While much of the U.S. starts to bundle up and rake leaves come fall, the Keys are still soaking up warm tropical breezes under clear blue skies. October and November in this archipelago stretch from Key Largo to Key West with fewer tourists and lower hotel prices. You won’t be battling for beach chairs or dinner reservations, and you’ll skip the heat and humidity that peak during summer.

The Keys hit that sweet spot in fall, known as the shoulder season. You still get all the postcard-worthy sunsets and turquoise waters, but with less of the summer chaos. Restaurants showcase seasonal seafood and hotel deals make high-end travel more attainable. Whether you’re exploring coral reefs, sipping cocktails at a bayside bar, or checking into a private island resort, fall in the Keys brings the goods. If you’re not sure where to begin, our guide will help you break down some of the best luxury stays, dining, activities, and tips to help you plan an unforgettable fall getaway in the Florida Keys.

Where to Stay

Starting in Key Largo, the northernmost of the Florida Keys, Playa Largo Resort & Spa, Autograph Collection offers upscale comfort with a tropical twist. The resort brings polished rooms and oceanfront bungalows together with an infinity pool that seems to pour right into the bay. There’s also a spa and private marina, so whether you’re seeking a couple hours of pampering or headed out on a boat for the day, it’s all conveniently on-site. Dining here is a highlight too—don’t miss Sol by the Sea, where Caribbean-style seafood dishes are served with a view and a salt-air breeze.

In Islamorada, Cheeca Lodge & Spa has been around since 1946. And while it’s picked up some polish over the decades, the Key Largo pine trees, wooden fishing pier, and palm-lined golf course preserve that timeless feel. The 27-acre property makes it easy to spread out, savor a waterfront dinner, or cast a line from the pier known for being one of the best sportfishing spots in the area.

Making your way down to Marathon, you’ll find Isla Bella Beach Resort, a relatively new resort with a clean, modern look that stretches along nearly a mile of private beach. You’ll find five pools peppered throughout the property, along with a wellness-focused spa and a restaurant that leans into Hawaiian influences (poke bowls, short ribs, tropical cocktails—the whole package).

At the far end of the Keys, Key West packs plenty of retreats worth a splurge. H2O Suites is an adults-only spot tucked just off lively Duval Street but designed to be an oasis from the action. Suites come with private plunge pools, and upstairs, the rooftop pool is the perfect place to sip something cold and fruity while taking in the sunset. It’s easy to walk to nightlife or come back and completely tune it out—it’s all up to you.

A truly unforgettable place to stay? That’s Little Palm Island Resort & Spa, technically located on Little Torch Key but known as a Key West-area escape. Accessible only by boat or seaplane, this private island resort is about as remote and luxurious as it gets. There are thatched-roof bungalows, lush landscaping, an intimate spa, and Michelin-rated food that rivals anything you’ll find mainland.

Where to Eat

Key Largo easily satisfies seafood cravings, starting with Snappers. This waterfront spot delivers fresh catch galore, known particularly for its Sunday jazz brunch and breezy outdoor seating. Another go-to in the area is the Buzzard’s Roost, where the famous Lobster Reuben draws curious foodies and loyal fans day after day. The waterfront deck is ideal at dusk, when both the temperature and the colors on the horizon mellow out perfectly.

Heading into Islamorada, Florida Keys Brewing Company is the spot for small-batch beer. While it’s more relaxed than refined, it works great as a pre-dinner stop or a low-key lunch hangout. The beer garden often features live music and rotating food trucks. Not far away, Lorelei Restaurant & Cabana Bar sets up some of the best sunset-watching in the Upper Keys with a cocktail menu that leans heavy on frozen delights. The seafood-heavy menu and sandy-floor seating add to the easygoing stretch of an afternoon or evening meal here.

In Marathon, make a reservation at Butterfly Café. Part of Tranquility Bay Resort, the restaurant focuses on flavor-forward plates, many made with local seafood and seasonal produce. The ambiance is casual-elegant and perfect for a nicer night out. If you’re in the mood for something a bit more playful, check out Porky’s Bayside Restaurant & Marina. This family-friendly joint has everything from BBQ and sushi to mini-golf—great for groups with mixed tastes or anyone looking to enjoy amazing food at a chilled-out place.

Key West is arguably the culinary hub of the Keys, and the Seaside Café at the Southernmost House keeps things easy and flavorful. Tuna poke bowls, lobster pizza, and conch fritters are top picks and the restaurant is right on the water, offering food with a view. For a dressier experience, Hot Tin Roof, perched above the Ocean Key Resort boasts contemporary coastal fare—plantain-crusted swordfish, filet mignon, and expertly crafted cocktails, all with waterfront views. For something a little different, Kaya Island Eats hits the spot with their playful menu of Caribbean fusion dishes. “Rasta Pasta” is a standout signature, and the lineup of creative sides makes this place memorable and fun.

Things to Do

You can’t visit the Keys without getting out on the water, and fall is an excellent time to explore the area’s marine life. Up in Key Largo, the nation’s first underwater park, John Pennekamp Coral Reef State Park offers guided snorkeling trips over colorful coral and through crystal-clear waters. Feeling adventurous? You can opt for scuba excursions to well-known spots like Molasses Reef or the intentionally sunk Vandenberg shipwreck off Key West, which now houses a thriving reef system.

Sunset cruises are always a popular option, and fall evenings are cooler and less humid—ideal for watching the sky fade to orange and pink while sipping a rum punch. Trips depart from multiple points including Key West, Islamorada, and Marathon, and options range from casual catamarans with live music to luxurious private charters. Fishing is also in full swing in the fall. It’s prime season for tarpon, snapper, and grouper.

If you love all things outdoors, make sure to visit the Big Pine Key’s National Key Deer Refuge. These tiny, endangered deer are only found here, and early mornings or twilight hours offer you one of the best chances for sightings. For birdwatchers and kayakers, the Great White Heron National Wildlife Refuge has quiet canoe trails and prime spots for spotting graceful egrets, herons, and more.

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Travel Tips

Weather-wise, fall is a sweet spot. Expect daytime highs in the mid-70s to mid-80s, which feels great for beach lounging or water activities. After early October, the amount of storms drops, and the sunshine sticks around—without the overwhelming summer humidity. Nights cool down just a bit, but you likely won’t need anything heavier than a light long-sleeved jacket.

Fall is also easier on the wallet. Compared to peak season (December through April), hotel and resort rates are lower, and you’ll most likely have more options to pick from. Booking just a few weeks out is often doable, which adds some flexibility to any last-minute trip planning. Just make sure to pack smart: bring light, breathable clothes, reef-safe sunscreen for all that snorkeling and swimming, and water shoes if you’re planning beach hikes or reef exploration. Having the right gear makes it easier to enjoy everything the Keys have to offer.

FAQs:

Q: What’s a convenient way to get to the Florida Keys in the fall?
A: One of the easiest ways to get to the Keys is to fly into Miami or Fort Lauderdale and drive down the scenic Overseas Highway (US-1). Key West also has a small airport with direct flights from several major U.S. cities.

Q: Do I need a rental car while visiting the Keys?
A: A rental car is handy if you’re exploring multiple islands. In Key West, you can get around easily by bike, scooter, or on foot.

Q: Are there mosquitoes in the Florida Keys during the fall?
A: Mosquito activity generally drops off by mid-fall, especially after October. Still, it’s smart to pack repellent if you plan to explore nature trails or visit mosquito-prone areas like Big Pine Key.

Q: Are luxury accommodations pet-friendly?
A: Some upscale resorts welcome pets, but policies vary. Always check ahead—many have breed or weight restrictions and may charge an additional cleaning fee.

Q: Is tipping expected at hotels and restaurants?
A: Yes, standard U.S. tipping applies. At restaurants, 18–20% is customary. Valets, bellhops, and housekeeping also appreciate tips for good service.

Q: Is Wi-Fi readily available across the Keys?
A: Most resorts, restaurants, and cafes offer complimentary Wi-Fi. Mobile service is generally reliable, though it can be spotty in more remote areas like parts of Big Pine Key.

Did we leave any of your favorite Florida fall activities off our list? Tell us in the comments below!