Contrasting Resorts in the Florida Keys


The Overseas Highway, the portion of U.S. Route 1 between mainland Florida and Key West, is one of the country’s most iconic drives. The 113-mile series of roads and causeways threading the Keys (“Key” comes from the Spanish word for small island, cayo) passes by mangroves, tropical forests, yacht-filled marinas, fishing-boat-lined piers, plush resorts, faded motels, modern strip malls and charming old seafood shacks. The highway’s view routinely opens onto the shallow islet-dotted sea surrounding the Keys, its bottom of white sand, coral reef and turtle grass flats creating a spectacular patchwork of blues ranging from deep lapis to almost iridescent turquoise. Causeways sometimes extend for miles between islands, and driving along them can be exhilarating — especially in a convertible.

The region offers myriad watery diversions, including excellent snorkeling, scuba diving, fishing, sailing and kayaking. Sunset cruises (with drinks included) are understandably popular, although sundowners on the beach are also delightful. There are a handful of formal restaurants, but for the most part, the Keys are a casual place to relax. Shorts and T-shirts constitute the local uniform. Paper napkins are at least as common as linen, and cocktails are more likely to appear in plastic cups than coupes. It won’t suit everyone, but it can be great fun. I loved discovering unpromising-looking weather-beaten restaurants that served superlatively fresh seafood, often procured from ships moored in an adjacent marina.

Shorts and T-shirts constitute the local uniform. Paper napkins are at least as common as linen, and cocktails are more likely to appear in plastic cups than coupes. It won’t suit everyone, but it can be great fun.

Perhaps most important to travelers in these uncertain times, the Keys have a reliably warm and dry climate in the winter, allowing one to enjoy a subtropical vacation without leaving the United States. Much of life is conducted outdoors, including dining and leisure activities. The Key West airport’s compact arrivals hall felt uncomfortably crowded — we were not the only ones intent on escaping to the warmest place in the continental U.S. — but for the most part, it was easy to avoid being indoors with substantial numbers of people. Reassuringly, most of the hotels at which we stayed took COVID-19 precautions quite seriously.

For many years, the only property we recommended between Miami and Key West was Little Palm Island, a 30-room resort on a private 5-acre islet south of Little Torch Key. The property suffered severe damage during 2017’s Hurricane Irma, as did much of the rest of the Keys. It rebuilt and renovated, reopening in early 2020, just in time for the pandemic to shut things down. I had been interested to revisit the hotel, but like most properties in the area, it raised rates dramatically in response to this year’s high demand. During 2021’s high season, Little Palm Island ranked among the most expensive hotels in the world, charging approximately $5,000 per night! A reassessment can wait until shoulder season.

Isla Bella Beach Resort

Beachside at Isla Bella Beach Resort, Marathon
Beachside at Isla Bella Beach Resort, Marathon - Photo by Andrew Harper editor

Instead, I decided to stay at two larger resorts at different points along Route 1, in the hopes of finding an additional recommendation that would allow travelers to make more of an itinerary in the Keys. First was the Isla Bella Beach Resort on Knights Key at the western end of Marathon, an hour from Key West and about two and a half hours from Miami. It opened in April 2019, and it still felt bright and new, although its gardens were already mature. An allée of palms leads from the front gate to the airy hacienda-style lobby building, which has a terrace facing the beach. More palms and hedges camouflage the parking lot and shade a walkway along the lengthy main building, containing 199 accommodations. All have seaview balconies or beachfront terraces.

We rolled our bags from our car to our suite (luggage assistance was available only on request due to COVID) and opened it with the yellow rubber bracelet that served as a key, breaking the seal indicating that the room had been sanitized. The front desk had upgraded us to a ground-level “Luxe Beachside Oceanfront 2-Bedroom 2 Bathroom Veranda, 2 King” suite, which had an inviting water-view terrace furnished with a sofa and two chairs. Inside, the immaculate suite positively gleamed. The two full baths, one with a shower-tub combination and one with a large walk-in stall, looked particularly pristine, with unblemished walls of white subway tile and well-lit white vanities.

Suite at Isla Bella Beach Resort - Isla Bella Beach Resort
Suite bath in Isla Bella Beach Resort - Isla Bella Beach Resort
Master bedroom of our Luxe Beachside Oceanfront 2-Bedroom 2 Bathroom Veranda, 2 King - Photo by Andrew Harper editor
Terrace of our master bedroom  - Photo by Andrew Harper editor
Main pool at Isla Bella Beach Resort - Photo by Andrew Harper editor
Beach at Isla Bella Beach Resort - Isla Bella Beach Resort

Since there were just two of us, we used the smaller, viewless bedroom as a walk-in closet and spent most of our time in the bright master bedroom, which had a smart color scheme of white, sapphire and sea-foam green. Silvery mercury-glass lamps flanking the very comfortable king bed added some luster, as did a gilded accent lamp and Henry Moore-like sculpture on the desk. Heavy drapes speckled with peacock-toned palms concealed sliding glass doors leading to our terrace that was just two or three stairs up from a broad stretch of firm sand. As soon as I saw the outdoor space, I placed an order for room service sushi, just to have an excuse to linger there. My lingering was postponed by a trip to the bar, however, in order to procure glasses of rosé to accompany the immense roll of lobster, eel and avocado. (The hotel does not allow the delivery of alcohol to guest rooms, because the staff “can’t card people over the phone.”) We dined overlooking the water, watching great white herons stalk the shallows, backdropped by a distant marina.

Although it faced the beach, our terrace felt relatively private because of our suite’s location at the opposite end of the resort from reception, the bar and the main (and only swimmable) beach. A stroll took me past numerous umbrella-shaded beach chairs and three small lounger-lined pools, including one open only for private bookings. Although these pools were popular, I preferred the much larger main swimming pool, with its sky-blue-striped umbrellas and easily accessible bar. A waiter served drinks but did not take orders; these were placed at the bar’s window. Families played together in the water, but the pool never seemed loud or crowded. I also enjoyed relaxing in one of the turquoise loungers lining the main beach. The silty sand exposed at low tide proved a popular place for children to hunt for crabs (we watched two enterprising girls build a “hermit crab hospital”). We also spent a pleasant hour on neighboring Pelican Point, where we took part in a complimentary yoga class in a shady grove of palm trees.

At the opposite side of the main beach is Il Postino, Isla Bella’s stylish Italian-inflected restaurant, open for breakfast and dinner. Our waitress in the morning remembered us after our first day, greeting us with good cheer and providing simple but well-presented breakfasts on the water-view terrace. In the evening, we dined at one of the tables on the adjacent stretch of palm-studded beach. As the sun sank behind the far-off arch of the Seven Mile Bridge, we feasted on fresh mussels in a classic sauce of white wine, garlic and butter, accompanied by slices of grilled ciabatta, and blackened mahi-mahi with roasted bell peppers and tangy tapenade. We liked to cap our evenings with cocktails at the nearby bar, at a romantic table beneath tall palms strung with lights. Although it came in a beach-safe plastic cup, the T&T cocktail (inspired by tequila and tonic) was excellent, a bittersweet and tart combination of reposado tequila, Aperol, pineapple, lime and agave syrup, garnished with rosemary.

We didn’t feel comfortable having treatments in the all-indoor spa, but we did try out a half-day snorkeling excursion organized by Dive Isla Bella. It was enjoyable and well organized, balancing the needs of both the snorkelers and scuba divers on board. The Isla Bella Marketplace, home to the resort’s activity center as well as a fashionable gift shop and café, can also arrange for fishing excursions, kayak and Jet Ski rentals, the use of complimentary bicycles and private charters of a Tiki boat (essentially a floating bar). And while on Marathon, we also made a point of visiting the Turtle Hospital, a wonderful facility dedicated to rehabilitating sick and injured sea turtles of various species.

My biggest problem with Isla Bella Beach Resort occurred before we arrived: The staff with whom I emailed never sent Marathon restaurant recommendations despite repeated requests. But since our time at the property was highly agreeable, I checked out with real regret.

- Hotel at a Glance -

Isla Bella Beach Resort    92Andrew Harper Bird


Our fresh and stylish suite; the immaculate housekeeping; the numerous inviting outdoor spaces in which to relax; the friendly service.


The poor communication before our arrival; the policy of allowing only nonalcoholic beverages to be delivered via room service.

Good to Know

Suites with direct beach access cost a bit more, but those on higher levels have more privacy; if booking a beachside suite, request one that’s not directly in front of a pool, and avoid 101 and 102, which have compromised views; low mangrove stands separate most of the beach from the water.

Rates: Oceanfront Balcony King, $1,520; Grand Oceanfront Residence Suite, $2,080.
Address: 1 Knights Key Boulevard, MM 47, Marathon
Telephone: (305) 481-9451

View Isla Bella Beach Resort Listing

Cheeca Lodge

Beach at Cheeca Lodge, Islamorada
Beach at Cheeca Lodge, Islamorada - Photo by Andrew Harper editor

We drove about an hour northeast to a much older property, the 214-room Cheeca Lodge, on Islamorada. Members often inquire about the state of the well-known resort, which has hosted a parade of celebrities over the past half-century. Since it had undergone major renovations in 2008 (after a fire destroyed the main building) and again in 2017-2018 (following damage caused by Hurricane Irma), it seemed like an opportune time to pay Cheeca Lodge an anonymous visit.

My first impression was unfavorable. A valet directed us to the front desk in the lobby-lounge, where we discovered two parties ahead of us, both of whom were sufficiently irritated by the wait that they engaged in a brief argument about who was next. After a few more minutes, we checked in and received cheap green plastic wristbands, worn in order to distinguish resort guests from visitors (who wear red bands). A valet followed us in a golf cart as we parked our car, and took us and our luggage to our Beach Bungalow, one of Cheeca Lodge’s oceanfront accommodations, up a flight of 13 stairs.

Located at the opposite end of the resort from the main building, these six accommodations occupy two buildings facing a quiet stretch of sand near the Pioneer Cemetery, which dates back to the 19th century. The view from our screened-in porch was very pretty, and I enjoyed having a room service breakfast overlooking the sea. Unfortunately, the rest of the traditionally decorated accommodation, in spite of its vaulted ceiling and fluffy king bed, was a disappointment. Whereas our suite at Isla Bella appeared immaculate, this room felt filmy. If I walked barefoot on the floor for any length of time, my feet ended up dirty (the room came with neither slippers nor robes, a serious omission considering the price). The rug around the bed was worn and faded, the dresser had dings, the walls had scuff marks, and the clothes pole in the closet was rusted. In the bath, the backsplash behind the dual vanity was sloppily tiled, three tap handles were missing pieces, and the slate tiles of the walk-in shower had holes as well as an unappealing coating of soap scum.

Resort pier at Cheeca Lodge - Photo by Andrew Harper editor
View from our Beach Bungalow at Cheeca Lodge - Photo by Andrew Harper editor
Our Beach Bungalow bedroom at Cheeca Lodge - Photo by Andrew Harper editor
Bath of our Beach Bungalow at Cheeca Lodge - Photo by Andrew Harper editor
Loungers in front of our Beach Bungalow at Cheeca Lodge - Photo by Andrew Harper editor
Adults-only pool at Cheeca Lodge - Photo by Andrew Harper editor

We fled first to a water-view swimming pool, but it was crowded with families, and the adjacent Tiki bar was also too busy for our comfort (Cheeca Lodge was hit and miss in terms of social distancing and mask wearing, in contrast to the more conscientious Isla Bella). We turned inland instead, heading to the spa’s large adults-only pool, lined with blue tented cabanas. All the loungers were occupied when we signed in, but we found a round daybed in the shade. A bar kept the pool’s thirsty occupants well watered, but though we spent over an hour there with our novels, the waitstaff never came our way.

Perhaps this was a blessing in disguise, because at the main restaurant, both at breakfast and dinner, the servers ranged from reasonably friendly to downright brusque. Even so, I enjoyed dishes such as the Chef’s Famous Pan-Roasted Octopus, a tender tentacle with edamame and squid ink-infused hummus, and the moist and fresh macadamia nut-crusted grouper fillet with tomato confit and a rich golden-raisin reduction. But at meals, our waitperson was just as likely to greet us with an abupt “Are you ready to order?” as a “Welcome to Atlantic’s Edge restaurant.” The resort also has an Italian-themed bistro with a wood-fired pizza oven and a sushi restaurant with a panoramic terrace above that of Atlantic’s Edge.

Cheeca Lodge did have its compensations. The sunrises each morning were sensational, and it was a great pleasure to relax after dinner on the beach, where we would take up residence in Adirondack-style chairs by a table with a fire pit at its center. On our first evening, a man played acoustic guitar nearby, and we sipped some Oremus Tokaji as a stupendous full moon rose up from behind the waves. We delayed returning to our room as long as possible.

- Hotel at a Glance -

Cheeca Lodge    86Andrew Harper Bird


Our tasty dinner at Atlantic’s Edge; the romantic beach bar area; our Beach Bungalow’s view; the separate adult and family swimming pools.


Our room stank of cheap air freshener, and its bath was in dire need of renovation; service at the restaurant could be standoffish; most accommodations don’t face the water.

Good to Know

One of the Keys’ finest restaurants, Pierre’s, is close by; the on-property nine-hole golf course is only partially open during ongoing renovations; if I were to return, heaven forbid, I’d reserve either a Lodge Oceanfront Suite in the main building or one of the Casitas that occupy a private enclave next to the main resort.

Rates: Beach Bungalow, $1,085; Lodge Oceanfront King Suite, $1,225
Address: 81801 Overseas Highway, Islamorada
Telephone: (305) 664-4651

Cheeca Lodge

Read more about our editor’s trip to the Florida Keys

By Andrew Harper Editor Andrew Harper editors travel the world anonymously to give you the unvarnished truth about luxury hotels. Hotels have no idea who the editors are, so they are treated exactly as you might be.