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5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free.

Photo gallery for 5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free.

Pool
Exterior
Private kitchen
Living area
Property grounds

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area
4 bedrooms0+ bathroomsSleeps 8

Popular amenities

  • Private pool
  • Hot tub on site
  • Garage parking available
  • Kitchen
  • Washer
  • Air conditioning

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪5 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪9 min walk‬
  • Place, Mallory Square
    ‪11 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪14 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 2

1 Queen Bed

Bedroom 3

2 Twin 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 HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free.

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 Waterfront Park is only 2 blocks away and comes 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.
Our prices include all fees. No hidden fees.

Add dates for prices

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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
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

About the neighborhood

Key West

Located in Old Town Key West, a neighborhood in Key West, this vacation home is near a water park and by the sea. 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. Jet skiing, kayaking, and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
View more Vacation Homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Duval Street - 5 min walk - 0.4 km
  • Harry S. Truman Little White House - 5 min walk - 0.4 km
  • Florida Keys National Marine Sanctuary - 8 min walk - 0.7 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
  • Mallory Square - 11 min walk - 0.9 km

Getting around

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

Restaurants

  • ‪Green Parrot Bar - ‬5 min walk
  • ‪Margaritaville - ‬8 min walk
  • ‪Blue Heaven - ‬9 min walk
  • ‪La Concha Bar - ‬9 min walk
  • ‪First Flight Island Restaurant & Brewery - ‬9 min walk

Frequently asked questions

Does 5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free. have a pool?

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

How much does it cost to stay at 5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free.?

As of May 6, 2026, prices found for a 1-night stay for 2 adults at 5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free. on May 7, 2026 start from $377, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is 5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free. pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at 5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free.?

Check-in begins at 4:00 PM.

What time is check-out at 5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free.?

Check-out is at 10:00 AM.

Where is 5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free. located?

Located in Old Town Key West, this vacation home is within a 10-minute walk of Truman Waterfront Park, 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 labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 57 out of 64 reviews
Rating 8 - Good. 6 out of 64 reviews
Rating 6 - Okay. 0 out of 64 reviews
Rating 4 - Poor. 0 out of 64 reviews
Rating 2 - Terrible. 1 out of 64 reviews

9.8/10

Cleanliness

8.0/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

John L.

Liked: Cleanliness, check-in, communication, listing accuracy
Great location, very comfortable floor plan – everything about it was perfect!
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Stacey V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home, very comfortable. A great location - you can’t beat it. Host was responsive to questions but honestly we didn’t need anything! Check in was easy, Penny was great. Would love to stay again when in Key West. THANK YOU!
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Colin B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice home. Great location. Would stay again.
Stayed 7 nights in Sep 2025
Verified

10/10 Excellent

Cheryl S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location. Wonderful house. Loved our daily pool time.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Megan H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful time during our stay in Key West. Penny's home was beautiful and well kept. Great location, close top everything but in a nice quiet neighborhood. The pool was pristine and a lifesaver in the Florida heat. We will definitely be back!
Stayed 7 nights in Jul 2025
Verified

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
Verified

10/10 Excellent

Tisha P.

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

Great Location Very Quiet

Our stay was great. Host was very responsive to a couple of unexpected issues that came up. We let our 4 kids (18, 19, 19 and 19) stay in the main house. My husband and I stayed in the "guest house" in back yard. That was perfect, we had so much privacy, it was like we were on a seperate vacation. The pool was perfect, we relaxed daily in it.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Mark L.

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

Family vacation

We had four generations for the week. Accommodations worked out great. Owner responded to all questions and resolved issues quickly. Walked to all restaurants and parks. Great vacation
Stayed 7 nights in Apr 2025
Verified

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
Verified

10/10 Excellent

Audrey C.

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

Family Time 3

This was one of the most lovely and accommodating properties we have ever stayed at. The photos didn't do justice to how beautiful and spacious it truly was. Especially the cottage. The house was perfect for our family of 6 to both come together, and spread out. There's even some small details that show how much love has gone into the comfort of this home. Many wonderful memories were made during our stay.
Stayed 7 nights in Jun 2025
Verified

8/10 Good

Darby S.

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

Wonderful Stay in a Prime Location

We had a fantastic time staying at this home! The location couldn't be better—just a short walk to Duval Street and Fort Zachary Taylor State Park, which made exploring Key West so convenient. The house itself was spotless and nestled in a beautiful, quiet neighborhood that felt both welcoming and private.We were initially concerned that the pool might be too small, but it turned out to be just right. It was perfect for a refreshing midday dip to cool off and relax. Overall, this place exceeded our expectations and was ideal for our trip.
Front of house
Neighborhood
Stayed 9 nights in May 2025
Verified

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
Verified

10/10 Excellent

Joe M.

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

Just like home

beautiful home in great condition and in a great location. We look forward to a return visit.
Stayed 7 nights in Feb 2020
Verified

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
Verified

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
Verified

10/10 Excellent

Joseph B.

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

Fabulous, Fabulous

In the heart of the Truman Annex, literally steps from major Key West attractions. Georgeous neighborhood, beautiful house, with pool and casita. WONDERFUL.....
Stayed 6 nights in Feb 2020
Verified

10/10 Excellent

Christine R.

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

High school Graduation present trip

My son wanted to go to Key West for his grad trip (we were supposed to travel Europe but Covid19 happen) so, I happened to find this cute lil home and we booked it.. beautiful neighborhood, felt safe, very close to everyone walking distance. The guest cottage was absolutely perfect. Would definitely stay here again (if we don’t buy one for us😁)
Stayed 7 nights in Aug 2020
Verified

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
Verified

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
Verified

10/10 Excellent

RICHARD T.

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

Family Vacation

Property and location were beautiful as described. We had a couple challenges but Penny the owner handled them right away. After researching many properties we were glad we chose this one. The Main house, pool and guest house gave us 7 adults plenty of room. Truly made a memorable vacation! Thank You!
Stayed 6 nights in Jul 2020
Verified

10/10 Excellent

Phillip F.

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

Awesome home.

The house was as advertised. The kitchen had most things needed for a week long stay. The bedrooms were very nice and we had plenty of room. The location was perfect, close to most things Key West had to offer. Only thing I would change is adding a second gate key so more than one person could have one.
Stayed 7 nights in Jun 2020
Verified

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
Verified

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
Verified

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
Verified

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.

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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