June Events Kick Off Our Key West Summer

southern skies waterfall
David

June events kick off our Key West summer and you can plan your much-needed vacation around these best times under the sun. From annual festivals to holiday celebrations, the fun never stops in Key West. We're looking forward to these upcoming events. For details on any event or planning a holiday vacation, contact our local team. We're happy to provide nearby vacation rental recommendations and the inside scoop on all things Key West. 

Key West Pride

Key West shows its Pride every day, and this is your chance to be a part of the celebration! The five-day schedule includes daytime pool and beach parties, late-night drag shows, on-the-water adventures ranging from snorkeling and kayaking to glass-bottom boat tours, a street fair, and pageants to select Mr., Miss and Ms. Key West Pride. June 2-6, 2021

Where To Stay: Bahama Getaway, Cayo Limon, My Happy Place, Southern Skies, Starfish, Steamplant 207, Steamplant 208, Steamplant 210, Steamplant 212  

I Love Stock Island Festival

This five-day festival is to feature one-of-a-kind Stock Island-inspired activities and authentic immersive experiences in the local community, culture, and art. It’s a great way to celebrate Father’s Day weekend with friends and family in the laidback atmosphere of Stock Island, just across the Cow Key Channel Bridge from Key West. June 16-20, 2021

Where To Stay: Bahama Getaway, Cayo Limon, My Happy Place, Southern Skies, Starfish, Steamplant 207, Steamplant 208, Steamplant 209, Steamplant 210, Steamplant 212 

Mango Fest Key West

Experience all things Mango through shopping, education and demonstrations. Stroll through Truman Waterfront Park to visit vendors, shop local shops, visit galleries, and order great food. June 23-27, 2021

Where To Stay: Villa Luxe, Fair Winds At The Foundry  

45th Annual Swim Around Key West

The officially sanctioned event is a 12.5 mile swim clockwise around the island of Key West that is open to all age groups. Individual swimmers and relay teams can compete. The route takes swimmers through the waters of the Atlantic Ocean and the Gulf of Mexico, ending where they began at Higgs Beach. June 26. 2021

Where To Stay: Seas The Day 

Booking your home is just the beginning! Historic Key West Vacation Rentals is here to help you plan the rest of your vacation. Our little Key West island offers endless fun-filled activities such as water excursions, historical tours, fishing charters, and transportation options for your vacationing pleasure.

Concierge Cindy is available via phone or text at 305.619.2252 or via email at cindy@historickw.com. 

Concierge Cindy is happy to arrange your fishing charters, snorkel trips, kayaking and paddleboarding, as well as day trips and excursions to the Dry Tortugas, ghost tours and more. Cindy makes it very easy and she can even arrange delivery of some transportation options to your vacation rental.