodations, as well as an outdoor pool.

Does 5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval. have a hot tub?

Yes, guests can enjoy a spa tub at this vacation home.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay free of charge?

No, pets aren't allowed at this vacation home.

Are there connecting rooms at this vacation home?

No, this vacation home doesn't feature connecting guestrooms.

How far is the airport from this vacation home?

The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 4.1 mi away (14 minutes by car).

Are there rooms with balconies at 5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval.?

Yes, every accommodation at 5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval. comes with a deck.

5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval. Reviews

9.8

Exceptional

9.8/10

Cleanliness

8.0/10

Amenities

10/10

Property conditions & facilities

8/10 Good

Carole G.

Mar 20, 2025

Liked: Cleanliness

Good place to stay

My family enjoyed the home and cottage. The home was furnished with everything we needed in the kitchen to be able to cook meals. The pool size was disappointing. Also, there was not much sunlight in the pool area. Only had about 3 hours of full sun to be able to sit by pool.My family enjoyed the fact that we could walk to many things in the area.I enjoyed the cottage and being able to have my own private place to relax in. The shower being so small was very challeging, but I made it work.

Stayed 7 nights in Mar 2025

10/10 Excellent

Marge O.

Mar 2, 2025

Liked: Cleanliness

The BEST place to stay on Key West!

This property has it all!! First, the location cannot be beat. You will be within walking distance of all the best restaurants, Duval Street shopping, Mallory Square, beaches, and historical sites, parks, and museums. The house is even more beautiful in person too! - the decor and amenities add a personal touch to make you feel instantly welcome and at home. Penny is a great communicator, and accommodating to our needs. The neighborhood is quiet, friendly, and beautifully landscaped. We especially enjoyed a cool dip in the pool and relaxing on the front porch after the day's activities. We've been to Key West many times over the past 10 years, staying in luxury hotels, and this is our favorite rental!

Stayed 6 nights in Feb 2025

10/10 Excellent

Jennifer R.

Jan 19, 2025

Liked: Cleanliness

Fabulous New Year Getaway

We were a family and friends group of 7 with 3 couples and one single. The house was perfect for our group and everyone had enough space while also being able to gather as a group for meals, games, etc. The location was amazing as well. We were close to the action on Duvall street, but you couldn’t hear in the house. It was also central to just about everything, so whether walking, cycling, or scootering, it was perfect! The house was clean and there was plenty of dishware, etc. to cook as needed. Only tiny disappointment was that, even though heated, the dipping pool was never warm enough to use, even with several days in the low 80’s. On the flip side, it encouraged us to go check out various beaches.Also, know that you will need to tell your Uber/Lyft driver to use the Southard entrance which was a little tricky. Overall 9.9 out of 10 experience and I would highly recommend!

Stayed 7 nights in Dec 2024

10/10 Excellent

Trudy S.

Jul 21, 2024

Liked: Cleanliness

Family Vacation

We enjoyed our stay, will be back one day.

Stayed 7 nights in Jul 2024

10/10 Excellent

KATHIE S.

Jul 14, 2024

Liked: Cleanliness

Wonderful location

The property was great. We had a non urgent problem with the pool and the owners had someone to fix the problem within 2 hours. The house is beautiful and highly recommend it

Stayed 7 nights in Jul 2024

10/10 Excellent

Michael J.

Jun 29, 2024

Liked: Cleanliness

Key West Is Best

Great setup for us with 3 generations of family all under one roof. Great access to walk to all the hot spots on the island. Great stay and we’d book again in the future.

Stayed 7 nights in Jun 2024

10/10 Excellent

Patricia K.

Feb 20, 2024

Liked: Cleanliness

Key West Truman Annex Home

The Truman Annex is a beautiful part of Key West that is set apart, quiet, safe, clean and still within walking distance of many venues and activities. It really is an ideal location. You do not want to drive much in Key West, it is just frustrating! The house is essentially a duplex and seems fairly new. The first floor living area is open and spacious with the kitchen as the hub with lots of counter space. One room with twin beds is on the first level and the large master room with bath and third bedroom with a queen are on the second level with another full hallway bath. All rooms have fans but the lower bedroom fan did not work and the master bathroom fan did not work. This was communicated to the owner who could not do anything about it during our stay. The kitchen was moderately appointed, sufficient for our crew and we did a fair amount of cooking. The "cocktail pool" was great though the water was chilly and the pool was in the shade most of the afternoon. This would be fine in really hot weather which we did not have. The kids still enjoyed it. The nearby state park beach was awesome as well as the waterfront playground and splash pad. A fun week for our extended family!

Stayed 7 nights in Feb 2024

10/10 Excellent

Ron B.

Aug 2, 2023

Liked: Cleanliness

Perfect Spot

We thoroughly enjoyed our week! Penny was responsive and we couldn't have been happier with our choice in houses.

Stayed 7 nights in Jul 2023

10/10 Excellent

Christina S.

Jul 6, 2023

Liked: Cleanliness

Such a great Experience

Everything was just perfect! The location is so ideal for all ages. We had a few littles that live the short walk to the splash pad. Our 19 year old loved the proximity to the park for her workouts and the adults enjoyed the location to mid Duval making it ideal for quick shopping and dining in either location. The house was perfect size and the pool was nice and private! We loved every minute of our stay!

Stayed 8 nights in Jun 2023

2/10 Terrible

Gina C.

Jun 7, 2023

Disliked: Cleanliness

BED BUGS

Unfortunately i believe you have bed bugs. I have been eaten up all up & down my arms & legs. I was unsure at first, thought maybe mosquitoes or sand somethings. Every day i had more & more bites and they zig zag & are in groups of 3. I found some evidence of them in the cottage & in the room with the twin beds. It was alittle more difficult to find in the master bedroom but that's where i was eaten up. My friend in the twin bedroom was also eaten up pretty bad. The other upstairs room didn't seem to be bothered but my friends that started in there are older & on medications that may be why they didn't get eaten up. I have pictures of my bites & what saw as some evidence of them, like the shell they shed as they eat & grow as well as some staining on the sheets. Also the base boards behind the bed in the cottage and the twin bedroom. I had a hard time in the master room bur was able to find a vet small one in the seams in the mattress top. The box springs & sides of the mattress made it difficult to see much there, also the whicker harbored would be a very good hiding place for them. I pray i am able to get my clothes & luggage in & cleaned up without infesting my house as exterminators are expensive. I am uncomfortable itching like crazy, embarrassed with all these bites on my body & i spent all my savings to go on this vacation & we were all excited to go, now we feel upset & frustrated. This was the most awful vacation i have ever experienced.

Stayed 7 nights in May 2023

10/10 Excellent

jay t.

Mar 6, 2023

Liked: Cleanliness

Great location

Super location with easy walk to Mallory Square, Duval, Hemmingway House and Southern Point. Plunge pool was great for cool off. Some plumbing issues were solved timely. Penny was great communicator.

Stayed 7 nights in Feb 2023

10/10 Excellent

Linda S., Discovery Bay, CA

Mar 1, 2023

Liked: Cleanliness

Beautiful Home in Perfect Location

This home is perfect for a group of 8 people. We were four couples and we were very comfortable. The three bedrooms in the main house are all good sizes and the cottage is a lovely spot with it’s own full bathroom and a little more privacy. The location can’t be beat. We rode bikes or walked everywhere. We rode bikes early in the morning to catch a fishing boat from the marina on Roosevelt. It only took about 15 minutes to get there. We rode to Smathers Beach and it only took about 15 minutes to get there by bike too. Jimmy Buffet was playing at the amphitheater when we were there and our bike ride to the amphitheater took probably less than 10 minutes. Duval Street is two short blocks away. Even though we were so close to everything, being in the complex is amazingly quiet. The home itself is clean, well cared for and beautifully decorated. Having the washer and dryer with plenty of laundry detergent was great. When we were home, we spent most of our time either in the pool or sitting outside by the pool. The instructions for locating and entering the home were very detailed and easy to understand. The owner responded very quickly whenever I had a question. My group and I all had a wonderful stay and highly recommend this beautiful home!

Stayed 7 nights in Feb 2023

10/10 Excellent

Jeff B.

Feb 7, 2023

Liked: Cleanliness

Great location in Key West

Everything was as expected and look forward to coming back in the future.

Stayed 12 nights in Jan 2023

10/10 Excellent

Pam

Traveled with family and small children

Dec 28, 2022

Liked: Cleanliness, amenities, property conditions & facilities

The property is in a great location with easy walking to tourist attractions, restaurants, and playgrounds. It is a very comfortable home with ample space so that you can enjoy being with your fellow housemates. The pool was enjoyable even though the temperatures in Key West were much cooler than normal. I did have an issue when I first arrived, but the owner answered my text promptly and the issue was resolved. I would highly recommend this property.

10/10 Excellent

andrew c.

Dec 1, 2022

Liked: Cleanliness

Wonderful home and location

The residence was great and located in the beautiful Truman Annex.

Stayed 7 nights in Nov 2022

10/10 Excellent

David T., temperance

Nov 17, 2022

Liked: Cleanliness

Excellent property and host

Great location. House was perfect for our needs and penny made the entire process simple and easy. Will definitely book again.

Stayed 7 nights in Nov 2022

10/10 Excellent

Rick L.

Oct 18, 2022

Liked: Cleanliness

A week of laughs to last a life time

Overall the property is awesome the only short coming for us the stairs to the up stairs bedrooms can be a little much at time. We all have homes on one level so are not used to it. The house is great and the area too.

Stayed 7 nights in Oct 2022

10/10 Excellent

Lisa H.

May 15, 2022

Liked: Cleanliness

Family vacation

The location was perfect with everything within easy walking distance. The house allowed us to easily spend time together (6 adults and two small children) with enough room so we didn’t feel crowded. We would definitely come back.

Stayed 7 nights in May 2022

10/10 Excellent

Brenda P.

May 9, 2022

Liked: Cleanliness

Great Stay

We enjoyed Our stay very much! A couple of cautions to future guests: Don't plan for a couple to stay in the back cottage. The shower is the smallest I have ever seen and there is no closet. It is more of a studio type structure. Also, be aware that the subdivision rules on parking are not user friendly and someone is assigned parking almost directly behind the driveway for this unit. All in all, a lovely property.

Stayed 6 nights in Apr 2022

10/10 Excellent

karyn r.

Mar 8, 2022

Liked: Cleanliness

Wonderful location, beautiful property

First stay in Truman Annex and it was wonderful. The location was quiet but two blocks from the action. Private space with pool for afternoon cocktails and beautiful front porch for morning coffee and watching the "doggy" parade! Property is very spacious and you immediately appreciate the details that make you feel at home. Penny was immediately responsive to any questions we had. Would not stay anywhere else in Key West!!

Stayed 7 nights in Feb 2022

10/10 Excellent

Rhonda F.

Feb 26, 2022

Liked: Cleanliness

Fantastic!

Very nice area and had everything we needed

Stayed 6 nights in Feb 2022

10/10 Excellent

Bruce P.

Jan 31, 2022

Liked: Cleanliness

Great house and great location

Great house and location. Would recommend this to anyone

Stayed 7 nights in Jan 2022

10/10 Excellent

David M.

Jan 26, 2022

Liked: Cleanliness

Excellent location and layout for large groups

Our sailing team stayed for an event. The proximity to the marina and downtown area are Excellent. Penny was a great host and accommodated us through the entire process.

Stayed 9 nights in Jan 2022

10/10 Excellent

Doreen C.

Jan 14, 2022

Liked: Cleanliness

Truman Annex

Gorgeous house. Perfect location. Excellent host.

Stayed 6 nights in Dec 2021

10/10 Excellent

Matt G., Tamp

Nov 22, 2021

Liked: Cleanliness

Ohh how I hate to give up a good spot I would want to keep for myself

For those of you lucky enough to consider renting this home, do not hesitate. The place is clean, well kept and the owner is amazing to deal with. Kitchen is stocked and ready for you to cook ( if that’s what you want to do) . Offstreet parking for one small vehicle and a great dipping pool to cool yourself off after long walks on Duval Street that is just a short four minute walk away. My friends and I cannot thank you enough for sharing your home for us.

Stayed 6 nights in Nov 2021