House in Key West, FL
8 guests · 4 bedrooms
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
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.
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.
Amenities at 5 STAR HOME 3/2 1/2 + 1 BR cottage, private pool, ready for your 28 day stay.
Free WiFi/internet
Air conditioning
Pool
Non-smoking
TV
Refridgerator
Kitchen
WiFi/Internet
Private pool access
Microwave
Dishwasher
Washing machine
Dryer
Patio
No pets allowed
Garden
Kettle
Oven
Stove
Laundry services
Bath or shower
Sofa bed
Ironing facilities
Towels
Desk
Hairdryer
Map of Key West, FL
Ratings and reviews
10.0 / 10.0Outstanding·Oct 2025
Nice home. Great location. Would stay again.
10.0 / 10.0Outstanding·Jul 2025
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!
10.0 / 10.0Outstanding·Jul 2025
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.
10.0 / 10.0Outstanding·Jul 2025
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.
$$$$
Top rated by guests
9.8Outstanding
(64 Ratings)
"Nice home. Great location. Would stay again."
Colin B.Don't miss out! Price and availability may change
