Key West condos rentals & Key West house rentals at AlwaysOnVacation®

Key West Boat Charter - Key West Vacation Rentals, Florida

Live aboard one of our yachts and be in the midst of Key West’s Historic Seaport. Sail to the reefs with our Captain and mate at the time of your choosing.

Walking distance to Duval St. and Sunset Festival… Leave your car... Fly in… we will pick you up at the airport or Ferry in… our boats are ste

No. Of Bedrooms: 2, No. Of Bathrooms: 2, Sleeps: 4

Historic Inn & Cottages in Old Town Key West - Key West Vacation Rentals, Florida

There are many rooms to chose from at this tropical downtown Key West Hotel Resort. The bed and breakfast, cottages, guesthouse, mansion and inn all housed on one large property known as Simonton Court Historic Inn & Cottages. The Inn was once a cigar factory where craftsmen hand rolled some of the

No. Of Bedrooms: 25, No. Of Bathrooms: 25.5, Sleeps: 50

BAHAMA HOUSE - Key West Vacation Rentals, Florida

This historic Bahamian-style Conch cottage is a perfect example of turn-of-the-century island architecture. The modest two bedroom, each with queen bed, two bath and queen sleeper-sofa is accented with Dade County pine walls, cathedral ceilings and island folk art, including original oil paintings,

No. Of Bedrooms: 2, No. Of Bathrooms: 2, Sleeps: 6

Luxurious Oceanfront Codo - Key West Vacation Rentals, Florida

This Key West, Florida vacation rental condo is an ideal place for enjoying beach vacations with your family. Located on the ocean behind the Little White House only two blocks from Duval Street, Mallory Square and old town Key West in Harbor Place within Truman Annex, this two bedrooms and two a

No. Of Bedrooms: 2, No. Of Bathrooms: 2.5, Sleeps: 4

Historic Luxury Home - Key West Vacation Rentals, Florida

Enjoy staying in this wonderful two story double porch classic that was recently fully restored with great care. The house, we believe, was originally built across town on Caroline Street before 1900. Sometime around 1908 it was cut in half and dragged by mules to it's present location. This home fe

No. Of Bedrooms: 4, No. Of Bathrooms: 3, Sleeps: 7

Beautiful Historic Seaport Home - Key West Vacation Rentals, Florida

House that sleeps 10 people close to the Historic Seaport and across from the Calvin Klein house in Old Town Key West. Built in the 1840's the beautiful restoration of this two and half story four bedroom "Conch" house, by a noted designer, offers space for gracious living. It is situated on a corne

No. Of Bedrooms: 4, No. Of Bathrooms: 4.5, Sleeps: 12

Tropical Retreat in Old Town - Key West Vacation Rentals, Florida

Enjoy the uniqueness of Key West while staying at the gorgeous historic four bedrooms, three bath home in Old Town. Originally built in the 1920's, this authentic Conch house was fully renovated and restored in 2007. Granite countertops, top of the line stainless steel appliances, and stunning Dade

No. Of Bedrooms: 4, No. Of Bathrooms: 3, Sleeps: 7

Artistic Mountain View Home - Key West Vacation Rentals, Florida

Escape from the frantic pace of your home and business life to our beautifully renovated historic shipbuilders Key West, Florida vacation rental home. Located across from the entrance of the historic Key West cemetery in Old Town Key West, our 2 bedrooms and one bath rental home

No. Of Bedrooms: 2, No. Of Bathrooms: 1, Sleeps: 6

The Sanctuary - Key West Vacation Rentals, Florida

The Sanctuary is located at the corner of South and Simonton Streets and consists of six studios, two street side (The Egret and Heron Studios) and four in a gated compound with lush tropical gardens (The Ibis, Osprey, Pelican, and Seagull Studios).

As you enter you will be welcomed into the ga

No. Of Bedrooms: 0, No. Of Bathrooms: 1, Sleeps: 2