Whether you’re planning a whirlwind weekend with three days in Key West or a relaxing week-long break from reality, this little island has no shortage of great resorts, inns, and hotels to please any traveler.
From Old Key West resort options right on Duval to Key West beach resorts (yes, there are a few!), here are five of my favorite Key West resorts.
The Best Key West Resorts for Your Island Getaway
If you’re looking for Key West all inclusive resorts, I have some bad news — there aren’t any.
But here’s the good news: There are plenty of great options in all the best areas to stay in Key West, from Old Key West resort experiences to modern, chic, and luxurious options in the new hot spots.
Here’s a look at the best Key West resorts for your next stay on the island.
1. Oceans Edge Resort and Marina
The Oceans Edge Resort in Key West offers a relaxing beachy getaway that combines luxury with the natural beauty of the Keys — it’s one of the best places to head for that authentic “Old Florida” feeling. Nestled right by the sea, it provides stunning views of the Atlantic. If you happen to be visiting the island by boat, they have a 111-slip marina for vessels up to 140 feet.
The resort features spacious rooms with modern amenities and tropical charm. Guests can enjoy various recreational activities, such as water sports and your choice of six different pools. Six! The resort also boasts an excellent on-site restaurant, the Yellowfin Bar and Kitchen.
Oceans Edge won the TripAdvisor Travelers Choice Award for 2024 and is rated the second-best resort in town by the site. Its serene atmosphere makes it ideal for couples seeking a romantic escape and families looking for a fun, laid-back vacation near Key West.
Wait, what? Near?
That’s right. Some of the best Key West resorts aren’t actually on Key West. Oceans Edge is on Stock Island, Key West’s secret, quiet, and more laid-back neighbor. It’s a 20-minute drive from the resort to Duval Street and Old Town.
2. Pier House Resort Key West
Ok, if I put you off with that ‘near’ Key West business, I’m sorry. This one is in Key West, I promise.
The Pier House Resort Key West is a charming waterfront retreat right on Key West Harbor. It’s at the edge of the Old Town, too. See, ‘in’ Key West! Just steps from Duval’s lively shops, bars, and restaurants — stumbling distance, you might say.
No, I kid you not. This resort’s address? One Duval Street. You. Cannot. Be. Closer.
The Pier House features elegant rooms and suites with beautiful ocean views and lush tropical gardens. The upper rooms have incredible views of the island. Guests can unwind at the resort’s small, private beach, take a dip in the pool, or enjoy a cocktail at the nearby Sunset Pier bar while watching the famous Key West sunset.
The hotel’s on-site dining options offer fresh seafood and Caribbean-inspired dishes in a relaxed, oceanside setting. While you’re there don’t miss out on Captain Zak’s favorite Key West bar, The Chart Room.
3. Margaritaville Beach House Key West
If you’re headed to Key West to waste away again, there’s no better place to do it than Margaritaville. This is, after all, how the song goes.
The Beach House is located on the south side of the town, right across from Smathers Beach on A1A, now and forever known as the Jimmy Buffett Memorial Highway. Plus, the hotel’s restaurant has a fun Jimmy-themed name: the Tin Cup Chalice Bar and Chill.
This resort is on the island of Key West, but it’s down by the airport and pretty much “out of town.” If you want to be technical, it’s in the Key West neighborhood called New Town, which is as far from Old Town and Duval as you can get while still being ‘on’ Key West. Consider yourself warned. It’s about a 15-minute drive, a 17-minute bike ride, or an hour’s walk over to Duval.
4. The Reach Key West
The Reach is one of the best Key West Beach resorts, hands down. Why? Because it actually has a decent beach! It’s a retreat with stunning Atlantic views on the island’s south shore, just a few blocks east of the Southernmost Point buoy. It’s near Old Town but not in the middle of it, so it makes a good base for exploring and finding all those unique things to do in Key West.
The resort provides spacious, comfortable rooms that surround a cool courtyard. There’s a huge private beach, pool, and options for water sports like kayaking. Oh, and they have these awesome sand sculptures you gotta see.
The on-site restaurant, Four Marlins, is great; they serve delicious seafood and island dishes.
The Reach Resort is a great choice for a relaxing and memorable Key West getaway. It’s in Old Town, but not in the middle of the party. And you can’t beat that private beach.
5. Ocean Key
Ocean Key Resort in Key West is a luxurious waterfront haven offering breathtaking views of the island and the harbor. It’s located near Mallory Square, home of the Key West sunset celebration. The pool at this hotel offers some incredible views out over Key West harbor. Count on live music every night along Sunset Pier.
Location-wise, you can’t ask for much better than being right on Sunset Pier, right? The poolside bar LIQUID has some of the best views in town. You’re right on Duval, but at the end of it, not the middle.
Not to be outdone by Pier House (located across the street), can you guess what this resort’s address is? Zero Duval Street! Take that, schmucks at Pier House!
The resort features spacious, clean rooms with private balconies and stunning views. Guests can unwind by the pool or indulge in delicious treats at the on-site restaurant, Hot Tin Roof. It’s an excellent spot for brunch.
With its prime location, you can easily explore Key West’s best offerings. Ocean Key was a Travelers Choice Award winner in 2024.
Ready to Book Your Key West Resort?
So, you’ve got places to stay. Don’t forget to plan a few activities while you’re here — things book up quickly during the busy times of year.
If you’re looking for a private boat charter out to the sandbar or to go snorkeling on the reefs, give me a ring, and I’ll have the Casual Monday ready to go when you get here.
