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March 31st
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Key West ~ Truman Annex Vacation Rentals

What is Truman Annex? 'Truman Annex' is a gated community that offers a Key West experience, in a class all its own. An impressive blend of historic and contemporary Key West architecture, from historic estates to Conch style cottages. Truman Waterfront Park and Fort Zachary Taylor Beach are right out the gate, on one side of this neighborhood. On the other side, is Downtown Old Town, near Mallory Square, acclaimed restaurants, and museums.

View our exclusive Key West vacation rentals. Vacation Homes of Key West can help you find the perfect vacation rental for your next Key West vacation. Don't pay booking fees, save money by booking directly with VHKW today.

* PLEASE NOTE: Some properties displayed may not be available for rent due to other inquiries and pending reservations. Please contact our office to be sure of availability. info@vhkw.com or 305-294-7358 ext. 1

There are no properties available that fit all of your search options. Please contact our office if you would like assistance. info@vhkw.com or 305-294-7358 ext. 1


key west poolside loft
New
special rates available

2BR 2BA



Monthly $4150

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Standard Rates: $4500 - $8850 per month

2BR 2BA - Sleeps 4
Overlooks Tropical Swimming Pool Garden
Shared Heated Pool w/ Caribbean Cabana
Truman Annex Neighborhood
Gates lead to Ft. Zachary Taylor Beach, Truman Waterfront, and Downtown Old Town Key West

You know that adage … An unexpected turn can lead to hidden treasures. If there were ever a place that meets that description, it's this 2BR 2BA Key West Poolside Loft. Cleverly tucked away, here you’re in a unique loft-style Key West cottage, with a private deck and beautiful down-look poolside view.

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tropical chill
special rates available

2BR 2BA

April 18- April 27

Weekly $2250

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Standard Rates: $2165 - $4140 per week

2BR 2BA - Sleeps 4
Overlooks Tropical Swimming Pool Garden
Shared Heated Pool w/ Caribbean Cabana
Truman Annex Neighborhood
Gates lead to Ft. Zachary Taylor Beach, Truman Waterfront, and Downtown Old Town Key West

If you’re looking for a place to chill-out in the tropical warmth of Key West, this cottage-style flat is a wonderful place to relax and take a breather from everyday life. 

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ocean view luxury villa

Standard Rates: $6970 - $10740 per week

3BR 4BA - Sleeps 6-8
Ocean View / Sun Deck
Private Heated Pool
Key West Truman Annex Neighborhood
Short Walk to Beach and Key West Waterfront Park Amphitheater
Pet Friendly

Gorgeous Old Town Key West Ocean View Luxury Home in immaculate gated neighborhood! Holding an enviable spot in Key West’s gated community of Truman Annex, this classic home offers an open water view, easy beach access, and is a short walking distance to Duval Street and downtown Old Town Key West..

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sweet sunshine garden flat
special rates available

2BR 1BA



Weekly $2575

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Standard Rates: $1485 - $3575 per week

2BR 1BA - Sleeps 4
Truman Annex Neighborhood
Steps to Truman Waterfront Park
Shared Heated Pool w/ Caribbean Cabana
2 Blocks from Duval Street
10 minute walk to the waters’ edge of Ft. Zachary Taylor Beach

Sweet Sunshine Garden Flat is perfectly situated for a week near the beach and downtown Old Town Key West. Looking north, you’re less than two blocks from downtown old town – looking south you’re less than two blocks from the Truman Waterfront Park and Fort Zachary Taylor State Park and Beach. 

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truman treasure

Standard Rates: $3745 - $8130 per week

3BR 2.5BA - Sleeps up to 5
Stroll to the Beach
Truman Annex residence with Ocean View from Bedroom Balconies
Short Walk to all Downtown Old Town Key West Features

Rent this Key West Luxury Home and Experience a Remarkable Piece of American Architectural History. A renovated 'Truman Treasure', in one of the most desirable Ocean Front Old Town Key West locations.

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island brownstone
special rates available

2BR 2BA


Weekly $2700

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Standard Rates: $1855 - $5520 per week

2BR 2.5BA - Sleeps 4-6
Stroll to downtown Old Town Key West
Short walk to Fort Zachary Taylor Park and beach

An exclusive island style brownstone town home offers a dramatic and spacious layout with features and details that include extra high ceilings, artistic crown molding, lots of windows and French doors. It is perfectly nestled in Key West’s most prominent gated waterfront neighborhood known as ‘Truman Annex.’

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