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Key West ~ Vacation Condos
Condos - A condo or town-house is one of a row of private houses joined by common sidewalls in a planned complex of two or more buildings. A condo or townhouse is an individually owned apartment style unit in a complex with a commonly owned grounds. Most condos and townhouses have two to three bedrooms.
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
Mar 21- Mar 28
Weekly $1975
Standard Rates: $1400 - $2550 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.
Standard Rates: $1675 - $3600 per week
2BR 2BA - Sleeps 2-4
1 Block from Duval Street
Oasis pool and hidden courtyard garden.
Private off-street parking
Just as you're inspired by an island oasis, so is this tropical island garden town home, cleverly hidden in the heart of Old Town Key West.
Standard Rates: $5000 - $8500 per month
2BR 2BA - Sleeps 2-4
1 Block from Duval Street
Upscale Renovation and Interior Design
Small Gated Town Home Complex
Large Heated Swimming Pool(shared)
Private off-street parking
Completely hidden from the thoroughfare, you would never know this small gated pool-garden complex is in the heart of Old Town Key West, less than one block from Duval Street. In this beautiful home, palettes of garden-green and Caribbean-blue take center stage so it claims the name, Casa Verde-Azure vacation rental.
Dec 12- Dec 21
Weekly $1550
8/9 Nights $1700
Standard Rates: $1500 - $2950 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.
Nov 17- Nov 23
Weekly $1975
Nightly $400
Jan 4- Jan 10
Six Nights $2575
Jan 22- Jan 25
Nightly $400
Standard Rates: $1800 - $4025 per week
3BR 2BA - Sleeps up to 6
Private Ocean-View Terrace
Resort-Style Shared Pool
If you’re craving a Key West beach accommodation with a bona fide front-line view to the sea, you can instantly gratify this need with a stay in this pretty vacation rental condominium, By The Beautiful Sea.
Standard Rates: $4200 - $7200 per month
2BR 2.5BR - Sleeps 6
Upscale Town home in gated bricked pool-garden courtyard
Shared Dipping pool with waterfall
Around the corner from trendy Petronia Street where you find Blue Heaven
Short Street from entrance to Fort Zachary Taylor Beach
Aspirational, luxurious, well appointed, and whimsical, are four attributes that make this courtyard townhome a lovely place to call home in Key West. Aptly named, Island Interlude, this 2-story property is situated around the corner from one of the most popular transitional urban scenes of Key West.
Standard Rates: $2600 - $6300 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.
Dec 1- Dec 12
7/8 nights $1500
Standard Rates: $1925 - $3625 per week
2BR 2BA - Sleeps 4
Manicured Tropical Swimming Pool Garden
Shared Heated Pool
Walk to Duval St. in 3 minutes
Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs. This is what you’ll experience as you make your entrance to this beautiful Bahamian ‘eyebrow’ style home, nestled away in private back corner of the small Old Town Key West gated community of Windward Park.
Jan 9- Jan 19
Weekly $2950
10 Nights $3350
Standard Rates: $1900 - $3950 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.’
Nov 14- Nov 23
Dec 17- Dec 21
Weekly $2100
Nightly $450
Jan 18- Jan 25
Weekly $2900
Mar 1- Mar 7
Six Nights $2900
Standard Rates: $1800 - $4025 per week
2BR 3BA
Designer Condominium Overlooking Key West Ocean Sanctuary
You can see for miles & miles & miles ... South over the turquoise ocean the White Street Pier stretches out in the near distance. Fresh Caribbean Breeze, great white herons wade in clear shallows below, relaxing on the balcony, southern sunrise, full moon rising ...
Nov 16- Nov 23
Dec 8- Dec 12
Dec 16- Dec 21
Weekly $1950
Nightly $400
Jan 4- Jan 6
Feb 18- Feb 22
Nightly $525
Standard Rates: $1850 - $3845 per week
3BR 2.5BA - Sleeps 6
A lush private tropical garden complete with large 40' X 16' swimming pool is the main focus of this unique island setting, and this traditional Key West town-home home is situated at the "pool-side" of the garden.
Nov 18 - Dec 21
Weekly $1750
Jan 8- Jan 18
Weekly $2900
10 Nights $3500
Standard Rates: $1900 - $3950 per week
2BR 2.5BA - Sleeps 4
Contemporary Interior Design Built in Historic Brick Architecture
Shared Pool in Gated Garden
Short Walk to Fort Zachary Beach
Close to Key West Water Park
Stroll to Downtown Old Town
A striking tri-level condominium situated in Key West's most historic gated Truman Annex waterfront luxury neighborhood, offers a beautiful combination of classic historic charm and refined modern ambience. Perfect location to enjoy the Truman Waterfron Park Ampitheater.
Nov 14- Dec 4
Dec 8- Dec 12
Dec 16- Dec 21
Weekly $1950
Nightly $400
Jan 4- Jan 11
Weekly $2400
Jan 11- Jan16
Jan 20- Jan 26
nightly $500
Feb 2- Feb 8
six nights $2800
Standard Rates: $1750 - $3845 per week
3BR 2.5BA - Sleeps 6-8
The artist-owner of this sun-lit pool-side town-home has created a delightful living space that welcomes you to an authentic tropical life-style in a unique Key West "pool garden compound."