Your Guide to Old Town Key West

Key West may be known for its stunning white sand beaches, but the Southernmost Point is also home to a rich and fascinating history. Step back in time in the neighborhood of Old Town Key West and discover the island’s architectural heritage, fascinating history, and renowned museums. Choose Rent Key West Vacations to host your getaway and stay in the heart of Old Town with our historic vacation rentals!

Discover the History of Old Town

Discover all the attractions in Old Town Key West with Old Town Trolley Tours, offering hop-on and off sightseeing tours! Or use this self-guided walking tour to discover the best of Old Town on your own! 

  • Start your journey back in time at the Key West Lighthouse, an iconic landmark that has stood for over 150 years! Ascend the lighthouse and marvel at the artifacts that give insight into our maritime history. 
  • Discover the world’s largest cache of Civil War armament at Fort Zachary Taylor Historic State Park. This historic fort also offers recreational opportunities like bicycling, fishing, hiking, paddling, and snorkeling.
  • Located in the heart of Old Town, Duval Street is a fantastic gateway to local history. Discover the island’s most famous shops, restaurants, and nightlife spots here, including Sloppy Joes!
  • Discover the homes of Key West’s most famous residents at the Hemingway Home & Museum and the Truman Little White House Museum!

Don’t Miss the Top Attractions in the Historic District

No visit to Key West would be complete without snapping a picture at the Southernmost Point Buoy! You can find some of Key West’s top attractions just a block from the buoy, such as the Key West Butterfly and Nature Conservatory. Further down the road, you can visit the Key West Aquarium to learn about local marine life!

Stick Around for Nightlife on Duval Street

End your day in Old Town Key West with some fun at Mallory Square! Join the nightly Sunset Celebration here and enjoy local musicians, comedy shows, artists, entertainment, and food vendors. Or return to Duval Street at night for the best nightlife on the island. Visit iconic bars like Sloppy Joes and Green Parrot Bar!

Stay in Our Old Town Key West Vacation Rentals

Rent Key West Vacations offers fantastic vacation rentals in Old Town Key West to host your getaway! Discover our collection of over 40 properties, all with their own distinct architecture and history. From the charming one-bedroom Portside Suite to the eleven-bedroom Watson House Grand Estate, we offer something for everyone! 

Key West Offers Treasure Trove of Original Art

Key West is known for its extremely vibrant arts scene. The island has been attracting artists inspired by its natural beauty, rich history, and diverse culture. Today there are dozens of Key West galleries and museums for visitors to discover, offering a vast variety of art mediums and styles from local and international artists. This week we are featuring a few of our very talented local friends! You can bring home an original piece of art or some unique hand-crafted gifts keeping a piece of paradise in your home, sharing Key West culture with others, and always keeping our unique island in your heart!

Sacred Space Key West

PHOTO: Sacred Space Key West

Barbara Sage & Lucy Hawk founded Sacred Space Gallery in August 2020. They needed an art studio and quickly realized there was room to feature artwork by others as well. They continue to seek out other local women who create unique artwork & gifts. 

They proudly highlight 25 female artists and have four working studios. They offer a variety of art classes including painting, sculpting, and many unique Keys Coastal Classes; such as:  ‘Broken But Beautiful” Seaglass Class. Participants create an original piece of seaglass art. Seaglass, pottery, shells, driftwood bits and all necessities are all provided along with detailed instruction. Everyone leaves with a one-of-a-kind framed piece.

Their carefully curated gallery offers a sense of wonder and whimsy and the magic can be found in the heart of Old Town Key West at 529 Southard Street, between Simonton & Duval Streets. They are also available by phone, 305 998-4801 and via their website.

Key West Pottery

PHOTO: Konk Life

Artists Kelly Lever and Adam Russell began their collaboration in 2009. They blend traditional production pottery (tableware and functional vessels) with their fine art pieces.  

Since its inception, they have grown their company to include multiple artisans, creatives, students and collaborators. The talented group works together to produce a modern expression of coastal life while always being authentic and not relying on cliché.

Over the years they have developed a brand of tropical modernism that is unique and diverse so it can fit into any home or collection. In addition to commissioned, bespoke pieces, they carry everything from the island’s best coffee mugs to award winning totems. Their distinctive gallery with its well-rounded program is located on iconic Duval Street at number 1203. You can also reach them by phone, 305-900-8303, and online.

Key West Collective Art Gallery

PHOTO: Keysnews.com

This beautifully curated local art gallery is filled with a collective of talented artists inspired by Key West. Photographer and founder, Rachel E. Ligon, a native Kentuckian, has made Key West her home for more than 20 years. 

Ligon has traveled the world capturing diverse environments and the faces living there. Ligon’s passion recently led to her opening the Key West Collective Art Gallery on Caroline Street.  

In addition to her photography, the critically curated collective features the work of some of the island’s best artists, artisans and authors. The Collective also offers regularly scheduled classes where people can gather techniques from the featured artists. The Gallery at 720 Caroline Street is open daily 10am to 5pm and can be reached by calling 305-395-1161. The artists and their works can also be seen on the Collective’s internet site.

Key West Art Center

In the mid-1930s the Great Depression had devastated the nation including the Florida Keys. The federal Works Progress Administration brought artists and writers to Key West to help revitalize the economy. Many art classes were taught at the Key West Community Art Center, believed to be the WPA’s first public art project, which eventually became the Key West Art Center. 

The Center’s HQ since 1960 is pictured above and the organization is the steward of their home in this historic wooden building dating back to the 1890s. The Art Center is the oldest artists’ nonprofit membership organization in the Keys and features the work of more than 50 Keys artists. 

Paintings in many mediums, ceramics, sculptures, prints, and even handcrafted jewelry are on display to draw guests’ attention. Artist members offer classes to share insights into various art disciplines. In addition, the center is renowned for presenting the annual open-air Key West Craft Show and Old Island Days Art Festival.  Visit them at 301 Front Street. Call them: 305-294-1241 or check them out on the Web.

Stay in Our Key West Vacation Rentals 

Find the perfect piece of art to take home with you at one of our inspiring Key West art galleries. After discovering our dynamic arts scene, return to your vacation rental with Rent Key West Vacations. Stay in one of our rentals in the historic district, and you will be within walking distance of the Old Town galleries. Plan your Key West getaway today!

When is the Best Time to Visit Key West?

With constant sunshine, warm weather, and turquoise waters, Key West offers an incredible year-round vacation destination. Deciding the best time to visit Key West depends on your personal preferences and what you want to do during your visit. Whether you are looking to escape the cold or want to enjoy fewer crowds during the slower seasons, Rent Key West Vacations has the perfect property waiting for you!

Winter (December-March)

Month High / Low (°F)

December 77° / 70°

January 75° / 67°

February 76° / 68

  Photo: The Florida Keys & Key West

Winter is the most popular time to visit Key West, attracting snowbirds from around the world looking to escape the cold. The average winter high is a beautiful 75 degrees and the low temperatures usually only fluctuate down 10 degrees, and winter offers minimal rainfall. Celebrate the holidays in Key West with annual events like the Key West Holiday Parade, Lighted Boat Parade, and New Year’s Eve at various countdowns and celebrations around the island. Discover more information about Events Welcoming the New Year with Rent Key West Vacations!

Keep in mind that the influx of tourists also makes this the most expensive season to plan your visit. Accommodations, tours, and experiences fill up fast in the peak season. Advanced reservations are highly recommended during our winter season of perpetual summer. 

People from around the globe descend upon the island in January for delicious delectables during the internationally acclaimed Key West Food and Wine Festival. January also gathers a multitude of readers and writers for the Key West Literary Seminar which always garners the highest reviews! In addition to tepid temperatures, February offers the longstanding Old Island Days Arts Festival featuring fine arts and crafts at events, galleries and openair street markets.

Spring (March-June)

Month High / Low (°F)

March 78° / 70°

April 82 ° / 74°

May 85° / 77°

Spring is a beautiful season to visit Key West, with warmer weather, and fewer crowds than the winter. The exception to this is spring break, usually around March, when many families, young professionals and some college students plan their visits. Spring is a popular time for swimming, fishing, snorkeling, visiting gardens, and wildlife watching. St. Patrick’s Day in Key West offers a myriad of activities from bar strolls, 5 & 10K walk/runs, to themed boat excursions and more.

A visit during April or May enables you to enjoy all your favorite activities without the spring break crowds! The annual Conch Republic Independence Celebration at the end of April offers a fun glimpse into how “Key West Seceded Where Others Have Failed”. Learn more about planning your Spring Getaway in Key West.

Summer (June-September)

Month High / Low (°F)

June 88° / 80°7 days

July 90° / 81°8 days

August 91° / 81°10 days

Key West summer is the hottest time of the year and the start of hurricane season, so be prepared for the possibility of some passing rain showers. Summer is the second most popular time to visit Key West, welcoming an influx of families enjoying school breaks. Water is at its clearest and warmest in the summer, ideal for swimming, snorkeling, and diving. 

Summer is the best time to visit Key West for travelers who want to join us for festivals! Key West Pride and MangoFest both occur in June. July 4th includes the traditional fireworks, festivities and The Mermaid and Key Lime Festivals; and Hemingway Days later in the month. Also, the very popular  Lobsterfest is held in August. 

Fall (September-November)

Month High / Low (°F)

September 89° / 80°

October 85° / 78°

November 79° / 72°

Photo: Tripadvisor

Fall is the low season in Key West and the best time to visit for travelers looking for fewer crowds, lower priced accommodations, and travel incentive flight pricing. The beginning of September offers the annual Key West BrewFest with tastings and pairings on the beach and at venues around the island.  The island also welcomes thousands of women for the event-packed annual WomenFest!   Fantasy Fest is at the end of October and is the most popular fall event, welcoming up to 75,000 travelers each year! Join us for ten days of costumes, parades, libations, and excitement this October!

November kicks off with the Race World Offshore Key West Championships featuring the world’s top power boat racers vying for the prestigious title, prizes and more.  Each November, also attracts film aficionados to the island for the highly praised Key West Film Festival. It always receives two thumbs up!

We all have a lot to be thankful for on this island of Key West, especially all of us who are fortunate enough to be able to celebrate Thanksgiving here in paradise.  Plan a Thanksgiving getaway with Rent Key West Vacations and celebrate the holiday island style!

Visit Key West

Year-Round with

Rent Key West Vacations

So, when is the best time to visit Key West? Anytime! Rent Key West Vacations offers excellent rental properties to host your getaway year-round. Browse over 60 Key West vacation rentals and let our knowledgeable staff help you customize your vacation. Please call our reservation specialists at 1-800-833-7368 for more information!

The Best Snorkeling While Visiting Key West

Key West offers some of the best snorkeling in the Florida Keys with a variety of shore entry snorkeling spots, reefs and shipwrecks accessible by boat.  The area’s clear, shallow waters and colorful marine life provide a great experience for snorkelers at all levels.

Key West is home to North America’s only living coral barrier reef! The Florida Reef stretches over 350 miles and is home to more than 6,000 species of marine life. Discover a magical underwater world of coral reefs, tropical fish, and shipwrecks at the best snorkeling spots around and nearby the island of Key West!

Let our team at Rent Key West Vacations help you find the perfect snorkel excursions.

Call us at 305-294-0990 to start planning your Florida Keys retreat today!

Shore-Entry Snorkeling Spots

Fort Zachary Taylor State Park Beach

This beach is considered one of the best shoreline snorkeling places in Key West. It’s located at the end of Southard Street in the Truman Annex. There are a variety of tropical fish species and living coral that will captivate your senses. Bring your own equipment or rent there. There is a per car, pedestrian/ bike entry fee.  Parking is included and the park offers beach rentals, concessions, showers and restrooms. In addition to snorkeling, explore the nature trails and the historic civil war era fort.

Higgs Beach & Key West Marine Park

The Key West Marine Park offers easily accessible snorkeling stretching from Higgs Beach to South Beach. Bring your snorkeling gear or rent on the spot.  This beach is located along Atlantic Boulevard close to White Street Pier. It features the only shore-accessible underwater marine park in the United States. These reefs are brain coral, sea fingers, sea whips, sea fans and more. It’s an excellent spot to see an abundance of butterflyfish, angelfish, and parrotfish around the pier. This is a great place for beginner snorkelers of all ages.

Smathers Beach

This large, family-friendly public beach with convenient vendors, water sports operators, umbrella/chair rental and restroom facilities also offers snorkeling from the shore.  Although the marine life is not as lively as at the outer reefs, it is a good option for snorkel beginners.  The shallow, current-free waters make it easy to get comfortable using your gear and you can encounter fish and some other sea creatures.

Off-Shore Snorkeling Excursions

Dry Tortugas National Park – Fort Jefferson

This park is worth the extra trip just 70 miles west of Key West. It is accessible by ferry, seaplane or private charter.  Here you will find the best snorkeling at the only living coral reef in the country! Over 100 unique corals make up the reef and more than 500 species of tropical fish call it their home. There are several snorkeling spots here, from the moat wall surrounding the fort to shipwreck sites.

The most cost-effective way to get there is by taking the Yankee Freedom III ferry. They include snorkel gear, beach picnic and tour of the historic fort. The seaplane excursion offers a faster and unique experience to get there and back more quickly and provides a bird’s-eye-view of the beautiful turquoise waters and tiny islands along the way.  There are a limited number of private charters available to the National Park and they customize day, overnight and longer trips.

Cottrell Key

Cottrell Key is 9 miles northwest of Key West. It was named after a captain of a lightship that was anchored there in the early 19th century. It is known for a unique sponge garden and large coral reefs. It’s also not unlikely to see dolphins, sharks, stingrays and Goliath groupers there. Cottrell Key is suitable for kids and families.

Little Africa Reef – Loggerhead Key

Loggerhead Key is the largest island in the Dry Tortugas and home to Loggerhead Lighthouse. Since this key is not reachable via public excursions and even private boats need a permit before entering the area, very few people come to this spot, so it remains a snorkeler’s paradise!

Little Africa is the name of the untouched reef on the north side of the island where you can explore fantastic aquatic life in calm, shallow waters. This is a very beginner and kid-friendly snorkel spot with many soft corals such as sea rods and sea fans, hard corals like brain and fire corals as well as juveniles of various fish species.

Avanti Dutch Wreck

The Avanti (AKA Dutch Wreck or Windjammer) is also situated in Dry Tortugas, a mile southwest of Loggerhead Key and it rests shallow enough to offer excellent snorkeling. Actually, some parts of it are even exposed at low tide and the maximum depth is 22’/ 6.7m.

This wreck is in amazing condition.  The ship split into two parts and those parts are scattered across the seafloor with healthy corals growing on and around them attracting huge schools of fish and many sea creatures.

Marquesas Keys

Marquesas Keys is a chain of 10 uninhabited islands west of Key West that were formed by a meteorite millions of years ago. In 1622, a Spanish Treasure Fleet sank in the area; the commander of the fleet was Marquis de Cadereita and this is why the island group was named Marquesas Keys.

Today Marquesas Keys is one of the most popular diving and snorkeling sites around Key West. Expect to find untouched reefs with large coral pinnacles and coral heads, interesting caves (Only Accessible by Scuba Diving) and crystal-clear waters. The strong currents attract larger pelagic species to the area so there is a high chance of spotting jackfish and sharks there.

Sambo Reef & The Western Sambo Ecological Reserve

The Sambo Reef system offers fantastic conditions for underwater adventurers at all levels. Situated near Boca Chica Key, it includes 3 large reef structures (Eastern, Middle, and Western). The Western Sambo Ecological Reserve contains the greatest diversity of habitat in the Lower Keys. It offers the best snorkeling because of its shallow waters (between 3-30’/0.9-9m). 

While snorkeling Western Sambo you will see healthy hard and stony coral structures (branch, brain and one of the last remaining stands of living elkhorn corals in the FL Keys). Anemones, crabs, starfish, sea cucumbers, sand dollars and sea urchins live in nearshore waters.  Huge gray angelfish, hogfish and a vast variety of fish live in the shallow waters of Western Sambo.

Sand Key Lighthouse Reef & Rock Key

Just seven miles west of Key West, Sand Key Sanctuary Preservation Area (SPA) is marked by an old red iron lighthouse that was completed in 1853. This protected area is a favorite among snorkeling enthusiasts. Thanks to its remote location and the strict no-take policy (no fishing, spearfishing or lobstering), the Sand Key Lighthouse Reef is one of the healthiest coral gardens of Florida.

The seas are often flat and calm which creates an optimal snorkeling experience for the entire family. Sand Key provides varying depths of 1’ to 15’ surrounding the lighthouse. You will see a variety of tropical fish species, sea turtles, sharks and more!

A little east of Sand Key Reef, lies Rock Key, an under-the-radar spot to go snorkeling while visiting Key West. It is part of the Sanctuary Preservation Area and Key West National Wildlife Refuge so it is well-protected. A variety of reef fish and sea creatures can be seen around the shallow bank reefs (the depth range is 5-35ft/1.5-10.6m) while the deeper and larger crevices provide habitat for morays, groupers and octopus.  You can also encounter turtles and sharks while snorkeling at Rock Key. In addition, the area has many shipwrecks to explore.

Snorkel Tours in Key West

Tours include all necessary equipment, knowledgeable guides, professional instruction, and complimentary beverages. Here are just a few offerings:

  • Fury Key West offers early trips to North America’s only living coral reef on a 65-foot catamaran with a seated sundeck, stairway to the sea, shaded lounge area, and restrooms.
  • Danger Charters: This tour allows you to sail, snorkel, and kayak with morning and afternoon tours to Key West National Wildlife Refuge.
  • Sebago Watersports: Join a small group for an epic snorkeling tour at the Florida Keys Reef!

Our team at Rent Key West Vacations is here to help you find the best snorkeling in Key West with our concierge services. We are happy to help you personalize your stay with the best Key West activities, from dinner recommendations to water adventures. Discover our collection of over 60 Key West Vacation Rentals and find your perfect home away from home in Florida’s southernmost city! Also, after you have booked your trip, you will have access to your Guest Portal with suggestions for private charters, water and land activities, restaurants, shopping and more!

Shop Local: Key West Farmers Market Guide

During your next Key West getaway, we encourage you to support our local community by shopping locally! Find a fantastic selection of locally grown produce and handcrafted goods at the farmers markets of Key West & The Florida Keys. Whether you are looking for fresh ingredients to prepare meals in your vacation home or want to find the perfect souvenir, you can find it all at our local, open-air markets. Choose Rent Key West Vacations to host your getaway and stay close to everything our slice of paradise has to offer!

Key West Farmers Market

When: Every Thursday, 2 pm – 7 pm

Where: Truman Waterfront

The Key West Farmers Market offers something for everyone! Shop for fresh produce grown in Homestead, gorgeous orchids & native plants, artisan selection of meats and cheeses, pickles, honey, nuts & dried fruits, natural soaps and so much more. You’ll find Key West crafts, gifts and the perfect souvenir to take home.  While browsing, fuel up with something from one of the food trucks with varying weekly options, like fresh seafood, Mediterranean, Indian, smoothies, and freshly brewed coffees and teas. There is ample parking, bike racks or take the FREE Duval Loop which conveniently stops close to the market. The entire park, market area, restrooms and parking lots are wheelchair accessible.

What else is there to do at the Truman Waterfront Park?

The USCG Ingham is a self-guided maritime museum open Tuesday – Saturday 10 am to 4 pm. $10 adults/$5 kids/$5 active military.

Truman Waterfront park features a splash park, playground and lots of grass to spread out a picnic. Restrooms & shower rinse stations are available.

The Quay faces the Gulf and often cruise ships and Navy cutters on duty will be docked nearby. There’s plenty of park benches to enjoy the view (but little shade, umbrella recommended),

Fort Zachary Taylor Beach & State Park is a National Historic Landmark on 54 acres and houses a civil war fortress and the best beach on Key West. Entrance fees start at $2.50 and up.

Florida Keys Eco Discovery Center is a kid-friendly & adult interesting educational exhibit open Tuesday – Saturday from 9 am to 4 pm. Admission is FREE.

Key West Artisan Market

When: Select Sundays, November-April, 10 am – 2 pm

Where: Key West Wildlife Center parking lot across from White Street Pier & Higgs Beach

The Key West Artisan Market, celebrating its 10th season, is a unique open air bazaar filled with artists, authors, chef-made cuisine, craftspeople, performers and fresh produce representing diversity, creativity, ingenuity and locally made products. Participants must live and also create/curate in the Keys in order to qualify for booth space.

Local artisans include culinary, textile, jewelry, wood, art & crafts, curiosities, fresh produce and lots of great, fresh food. Each week is a different theme focused on island living and local charities. Guests are encouraged to go green and ride bikes. There is limited free parking and marked handicapped spots at the park. Please BYOB (bring your own bags). Find your beach reading material at the Local Authors Nook and enjoy live entertainment at the weekly variety show. 

What else is there to do at Higgs Beach?

Higgs Beach offers a Civil War Era Fort, Fort West Martello home of the Key West Garden Club that is listed on the National Register of Historic Places, a beachside café, the African Refugee Memorial and burial site, and an AIDS memorial. Activities available include swimming, snorkeling, sunbathing, beach volleyball, tennis, pickleball, and a children’s playground. 

Higgs Beach Park also hosts the only shore-accessible underwater marine park in the United States and is the end of the Florida Overseas Heritage Trail, one of only 31 nationally designated All American Highways in the United States.

A beach concessionaire offers beach items for rent including chairs, umbrellas, kayaks, and paddleboards, among others. The Key West Garden Club offers free self-guided tours at Fort West Martello and its nearly two acres of beautiful gardens. The park also hosts a large dog park with separate runs for small and large dogs.

Florida Keys Farmers Market

When: Every Sunday, Year Round, Rain or Shine, 10 am – 3 pm – 305-432-6900

Where: Islamorada Gardens Plaza parking lot, 81001 Overseas Hwy, Islamorada, FL 33036

Local, Fresh, Organic & Sustainable Shopping just under a two hour drive from Key West. Walk through an outdoor oasis featuring colorful artwork and murals by Miami artist DaveL @davel_art on Instagram. Each week features a rotating line up of vendors passionate about their craft. Find Artisan cheeses, select meats, fresh and local seafood, delicious baked goods, farmstand fresh juices, natural and organic produce, local art, orchids and so much more!

Bahia Honda State Park is on the drive and one of the most popular state parks in the Florida Keys. This is where you will find another icon of the Florida Keys, the Old Bahia Honda railway bridge. You can see the old bridge if you continue your drive without stopping at Bahia Honda State Park. But if you do stop at Bahia Honda State Park, you can get a classic view of the old bridge.  Bahia Honda State Park also has picnic tables so it can provide the perfect stop for a picnic with views! There are snorkel gear and kayak rentals at Bahia Honda State Park as well.

You will also drive across the iconic Seven Mile Bridge! There are parking areas on either side of the bridge for amazing views and photo opportunities.

Enjoy the Amenities at Our Key West Vacation Rentals 

Shop local at our Key West farmers markets during your Florida Keys getaway and keep money within our communities! Discover Rent Key West Vacations collection of vacation rentals complete with fully equipped kitchens, linens, and laundry facilities. Many of our properties also come with private pools, hot tubs, and tennis courts. If you need help customizing your Key West vacation, please get in touch with us at 1-800-833-7368.