Vacation Homes of Key West - VHKW

Vacation Homes of Key West - VHKW VHKW - Vacation Homes of Key West is a boutique vacation rental company since 1997. We are located at 507 Whitehead St., Key West, FL.

We offer: One-of-a-kind rental Homes from Luxury to Boho; Full Management Services; Unique Guest Experiences, Concierge. In-house Concierge for Vacation Rental Guests and Key West Travelers; Full Service Property Management of Privately Owned Homes in Key West

Stay in true island luxury at Sunset Sonnet Luxury Villa on exclusive Sunset Key. Just a 5-minute ferry ride from Key We...
04/24/2025

Stay in true island luxury at Sunset Sonnet Luxury Villa on exclusive Sunset Key. Just a 5-minute ferry ride from Key West, but it feels like a world away.

🏝 2 Bedrooms, Sleeps 4, Monthly Rental
🚤 Private 24-hour ferry access
🌅 Secluded Caribbean-style retreat

Perfect for those who want the beauty of Key West with the privacy of an exclusive island.

The Keys are calling. Book your stay. 🌺
vhkw.com

Key West has always been a refuge for artists, dreamers, and free spirits. That legacy lives on in our historic gorgeous...
04/16/2025

Key West has always been a refuge for artists, dreamers, and free spirits. That legacy lives on in our historic gorgeous homes.

Experience authentic Key West. 🌺
vhkw.com

Wake up to the sound of the waves, spend your days in paradise, and end each evening with a postcard-worthy view of the ...
04/14/2025

Wake up to the sound of the waves, spend your days in paradise, and end each evening with a postcard-worthy view of the sunset.

Villa Porta del Sole - 2 Bedrooms, sleeps 4, and available for monthly rental.

The Keys are calling. Book your stay. 🌺
vhkw.com

Experience Key West authentically. 🌺 Our collection of handpicked homes lets you experience Key West as it’s meant to be...
04/08/2025

Experience Key West authentically. 🌺

Our collection of handpicked homes lets you experience Key West as it’s meant to be. Laid-back, colorful, and full of character.

Book your stay 👉🏻 vhkw.com

Art has always been a priority at VHKW- Vacation Homes of Key West. Artist / Sailor Captain David Wegman is a decades lo...
04/08/2025

Art has always been a priority at VHKW- Vacation Homes of Key West. Artist / Sailor Captain David Wegman is a decades long friend and his Caribbean folk art was an early inspiration in the design of our business.

Over the decades we celebrated David’s lifestyle, collected his art, and featured his art through murals, paintings, and sculptures in several of our vacation properties including “Wabi Sabi,” “Amelia’s Hideaway,” “Pavilion Villa, “Heavenly Hideout,” “Elegant Key West Tree House,” and our VHKW office in Key West

From now until April 24, artist Wegman has an exhibition of original paintings and drawings at The Studios of Key West. Titled “A Fifty Year Retrospective.” Collectors of his art include infamous musicians such as Kenny Chesney, Zac Brown, and the late Jimmy Buffet. https://tskw.org/a-fifty-year-retrospective-by-david-wegman/

David recently published a book titled, “Fifty Years of David Wegman,” featuring a collection of his paintings and stories about the experiences that inspired him. https://shopgreenparrot.com/products/fifty-years-of-david-wegman

If you’re not in Key West, no problem. Explore his works on David Wegman’s online gallery: https://tskw.org/david-wegman-online/

If you’d like to stay in a VHKW vacation home that features David’s work, follow these links:

https://vacationhomesofkeywest.com/properties/amelias-hideaway/

https://vacationhomesofkeywest.com/properties/key-west-wabi-sabi/

https://vacationhomesofkeywest.com/properties/pavilion-villa/

https://vacationhomesofkeywest.com/properties/heavenly-hideout-at-rainbows-end/

https://vacationhomesofkeywest.com/properties/elegant-key-west-tree-house/

Stay in an authentic 1880s cottage with modern comforts in the heart of Old Town Key West. Blue Porch Cottage is a caref...
04/06/2025

Stay in an authentic 1880s cottage with modern comforts in the heart of Old Town Key West. Blue Porch Cottage is a carefully restored 1-bedroom retreat perfect for a quiet retreat with Old Town at your doorstep.

🏡 Sleeps 2-4 | Monthly Rental
🌿 Original Dade County Pine & counterweight windows
💙 Quintessential blue porch for relaxing Key West-style

The Keys are calling. Check complete list of amenities and availability. 🌺
vhkw.com

Not just another rental. Romance on William is a 1902 Victorian home listed on the National Historic Registry. Located i...
04/05/2025

Not just another rental. Romance on William is a 1902 Victorian home listed on the National Historic Registry. Located in the heart of Old Town Key West, it’s perfect for a long-term stay.

🏡 3-3.5 Bedrooms | 3.5 Baths | Sleeps 6-8
🌴 Private & peaceful, yet steps from Key West’s best
📍 528 William St | Monthly Rental

Stay in a home with history, elegance, and a prime location.

The Keys are calling. 🌺
vhkw.com

We’ve updated our website to make finding your perfect slice of island life even smoother. 😍Take a peek, get inspired, a...
04/03/2025

We’ve updated our website to make finding your perfect slice of island life even smoother. 😍

Take a peek, get inspired, and start planning your Key West escape.
🌺 vhkw.com

Good vibes, great sunsets, and that unmistakable island magic. Sunset taken from Mallory Square. ✨
03/23/2025

Good vibes, great sunsets, and that unmistakable island magic. Sunset taken from Mallory Square. ✨

This Key West villa is a rare find!Ocean View Luxury Villa is one of the few true beachfront homes in Key West, offering...
03/21/2025

This Key West villa is a rare find!

Ocean View Luxury Villa is one of the few true beachfront homes in Key West, offering breathtaking open-water views and direct access to Key West’s very best beach, Fort Zachary Taylor.

It is also just minutes from Old Town’s restaurants and nightlife.

Available for weekly stays.
vhkw.com

Key West may be small, but its beaches are packed with personality. 🏖 Smathers Beach – The largest & best for swimming, ...
03/18/2025

Key West may be small, but its beaches are packed with personality.

🏖 Smathers Beach – The largest & best for swimming, sunbathing, and water sports

🌅 Rest Beach – A peaceful spot, perfect for sunrise views & relaxation

🌊 Higgs Beach – Features a pier, picnic areas, and a dog-friendly section

🐾 Dog Beach – A small, rocky beach just for pups to splash around

🤿 Fort Zachary Taylor Beach – The best snorkeling with clear water & rocky shore

Which beach fits your vibe?

Tucked away near Bahama Village, Governor’s Retreat blends historic charm with modern island luxury. This 3BR/2.5BA home...
03/16/2025

Tucked away near Bahama Village, Governor’s Retreat blends historic charm with modern island luxury.

This 3BR/2.5BA home is a nod to Hemingway’s Key West, with curated books, vintage photos, and a porch made for cocktails at sunset.

Steps from the Hemingway Home & Museum, yet hidden on a quiet lane.

Availably for monthly stays.
vhkw.com

This is your cozy getaway in the heart of Key West. Island Sunshine Bungalow combines historic charm with modern design,...
03/09/2025

This is your cozy getaway in the heart of Key West.

Island Sunshine Bungalow combines historic charm with modern design, featuring vaulted ceilings, heart pine wood flooring, and a fully equipped chef’s kitchen.

Just a short stroll to the Key West Historic Seaport and vibrant Duval Street.

Sleeps 4 | Monthly rental

Book your stay.
vhkw.com

Unwind in Tropical Chill, a charming cottage-style flat in Truman Annex. One of Key West’s most exclusive gated communit...
03/07/2025

Unwind in Tropical Chill, a charming cottage-style flat in Truman Annex. One of Key West’s most exclusive gated communities.

This 2BR retreat (sleeps 4) offers a peaceful escape with lush surroundings, a private balcony, and easy access to Old Town’s vibrant energy.

Stroll to Duval Street, the beach, and local hotspots, then return to the serenity of Shipyard’s secure and luxurious setting.

Available for weekly stays.
vhkw.com

Duval Street is where Key West comes alive. By day, it’s a charming stretch of cafés, art galleries, and historic landma...
03/04/2025

Duval Street is where Key West comes alive. By day, it’s a charming stretch of cafés, art galleries, and historic landmarks. By night, it transforms into a vibrant scene of live music, famous bars like Sloppy Joe’s, and nonstop energy.

How will you spend your time on Duval?

This beach house on Sunset Key is the definition of VIP island living with a private pool overlooking the ocean. Set on ...
03/02/2025

This beach house on Sunset Key is the definition of VIP island living with a private pool overlooking the ocean.

Set on a 27-acre private island, this home offers the tranquility of no cars, soft sandy beaches, and exclusive resort amenities, including a luxury spa, fine dining, and a world-class bar.

Just a short ferry ride from Key West, but a world away from the ordinary.

📍 Private Island Key West Beach House, Sunset Key
Sleeps 6 | Monthly rental

Book your stay.
vhkw.com

Live music is back at Salute! Every Saturday & Sunday evening, Salute brings back live music from the pavilions on the b...
02/28/2025

Live music is back at Salute!

Every Saturday & Sunday evening, Salute brings back live music from the pavilions on the beach. Locals know. You should too.

Bring a beach chair or blanket to relax on the sand, or grab a table at Salute for dinner with a view.

See you there!

Address

507 Whitehead Street
Key West, FL
33040

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm
Saturday 9am - 5pm
Sunday 9am - 5pm

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About Vacation Homes of Key West

Welcome to Vacation Homes of Key West ~ VHKW, a locally owned and operated full service vacation rental and vacation property management company. Since 1997 we have helped pave the way for licensed vacation rentals in Key West, Florida. We dedicate ourselves to helping visitors discover the lifestyle of Key West by renting authentic privately owned homes, while managing and maintaining these homes for property owners with our hands-on care.

Our company was founded on the belief that Key West's historic homes and neighborhoods are an important tangible investment in our community heritage and economy, and one of our island's most treasured sustainable resources to be preserved for generations to come. We are proud to offer a wide range of unique vacation rentals (something for everyone), from intimate charming cottages, to ocean view condos, to luxury island estates - each reflecting the island style of their individual owners. Our website provides detailed information about each home, a descriptive map of the neighborhoods of Key West where they are located, vacation rental management services, and vacation rentals as an investment.