Key West Time
December 21st
7:30am · 65°F
December 21st
7:30am · 65°F
What Are 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
1 BR 2 BA
Standard Rates: $4,900 - $9,150 per month
1BR 2BA
Sleeps 2 - 4
Stunning 2-Story Luxury Condo
Hidden in a Heritage Victorian
Private open-air deck
Shared Zen-pool and spa
2 Streets from Historic Seaport
Rooftop Renaissance falls into a unique architectural category of Heritage Victorian - Meets Modern Luxury. This one-of-a-kind monthly rental is situated on the 2nd and 3rd level of a historic Victorian house on Caroline Street. An exquisite 1BR 2BA luxury accommodation, it was redesigned to offer all the accoutrements of a 5-Star condominium.
2 BR 2.5 BA
Monthly
Standard Rates: $6,200 - $17,610 per month
2BR 2.5BA - Sleeps 4
Located in Small Gated Enclave w/in Truman Annex Neighborhood
Large Shared Heated Pool and Jacuzzi
Private Gate is Steps to Downtown Old Town
Short stroll to Truman Waterfront Park and Ft. Zacharay Taylor Beach
Close your eyes for a moment and take a deep breath ... Now imagine yourself on an extraordinary Old Town Key West vacation. This luxury townhome vacation rental stands on a serene street, tucked in a tiny enclave called Key West Porter Court. A bit of a secret, it’s nicely hidden within the stunning neighborhood of Truman Annex where the gated grounds are park-like and immaculate. It’s as if you’re in a dream.
2BR 1.5BA
Standard Rates: $450 - $9,965 per month
2BR 1.5BA
Sleeps 2 - 4
Limited Edition 2-Story Condo
2 Streets from Historic Seaport
Private Porches and Courtyard Garden
Hidden from View in Heritage Building
Magic happened when this Key West wooden heritage building was redesigned. Now offers limited-edition condominiums. A case in point is this 2BR 1.5BA Seaport Hideaway. Architecturally intriguing. Epic historic atrium stairwell. Masterfully tucked away on Fleming Street. A special residence ideally located 2 short blocks from the docks, at the Key West Historic Seaport neighborhood.
2BR 2BA
Monthly
Monthly $
Standard Rates: $4,725 - $9,475 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.
2BR 2BA
Standard Rates: $2,230 - $4,260 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.
2BR 2BA
Dec 16 - Dec 22
Weekly $2400
Nightly $525
Jan 26- Feb 5
Weekly $4200
Nightly $850
Standard Rates: $2,580 - $6,200 per week
2BR 2BA - Sleeps 4
2nd FL Condo Suite plus private back deck on ground level
Downtown - 1 block off 500 block of Duval Street near Margaritaville
Private Heated Pool
Sun deck on ground level
When taking a selfie at the iconic Key West Mile Marker 0 just isn’t enough, now you can luxuriously live right next to this famous landmark ... in luxury and style!
3BR 2BA
Jan 28 - Feb 4
Nightly $650
Weekly $3500
Standard Rates: $2,580 - $5,775 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.
2BR 3BA
Standard Rates: $2,530 - $5,775 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 ...
2BR 1BA
Standard Rates: $1,800 - $3,675 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.
2BR 2.5BA
Standard Rates: $4,900 - $10,125 per month
2BR 2.5BA - Sleeps 4
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: $3,900 - $7,557 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.
2 BR 1 BA
Dec 12 - Dec 24
Jan 10 - Jan 16
Jan 26 - Jan 30
Nightly $450
Weekly $2100
Standard Rates: $2,200 - $4,380 per week
2BR 1BA - Sleeps 4-6
Overlooks large tropical garden with very large shared pool.
Boho style. Great value.
The Tree Tops Suite vacation rental is has a classic undying Key West charm that exudes a real down-island vacation feel. Approximately 750 square feet of living space offering an open floor plan joining the beamed ceiling living room and galley kitchen.
3 BR 2 BA
Jan 10 - Jan 22
Jan 26- Jan 30
Nightly $525
Weekly $2900
Standard Rates: $2,800 - $5,430 per week
3BR 2BA - Sleeps 6
Situated in Gated Tropical Garden
Expansive covered porch
Very Large Pool.
Boho Style Decor
Great value.
The allure of the bohemian style Garden Suite vacation rental comes from its one-of-a-kind architectural design, the original wood it is built with, the fun decor, and its authentic Key West pool garden setting. Garden Suite offers over 1200 square feet of living space and features a large living room with cathedral ceilings.
3BR 2.5BA
Jan 27 - Jan 30
Nightly $650
Feb 9 - Feb 15
Feb 22 - Feb 28
Nightly $750
Standard Rates: $2,600 - $5,660 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."
