Authentic Key West Vacation Rentals ...

where you can really live your Key West vacation island style.

Summer Rates
Call now to receive special summer rates on select properties: +1 (305) 294-7358.
Dancing Palms Villa
This completely renovated home has the architectural allure of a vintage design, with all the advantages of a modern luxury home.
New Monthly Vacation rental
This property is located 2 blocks from the Historic Key West Seaport, and just 2 blocks off Duval Street.
Ultimate Key West Beach House
Perfectly positioned on Sunset Key, 'the islands island,' the Ultimate Key West Beach House ~ Sunset Key VIP, is within 500 yards off-shore of the 'main island' of Key West.
Key West Wabi Sabi
Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island living.
Heavenly Hideout at Rainbow's End
Welcome to the end (and the beginning) of the road. Literally the first and last vacation rental in on U.S. Highway 1- Mile 0.
Classic Key West Estate
Classic Key West Estate is a meticulously maintained grand wooden estate home available as a weekly Key West vacation rental.
Island Elegance ~ Near The Beach
Strikingly set in the oft-missed Key West Beachside neighborhood, showing a tall white privacy wall topped with shimmering green louvers.
The Caroline House Estate
An exceptional degree of refinement was reserved for the sophisticated renovation and d├ęcor of this circa 1930's Key West Victorian house plus Caribbean bungalow cottage.

Vacation Homes of Key West invites you to truly embrace the island lifestyle by renting private Key West vacation rentals. Whether you want to rent an amazing Duval Street penthouse, an authentic historic home in Key West's Old Town, a modern island villa, a romantic Caribbean cottage, or an oceanfront luxury condo, here you'll find truly unique Key West rentals.

Did you know that Key West vacation rentals are a great alternative to hotels, offering more space, comfort, privacy and affordability? From weekly rentals to monthly rentals, from charming little cottages to luxury island estates; we offer a select number of privately owned top quality Key West houses, villas, cottages, townhouses, condos, penthouses, suites, and estates. Our private rentals offer luxury amenities including full kitchens, swimming pools, Jacuzzi tubs, and lush tropical gardens.

Vacation Homes of Key West is a locally owned and operated company and this means we know our island well. We have filled this exclusive website with detailed information about all our vacation homes and the unique neighborhoods where they are found. Our customized interactive Key West map not only helps you navigate around the island, you can read about the Key West neighborhoods in detail and learn a little bit about their history too. Our map also includes beautiful photography of Key West beaches, parks, museums, and many other points of interest.

For an entertaining way to visualize the benefits of renting a private vacation rental and see the huge variety of things to do in Key West, be sure to view our ever-growing Key West Videos page. As you plan your Key West vacation or Key West wedding, please review our extensive list of Things to Do in Key West with recommendations for Key West restaurants, art galleries, shopping, theater, clubs, marinas, museums, gardens, and water-sports, to name a few. Be sure to check out our Key West Beach Guide. And to keep you informed about what's going on around the island we offer a detailed list of Key West Events including world staged events like Yacht Race Week, popular local events like the House and Garden Tours and Fishing Tournaments, and famous off-beat events like Fantasy Fest. On top of all that, a special feature our website is the unique on-line Key West Picture Gallery. Visit this gallery and here you can direct purchase amazing Key West photography prints from renowned local photographers established in their own art form.

Beyond all of these website features, we're also committed to providing you with updated and interesting information about Key West vacation rentals, the vacation rental business and life in Key West. So we invite you to enjoy our 'not so typical' Key West Vacation Rental Blog. And towards that same effort, we invite you to visit us on facebook, Twitter, and YouTube. Your Key West vacation becomes personalized and even more memorable when you utilize our website and choose your own private rental from our exclusive selection of vacation rentals. Vacation Homes of Key West wants you to experience the real Key West lifestyle. Come live your island dream.


key west map

Neighborhoods of Key West ~ Ultimate Key West Map

Our personalized interactive Google map of Key West helps you navigate around the island, plus you can read about the unique island neighborhoods. We pin-point and describe major points of interest around the island that are illustrated with unique professional photographs. Beneath the Google map, we highlight and define the real estate rental districts of Key West and locate each of our rentals to assist you in choosing your vacation rental property.


key west webcam

US 1 Mile Marker 0 ~ Key West Live Webcam

Welcome to the end (and the beginning) of U.S. Highway 1. Mile Marker 0 in Key West, Florida, the famous small green road sign that marks the southernmost tip of the Overseas Highway, U.S. 1. The 'end of the road,' that begins at Fort Kent, Maine at the Canadian border and ends at the junction of Fleming and Whitehead Streets. One of the most famous photo-ops on the island, now you can check it out anytime you want. When you visit Key West, call your friends from Mile Marker 0 and give them a 'real-time' wave. Better than emailing a photo, send them to our website: mile0webcam.com


key west beaches

Ultimate Key West Beach Guide ~ Key West Beaches

Key West beaches are similar to The Bahamas, with white sand, coral rocks, and shallow turquoise water with tropical fish and living reefs right off shore. This is because Key West and the Florida Keys are flat coral islands, the top remnants of former coral reefs. The living coral reef line is 7 miles offshore and protects the flat islands of the Florida Keys from crashing waves. Our Key West Beach Guide will help you locate and learn about how you can experience first-hand Key West's Caribbean beaches.


key west vacation rental blog

Key West Vacation Rental Blog

Not your usual vacation rental blog. Notes and opinions, quips and quirks about life in the Key West vacation rental business. Read personal stories and first hand accounts about things like how we got started and what continues to inspire us about Key West cottages, the people who live here, and the charm of the island. We've lived in Key West for a very long time and we've been helping people plan Key West vacations since the internet first got started.


things to do in key west

Things To Do in Key West

The tiny island of Key West is blessed with an amazing variety of fine international cuisine, nationally recognized music and entertainment, beautiful art galleries, creative shops and services, and historic museums, parks, and gardens. Vacation Homes of Key West gives you an extensive selection of "things to see and do" from our own personal "well worn path" from decades of living and loving in Key West. Regardless of the inevitable changes brought with time, we continue to love and enjoy this island year after year.


events in key west

Key West Events

Vacation Homes of Key West brings you an updated calendar Key West Events to help you plan the trip you are dreaming about. Choosing a vacation rental property from Vacation Homes of Key West will provide you with a beautiful, and usually the most affordable place to stay for your favorite Key West events. If you are planning to come to the island for a more popular event, such as Fantasy Fest or New Years, we suggest you reserve your vacation rental well in advance so you don't miss out on your favorite place to stay.


Vacation Rentals

Sunset Key

sunset key

Villas

villas

Cottages

cottages

Condos

town houses and condos

Suites

suites

Compounds

compounds

Penthouses

penthouses

Estates

estates



Featured Businesses

Around Key West

around key west

Key West Golf Club

key west golf club

Best Key West Rentals

best key west rentals