Key West Vacation Rentals

Featured Properties

Weekly

By The Beautiful Sea ~ A Key West Beach Front Condo

3 Bedrooms
2 Bathrooms
6 Sleeps

From $482 / night
4.7

Weekly

Family Reunion Compound

8 Bedrooms
6 + Bathrooms
21 Sleeps

From $1462 / night
5.0

Weekly

Old Town Caribbean Estate

10 Bedrooms
7 + Bathrooms
21 Sleeps

From $1010 / night
4.9

Weekly

Down Island Digs

2 Bedrooms
2 Bathrooms
6 Sleeps

From $517 / night
4.7

Weekly

Tropical Chill

2 Bedrooms
2 Bathrooms
4 Sleeps

From $347 / night
5.0

Weekly

Amelia’s Hideaway

4 Bedrooms
4 Bathrooms
10 Sleeps

From $864 / night
4.7

Weekly

Cockadoodle Cottage On Duval

2 Bedrooms
2 Bathrooms
4 Sleeps

From $390 / night
4.8

Monthly

Rooftop Renaissance

1 Bedroom
2 Bathrooms
4 Sleeps

From $154 / night

Weekly

Exclusive Key West Beach Front

2 Bedrooms
3 Bathrooms
6 Sleeps

From $487 / night
4.7

Weekly

Twice as Nice on Duval Street

4 Bedrooms
4 Bathrooms
8 Sleeps

From $808 / night
4.9

View all Rentals

Reviews from Real Renters

“Absolutely great experience. The cottage was immaculate…”

Read Full Testimonial
Dale H.

February 2025

Absolutely great experience. The cottage was immaculate when we arrived and we had a wonderful stay.

Dale H. – February 2025

Reviews from Real Renters

“…Was nicer than the pictures. VHKW is the best rental company in the keys…”

Read Full Testimonial
James C.

December 2024

The house was super clean, pool was amazing. Was nicer than the pictures. VHKW is the best rental company in the keys. We have rented from many of the local co and they do not come close. Their customer service is great, from the beginning to the end.

James C. – December 2024

Reviews from Real Renters

“Excellent at communicating. Very easy to check in and check out…”

Read Full Testimonial
Delilah M.

January 2025

Excellent at communicating. Very easy to check in and check out. Stellar property.We will book with VHKW again.

Delilah M. – January 2025

Reviews from Real Renters

“…excellent condition. Would definitely rent from VHKW again!“

Read Full Testimonial
Jessica C.

December 2024

Communication was amazing! Unit was as described and in excellent condition. Would definitely rent from VHKW again!

Jessica C. – December 2024

Access the Best of Key West

Featured Key West
Vacation Destinations

Old Town

Sunset Key

4 Miles of Fun Times

Explore Key West Neighborhoods

Iguana

Plan Your Vacation in

Key West Florida

Ultimate Key West Activities Guide

Ultimate Key West Beach Guide

Your Ultimate Insider’s Guide to Key West

Explore Resources & Guides

Why Book Direct?

Book your stay in one of our Key West Vacation Rentals directly with us for guaranteed lowest rates and hassle-free online reservations. While we list our exclusive rentals on trusted sites, they often add over 10% in booking fees with no extra value. Booking directly with us ensures you the best price—guaranteed!

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Key West Vacation Rentals

By The Beautiful Sea ~ A Key West Beach Front Condo

Family Reunion Compound

Old Town Caribbean Estate

Down Island Digs

Tropical Chill

Amelia’s Hideaway

Cockadoodle Cottage On Duval

Rooftop Renaissance

Exclusive Key West Beach Front

Twice as Nice on Duval Street

“Absolutely great experience. The cottage was immaculate…”

Dale H.

“…Was nicer than the pictures. VHKW is the best rental company in the keys…”

James C.

“Excellent at communicating. Very easy to check in and check out…”

Delilah M.

“…excellent condition. Would definitely rent from VHKW again!“

Jessica C.

Featured Key West
Vacation Destinations

Old Town

Sunset Key

Explore Key West Neighborhoods

Key West Vacation Rental

Key West Florida

Ultimate Key West Activities Guide

Ultimate Key West Beach Guide

Your Ultimate Insider’s Guide to Key West

Why Book Direct?

Questions About Booking?

(305) 294-7358

Key west

Key West Vacation Rentals

By The Beautiful Sea ~ A Key West Beach Front Condo

Family Reunion Compound

Old Town Caribbean Estate

Down Island Digs

Tropical Chill

Amelia’s Hideaway

Cockadoodle Cottage On Duval

Rooftop Renaissance

Exclusive Key West Beach Front

Twice as Nice on Duval Street

“Absolutely great experience. The cottage was immaculate…”

Dale H.

“…Was nicer than the pictures. VHKW is the best rental company in the keys…”

James C.

“Excellent at communicating. Very easy to check in and check out…”

Delilah M.

“…excellent condition. Would definitely rent from VHKW again!“

Jessica C.

Featured Key West Vacation Destinations

Old Town

Sunset Key

Explore Key West Neighborhoods

Key West Vacation Rental

Key West Florida

Ultimate Key West Activities Guide

Ultimate Key West Beach Guide

Your Ultimate Insider’s Guide to Key West

Why Book Direct?

Questions About Booking?

(305) 294-7358

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Featured Key West
Vacation Destinations