Key West Vacation Guide

Key West is a VERY dog-friendly town! Furry friends are even allowed in some bars and restaurants on our island. There are also several dog parks and even a dog beach! If you wish to travel with your dog(s), we do have dog-friendly vacation homes available.

open floor plan at ashe house monthly vacation rental
Birds of a feather flock to Key West for the winter. We refer to them as Snowbirds and we're happy to call them our friends. Year after year, we enjoy hosting guests from Canada, New York, Connecticut, Boston, Chicago, Washington DC and other very cold...Read more
Christmas in Key West
Twas the Bight before Christmas and all through the house. Not a creature was stirring. Not even a dog slipping into a life vest to go kayaking the mangroves. Fortunately, Historic Key West Vacation Rentals has a full collection of luxury boutique vacation rentals, many...Read more
open space living at lola's place monthly rental
Historic Key West Vacation Rentals presents these six Key West Spots for laptops and lapdogs . We've spent most of this year in Zoom meetings, virtual learning environments and in close communion with our dogs. We could all use a much-needed change of environment and...Read more
solaris cottage
Solaris Cottage is a pet-friendly Key West retreat for dog lovers. This splendid luxury boutique is located on one of Key West’s most private slow lanes. The moment you step onto the front porch and into the cool, sun-dappled living area, stresses will melt away...Read more
dog on the beach in key west
Set a place for fido in pet-friendly Key West at these eight boutique luxury vacation rentals at Thanksgiving. Traveling to Key West with a dog is easy during the holidays. We're in a very dog-friendly destination. Furry friends are even allowed in some bars and...Read more
seas the day
Seas The Day in Key West for your weeklong adventures. Historic Key West Vacation Rentals invites you to enjoy this vacation rental aptly named "Seas the Day!" This newly updated 2 bedroom, 1 bath, first-floor condo is located in the Shipyard section of the Truman...Read more
john truman bedroom
Fall is the perfect time to experience Key West retreats at Truman Suites. The Truman Suites offers five separate fully equipped suites just a few steps from famous Duval Street. The two-story complex offers 7 bedrooms, 5 bathrooms and sleeps up to 18. The Truman...Read more
key west palms at sunset
Our Key West weather is absolutely perfect from October through January making it the ideal getaway destination for extended vacations. Warm enough to lounge by the pool, snorkel our reefs and to kayak along the mangroves. Visiting couples, seniors and families will find it the...Read more
island days pool
Historic Key West Vacation Rentals has the premier collection of boutique luxury homes and we're happy to present to you these eight Caribbean homes for the holidays! You've spent most of the year quarantined and landlocked while dreaming of an exotic, tropical getaway. Key West...Read more
al fresco dining at Inn Cogneato in Key West
Inn Cogneato is a newly renovated beautiful 2 bedroom 2 bath home located in one of the oldest parts of Historic Key West. We so excited to share the updates with you this luxury boutique rental comes with a very special tropical rate for November...Read more

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