Entire home

Key West Oasis - Truman Annex Estate

Holiday home with an outdoor pool, 9-minute walk to Duval Street

Photo gallery for Key West Oasis - Truman Annex Estate

Pool
Exterior
Living area
Dining
Dining

Reviews

10 out of 10
Exceptional
5 bedrooms4+ bathroomsSleeps 8301.9 sq m

Popular amenities

  • Dryer
  • Hot tub
  • Washer
  • Parking available
  • Kitchen

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪8 min walk‬
  • Place, Mallory Square
    ‪11 min walk‬
  • Place, Southernmost Point
    ‪16 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪10 min drive‬

Rooms & beds

5 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Double Bed

Bedroom 4

1 Double Bed

Bedroom 5

1 Queen Bed

4 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Bathtub · Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Kitchenette
Balcony
Separate dining area
Outdoor play area
Garden
Dining area

About this property

Key West Oasis - Truman Annex Estate

Welcome to Key West Oasis

Luxury | Privacy | Iconic Location in Truman Annex

Tucked away on one of the most exclusive lanes in the Truman Annex, Key West Oasis is a sophisticated, meticulously maintained estate that offers an unparalleled island escape. With 5 bedrooms, 5.5 bathrooms, and over 2,796 sq. ft. of beautifully designed living space, this estate is the ideal sanctuary for discerning travelers seeking comfort, style, and an unbeatable location.

PROPERTY HIGHLIGHTS:

Total of 5 bedrooms / 5.5 bathrooms

4-bedroom main house + 1-bedroom guest cottage

Lagoon-style heated saltwater pool & spa

Rooftop observation deck with panoramic 360° Key West views

Located steps from Truman Waterfront Park, Duval Street & the beach

4 cruiser bikes included

Gated carport & lush tropical landscaping

Maximum 8 guests | No pets | No events

MAIN HOUSE (4 Bed / 4.5 Bath)

Main Floor:
Step into elegance with gleaming mahogany wood floors, a formal dining room with seating for 8, and an adjacent study complete with a built-in workstation. The open-concept kitchen connects seamlessly to the living area and features black granite countertops, stainless steel appliances, breakfast bar for 4, and fully stocked cooking essentials.
The living room is centered around a 75” smart TV with sound system and opens directly to the stunning outdoor patio and pool area.

Second Floor:
Two guest bedrooms share a balcony overlooking charming Noah Lane—one with a queen bed, the other a full—plus a shared full bath. The spacious primary suite features a king-size bed, 55” smart TV, large walk-in closet, and a spa-like en-suite bath with soaking tub, dual vanities, and walk-in shower. French doors open to an expansive Ipe balcony—perfect for sunset cocktails.

Third Floor + Rooftop:
The third floor features a cozy 4th bedroom with a full bed and an adjacent full bathroom. A second flexible room serves as an office, yoga studio, or meditation space, and includes a wet bar. French doors lead to a ship ladder ascending to the rooftop observation deck, offering 360-degree views of Key West and the surrounding turquoise waters.

GUEST COTTAGE (1 Bed / 1 Bath)

Detached for maximum privacy, the 239 sq. ft. guest cottage includes a queen bed, 55” smart TV, full bathroom, mini kitchen, and closet—ideal for visiting friends or family.

OUTDOOR LIVING

Lagoon-Style Saltwater Pool & Spa – Heated with tranquil water feature

Outdoor Dining & Lounge Areas – With ceiling fans for warm afternoons

Gas Grill – Perfect for al fresco BBQs

Outdoor Shower – Ideal after beach or pool time

Tropical Landscaping & Lighting – Enhancing the charm and ambiance of this classic Conch-style estate

CARPORT & TRANSPORTATION

Gated carport with space for vehicle or golf cart

4 cruiser bikes provided—ride to the beach or Duval Street in minutes

LOCATION, LOCATION, LOCATION

Steps from Truman Waterfront Park and Amphitheater

Walk to Fort Zachary Taylor Beach

Minutes from Duval Street, Mallory Square, and top-rated restaurants, bars, and galleries

GOOD TO KNOW

Strict maximum of 8 registered guests

No parties, events, or amplified noise allowed

No pets permitted

Security cameras on exterior only (front, rear entry, and driveway)

Professionally maintained and cleaned to the highest standards

Experience Key West at its finest. Whether you’re sipping cocktails on the rooftop deck, enjoying a morning swim, or biking to local favorites, Key West Oasis is the perfect blend of luxury, privacy, and island charm.

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
Guests count maximums include infants/toddlers.
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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

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
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

About the area

Key West

Located near the beach, this holiday home is in Old Town Key West, a neighbourhood in Key West. 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 Florida Keys Eco - Discovery Center are also worth visiting.
Map
Key West, FL

What's nearby

  • Fort Zachary Taylor Historic State Park - 6 min walk - 0.6 km
  • Duval Street - 8 min walk - 0.7 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
  • Mallory Square - 11 min walk - 1.0 km
  • Southernmost Point - 16 min walk - 1.4 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 16 min drive

Restaurants

  • ‪Green Parrot Bar - ‬6 min walk
  • ‪Margaritaville - ‬10 min walk
  • ‪Blue Heaven - ‬10 min walk
  • ‪Rams Head Southernmost - ‬9 min walk
  • ‪Santiago's Bodega - ‬6 min walk

Frequently asked questions

Does Key West Oasis - Truman Annex Estate have a pool?

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

Is Key West Oasis - Truman Annex Estate pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Key West Oasis - Truman Annex Estate?

Check-in begins at 4:00 PM.

What time is check-out at Key West Oasis - Truman Annex Estate?

Checkout is at 10:00 AM.

Where is Key West Oasis - Truman Annex Estate located?

Located in Old Town Key West, this holiday home is within a 10-minute walk of USCGC Ingham Maritime Museum, Duval Street and Fort Zachary Taylor Historic State Park. Florida Keys Beaches and Mallory Square are also within 15 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Melissa S.

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

Close to perfect

A group of 6 of us here for the boat races. The location was wonderful and close enough to walk/ride the bicycles everywhere. There were plenty of extra linens and well-stocked supplies that we have ever had in a VRBO house. Pool had some issues, but management was quick to assist. The only complaint was the need for labels for the light switches and easier technology to use.
Stayed 7 nights in Nov 2023

10/10 Excellent

Willow F.

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

Gorgeous Property

My husband and I stayed 10 days with our 12 year old son. The property was exactly as described. We had plenty of room and spent a great deal of time around the pool. It’s very close to Duval, but also very quiet. We are excited to return again next year.
Stayed 9 nights in Oct 2023

10/10 Excellent

john c.

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

key west truman

Excellent property and location. Super nice home, perfect for 8 pep. Close enough to walk to places yet far enough to avoid congestion.
Stayed 9 nights in Jul 2022

About the host

Hosted by Conch Collection

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Languages:

English

Premier Host

They consistently provide great experiences for their guests