Entire home
Truman House - Private Pool Home in the Heart of Old Town Key West!
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Reviews
9.4 out of 10
Exceptional
4 bedrooms3 bathroomsSleeps 102050 sq ft
Popular amenities
Explore the area

Key West, FL
- Place, Duval Street6 min walk
- Place, Ernest Hemingway Home and Museum9 min walk
- Place, Southernmost Point16 min walk
- Airport, Key West, FL (EYW-Key West Intl.)13 min drive
Rooms & beds
4 bedrooms (sleeps 10)
Bedroom 1
1 Queen Bed
Bedroom 2
1 King Bed
Bedroom 3
2 Single Beds
Bedroom 4
2 Single Beds
Living Room 1
1 Queen Sofa Bed
3 bathrooms
Bathroom 1
Bathroom 2
Bathroom 3
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden
Dining area
About this property
Truman House - Private Pool Home in the Heart of Old Town Key West!
The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly home is located on an upscale and tranquil residential street within easy walking distance of all the "must-do's" in your Key West guidebook.
The design mantra for Truman House must have gone like this: all doors should lead poolside. Even the second-floor master bedroom balcony overlooks this area and for good reason. The very private rear of the home is paradise perfect. It starts with a natural wood deck, one part under an overhang that shades a glass-top table and six cushioned chairs. Just beyond, chaise lounges and chairs dot the open space in case you want to work on your tan, or just open up the green market umbrella for some additional shade. Three steps down bring you to tile decking. To one side is a delightful pergola. At the same end a unique and imposing white tarpon sculpture watches over the heated oversized pool and spa with round fish eyes and open lips. Tropical foliage rings the area, creating privacy and beauty. Swim, float, spa, lounge, barbecue, and eat your feast al fresco at the deck table. Maybe include a glass or two of wine. So many opportunities to enjoy your vacation any way you want.
But let's be practical; you can't spend all your time outside. And that's fine because Truman House offers a bright and spacious interior with high ceilings and a tropical color pallet. Right inside the front door is the great room, including a dining area with a rectangular table and six spindle-back chairs with cushions. Nearby is a large hutch for dishes and knickknacks. The area rug below picks up the Key Lime green walls. This area flows into the living area, also delineated by an area rug over antique wide-plank flooring. A large sleeper sofa and three armchairs circle a coffee table, forming a great conversation area. Sit here to enjoy friends and family. Maybe that means a card game of some sort with a cool glass of ice tea or lemonade. Or maybe you'll prefer to use the family room on the other side of the kitchen for social activities. Lamps and windows provide ample light for the living area, while Florida-themed wall art adds color and interest. A paddle ceiling fan with light whirrs above adding circulation, brightness, and tropical ambience.
Directly behind the living room is a small bedroom with twin beds and dresser with four drawers. A door on one wall leads to the laundry room, which then opens to the pool area. Next comes the gourmet kitchen with plenty of gleaming white cabinetry, butcher-block island, and eat-in corner area. The walls in this room are the hue of a grove-fresh orange. All the appliances you'd expect are tucked in neatly with plenty of counter space for food preparation. Glass doors open wide from here to the deck and pool. The view is spectacular, not to mention the balmy weather the open doors let in. You may even find yourself preparing more food than you had intended on your vacation because the kitchen is so inviting.
Next to the kitchen is the family room, painted in fresh lemon yellow. This room has a sofa, armchairs, coffee table, and of course cable, wireless high-speed Internet, stereo, and DVD player. Windows on three walls provide garden views while French doors open on one wall to the deck and pool. Two guest bedrooms account for the rest of the first floor. The first has a king bed and en suite full bath. The second has twin beds with another full bath just steps away, one conveniently accessible from the dining room and bedroom.
At the top of gleaming hardwood stairs, you'll find the master suite. It starts with a small, cedar-lined room that is quite an unusual amenity for Key West: a real walk-in closet. In fact eight people could walk in at once and hang around. The rest of the second floor is the master suite. There are plenty of windows, a queen bed, dresser, side tables, and a full bath with striking ocean blue tiles. Best of all are the French doors to a small deck with table and two chairs overlooking the pool, Jacuzzi, and tropical garden. Maybe like Goldilocks you want to try each of the four bedrooms or maybe you already know this one is for you. This home is Pet (Dog) Friendly**(please see below or our FAQ page for rules and restrictions)
When you're ready to explore your neighborhood and the rest of Key West, everything is within walking distance. The Historic Seaport is only four streets over. Follow the boardwalk along the Gulf of Mexico to find historic tall ships offering day and sunset cruises or take an all-day ferry excursion to the Dry Tortugas. If you're interested in watersports, there's all kinds like diving, fishing, parasailing, snorkeling, and jet skiing. If you get hungry, a dozen or so restaurants of varying levels of informality ring the harbor. Maybe stop at Schooner Wharf or BO's Fish Wagon for a fresh Mahi sandwich and listen to local musicians. Continue on to Mallory Square where crowds of visitors and locals alike gather to witness the sun sinking into the horizon. Then hang around for the party as artists and street performers entertain the crowd. From Mallory Square, the famous Duval Street is within two blocks in case you're interested in tours, museums, shopping, over two hundred restaurants, and bars. If beaches call to you, there are two within easy biking distance.
The Property may only be used for residential accommodations. No special events, parties, or functions of any kind are permitted on the Property.
If this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We DO NOT guarantee that the information VRBO (and affiliated sites) scrapes from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information.
**For Pet Friendly (dog) homes there are restrictions that include, but may not be limited to, the following: pet friendly means dogs, no other animal is permitted. Dogs are restricted to one (1) large dog or two (2) small dogs per stay. Due to Homeowner Insurance restrictions we are unable to accommodate the following breeds: Pit Bull Terriers, Staffordshire Terriers, Rottweilers, German Shepherds, Presa Canarios, Chows Chows, Doberman Pinschers, Akitas, Wolf-hybrids, Mastiffs, Cane Corsos, Great Danes, Alaskan Malamutes, Siberian Huskies nor any mixed breed that contain one of the preceding as part of that mix. Guest is responsible for an additional pet fee of $200.
The design mantra for Truman House must have gone like this: all doors should lead poolside. Even the second-floor master bedroom balcony overlooks this area and for good reason. The very private rear of the home is paradise perfect. It starts with a natural wood deck, one part under an overhang that shades a glass-top table and six cushioned chairs. Just beyond, chaise lounges and chairs dot the open space in case you want to work on your tan, or just open up the green market umbrella for some additional shade. Three steps down bring you to tile decking. To one side is a delightful pergola. At the same end a unique and imposing white tarpon sculpture watches over the heated oversized pool and spa with round fish eyes and open lips. Tropical foliage rings the area, creating privacy and beauty. Swim, float, spa, lounge, barbecue, and eat your feast al fresco at the deck table. Maybe include a glass or two of wine. So many opportunities to enjoy your vacation any way you want.
But let's be practical; you can't spend all your time outside. And that's fine because Truman House offers a bright and spacious interior with high ceilings and a tropical color pallet. Right inside the front door is the great room, including a dining area with a rectangular table and six spindle-back chairs with cushions. Nearby is a large hutch for dishes and knickknacks. The area rug below picks up the Key Lime green walls. This area flows into the living area, also delineated by an area rug over antique wide-plank flooring. A large sleeper sofa and three armchairs circle a coffee table, forming a great conversation area. Sit here to enjoy friends and family. Maybe that means a card game of some sort with a cool glass of ice tea or lemonade. Or maybe you'll prefer to use the family room on the other side of the kitchen for social activities. Lamps and windows provide ample light for the living area, while Florida-themed wall art adds color and interest. A paddle ceiling fan with light whirrs above adding circulation, brightness, and tropical ambience.
Directly behind the living room is a small bedroom with twin beds and dresser with four drawers. A door on one wall leads to the laundry room, which then opens to the pool area. Next comes the gourmet kitchen with plenty of gleaming white cabinetry, butcher-block island, and eat-in corner area. The walls in this room are the hue of a grove-fresh orange. All the appliances you'd expect are tucked in neatly with plenty of counter space for food preparation. Glass doors open wide from here to the deck and pool. The view is spectacular, not to mention the balmy weather the open doors let in. You may even find yourself preparing more food than you had intended on your vacation because the kitchen is so inviting.
Next to the kitchen is the family room, painted in fresh lemon yellow. This room has a sofa, armchairs, coffee table, and of course cable, wireless high-speed Internet, stereo, and DVD player. Windows on three walls provide garden views while French doors open on one wall to the deck and pool. Two guest bedrooms account for the rest of the first floor. The first has a king bed and en suite full bath. The second has twin beds with another full bath just steps away, one conveniently accessible from the dining room and bedroom.
At the top of gleaming hardwood stairs, you'll find the master suite. It starts with a small, cedar-lined room that is quite an unusual amenity for Key West: a real walk-in closet. In fact eight people could walk in at once and hang around. The rest of the second floor is the master suite. There are plenty of windows, a queen bed, dresser, side tables, and a full bath with striking ocean blue tiles. Best of all are the French doors to a small deck with table and two chairs overlooking the pool, Jacuzzi, and tropical garden. Maybe like Goldilocks you want to try each of the four bedrooms or maybe you already know this one is for you. This home is Pet (Dog) Friendly**(please see below or our FAQ page for rules and restrictions)
When you're ready to explore your neighborhood and the rest of Key West, everything is within walking distance. The Historic Seaport is only four streets over. Follow the boardwalk along the Gulf of Mexico to find historic tall ships offering day and sunset cruises or take an all-day ferry excursion to the Dry Tortugas. If you're interested in watersports, there's all kinds like diving, fishing, parasailing, snorkeling, and jet skiing. If you get hungry, a dozen or so restaurants of varying levels of informality ring the harbor. Maybe stop at Schooner Wharf or BO's Fish Wagon for a fresh Mahi sandwich and listen to local musicians. Continue on to Mallory Square where crowds of visitors and locals alike gather to witness the sun sinking into the horizon. Then hang around for the party as artists and street performers entertain the crowd. From Mallory Square, the famous Duval Street is within two blocks in case you're interested in tours, museums, shopping, over two hundred restaurants, and bars. If beaches call to you, there are two within easy biking distance.
The Property may only be used for residential accommodations. No special events, parties, or functions of any kind are permitted on the Property.
If this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We DO NOT guarantee that the information VRBO (and affiliated sites) scrapes from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information.
**For Pet Friendly (dog) homes there are restrictions that include, but may not be limited to, the following: pet friendly means dogs, no other animal is permitted. Dogs are restricted to one (1) large dog or two (2) small dogs per stay. Due to Homeowner Insurance restrictions we are unable to accommodate the following breeds: Pit Bull Terriers, Staffordshire Terriers, Rottweilers, German Shepherds, Presa Canarios, Chows Chows, Doberman Pinschers, Akitas, Wolf-hybrids, Mastiffs, Cane Corsos, Great Danes, Alaskan Malamutes, Siberian Huskies nor any mixed breed that contain one of the preceding as part of that mix. Guest is responsible for an additional pet fee of $200.
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi
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9.8 out of 10, Exceptional, (157 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Children Allowed
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Smoking is not allowed.
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
Long-term renters welcome
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
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
We should mention
This property does not have any lifts
About the area
Key West
Located near the beach, this holiday home is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and Florida Keys Beaches. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Key West, FL
What's nearby
- Duval Street - 6 min walk - 0.6 km
- Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
- South Beach - 14 min walk - 1.2 km
- Key West Butterfly and Nature Conservatory - 14 min walk - 1.2 km
- Southernmost Point - 16 min walk - 1.3 km
Getting around
Restaurants
- Willie T's - 7 min walk
- Mangoes Restaurant - 8 min walk
- Kaya Island Eats - 8 min walk
- DJ's Clam Shack - 8 min walk
- The Cafe - 6 min walk
Frequently asked questions
Reviews
9.4
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.8/10
Cleanliness
9.8/10
Check-in
9.6/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
23 Sept, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Sep 2025
10/10 Excellent
Julie S.
10 Jan, 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy



Julie S.
Stayed 7 nights in Jan 2026
10/10 Excellent
Amy H.
14 Jul, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy

Amy H.
Stayed 5 nights in Jul 2025
8/10 Good
Chrisanne S.
19 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chrisanne S.
Stayed 5 nights in Oct 2025
10/10 Excellent
Karyn M.
6 Feb, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Large house - within walking to all main activities in KW
Karyn M.
Stayed 9 nights in Jan 2025
8/10 Good
Rachel S.
19 Feb, 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Rachel S.
Stayed 4 nights in Feb 2026
10/10 Excellent
Thomas A.
25 Jan, 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Thomas A.
Stayed 5 nights in Jan 2026
10/10 Excellent
Tracie C.
4 Jan, 2026
Tracie C.
Stayed 5 nights in Dec 2025
8/10 Good
Matthew O.
29 Jan, 2025
Matthew O.
Stayed 7 nights in Dec 2024
About the host
Hosted by Historic Hideaways
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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