5 STAR HOME 4 BR 3/1/2 baths, pool. Extremely discounted for 28 day 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 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
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
Truman Annex
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
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
Property # 1395775vb
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Key West
Located in Old Town Key West, a neighbourhood in Key West, this holiday 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 Smathers 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.
Harry S. Truman Little White House - 5 min walk - 0.4 km
Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
Mallory Square - 9 min walk - 0.8 km
Fort Zachary Taylor Historic State Park - 11 min walk - 0.9 km
Getting around
Key West, FL (EYW-Key West Intl.) - 14 min drive
Restaurants
Green Parrot Bar - 5 min walk
Blue Heaven - 9 min walk
Margaritaville - 8 min walk
Wendy's - 9 min walk
Mangoes Restaurant - 8 min walk
Frequently asked questions
Does 5 STAR HOME 4 BR 3/1/2 baths, pool. Extremely discounted for 28 day rental. 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 4 BR 3/1/2 baths, pool. Extremely discounted for 28 day rental.?
As of 18 Aug 2026, prices found for a 1-night stay for 2 adults at 5 STAR HOME 4 BR 3/1/2 baths, pool. Extremely discounted for 28 day rental. on 1 Sept 2026 start from £7,386, 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 4 BR 3/1/2 baths, pool. Extremely discounted for 28 day rental. pet-friendly?
No, pets are not allowed at this property.
How much is parking at 5 STAR HOME 4 BR 3/1/2 baths, pool. Extremely discounted for 28 day rental.?
On-site parking is available at the property.
What time is check-in at 5 STAR HOME 4 BR 3/1/2 baths, pool. Extremely discounted for 28 day rental.?
Check-in begins at 4:00 PM.
What time is check-out at 5 STAR HOME 4 BR 3/1/2 baths, pool. Extremely discounted for 28 day rental.?
Checkout is at 10:00 AM.
Where is 5 STAR HOME 4 BR 3/1/2 baths, pool. Extremely discounted for 28 day rental. located?
Located in Old Town Key West, this holiday 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.
About the host
Hosted by Penny Feeser
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
Premier Host
They consistently provide great experiences for their guests