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





Reviews
10 out of 10
Exceptional
5 bedrooms4+ bathroomsSleeps 8301.9 sq m
Popular amenities
Explore the area

Key West, FL
- Place, Fort Zachary Taylor Historic State Park6 min walk
- Place, Duval Street8 min walk
- Place, Mallory Square11 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.
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
Children
Children allowed: ages 0–17
Guests count maximums include infants/toddlers.
Events
No events allowed
Pets
No pets 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
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 Smathers Beach. USCGC Ingham Maritime Museum and Florida Keys Eco - Discovery Center are also worth visiting.

Key West, FL
What's nearby
- 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 - 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
Getting around
Restaurants
- Green Parrot Bar - 6 min walk
- Margaritaville - 10 min walk
- Blue Heaven - 10 min walk
- Santiago's Bodega - 6 min walk
- Rams Head Southernmost - 9 min walk
Frequently asked questions
About the host
Hosted by Conch Collection
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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