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.

shell cornucopia
Historic Key West Vacation Rentals has the premier collection of boutique luxury homes and we're happy to present to you these nine 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 October...Read more
southard comfort pool
Chances are you're ready to turn the page and to say goodbye to 2020. We couldn't agree more and we also can't think of a better time to wrap this one up, put a bow on it, load it into a fireworks cannon and blast...Read more
Have yourself a socially distant Key West Christmas and for this moment in time, your troubles will be far away. Historic Key West Vacation Rentals invites you to experience our collection of boutique luxury vacation homes with plenty of yuletides for days. Faithful friends who...Read more
thanksgiving feast
The centerpiece of Thanksgiving is always a large meal centered around a large turkey with lots of side dishes and desserts and traditions that celebrate family and friends and culture. This is a year when coming together for mashed potatoes, stuffing, cranberry sauce, hugs and...Read more
a Christmas wreath at Lemonade Mermaid Vacation Rentals in Key West.
Key West is known for its community spirit where all are welcome to join in joyous celebrations of Thanksgiving, Christmas and New Year's. These are the times we decorate for the season and regale locals and visitors alike with art, fine food and holiday libations...Read more
little miss magic den
2020 is not the year to be hoarding your vacation days. We all need time away from work and routines and that's especially important when we're spending much more time in our homes. You may be able to roll over some of your vacation days,...Read more
waterfall feature at southard comfort vacation rentals
If you're currently balancing virtual school for your children and meeting deadlines while working from home, it's time for a change of scenery. Trade in the drudgery for creativity and outdoor activities that translate into learning, plant life, moon phases, star gazing, and assorted natural...Read more
the commercial kitchen at villa luxe
If you've been working from home, virtual learning from home, social distancing at home, and, well, been at home more often than not this year, you've earned a luxury Key West Getaway. It's time to pack up your laptop, cell phone, project files, virtual school...Read more
castaway cove is for kayakers
Welcome to Castaway Cove Castaway Cove is a recently renovated monthly rental (28-night minimum) and comes with all the comforts you would find at home. This home boasts hardwood bamboo flooring throughout and has an open floor plan downstairs. The living area features a comfy...Read more

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