Work, Play And Stay In Key West

copa cabana pool

Work, play and stay in Key West all summer. Historic Key West Vacation Rentals features luxury boutique vacation rentals that feature free Internet so you can remote work and remote learn. Stretch your Caribbean vacation into your most memorable travel experience. We feature nightly, weekly and monthly rentals and we're happy to help you plan your long-term stays for even more productive work and learning opportunities. Just look at some of the opportunities for recreation, the arts, culinary and exploratory adventures coming up soon.

Key Lime Festival

July 1-5, enjoy a full 4 days of culinary events for every taste, including favorites from past years such as the Key Lime Cocktail Sip & Stroll and Key Lime Pie Hop and new favorites for Key Lime lovers like a Key Lime Scavenger Hunt and Key Lime University! Organizers have also added a few intimate culinary events for VIP Key Lime lovers! Where To Stay: Bahama Getaway, Fish Camp, Poppy Cottage

The 2nd Annual Key West Mermaid Festival

July 1-5, #TheTakeOverIsReel we like to say, and we look forward to getting salty with all of the captains and mermaids who work hard to make Key West and the Florida Keys a better place for all who live the island life and our visitors. Where To Stay: Bahama Getaway, Fish Camp, Poppy Cottage

4th of July Fireworks and VIP Dinner

Bring the whole family to the Patriotic Party by the Ed Knight Pier. Enjoy food, music, and of course, fireworks. Get your tickets now for the VIP Fireworks Dinner-- featuring a plated dinner by Catered Affairs, private cash bar, music, and prime view for the fireworks. Space is limited; and seating will begin @6PMIn addition to the VIP seating. Where To Stay: Casablanca Too, Bahama Getaway, Fish Camp, Poppy Cottage, Sea Conch, Villa Josine


40th Annual Hemingway Days

July 20-25, with the annual Hemingway Days festivities. Scheduled events include a three-day marlin tournament recalling Ernest’s passion for deep-sea angling, virtual symposium presentations, poetry readings, a street fair celebrating Key West’s lively spirit, a museum exhibit of rare Hemingway memorabilia, a commemoration of the 121st anniversary of the author’s July 21 birth and a 5k run that salutes his sporting interests. Hemingway Look-Alike Contest is scheduled July 22-24, 2021. Where To Stay: Bahama GetawayFish Camp, Poppy Cottage

2020 Mini Lobster Season

July 28-29, 2021 (last consecutive Wednesday and Thursday of July each year) Daily Bag Limit: 6 per person for Monroe County and Biscayne National Park; 12 per person for rest of Florida.  Where To Stay: Bahama Getaway, Fish Camp, Poppy Cottage


Key West Tropical Heat

The temperature is not the only thing that will rise during Tropical Heat. The all-male theme parties, pool parties, and adult-oriented entertainment. August 11-15. Where To Stay: Bahama Getaway, Butterfly Cottage, Cayo Limon, Copa CabanaFish Camp, My Happy PlacePetunia Cottage, Poppy Cottage, Southern Skies, Starfish, Steamplant (207, 209), The Escape At Sunset Key

25th Annual Key West Lobsterfest

August 12th, Seafood lovers can chow down on Florida’s clawless lobster during a tasty “feast-ival” that features a savory schedule of events ranging from a traditional lobster boil to a lively street fair starring the sensational crustacean prepared in a variety of ways. Where To Stay: Bahama Getaway, Butterfly Cottage, Cayo Limon, Copa Cabana, Fish Camp, My Happy Place, Petunia Cottage, Poinciana Treetop, Poppy Cottage, Southern Skies, Starfish, Steamplant (207, 209), The Escape At Sunset Key

Plan Your Vacation The Right Way. Work, Stay and Play in Key West all summer. Reserve your favorite nightly, weekly or monthly rental right on our website or with our very summer-loving vacation planners. This summer we're ready to open up and let the sunshine in. You're invited, too!