Destinations · Key West, Florida Keys

Key West

5 Nights · Old Town, the reef, and the end of the road.

The Classic
From $1,200pp
The Gardens Hotel
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The Grand Resort
From $2,100pp
Casa Marina, Curio Collection
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✦ Ultimate Experience
The Private Island
From $7,600pp
Little Palm Island Resort & Spa
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The Island at the End of the Road

Key West

The last of the Florida Keys, closer to Havana than to Miami, and the most welcoming town in America. Days here run slow: the gingerbread conch houses and shaded lanes of Old Town, the only living coral reef in North America a few miles offshore, and the ritual of the Mallory Square sunset. It is where Hemingway wrote and the six-toed cats still roam, where Duval Street never quite sleeps, and where a rainbow has flown over the harbor for fifty years. Five nights in the heart of it. Gay-owned, and welcoming to all.

Where You Stay

The Classic

The most refined small hotel in Old Town: a walled tropical garden, a handful of rooms, and the quiet the rest of the island does not always keep. Or step up to the grand resort, or the private island, just below.

A garden-view king room with a carved four-poster bed at The Gardens Hotel, Key West Aerial view of the pool set in the tropical garden at The Gardens Hotel, Key West A historic conch-house building in the tropical garden at The Gardens Hotel The wine room at The Gardens Hotel, Key West
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Old Town · 5 nights

The Gardens Hotel

A city block of walled tropical garden in the heart of Old Town, and one of the most highly rated hotels on the island. Seventeen rooms among the orchids and palms, a garden pool, and the Marquesa-quiet that hides you a block off Duval, close enough to walk everywhere and far enough to sleep.

  • A garden-view king room among the tropical grounds
  • Breakfast daily and a welcome drink, with an upgrade where available
  • A block off Duval, walking distance to the whole of Old Town

The Classic · 6 Days

Old Town, Key West
  • Five nights at The Gardens Hotel
  • A garden-view king room
  • Breakfast daily
  • Elevida amenities and a welcome drink
From $1,200 per person
double occupancy · airfare and transfers quoted separately
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Or, the grand old resort

The Grand Resort

The landmark of Key West: Henry Flagler's 1920 oceanfront resort, with the only private beach in town, marble and royal palms, and a century of history on the water.

A Key West View King room at Casa Marina, Key West The palm-lined facade and reflecting pools of Casa Marina, Key West The beachfront and pier at Casa Marina at sunset, Key West The oceanfront terrace dining at Casa Marina, Key West
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Oceanfront · 5 nights

Casa Marina, Curio Collection

Built by railroad magnate Henry Flagler in 1920 and still the grand dame of the island: a Mediterranean landmark on the only private beach in Key West, with a great lawn to the water, two oceanfront pools, and a lobby of marble and dark wood. The recognizable name, at the ocean end of Old Town.

  • A Key West View king room at the Flagler landmark
  • Breakfast daily and Signature amenities, with an upgrade where available
  • The only private beach in town, two oceanfront pools, the spa

The Grand Resort · 6 Days

Oceanfront, Key West
  • Five nights at Casa Marina, Curio Collection
  • A Key West View king room
  • Breakfast daily and Signature amenities
  • The private beach, the oceanfront pools, the spa
From $2,100 per person
double occupancy · airfare and transfers quoted separately
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Or, the private island

✦ Ultimate Experience

The Private Island

Off the chain of islands and onto your own: a thatched-bungalow resort on a five-acre private island, reached only by the resort's launch or a seaplane. Adults only, no clocks, no crowds. The finest address in the Keys.

An island suite with a four-poster bed at Little Palm Island Resort & Spa The private beach and lagoon at Little Palm Island Resort & Spa An island romance suite at Little Palm Island Resort & Spa A thatched island suite interior at Little Palm Island Resort & Spa The island suite terrace at Little Palm Island Resort & Spa
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Little Torch Key · 5 nights

Little Palm Island Resort & Spa

A five-acre private island in the Lower Keys, thirty rooms in thatched bungalows scattered among the palms, reached only by the resort's launch or by seaplane. No televisions, no clocks, no children: only the lagoon, the spa, and dinner by candlelight at the water's edge. The most private address in the Keys.

  • An Island Escape Suite with a four-poster bed and a sundeck
  • Breakfast daily, the launch from the mainland, adults only
  • The private beach, the lagoon, the spa, dining at the water's edge

The Private Island · 6 Days

Little Palm Island
  • Five nights at Little Palm Island Resort & Spa
  • An Island Escape Suite
  • Breakfast daily and the resort's island launch
  • Adults only, the spa, the private beach
From $7,600 per person
double occupancy · airfare and transfers quoted separately
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Add as You Like

Experiences

Private days on the water and through the lanes of Old Town, timed around your stay. Add the ones that suit you, and we book and time them for you.

A classic schooner sailing at sunset off Key West
Private Sunset Sail
A classic schooner across the Gulf as the sky turns, champagne aboard
On Requestbespoke
Fort Jefferson and the turquoise shallows of Dry Tortugas National Park
Dry Tortugas by Seaplane
Fort Jefferson and the clear shallows, seventy miles out, with snorkeling
On Requestbespoke
Snorkeling the coral reef off Key West
The Living Reef
A private charter to North America's only barrier reef, to snorkel the coral
On Requestbespoke
The Hemingway Home and the lanes of Old Town, Key West
Old Town, on Foot
A private walk: Hemingway's house and its cats, the Southernmost Point, the lanes off Duval
On Requestbespoke
A flats skiff in the mangroves and backcountry of the Lower Keys
Backcountry Flats
A private skiff into the mangroves and flats for tarpon, bonefish and permit
On Requestbespoke
A seaplane over the turquoise water of the Florida Keys
Key West by Air
A champagne seaplane loop over the reef, the backcountry and the island chain
On Requestbespoke

We book and time each experience around your stay, and confirm the dates with the guides ahead of arrival.

Good to Know

Before you go

When to go

December to April

The dry season, and the height of Key West: warm days, low humidity, blue water, and the calendar full. December through April is the peak, and the finest rooms sell first.

The summer is hot and green with afternoon storms, and the rates ease; hurricane season runs June to November. Fantasy Fest lands in late October.

Getting there

Direct to EYW

Nonstop flights reach Key West (EYW) from a growing list of US cities. Or fly into Miami or Fort Lauderdale and drive the Overseas Highway down US-1, one of the great American drives, about three and a half hours. No passport needed. For the private island, it is about forty minutes from Key West to the Little Torch Key marina, then the resort's launch across, which is included in the rate. Airport transfers we arrange on request.

The Elevida difference

Handled for you

The right hotel, the right room, the launch to the island, and every guide and day you choose, all arranged. You arrive to breakfast, amenities, and the details you only know to ask for once you have been.

A couple together at the water at golden sunset in Key West

Gay-owned · Welcoming to all

Planned by people who travel like you

Elevida is gay-owned, and Key West has been a haven for as long as anyone can remember. We build the trip we would want for ourselves: the right hotel, the right room, and the kind of details you only know to ask for once you have been. Tell us your dates and we will shape this around you.

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From prices are per person, double occupancy, based on a five-night stay in the room categories shown, with Elevida amenities. The Classic uses a garden-view king at The Gardens Hotel; The Grand Resort uses a Key West View king at Casa Marina, Curio Collection; The Private Island uses an Island Escape Suite at Little Palm Island Resort & Spa. Breakfast is included on every stay, and the Little Palm rate includes the resort's island launch. Airfare and airport transfers are quoted separately. Experience prices are from, per person unless noted, and confirmed with the guides ahead of arrival. Pricing varies by travel date, room category and availability.
Elevida Luxury Journeys · An LGBTQ+-owned luxury travel advisory · Welcoming to all