Things to Do During Key West Pride Week

Known for its open and accepting atmosphere, Key West has long been a sanctuary for LGBTQ+ travelers. Plan your trip to our tropical paradise in June and join us for one of the best Pride Month celebrations in the country. With street fairs, parades, drag shows, pool parties, and gay history tours, we know how to celebrate Pride in Key West. Find lodging for everyone in your group with Rent Key West Vacations, and start planning your trip today!

Learn About LGBTQ+ History in Key West

Key West is a haven for the LGBTQ+ community. Did you know we were the first city in North America to elect an openly gay Mayor? Or that we have the only gay and lesbian trolley tour? Before joining us for Pride Week in Key West, check out this article How the Gays Saved Key West to learn about the island’s LGBTQ+ history!

Key West Pride Events and Activities

Key West Pride is an annual celebration taking place every June during Pride Month. Find the complete schedule of events here and discover some of the highlights of the week below:

Throughout the week, you will find many activities happening throughout the island, including pride-themed karaoke nights, bike tours, trolley rides, pool parties, comedy shows, art exhibitions, sunset sails, and brunches.
One of the most popular events is the Street Fair and Dance Party, featuring live performances and eclectic vendors on Duval Street.
For nearly 50 years, La Te Da has hosted a Tea Dance every Sunday. During Pride Week, they host a special celebration on the last day, where you can join in the historic party.
Pride closes with the annual parade down Key West’s historic streets. If you’re interested in participating, consider volunteering to help carry the 100-foot flag!

Reserve Your Key West Vacation Rental for Pride Week

Rent Key West Vacations offers the perfect lodging for everyone visiting during Pride Week! Our collection of vacation homes and condos offers everything you need for a comfortable stay, including fully equipped kitchens, linens, and laundry facilities. Book one of our homes in the historic district and stay close to the events happening on Duval Street. Or reserve a home near the beach and easily access Key West’s breathtaking beaches. If you need assistance finding the right vacation rental, please contact us at 1-800-833-7368!

Key West Day Trip Destinations: Dry Tortugas & Florida Keys Islands

The Overseas Highway travels 113 miles from Key Largo to Key West, offering a unique way to travel between the Florida Keys and experience all it has to offer. Plan an epic road trip to Key West from Florida’s mainland, or fly into our local airport and start your exploration from the Southernmost City. Drive to islands along the Florida Keys, like Big Pine Key, Marathon, Islamorada, and Key Largo. Or head out on the water and take a ferry to the remote Dry Tortugas National Park. No matter where you want to explore, Rent Key West Vacations offers the perfect lodging in Key West!

Dry Tortugas

Located 70 miles west of Key West is Dry Tortugas National Park, a one-of-a-kind destination where you can explore remote islands and discover fascinating history. Get to the park on the Yankee Freedom Ferry and disembark at Fort Jefferson, one of the nation’s largest 19th-century forts. After touring the fort, you will have free time to snorkel coral reefs, swim in the crystal clear water, and watch wildlife.

Day Trip to Florida Keys Islands

Start your journey in Key West and drive along Highway 1 to access several Florida Keys Islands:

The Lower Keys

Traveling east from Key West will take you through the Lower Keys, the most natural and unpopulated area in the Keys. Experience the wilder side of the Keys at national wildlife refuges, marine sanctuaries, and remote beaches. Don’t miss Bahia Honda State Park!

Marathon

Just over an hour from Key West, Marathon is best known for its rich maritime history and family-friendly vibe. Enjoy prime boating access, explore Curry Hammock State Park, and learn about local wildlife at Turtle Beach or the Florida Keys Aquarium.

Islamorada

Islamorada is known as the sport fishing capital of the world, just under two hours from Key West. Experience an epic day of fishing and discover the island’s rich history, vibrant arts scene, and nature activities. Some of the most popular attractions in Islamorada include feeding fish at Robbie’s Marina, exploring the quirky art at Rain Barrel Village, and learning history at the Diving Museum.

Key Largo

Key Largo is the furthest island from Key West, approximately two hours and twenty minutes away. This is the longest island in the Keys, known for its fantastic diving, snorkeling, and fishing. Explore the underwater world of John Pennekamp Coral Reef State Park, explore the natural wonders of Everglades National Park, and cruise on the famous African Queen steamboat.

Book Your Vacation Rental on Key West

Whether Key West is at the beginning or end of your Florida Keys exploration, Rent Key West Vacations offers the ideal place to stay. We are one of the longest-standing vacation rental companies on the island, representing more than 100 properties. Book one of our rentals near Key West’s most famous beaches, or stay in Old Town and immerse yourself in the island’s historic charm. Book with us online or contact our local reservationist at 1-800-833-7368 to start customizing your Florida Keys vacation!

Explore the Natural Beauty of Key West on a Jet Ski Tour

One of the best ways to experience Key West is from the water. While there are many ways to explore the island’s coastline, one of the most fun ways is by jet skiing. Sign up for a jet-skiing tour and let a local guide show you the best of Key West on an adrenaline-pumping adventure. Hit the throttle and explore the crystal-clear water while looking for marine life, taking a dip at local sandbars, and admiring coastline views. Stay close to the water with Rent Key West Vacations and find the perfect lodging for your island getaway!

Jet Ski Tours vs Rentals

When you are looking for jet-skiing experiences, you may be curious why you can’t find any rentals on the island. That’s because Key West is located within the protected Florida Marine Sanctuary, and jet skiing in certain areas can cause harm to the natural environment. As a result, guided jet ski tours are the preferred option, ensuring you can enjoy the experience while avoiding restricted areas.

Key West Jet Ski Tours

If you were born in 1988 or later, you must complete the Florida Boating Certificate before heading out for the tour. For the ultimate convenience, Rent Key West Vacations has partnered with local operators like Fury Water Adventures and Barefoot Billy’s, so you can book a jet ski tour directly from our website:

Fury Water Adventures

Embark on a 28-mile jet ski tour with Fury Water Adventures. Travel through the backcountry on their top-of-the-line jet skis and take in the sights of the stunning coastline while keeping your eyes peeled for bottle-nose dolphins and sea turtles. Along the way, you will stop at a sandbar to cool down and have a refreshing swim.

Barefoot Billy’s

Sign up for the Casa Marina Island Jet Ski Tour with Barefoot Billy’s. Travel around the island and stop at five locations along the way as you learn about local history from your guide. If you are interested in a freestyle experience, they also offer a trip where you can play around in a designated ride area and try out some tricks.

Book Key West Condo Rentals near the Beach

Book even more water adventures for your Key West getaway directly on our website. From snorkeling tours to fishing trips and kayak rentals, we have something for everyone! Stay close to the action with our Key West condo rentals near the beach or with an ocean view. No matter which property you choose, you will have access to fully-equipped kitchens, laundry facilities, and open-concept living spaces. Book with us online or speak to a reservation specialist at 800-833-7368 for assistance customizing your Key West getaway!

Discover the Life of Ernest Hemingway in Key West, Florida

Key West has long attracted artists and writers. Among these writers was one of the most famous American writers of the 20th century– Ernest Hemingway. Inhabiting the island for nearly a decade, Hemingway wrote some of his most prolific works on Key West, drawing inspiration from the island’s landscapes, people, and history. Today, his presence can still be felt throughout the island. Visit the Hemingway Home and explore where the famous author resided during the 1930s, grab a drink at one of his local haunts, and join the annual Hemingway Days Festival celebration. Find the perfect lodging with Rent Key West Vacations and follow in the footsteps of Hemingway during your visit:

Hemingway Home

Hemingway resided in the Whitehead Street home for most of his time in Key West. Today, the Hemingway Home is open for tours so that visitors can explore the home, gardens, and grounds:

Inside the home, you can see the writing studio, where he wrote famous works like To Have and Have Not. Walk through the living room and see many photos of Hemingway and his fishing adventures.
On the property grounds, you will see the in-ground swimming pool he constructed, which was the first pool on the island and cost $20,000 to build.
While on the Key West, a local ship captain gave Hemingway a white six-toed cat. Today, the grounds are home to nearly 60 cats, some descended from his original cat, that you can pet and hang out with!

More Hemingway Haunts on Key West

Opened in 1933, Sloppy Joe’s Bar was one of Hemingway’s favorite watering holes, owned by his friend Josie Russel. The original Sloppy Joe’s, where Ernest Hemingway frequented, is now Captain Tony’s Saloon. Stop at Captain Tony’s for a drink in his honor!

Most of the other sites mentioned by Hemingway no longer exist on the island, but you can still visit the locations where they once stood. For example, the grounds now home to Blue Heaven Restaurant were once the site of the Key West Arena, where Hemingway refereed boxing matches.

Hemingway Days Festival

Plan your getaway around the annual Hemingway Days Festival and celebrate Hemingway’s life and literary accomplishments with other fans. Events throughout the festival include a look-a-like contest, a fishing tournament, literary readings, a street fair, and a short story competition.

Book Your Key West Vacation Rental and Explore the Island

Stay in Old Town Key West with Rent Key West Vacations and access the Hemingway Home just blocks from your vacation home. Our charming conch-style cottages perfectly encapsulate the historic charm of the island. These homes are also a short walk from the famous Duval Street, where you can enjoy restaurants, shops, history, and many attractions. Book your Key West getaway with us today!

Where to Watch the Sunset in Key West, FL

Key West, FL, offers countless stunning spots to catch a sunset, and Rent Key West Vacations is here to guide you to the very best ones. Check the sunset time online and watch the sun dip below the horizon as you take in ocean views and admire the vibrant shades of orange, pink, and blue. Whether you want to watch the sunset with a cocktail at our local restaurants or join the legendary Sunset Celebration at Mallory Square, there is an experience for everyone. You can even reserve sunset cruises directly on our website. Read on to discover the best places to catch the sunset during your stay!

Sunset Cruises

One of the best places to watch the sunset is from the water. Browse the tour options on our website and find the perfect sunset cruise for your group:

Sign up for a sunset cruise with Fury Water Adventures, offering everything from champagne sunset cruises on a motorized catamaran to combination tours that include snorkeling, sunset sails, and reggae music.
Enjoy the sunset from your very own private tiki bar with Crusin Tikis Key West.
Embark on a private romantic sunset sail with Key West Eco Tours or Danger Charters.

Mallory Square Sunset Celebration

Join the nightly Sunset Celebration at Mallory Square, a Key West tradition since the 1960s. Head to Mallory Square two hours before sunset and shop from local vendors, listen to live music, watch stunt performers, and laugh at the comedy shows. Then, find a spot along the Square and watch the sunset with the nightly crowd while enjoying the lively atmosphere.

Sunset Views at Local Restaurants

Several of our local restaurants offer fantastic sunset views. Enjoy delicious food and refreshing drinks as you watch the spectacular event from one of these bars or restaurants:

Sunset Spots Across the Island

Find even more sunset spots across the island, from our beaches, parks, and waterfronts:

Visit Fort Zachary Taylor and enjoy sunset views in a natural setting.
If you want to avoid the crowds of Mallory Square, we recommend heading to Truman Waterfront for sunset views in a more relaxed setting.
Stroll down the walkway of White Street Pier and watch the sunset.

Visit Key West and Watch the Sunset During Your Stay

No trip to Key West is complete without experiencing one of our world-famous sunsets. Book your getaway with Rent Key West Vacations and enjoy breathtaking sunset views throughout the island. Browse our collection of Key West vacation rentals and find the perfect basecamp for your adventures. Elevate your stay with our concierge services and reserve in-home chefs, gift baskets, and specialty services. Reserve your Florida Keys vacation today!