Key West Travel: Top Resorts, Secrets & Fun Tips

There’s something about Key West that just feels… different. It’s not the prettiest island I’ve been to. It’s not the cheapest either. But wow—this place has a soul.

I arrived with sand in my shoes, no real plan, and one mission: to trade stress for sunsets. What I found was an island that doesn’t try too hard. It doesn’t need to. Between the conch-style cottages, six-toed cats, rum cocktails, and pastel skies, Key West gets under your skin in the best possible way.

Here’s everything I loved, hated (okay, not much), and highly recommend you eat, book, or jump into—whether you’re going full luxury or just chasing sunshine.

🌴 Where to Stay in Key West (And Why It Really Matters)

Picking a place to stay here is like choosing a character in a novel—it sets the tone for your whole story. I stayed in two spots and visited three others just to snoop (for research, of course).

🛎️ I booked via Booking, but honestly? Always check TripAdvisor, Expedia, and Hotels too. Prices + perks vary like crazy. Sunset Key had free breakfast and boat transfers through VRBO, but not through others. Just sayin’.

🧡 Ocean Key Resort & Spa

Front-row seat to the famous sunset at Mallory Square. Expect noise (in a good way), music, boats, and a view that slaps. Rooms are full of local art, and the Hot Tin Roof restaurant? 10/10 on my ceviche scale.

🌊 Sunset Key Cottages

You get there by ferry. You feel like Beyoncé on vacation. I didn’t stay overnight, but I had lunch at Latitudes and wandered the grounds like I belonged. It’s drop-dead gorgeous and outrageously private. Pricey? Yep. Worth it? If you’re splurging.

🏡 The Marquesa Hotel

This one’s for the introverts and aesthetes. Tucked behind tropical gardens in Old Town, it feels like staying in a painting. Bonus points for Café Marquesa—the food is dreamy.

🎨 Key West Culture: Cats, Presidents & Chickens

Ernest Hemingway lived here, wrote here, drank here, and left behind a legacy that now includes 60+ polydactyl cats(that’s six toes, FYI).

Don’t miss:

• The Hemingway Home & Museum — even if you’re not into literature, it’s weirdly charming.
• Truman’s Little White House — feels like walking through forgotten history.
• The Key West Cemetery — funny, strange, and full of character. My favorite headstone? “I told you I was sick.”

And if you see chickens crossing the road… yep, that’s normal.

🌅 Mallory Square: Sunset Theater, Every Night

You haven’t done Key West until you’ve clapped for the sunset with 500 strangers, half of whom are drinking mojitos out of pineapples.

• Street performers everywhere
• Handmade crafts
• Food stalls with grilled shrimp + conch fritters
• Vibe: chaotic, wonderful, and uniquely Key West

🌊 Island Adventures I’d Totally Do Again

There’s no shortage of excursions, but these stood out:

💡 Travel tip: Book activities through bundles on KAYAK or MOMONDO. I got my snorkel tour half-off by pairing it with a hotel.

🧭 Getting Around Without Losing Your Mind

• Don’t rent a car. Parking will make you hate vacation.
• Do rent a bike (aka “Conch Cruiser”). About $15/day.
• The Duval Loop is a FREE hop-on-hop-off shuttle.
• Ubers work, but they’re not always available.

🍽️ What to Eat (And What to Avoid)

You’re on an island. Order seafood. Trust me.

• 🐠 Cuban mix sandwich at El Meson de Pepe
• 🍤 Pink shrimp tacos at Turtle Kraals
• 🥧 Frozen key lime pie on a stick at Kermit’s

Avoid: cheap all-you-can-eat buffets. The food isn’t fresh, and you’re in Key West for flavor, not quantity.

🛡️ Don’t Be That Tourist: Stay Safe Online

I don’t travel without a VPN anymore—especially in places where I’m constantly logging into hotel Wi-Fi, checking my bank, or streaming Netflix while waiting for the rain to pass.

These are my ride-or-dies:

• NordVPN – Fast, secure, works even on cruise ships
• Surfshark – Cheap and lets you connect unlimited devices
• ExpressVPN – Never fails me, especially on public Wi-Fi
• CyberGhost – Perfect for streaming
• Proton VPN – Free tier is great for short trips

✈️ Getting to Key West

Unless you’re road-tripping the Overseas Highway (which you absolutely should one day), your best bet is to fly into Key West International (EYW).

💡 I book flights through KIWI because I’m cheap and flexible, or AGODA when I’m bundling hotels and flights.

💬 Final Thought: Why I Fell for Key West

It’s not just the sunsets or the pastel houses. It’s the attitude. This little island, stuck between the Gulf and the Atlantic, somehow gives you permission to slow down, laugh louder, wear flip-flops to dinner, and order a margarita at noon.

You don’t just visit Key West. You let it absorb you.

And if you do it right, you’ll go home a little saltier, a little happier, and a lot more relaxed.

Anna

My name is Anna, and my daily life is a balancing act between family logistics, work responsibilities, and trying not to lose myself in the process. I cherish the moments when everything comes together – a good cup of tea, a calm morning, and our family all in one place. I'm not a perfectionist, but I do like things in order (especially in my head). I love planning trips, trying new recipes, and creating a home that feels good not just for us, but for anyone who walks through the door. And even when life gets a little chaotic, I believe that humor, openness, and love can do more than the most perfect plan ever could.

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