Key West Vacation Rentals

Key West Rentals & Property Categories

At Home Key West vacation rentals specializes in a variety of Key West rentals for travelers, with a great selection of amenities and locations to choose from; the possibilities are nearly endless when a guest is seeking their ideal Key West vacation rental.

Whether you prefer air conditioning and an iPod dock or a flat screen TV and an ocean view, At Home Key West has you covered with the conveniences guests deserve and have come to expect from our Key West rentals. Browse our categories to find the perfect rental home or condo for your Key West vacation.

Key West Rental Options

At Home Key West knows you have many choices when it comes to lodging in Key West, so we are here to make the process of finding a rental the easiest it can be; when you arrive for your much deserved tropical getaway, the only thing you have to worry about is how quickly you can get to the beach.


Gated Community    

Gated communities are a perfect opportunity to access amenities such as community pool while offering security within the complex.

Pool/Beach Towels    

Pool/Beach Towels are provided at all of our vacation rentals; pack light with essential shorts, swimsuits and flip flops.

Private Pool    

Down south it's hard to find a home that doesn't have its very own private pool; Key West is no exception. Our selection of Key West vacation homes includes a private pool where you and your guests can enjoy pool parties, relaxation and good times with friends.


Vacation houses in Key West are designed to offer you a casual comfortable "home away from home", including modern conveniences such as WIFI.


Bicycles are not just a mode of transportation; they are an opportunity to express our individuality.

Monthly Rental    

Key West vacation homes in Florida, like the ones offered by At Home Key West, have been adored by all who set foot on our sands. Harry S. Truman spent his winter down here, and Ernest Hemingway called the island his home for many years.

Pets Considered    

Choose from over 25 Key West pet friendly vacation homes. Bring the whole family!


Most of our homes have either private or community pool

Beach View    

Beach View condos are located on the south side of the island where tropical breezes nourish your spirit.

Community Pool    

Key West vacation rentals with access to a community pool.

Free Concierge Service    

At Home In Key West has experts that can help you with everything Key West. Let us suggest great restaurants, fabulous activities or the latest local hot spot.

Housekeeper Optional    

amenity: Housekeeper Optional


Old Town    

The properties listed below are located in the Old Town area of Key West, Florida. These properties are within walking distance to many of the attractions, restaurants, bars and shopping that make Key West famous.

Truman Annex    

Just steps away from Key West's historic Old Town, and at the rim of the sea where the Gulf meets the Atlantic sits the premier gated community known as Truman Annex.

Key West Golf Club    

The Key West Golf Club is only minutes away from downtown Key West and located on Stock Island which offers several full service marinas and several excellent restaurants that are popular with many of the "locals".

Coral Hammock    

This resort community of town homes recalls the romantic charm of old Key West. Inspired designs with custom details feature spacious 2 & 3 bedroom floor plans, vaulted ceilings, "Conch" style porches and the traditional metal roof.

Mid Town    

The properties listed below are centrally located on Key West, just a short bike ride to Old Town or the beaches.

Stock Island    

Stock Island is an island in the lower Florida Keys immediately east of Key West. It is considered part of Key West proper, just about 5 miles from the Old Town historic district.

Smathers Beach    

Key West's largest beach runs along the southern shore of the island for almost 2 miles. Beach activity ranges from tanning, volleyball, and watersport/beachsport rentals.

Historic Seaport    

At Key West Historic Seaport and Harbor Walk you will find a multitude of restaurants, attractions and activities and take in some breathtaking views at the same time.

Property Types


Magnificent private luxury condominiums that provide high end vacations for the discriminating vacationer. Spectacular vacation getaways with your every desire in mind, ultra chic, one of kind private homes with your every comfort provided for.


Don't pass up the opportunity to stay in a private home in Key West, Florida. The added privacy and space will truly add to your "live like a local" Key West experience.


Key West condo rentals are a charming and comfortable way to spend your vacation in Key West, Florida. Many condo rentals in Key West Florida boast a community pool and hot tub for guest use throughout your stay.


Townhomes are a great alternative Key West, Florida vacation rental if you want more than an apartment and not as much room as a private home would offer.


Cottages in Key West, Florida are small, quaint and historic in nature; all are located in the Old Town historic district in the heart of our island paradise.


Villas in Key West, Florida offer the ultimate in Key West island experience that you'll remember for a lifetime.

Private Home    

type: Private Home