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

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

Pool
Exterior
Private kitchen
Living area
Property grounds

Reviews

9.8 out of 10
Exceptional
4 bedrooms0+ bathroomsSleeps 8167.2 sq m

Popular amenities

  • Dryer
  • Hot tub
  • Washer
  • Parking available
  • Kitchen

Explore the area

Map
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

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

Cottage Bedroom

1 Queen Bed

Living room

1 Double Sofa Bed

Master Bedroom

1 King Bed

1 half bathroom

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Hair dryer

Bathroom 2

Toilet · Shower only

Bathroom 3

Bathtub or shower · Toilet

Bathroom 4

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden
Dining area

About this property

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.

Property manager

Penny Feeser
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
See rental agreement for cancellation policy, some refunds. This is a private nicely furnished home, not a party house.
No oversized cars or trucks Vehicles over 15 feet long or 80 inches wide strictly prohibited. They will be towed, they must fit in garage.

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 indicated that there is a carbon monoxide detector on the property
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 not required for transport to and from this property

About the area

Key West

Located by the sea, 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 Mel Fisher Maritime Museum are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Key West, FL

What's nearby

  • Duval Street - 8 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park - 9 min walk - 0.8 km
  • Ernest Hemingway Home and Museum - 10 min walk - 0.9 km
  • Mallory Square - 12 min walk - 1.0 km
  • Southernmost Point - 17 min walk - 1.5 km

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 - ‬7 min walk
  • ‪Willie T's - ‬7 min walk
  • ‪Mattheessen's - ‬9 min walk

Frequently asked questions

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

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

Is 5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval. pet-friendly?

No, pets are not allowed at this property.

What time is check-in at 5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval.?

Check-in begins at 4:00 PM.

What time is check-out at 5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval.?

Checkout is at 10:00 AM.

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

Located in Old Town Key West, this 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.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 49 out of 55 reviews
Rating 8 - Good. 5 out of 55 reviews
Rating 6 - Okay. 0 out of 55 reviews
Rating 4 - Poor. 0 out of 55 reviews
Rating 2 - Terrible. 1 out of 55 reviews

9.8/10

Cleanliness

8.0/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

8/10 Good

Carole G.

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

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.

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

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.

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

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.

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

Family Vacation

We enjoyed our stay, will be back one day.
Stayed 7 nights in Jul 2024

10/10 Excellent

KATHIE S.

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

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.

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

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.

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

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.

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

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.

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

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.

Liked: Check-in, location, listing accuracy
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.

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

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

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

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.

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

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

Liked: Cleanliness, amenities, property conditions & facilities, communication
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.

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

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

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

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.

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

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.

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

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.

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

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.

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

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.

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

Fantastic!

Very nice area and had everything we needed
Stayed 6 nights in Feb 2022

10/10 Excellent

Bruce P.

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

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.

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

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.

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

Truman Annex

Gorgeous house. Perfect location. Excellent host.
Stayed 6 nights in Dec 2021

10/10 Excellent

Matt G., Tamp

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

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

About the host

Hosted by Penny Feeser

Host profile image
We are outdoors people and we love to bike ride throughout this beautiful community of Truman Annex and Old Town Key West. Everything we do, dining, bar hopping, sports, beaches, and beautiful sunsets are all within walking distance. We have been coming to Key West for 43 years and just love everything about it.

Why they chose this property

This is our third property in Truman Annex. We have just kept getting bigger and bigger homes until we reached this one which is perfect for us. The main house has 3 large bedrooms and 2 1/2 baths. The detached cottage is great for company, teenagers, or in-laws.

It is located 2 blocks to Duval Street and the beach is at the end of the street. You can walk or ride a bike to everything in Old Town Key West, including Mallory Square where "FREE" nightly entertainment is provided prior to the fabulous sunsets.

The Fantasy Fest parade rolls just 1/2 block from our home. Ft. Zackary Taylor is at the end of the street and has an awesome beach, perfect for snorkeling and fishing.

All types of watersports are nearby; snorkeling, fishing, diving, paddle boarding, kayaking, sailing, and sunset dinner cruises.

Night life starts just one block away with The Green Parrot, the first and last bar on US 1. Duval is another block away and this is where you will find fantastic dining, bars with live music, shopping, and plenty of sights to see. You never know when you will dine with a pirate or a mermaid. Key West is full of colorful characters and street performers.

Feel free to contact Penny for more information.

What makes this property unique

This home is in a very beautiful location and private neighborhood. It is within walking distance to everything people come to Key West for, yet very quite. The new Truman Annex Waterfront Park is one block away.

It is the perfect place to sit and watch sunsets more privately. You will literally have the very best of old town.

The heated cocktail pool is the perfect place to start or end your days.

Languages:

English

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