Key West Hotels: A Hit and Two Misses


Improbably, Key West was the richest city (per capita) in the United States in the mid-1800s. Locals would salvage the cargoes of ships wrecked on the shallow reefs surrounding much of the island. The most successful salvagers built grand mansions, many of which still stand to this day. Indeed, much of the city’s old center appears as it did a century ago. These neighborhoods are sharply contrasted by the raucous atmosphere of upper Duval Street, reminiscent of Bourbon Street in New Orleans, lined by souvenir shops, kitschy “art galleries” and margarita-fueled watering holes.

But Key West has at least as much to offer in terms of literature and history as it does alcohol and revelry. Ernest Hemingway famously lived there, working on novels such as “A Farewell to Arms” and “To Have and Have Not.” Other major literary figures associated with Key West include Tennessee Williams and Wallace Stevens. Shel Silverstein bought a house on William Street in the 1980s, and Meg Cabot still has a home on the island, as does Judy Blume, who (in nonpandemic times) can often be found in her delightful bookshop, Books & Books. Key West is also home to the Little White House, where Harry Truman spent some 175 days of his presidency, debating major postwar policies such as the Truman Doctrine and the Marshall Plan. (And I always make a pilgrimage to the little white house that served as the original office of Pan American World Airways. The airline ran the country’s first international commercial flights, connecting Key West and Havana. A microbrewery and restaurant now occupy the building.)

Sunset Key Cottages

Main beach at Sunset Key Cottages, Key West, Florida
Main beach at Sunset Key Cottages, Key West, Florida - Photo by Andrew Harper editor

Aside from the inn we currently recommend, The Gardens Hotel, the property in Key West about which I receive the most inquiries is Sunset Key Cottages. This 40-room resort went through phases as a Hilton, a Westin and a Luxury Collection member, and it is now independently owned. I had hoped that its location on 27-acre Sunset Key, an artificial island accessible only via a short ferry ride from Key West, would give the property the feel of a hideaway, removed from the bustle but easy to reach from downtown. Certainly its price indicates that Sunset Key Cottages regards itself as a luxury resort of the highest order.

What one pays for, more than anything else, is a large accommodation on an exclusive island. We reserved a Two Bedroom Oceanfront Cottage (the one-bedroom cottages are all garden-view), and the freestanding house could have comfortably sheltered a family of four to six. A terrace wrapped around half the traditionally designed cottage, with rockers facing the beach. Inside, we found a sunny great room with a floor tiled to imitate travertine, white walls and furnishings in blues, teals and butter yellow. Framed photos of Keys scenes clustered above the sofa. The kitchen offered a cooktop, a full-size fridge (stocked on request) and a Nespresso machine. Both spacious bedrooms had an en suite tile bath, one with a large walk-in shower and the other with a shower-tub combination; a third bath came with a small shower stall. Each bath had a ceiling vent, in which the dust of the ages had accumulated.

View of Sunset Key Cottages from our ferry - Photo by Andrew Harper editor
Beach at Sunset Key Cottages - Photo by Andrew Harper editor
Bedroom in our Two Bedroom Oceanfront Cottage at Sunset Key Cottages - Photo by Andrew Harper editor
Sitting area of our Two Bedroom Oceanfront Cottage at Sunset Key Cottages - Photo by Andrew Harper editor
Bath of our Two Bedroom Oceanfront Cottage at Sunset Key Cottages - Photo by Andrew Harper editor
Veranda of our Two Bedroom Oceanfront Cottage at Sunset Key Cottages - Photo by Andrew Harper editor

Vent dust aside, I quite liked our sprawling accommodations. It was Sunset Key Cottages’ service that proved a great disappointment. Problems began even before we arrived, when we tried to confirm a table on the patio of the main restaurant, Latitudes, which is open to the public. “It’s best to arrive at 5 p.m. if you want to be sure to have an outside table,” the restaurant host told us over the phone. “People start arriving and pointing to empty tables, asking, ‘Why can’t we have that one?’ And we have to give it to them.” Perhaps when a restaurant devises a system to reserve specific tables for specific parties, it can train Latitudes in the procedure. (Dinner, it must be said, was delicious and well presented, and the view of the sunset was sensational.)

There was no golf cart, luxury or otherwise, and no ambassador. Instead, we were greeted by a condescending bellman, who angled for a tip after failing to convince us to take our own luggage to the boat.

A restaurant at a luxury resort should consider giving seating priority to those who are paying upward of $2,000 a night to stay there. A luxury resort should also, in general, try to take every opportunity to delight its guests. Sunset Key Cottages squandered almost every such opportunity from start to finish. According to the hotel’s website, arrivals should check in at “Opal Key West Resort & Marina, where they will be greeted by an Island Ambassador and whisked away via luxury golf cart to a ferry.” There was no golf cart, luxury or otherwise, and no ambassador. Instead, we were greeted by a condescending bellman, who angled for a tip after failing to convince us to take our own luggage to the boat. When we arrived at Sunset Key Cottages’ pier on the public ferry, there were no chilled towels or welcome drinks, as one might expect. There was no one at all, in fact. We wandered, unaccompanied, until we stumbled on reception. While waiting for our cottage to be ready, we lunched at Flipper’s Pool Bar, which had a cocktail list that included drinks made with cheap well-level spirits. And I understand the need to serve beverages in plastic cups at a poolside restaurant, but is it also necessary to use plastic cutlery?

Room service also suffered in terms of presentation. Cocktails we ordered from Latitudes arrived in plastic cups set in a cardboard tray, like drinks from a drive-thru. How much nicer it would have been had the cocktails arrived in shakers, ready to be poured into actual glasses. The included “breakfast basket” also disappointed. It consisted of a handful of croissants and mini-quiches, all wrapped in plastic and piled at the bottom of a thermal bag. I could continue enumerating missed opportunities and outright service gaffes, if space permitted. Suffice it to say that Sunset Key Cottages’ rates set expectations that the staff time and again failed to meet.

- Hotel at a Glance -

Sunset Key Cottages    88Andrew Harper Bird


The ample size of our Two Bedroom Oceanfront Cottage; the memorable views from the main restaurant; the spa treatment rooms that open onto private patios, allowing fresh air to circulate; the location removed from the bustle of Key West.


The unwillingness of the restaurant to guarantee hotel guests a patio table; the unfriendly check-in at Opal Key West Resort; the lack of a special welcome of any kind on arrival at Sunset Key; the unappealing room-service presentations; the dated baths in our cottage; the dust clogging our baths’ fan vents; the stratospheric rates.

Good to Know

Latitudes restaurant is open to the public, making it important to make reservations (including for lunch) in advance; the resort’s beach is also open to the public, though only guests can use the loungers; the ferry between Sunset Key and Key West runs 24 hours.

Rates: Two Bedroom Oceanfront Cottage, $2,160; Four Bedroom Oceanfront Cottage, $4,465
Address: 245 Front Street, Key West
Telephone: (305) 292-5300

Sunset Key Cottages

Ocean Key Resort & Spa

Swimming pool at Ocean Key Resort, Key West, Florida
Swimming pool at Ocean Key Resort, Key West, Florida - Photo by Andrew Harper editor

Unfortunately, we fared little better at our next hotel, the Ocean Key Resort & Spa. This 100-room property at the top of Duval Street is part of the same hotel group as Little Palm Island, which gave me hope that it would have similarly high standards. The concierge, Charlie, was the best part about our stay. He offered helpful restaurant advice, made us a number of reservations and arranged for an excellent sunset cruise. Professional concierge-style service is a rarity in the Keys; we encountered it only here and at The Gardens Hotel.

In most other respects, however, the Ocean Key Resort did not live up to the expectations set by its rates. The lobby was attractive and welcoming, but I was quickly put off by the series of dark hallways extending back from it, as well as the confusing layout. Since it required two different elevators or staircases to reach our room from the lobby, we took to entering and exiting from the parking lot at the hotel’s center. (A garden canopy covered it, hiding the lot from the outdoor corridors that border the accommodations.)

View of Ocean Key Resort from our ferry - Photo by Andrew Harper editor
Bedroom of our Partial Oceanview Junior Suite - Photo by Andrew Harper editor
Sitting area of our Partial Oceanview Junior Suite - Photo by Andrew Harper editor
Bath of our Partial Oceanview Junior Suite - Photo by Andrew Harper editor
Balcony of our Partial Oceanview Junior Suite - Photo by Andrew Harper editor
View from our Partial Oceanview Junior Suite - Photo by Andrew Harper editor

Our colorful Partial Oceanview Junior Suite also had an unfortunate layout, which was quite different from the one shown on the hotel’s website. Instead of an open-plan accommodation, with a living area abutting the furnished balcony, we had a full suite. This was not a plus. The separate living room had a window facing the exterior hallway, and though it had bright upholsteries and cheerful framed watercolor prints, it felt dark. We spent little time there. The light-filled bedroom, with a French door opening onto a balcony with views of Mallory Square and the Gulf, was much more appealing. The bath was less so. It had a new digital mirror with a Bluetooth connection, as well as ample counter space and a jetted tub. But the paint job was sloppy, and the limestone tile floor near the curtained walk-in shower was heavily water damaged. Elsewhere in the hotel, it wasn’t difficult to find dirty corners and scuffed paint.

We had a pleasant sunset-view dinner on the terrace of Ocean Key’s Hot Tin Roof restaurant, enjoying roasted beets with goat cheese and pecans, and Key West pink shrimp in a tangy charred-tomato vinaigrette accompanied by mascarpone-enriched risotto. But at breakfast, the restaurant sometimes lacked the staff to handle the number of guests. Understaffing was also an issue at the otherwise attractive Gulf-view swimming pool. The lone bartender there worked hard but couldn’t keep up with the harder-drinking crowd. Lounger space was scarce enough that by 8:30 a.m. people had placed novels and other tokens on chairs to reserve them. I imagine everyone was up early because of the roosters that started crowing well before sunrise each day. I left the hotel with a craving for coq au vin.

- Hotel at a Glance -

Ocean Key Resort & Spa    87Andrew Harper Bird


The very helpful concierge; the location near all the action at the top of Duval Street; our Junior Suite’s views of Mallory Square and the water; the colorful décor; the restaurant’s memorable sunset views.


Signs of wear in our room and throughout the hotel; the confusing layout; the overcrowded pool area; the aggressive rates; the loud roosters.

Good to Know

Key West is ordinarily a popular stop with cruise ships, and the larger ones can block the water view of accommodations overlooking Mallory Square.

Rates: Partial Oceanview Junior Suite, $1,200; Oceanfront One Bedroom Suite, $1,780
Address: 0 Duval Street, Key West
Telephone: (305) 809-8072

Ocean Key Resort & Spa

The Gardens Hotel

Courtyard at The Gardens Hotel, Key West, Florida
Courtyard at The Gardens Hotel, Key West, Florida - Bob Miano TV

With neither the poorly serviced Sunset Key Cottages nor the worn Ocean Key Resort & Spa recommendable, that left our current choice of The Gardens Hotel. We have received one or two complaints about the property over the years, and indeed, it’s not a perfect hotel. Most concerning were the staff’s comments, direct and indirect, about management. One employee seemed frightened of being reprimanded when we brought up a housekeeping issue in our room and was profusely grateful that we hadn’t gone to the front desk. Another complained to us, inappropriately, about various management policies that rankled.

That said, we had an enjoyable stay at this centrally located hotel, set on a quiet street a couple of minutes’ walk from the more stylish end of Duval Street. Its 22 rooms occupy several traditional colonial-style buildings, including the upper level of a 19th-century mansion that also houses reception, a homey lounge and a grand piano. One evening, a pianist provided live music as we relaxed on the shady patio nearby, sipping selections from the hotel’s self-serve D’vine Wine Gallery, a collection of Enomatic machines offering almost 30 bottlings by the glass (a card records one’s consumption). The patio overlooks the main swimming pool, the pool bar and a gazebo that sometimes hosts live jazz combos. Extravagantly lush botanical gardens dating to the 1930s fill the property, laced with brick paths and dotted with large sculptures.

Bedroom of our Courtyard Room at The Gardens Hotel - Photo by Andrew Harper editor
Terrace of our Courtyard Room at The Gardens Hotel - Photo by Andrew Harper editor
Breakfast from Croissants de France on the terrace of our Courtyard Room, The Gardens Hotel   - Photo by Andrew Harper editor
Bath of our Courtyard Room, The Gardens Hotel - Photo by Andrew Harper editor
The main swimming pool at The Gardens Hotel - Photo by Andrew Harper editor
Bar at The Gardens Hotel - Bob Miano TV
The Queen's Residence, part of the resort, a home available for 28-day rentals at The Gardens Hotel - Photo by Andrew Harper editor

Our second-floor Courtyard Room overlooked a smaller patio, centered on a charming quatrefoil fountain surmounted by a copper frog. We shared our broad, furnished veranda with the neighboring room, but a curtain afforded some privacy. Because the hotel had canceled its usual breakfast service in the wake of COVID-19, we started each morning on the veranda instead, fortifying ourselves with pastries procured from nearby Croissants de France. The interior of the wood-floored room wasn’t large, but it had a well-considered layout. An elaborately turned four-poster bed dominated the space, flanked by palm-shaped bronze accent lamps. To its left was an antique desk bearing a basket of snacks, over which hung a vibrant painting by local artist Carrie Disrud. A nook to the right contained a love seat upholstered in faux alligator, facing a coffee table and a small dresser with a coffee maker. The shower-only bath, done in black, white and chrome, was also compact but striking and well designed.

Although we experienced some service missteps, the staff were unfailingly friendly and eager to make us feel welcome. The front desk started things off on the right foot, providing us with flutes of Prosecco and an array of restaurant coupons when we arrived. And it didn’t take long for staff members to start greeting us by name.

Considering the warmth of its service and the idyllic, tranquil setting, The Gardens Hotel remains my top choice in Key West. I recommend reserving one of the four Cottage accommodations that form a private enclave (with its own small swimming pool) adjacent to the main part of the resort. The Master Suite and Eyebrow Cottage are also excellent choices. Nowhere in Key West offers luxury-level service, in spite of what the high-season rates might lead one to believe, and The Gardens Hotel is no exception. But for those in the mood for an easygoing atmosphere somewhere reliably warm, Key West is an ideal getaway. The fresh seafood is a delight, the historic surroundings are fascinating, and it’s a fine base for snorkeling and sailing excursions.

- Hotel at a Glance -

The Gardens Hotel    90Andrew Harper Bird


The idyllic leafy setting; the central but quiet location; the welcoming staff; the traditional and very comfortable accommodations; the self-serve wine bar; the convivial pool bar; the property’s sense of history.


The staff’s complaining to us about management policies; housekeeping issues such as an unwashed coffee mug and hair in the shower drain.

Good to Know

As of this writing, breakfast service has been canceled due to COVID, but numerous restaurants are within walking distance; The Gardens also has an impressive home available for longer-term rentals; no guests under 16 are permitted.

Rates: Courtyard Room, $600; Cottage 4, $690
Address: 526 Angela Street, Key West
Telephone: (305) 294-2661

View The Gardens Hotel Listing

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.

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