Entire home

Key West Oasis - Truman Annex Estate

Photo gallery for Key West Oasis - Truman Annex Estate

A two-story building with a pool, surrounded by palm trees and greenery. - Key West Oasis - Truman Annex Estate (Key West)
A two-story white building with a balcony, surrounded by a white picket fence and palm trees. - Key West Oasis - Truman Annex Estate (Key West)
A covered porch with a ceiling fan, wicker furniture, and a view of palm trees. - Key West Oasis - Truman Annex Estate (Key West)
A spacious living room with a beige sofa, a brown leather couch, and a large window with blinds. - Key West Oasis - Truman Annex Estate (Key West)
A dining area with a wooden table and chairs, a chandelier, and a view of the kitchen. - Key West Oasis - Truman Annex Estate (Key West)
Close to Fort Zachary Taylor Historic State Park and Duval Street, Key West Oasis - Truman Annex Estate provides a garden, a playground, and laundry facilities. For some rest and relaxation, visit the hot tub. Stay connected with free in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 8302 sq m

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

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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.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Heated pool
  • Hot tub
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchenette
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 4.5 bathrooms
  • Bathtub
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Separate dining area

Entertainment

  • Smart TV
  • Stereo

Outdoor areas

  • Balcony
  • Fenced yard
  • Garden
  • Gas grill

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair
  • Printer

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Hardwood flooring in public areas
  • Smoking not allowed

Services and conveniences

  • Concierge services
  • Iron/ironing board

Location highlights

  • In a village
  • In the city center

Things to do

  • Heated pool

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Garden
  • Unit size: 3,250 square feet

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome
Note from host: Guests count maximums include infants/toddlers.

Events

No events allowed

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
Onsite 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
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the neighborhood

Located near the beach, this vacation home is in Old Town Key West, a neighborhood 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. Visit our Key West travel guide
View more Vacation Homes in Key West
Map
Key West, FL

What's nearby

  • A military jet flying low over a concrete path surrounded by vegetation.
    Key West Naval Station
    1 min walk - 0.2 km
  • A yellow exhibit labeled 'NOAA's AQUARIUS UNDERSEA LAB' with a circular window and a door.
    Florida Keys Eco - Discovery Center
    2 min walk - 0.2 km
  • A brick corridor with arched ceilings and benches.
    Fort Zachary Taylor Historic State Park
    6 min walk - 0.6 km
  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    9 min walk - 0.8 km
  • Florida Keys National Marine Sanctuary
    3 min walk - 0.3 km

Getting around

  • Key West Intl. Airport (EYW)
    16 min drive

Restaurants

  • Blue Heaven
    10 min walk
  • Green Parrot Bar
    6 min walk
  • Margaritaville
    10 min walk
  • Mangoes Restaurant
    9 min walk
  • Kaya Island Eats
    9 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.

How much is parking?

Onsite parking is available at the 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?

Check-out is at 10:00 AM.

Where is Key West Oasis - Truman Annex Estate located?

Located in Old Town Key West, this vacation home is within a 10-minute walk of Truman Waterfront Park, Duval Street, and Fort Zachary Taylor Historic State Park. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 15 minutes.

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