The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
Discover nearby landmarks
Walk to Duval Street
5 bedrooms4+ bathroomsSleeps 8
Popular amenities
Balcony
Hot tub on site
Private pool
Kitchenette
Gas barbecue
Free Wi-Fi
Explore the area
Key West, FL
Florida Keys National Marine Sanctuary
Place, Florida Keys National Marine Sanctuary
3 min walk
Fort Zachary Taylor Historic State Park
Place, Fort Zachary Taylor Historic State Park
6 min walk
Duval Street
Place, Duval Street
9 min walk
Key West, FL (EYW-Key West Intl.)
Airport, Key West, FL (EYW-Key West Intl.)
15 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.
Our prices include all fees. No hidden fees.
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If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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. Southernmost Point 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.
Florida Keys Eco - Discovery Center - 2 min walk - 0.2 km
Florida Keys National Marine Sanctuary - 3 min walk - 0.3 km
Fort Zachary Taylor Historic State Park - 6 min walk - 0.6 km
Duval Street - 9 min walk - 0.8 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
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.
How much does it cost to stay at Key West Oasis - Truman Annex Estate?
As of 8 Jun 2026, prices found for a 1-night stay for 2 adults at Key West Oasis - Truman Annex Estate on 7 Sept 2026 start from £1,420, 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 Key West Oasis - Truman Annex Estate pet-friendly?
No, pets are not allowed at this property.
How much is parking at Key West Oasis - Truman Annex Estate?
On-site 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?
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 Truman Waterfront Park, 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.
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.
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.