Dreaming of a Key West vacation but unsure where to start? More than just sand and sun, Key West has amazing accommodations, beachside activities and historic landmarks. There’s something for everyone from couples and families to solo travelers.
However, with so many options, it can be hard to create an itinerary. I’m here to help with recommendations from my recent trip. I loved every minute from my comfy suite to long days at the beach.
Keep reading for the best of Key West beaches, lodging and things to do.
CONTENTS:
- Ocean Key Resort & Spa
- Jet Ski Tour
- Fort Zachary Taylor Beach
- Old Town Key West
- Truman Little White House
- Weatherstation Inn
- The Shops at Mallory Square
Ocean Key Resort & Spa
Picking a place to stay is the toughest part of planning a Key West vacation. Each resort, hotel and inn has its own unique blend of style and amenities.
I recommend Ocean Key Resort & Spa for its prime location, classic style and water sport offerings. It’s right on the beach with its own pier and rentals. Rooms are styled in the classic “beachy” Key West aesthetic and offer unbelievable ocean views.

You can spend your days out on the water and nights down at the Sunset Pier bar. It’s full of friendly people and the type of drinks that just scream “vacation”.


Jet Ski Tour from Ocean Key
Getting out into the water is easy with Ocean Key’s lineup of water sport activities. I love to jet ski, so we reserved a tour with the resort.
You can book the jet ski tour or just reserve a jet ski to ride around shore. The tour goes from the pier, past Wisteria Island to Sunset Key and back.

Jet skis are docked right on the resort pier, making it so easy to just walk down for your activity. No Uber rides here! Plus, if anything goes wrong with the reservation, you can handle it with the resort’s friendly staff.
I do wish there was an option to book online. Instead, you must book through the concierge at 305-295-7005 or concierge@oceankey.com.
Fort Zachary Taylor Beach
At the southern tip of town lies the best beach in Key West to sit and relax. The beach at Fort Zachary Taylor State Park has gorgeous white sand and crystal clear water.


Hidden behind a stretch of trees, this sunny beach features corals and other marine life. As a result, you can take part in essential Key West activities like fishing, snorkeling and rafting. Rentals are available on-site.
I visited in February and was surprised how perfectly warm the weather was. The sky was bright and clear, and the beach wasn’t crowded at all.
The beach is part of a larger 54-acre state park, so there’s even more to explore. Feeling adventurous? Take off on a hike or bike along the trails.
The park is named after Fort Taylor, which dates back to the civil war era. The fort still stands within the park where you tune in to a narrated tour. You can even check out authentic cannons from the era.


Old Town Key West
The Little White House
Another Key West must-do is visiting the Harry S. Truman’s Little White House. This massive historic house is home to a museum showcasing a century of US history.
Originally built as a home for military commanders, it has served many significant purposes. US leaders, inventors and historical figures have lived here for various stints. It was even a Navy command center during WWII. Its namesake, former US President Harry Truman, visited several times during and after his term.
Located in Old Town Key West, the Little White House is one of several beautifully preserved historic buildings. It’s a gorgeous area to walk around and explore the architecture.


Weatherstation Inn
Another gem of a place to stay is the lovely Weatherstation Inn. This adult-only hotel is perfect for a more relaxed Key West vacation. Think of couples escapes and extended trips as the perfect occasion to stay here.

In contrast to the resorts in Key West, Weatherstation Inn offers a calmer experience. With a small number of rooms and more home-like environment, you can expect some peace and quiet.
Like the rest of old town, the inn was built in the early 1900s. It’s converted from an office that originally housed the US Weather Bureau. Then it served as residential military housing. As such, it’s a well-preserved portal to the past.
The Shops at Mallory Square
If history isn’t your thing, maybe you’ll enjoy some shopping and sightseeing. If so, Mallory Square is the place you want to be.
This is Key West’s go-to district with everything from shopping to art galleries, restaurants and historic sites.


It’s a lively, vibrant area with a mix of popular brands and small boutiques. You can find the perfect souvenir or gift to commemorate your Key West trip.
Conclusion
You can’t go wrong with a Key West vacation, no matter your travel style. Start your itinerary with some of these recommendations and build your perfect trip from there.
Are obsessed with beach vacations? Explore this guide to Santa Monica beach in California.

