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Tropical Oasis in the Truman Annex with a private pool

Photo gallery for Tropical Oasis in the Truman Annex with a private pool

Exterior detail
Private backyard and pool.
Pool
Living / Dining Room
Living Room

Reviews

10 out of 10, Loved by Guests
Top 10% based on
2 bedrooms2+ bathroomsSleeps 61360 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Key West, FL
  • Place, Harry S. Truman Little White House
    ‪3 min walk‬
  • Place, Duval Street
    ‪5 min walk‬
  • Place, Mallory Square
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪14 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Living Room 1

1 Queen Sofa Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Towels provided · Toilet · Shower only · Hair dryer

Bathroom 2

Towels provided · Toilet · Shower only · Hair dryer

Half Bath Downstairs

Toilet

Spaces

Deck or patio
Kitchen
Balcony
Separate dining area
Garden
Dining area

About this property

Tropical Oasis in the Truman Annex with a private pool

Searching for the perfect vacation home away from it all? Your hunt ends in here! A Wave from it All is a remodeled and tastefully decorated 2-story townhome with its own private pool that epitomizes island living at its finest while offering all the comforts of home. Best of all, this home is nestled in the Truman Annex, a palm tree lined residential community with many historic buildings including the Truman Little Whitehouse, walking distance to many of Key West’s finest dining establishments, two blocks from the world-famous Duval Street, two blocks from the nightly sunset celebration at Mallory Square, and less than a half mile from the beach at Fort Zachary Taylor State Park. Break away from the ‘high seas’ of everyday life while you settle into for what’s sure to be a memorable Key West vacation!

The double set of sliding glass doors on the back of the home open up to provide a private spacious tropical oasis of indoor/outdoor living space with a private pool. A large flat screen HD SMART TV hangs on the wall in front of comfortable seating options. The fully equipped kitchen has all the appliances and tools needed to prepare meals at home, on those nights that you chose to dine home with your pick of indoor or outdoor dining.

Truman Annex is the most exclusive private residence community in Old Town Key West. Located just off the main drag of Duval Street, The Truman Annex is an oasis of calm, quiet palm tree lined streets with many historic homes, 24-hour staff and restricted access in the evenings where you can use the entry gate keys to come and go on foot.

Property includes..
Central Heat and A/C, Ceiling Fans, Flat Screen TVs in Living Room & All Bedrooms, Fully Equipped Kitchen, Laundry Room with full size Washer and Dryer, Starter supply of paper products & cleaning supplies, Linens and Towels provided, Wireless high-speed Internet access & full cable included.

** Fully Fenced & Lushly Landscaped Private Yard with Pool. Pool can be heated for an additional charge.

** Designated Covered Off-Street Parking (one space)

** This property will accommodate up to 4 adults

** No Pets Allowed

**The entire property is NON smoking or vaping
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 13-17
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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
THIS IS A SMOKE / VAPE FREE, DRUG FREE, FIREARM/WEAPON FREE AND FIREWORK FREE PROPERTY. ANY VIOLATION IS SUBJECT TO IMMEDIATE EVICTION.
PETS are not permitted at the property. Pets include but are not limited to dogs, cats and/or caged animals such as reptiles, rabbits, gerbils, etc.
ALL renters must abide by the Rules / Regulations of Truman Annex HOA. The Rules / Regs can be found at https://----------------

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
This property uses eco-friendly cleaning products
Host has indicated there are no carbon monoxide detectors or gas appliances 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
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

We should mention

This property does not have elevators

About the neighborhood

Key West

Old Town Key West, a neighborhood in Key West, is home to this vacation home. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. USCGC Ingham Maritime Museum and Florida Keys Eco - Discovery Center are also worth visiting. Be sure to check out the area's animals with activities such as game walks and birdwatching.
View more Vacation Homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Harry S. Truman Little White House - 3 min walk - 0.3 km
  • Duval Street - 5 min walk - 0.4 km
  • Florida Keys National Marine Sanctuary - 6 min walk - 0.6 km
  • Mallory Square - 8 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park - 9 min walk - 0.8 km

Getting around

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

Restaurants

  • ‪Green Parrot Bar - ‬5 min walk
  • ‪Margaritaville - ‬5 min walk
  • ‪Willie T's - ‬6 min walk
  • ‪Blue Heaven - ‬9 min walk
  • ‪First Flight Island Restaurant & Brewery - ‬7 min walk

Frequently asked questions

Does Tropical Oasis in the Truman Annex with a private pool have a pool?

Yes, this property has a pool.

How much does it cost to stay at Tropical Oasis in the Truman Annex with a private pool?

As of Mar 31, 2026, prices found for a 1-night stay for 2 adults at Tropical Oasis in the Truman Annex with a private pool on Nov 19, 2026 start from $570, 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 Tropical Oasis in the Truman Annex with a private pool 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 Tropical Oasis in the Truman Annex with a private pool?

Check-in begins at 4:00 PM.

What time is check-out at Tropical Oasis in the Truman Annex with a private pool?

Check-out is at 11:00 AM.

Where is Tropical Oasis in the Truman Annex with a private pool located?

Located in Old Town Key West, this vacation home is within a 5-minute walk of Jackson Square and Duval Street. Mallory Square and Ernest Hemingway Home and Museum are also within 15 minutes.

Reviews

10

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. 35 out of 36 reviews
Rating 8 - Good. 0 out of 36 reviews
Rating 6 - Okay. 1 out of 36 reviews
Rating 4 - Poor. 0 out of 36 reviews
Rating 2 - Terrible. 0 out of 36 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jay P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice place to stay. Great location.
Stayed 4 nights in Dec 2025
Verified

10/10 Excellent

Paul D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Property was very nice, particularly the pool area in rear of house
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Gail R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property is very nice and clean. The beds were very comfortable too. It was very close to everything so that made our stay perfect. We would definitely stay there again. The hostess Don was very nice and helpful.
Stayed 5 nights in Oct 2025
Verified

10/10 Excellent

Jennifer s.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house! The house was equipped with every kitchen appliance and gadget needed. The pool was the perfect size with a sitting ledge inside, so no raft needed. Owner was very nice and responsive with any questions we had. We plan on staying here in the future
Stayed 5 nights in Dec 2025
Verified

10/10 Excellent

Lora S.

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

Fabulous property! Great stay!

We had a fabulous time at this beautiful property. Perfectly maintained and excellent location, within walking distance of so many sites!
Stayed 4 nights in May 2025
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great host. Easy with communication. Great house, convenient location, clean, everything we needed.
Stayed 4 nights in Jul 2025
Verified

10/10 Excellent

Ronald W.

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

2025 Key West Vacation

Absolutely worth staying here! Beautiful home location was perfect.
Stayed 7 nights in Jan 2025
Verified

10/10 Excellent

Michelle s.

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

Wonderful stay!

Wonderful location and beautiful home. Great communication. We had a lovely time!
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Hannah C.

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

Perfect!

This place was amazing. Host provided everything we needed. Everything was clean and comfy.
Stayed 4 nights in May 2025
Verified

10/10 Excellent

Kathy G.

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

Relaxation vacation

Beautiful property! Great location! Amazing pool.We will return! Owner is very nice and helpful!
Stayed 6 nights in May 2025
Verified

10/10 Excellent

David S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was very nice and well appointed. The location is great to get everywhere you would like to go on in Key West. The private patio and pool were great to come back to after a warm day walking to the nearby restaurants, museums, and bars!The owner was very helpful and quick to respond via text message. I would highly recommend staying at 504 Porter!!!
Stayed 4 nights in Jun 2025
Verified

10/10 Excellent

Danielle C.

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

Key West Tropical Oasis

Everything was wonderful from check in to check out @ The owners of this property are AMAZING!
Stayed 4 nights in Aug 2024
Verified

10/10 Excellent

bob k.

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

July 4th Holiday Week

Gorgeous property perfectly situated in a quiet Truman Annex neighborhood. Still an easy walk to Old Town. Backyard pool is perfect for cooling off at any time. Our family loved it!
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Brad H.

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

Truman annex Key West

Property is beautiful and well maintained. Short walk to Duvall Street. Was not disappointed in any way.
Stayed 4 nights in May 2025
Verified

10/10 Excellent

Colleen W.

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

Great house

Nice house. Good location. Great communication with property manager. Highly recommend
Stayed 5 nights in Apr 2025
Verified

10/10 Excellent

Ashley M.

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

Can’t wait to go back!

Amazing property! Great location! Very responsive host! Would definitely stay here again!
Stayed 5 nights in Nov 2023
Verified

10/10 Excellent

Verified traveler

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

Perfect Key West Vacation

We loved this home so much. It has always been our dream to stay in the Truman Annex. The home was spotless and well equipped with everything that you would ever need.The pool is beautiful and being near Ft Zachary was an added bonus.We hope to be back in the not too distant future.
Stayed 4 nights in Apr 2025
Verified

10/10 Excellent

Ann L.

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

Best Key West Location

Highly recommend and will definitely return.
Stayed 7 nights in Dec 2023
Verified

10/10 Excellent

richard m.

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

Everything was fantastic

Property was great.
Stayed 4 nights in Aug 2024
Verified

10/10 Excellent

Michelle B.

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

Beautiful Truman Annex home

We had a wonderful stay in this beautiful and well appointed home. We hope to stay here again in the near future. The owners were very responsive and hospitable.
Stayed 4 nights in Apr 2024
Verified

10/10 Excellent

Mickie K.

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

Outstanding property and host

This was meant to be a relaxing vacation and it was. The pool was perfect and the proximity to downtown was ideal. The host was responsive and helpful. Overall, it was just what I needed and allowed me to relax, recharge, and enjoy the local area.
Stayed 7 nights in Dec 2024
Verified

10/10 Excellent

Evan M.

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

Beautiful

Loved the house. Don is great.
Stayed 4 nights in Jul 2024
Verified

10/10 Excellent

Amy K.

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

Perfect location!

Want to be steps from the fun, but not hear a thing when you go to bed at night? What about a private pool surrounded by lush greenery? This place in the Truman Annex is just perfect for 2 couples hoping to get away for a few days. Your host, Don, is super responsive and ensures your satisfaction. We will surely return!
Stayed 4 nights in Apr 2025
Verified

10/10 Excellent

Jason W.

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

5 stars!

Perfect location. Very clean. Great host!
Stayed 4 nights in Jun 2024
Verified

10/10 Excellent

Maria H.

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

Fun in the Sun

Loved our stay! The place is beautiful, quiet and close to everything. We loved the host’s attention to detail that included restaurant recommendations. We will be back. Thanks so much!
Stayed 4 nights in Jul 2024

About the host

Hosted by Don Roberts

Host profile image

Languages:

English
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