You don’t need to leave the country to experience turquoise waters, coral reefs, and luxurious accommodations. In fact, paradise may be closer than you think. Have you been to the Florida Keys? This chain of small islands, connected by 42 bridges, runs 125 miles from the southern tip of Florida’s mainland. The drive time from Fort Lauderdale to the Key West, the southern most tip of the Florida Keys, is about 3.5 hours and the views are breathtaking. But, you can opt for a shorter drive to your destination as there are plenty of islands north of Key West. In fact, there are 44 main islands, and over 1,700 small islands, that make up the Keys. You can also opt to fly directly into Key West.
Listed below are five luxury accommodations found throughout the Keys. But, please know that there are plenty of price points available throughout the Keys. If the five below are more than you’d like to spend, check out this visitors guide as there are plenty of affordable places on this stretch of islands.
And, keep scrolling to the end of this article for an insider’s tip on a place to rent that is refreshingly affordable and that my family has stayed at three times.
5 Luxurious Places to Stay in the Florida Keys
Little Palm Island Resort & Spa
This resort brings exclusivity and privacy as the property takes up the entire island. Little Palm Island Resort & Spa is pretty much synonymous with luxury and great service. Condé Nast awarded this resort the prestigious Top 50 Resorts in the World ranking for 2020 and a Top 10 Resorts in the US ranking for 2020 as well. This is where you go when you want to relax and unwind. And, it’s just a short 36-minute drive time from Key West International Airport.
Sunset Key Cottages
Minutes away from the Key West airport (seven minutes to be exact), is another island locale. Simply check in at the Margaritaville Resort and Marina, get on the boat, and you will soon be on your 27-acre secluded island, suitable for families and couples alike. Choose from a one-room cottage up to a four-room cottage, and experience dining in the sand and a first-rate spa. Bliss!
The Moorings Village
Long before Netflix’s show Bloodline made this place even more famous, The Moorings Village has been attracting discerning travelers. Having recently sold part of the northern part of the property, including two restaurants and 10 cottages, to neighboring Cheeca Lodge, which is the next property on this list, The Moorings Village is now made up of eight cottages, on 11 acres of oceanfront property. Imagine walking down paths with orchids growing from trees next to a beautiful sandy beach with tall palm trees that filter the light just so perfectly. It’s a photographer’s dream, as the light is so special here, and thus the property is a darling of production companies.
Perfect for people wanting to get away, but feel like you are staying at a friend’s guest house, The Moorings Village is located in Islamorada, a group of islands known for its beautiful coral reefs and fabulous fishing. This area an ideal destination for anyone who loves to snorkel, scuba dive, or fish.
Cheeca Lodge & Spa
This is a largest resort on this list and it’s filled with amenities and gorgeous views. As mentioned above, this property directly neighbors The Moorings Village. Last time I was driving through, a guest had just arrived by helicopter and I believe it landed next to the golf course. But, rest assured that most people arrive by car! There are 214 room accommodations, three heated pools, a nine-hole golf course, three restaurants, and two tiki bars. This lodge has been a long-time favorite for families, with generations of happy memories here. For a family who wants to stay busy without ever leaving the resort, this is your place.
Casa Marina, a Waldorf-Astoria Resort
On New Year’s Eve 1920, over 100 years ago, Casa Marina opened and instantly became Key West’s most glamorous destination. Fast-forward to the present day and this resort continues to shine brightly, but not without some seriously intriguing historical side steps. Its history includes being purchased by the US Navy in 1942 for officers’ quarters during World War II, housing the US Army’s Sixth Missile Battalion during the Cuban Missile Crisis, and serving as a training center for 300 volunteers for the new Peace Corps in 1966. After being closed for more than a decade, and then undergoing extensive renovations, the property today is a luxurious place to stay with multiple options for rooms and suites, and the largest private beach on Key West.
Insider Tip for an Affordable Place to Stay in Key West: Angler’s Reef
While I love luxury hotels and the wonders that come from the service and amenities each one provides, there is a great community to rent from in the Keys, and it’s a great tip to keep in your back pocket when planning a trip that won’t break the bank.
Angler’s Reef is a community in Islamorada that has rental homes. My family has stayed here three times and the location is great. There is a bit of a sandy stretch of beach, a nice pool, and boat slips to rent on-property. I really adore the variation of plants and trees in this gated community, which I have enjoyed on morning and nightly walks.
From my experience, and looking online before the publication date of this article, most homes rent between $355-$700 a night. I suggest renting through VRBO for the most options.
Looking for a gift for the person who loves to fish? Check out this article about two fishing lodges, one in Belize and one in the Florida Keys.
For more destinations to add to your bucket list, visit our Travel archives!