1 . Reach Resort

Key West, Florida

CALL DIRECT: +1 (866) 537 - 5241

WEBSITE

If the Key West luxury vacation of your dreams has always seemed just beyond your reach, our No. 1 pick should place it firmly back in your hands. From pampering spa treatments that restore your glowing complexion to gourmet dining that exceeds all expectations, every Key West vacation dream is realized at Reach Resort!

With so much surf, sand and luxury in one incredible Key West location, it’s hard to decide which to reach for first! You could pick up the phone and book a mind, body and soul transforming treatment at Reach Resort’s spa-inspired Massage Studio. You could get a firm grasp on your knife and fork as you savor the Strip House restaurant’s savory menu of sirloin steaks paired with black truffle side dishes. Or, you could do what we did – release all hold on reality as you surrender to the sleep-inducing comfort of your Reach Resort room or suite! Inside Reach Resort’s exquisite collection of luxury accommodations, colorful splashes of coral blend beautifully with an otherwise neutral décor – a striking complement to the turquoise waters just beyond the balcony’s borders. And outside, this Key West luxury retreat boasts a generous stretch of white sand beach and a laidback tropical ambiance that rivals that of the most opulent Caribbean resorts!

Highlights

Reach Resort’s Massage Studio offers a range of relaxing Swedish and deep tissue massage styles, plus an invigorating selection of aromatherapy and reflexology treatments.

Related activities

Designed by golf legend Rees Jones, Key West Golf Course’s 6,500-yard course offers 18 holes of challenging and scenic Florida golf.

Related Onsite Offerings

Wake to a delightful breakfast overlooking the pool’s sparkling waters with a bed and breakfast package from Reach Resort.

2 . Casa Marina Resort & Beach Club

Key West, Florida

CALL DIRECT: +1 (866) 397 - 6342

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If you’ve secretly harbored dreams of one day owning a house by the sea, our No. 2 selection should fulfill your oceanfront real estate aspirations. Then again, with an intoxicating blend of timeless elegance and no-limits luxury, Casa Marina Resort is destined to surpass even the most extravagant Key West fantasy!

Imagine a place where the lackluster sod and pink flamingo statues of your current backyard are replaced with emerald lawns shaded by towering palms, vast expanses of white sand beach and turquoise waters as far as the eye can see. Now open your eyes and feast them upon the breathtaking landscape that serves as the backdrop to your Key West luxury vacation, courtesy of Casa Marina Resort! Pinch yourself if you think we’d deceive you, but all this and more truly awaits you at this Key West outpost of the prestigious Waldorf Astoria Collection. If you thought the lawns were a dream, wait until you step into the lavish surrounds of your Casa Marina Resort suite. A splash of cold water may be needed to truly take in your Key West luxury suite’s flat screen TV, soaring ceilings and private balcony overlooking Flagler’s Beach. And if you’re still in need of a refresher, head to Casa Marina’s private beach club and marina for an eye-opening wave runner, deep sea fishing or SCUBA diving adventure in Key West’s waters!

Related Onsite Offerings

Casa Marina Resort boasts two oceanfront swimming pools, beachfront hammocks, a private pier and water equipment rentals right on the beach.

Fun facts

Casa Marina Resort was built in 1920 and is currently listed in the National Register for Historic Places.

Highlights

Key West weddings practically plan themselves at this idyllic Florida luxury retreat. But don’t limit your Casa Marina Resort experience to just one day; stay for a memorable honeymoon on Key West’s shores!

3 . Parrot Key Resort

Key West, Florida

CALL DIRECT: +1 (866) 939 - 3715

WEBSITE

For a spacious and luxurious vacation head down to Parrot Key Resort! Here, you'll find the largest rooms in the Key West.

Nestled on five acres gorgeous sandy beaches you'll find your piece of paradise; the luxurious Parrot Key Resort. Every detail of the resort is designed to offer the best and finest of the Florida Keys. In room amenities feature flat-screen tv's, the finest linens, local island artwork and handcrafted furniture. Spend your days lounging on the white sandy beaches, walking through the tropical gardens or just enjoying the view from your private balcony!

Address

2801 N. Roosevelt Boulevard, Key West, FL 33040

Related activities

Guests can enjoy a long list of activities including fishing excursions, snorkeling, diving, historic district tour and much more!

Fun facts

The resort is located on the waterfront providing a unique landscaped scenery that is truly unmatched in Key West!

4 . Sunset Key Guest Cottages

Key West, Florida

CALL DIRECT: +1 (877) 564 - 1273

WEBSITE

You’ll find the sister property to our No. 4 pick a few spots down on our Top 10 Key West Luxury Resorts list, but the similarities end at their shared Westin name. Where our No. 10 spot offers traditional touches, Sunset Key Guest Cottages’ specialty is bringing to life your Key West vacation dreams.

Palm trees swaying in the fragrant tropical breeze. A lacy white hammock centered between their towering forms. And a pristine stretch of wide sand beach bordered by impossibly blue Atlantic waters. If that’s not your idea of a Key West vacation straight from heaven’s doors, you’ll be disappointed by our No. 4 pick. But if spectacular Key West sunsets, blooming tropical gardens and the luxurious comfort of Florida’s finest accommodations are something you could get used to, you’ll love – and who wouldn’t – what’s in store at Sunset Key Guest Cottages. With whimsical pastel exteriors and tin roofs straight out of Key West’s storied past, Westin’s Sunset Key Guest Cottages prove worthy of their tropical surroundings. Tasteful one-, two- and three-bedroom cottages capture Key West’s charm, while a spacious porch perfectly frames the Florida sun as it rises and sets over the Gulf of Mexico’s turquoise waters. And a scrumptious Sunset Key breakfast basket accompanied by a glass of sparkling champagne – and a breathtaking view – is the perfect beginning to each morning of your Key West luxury vacation!

Related activities

Nearby Key West offers water sports, golf courses, museums, theaters, shops, restaurants and more to take advantage of on your Florida luxury vacation.

Related Onsite Offerings

Sunset Key’s Latitudes Beach Cafe offers an upscale yet casual setting with al fresco beachfront dining overlooking the Gulf of Mexico.

Fun facts

Sunset Key Guest Cottages, a Westin Resort, is located on Sunset Key, a luxury island only 500 yards from Key West.

5 . Santa Maria Suites Resort

Key West, Florida

CALL DIRECT: +1 (866) 726 - 8259

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They say walking is the new driving, and it’s an easy switch when you’re mere blocks from Key West’s most notable sights and attractions. Of course, it’s practically effortless to spend all day exploring when your nights are passed in the restful comfort of the sophisticated all-suite hotel in our No. 5 spot, Santa Maria Suites Resort.

This Key West luxury resort’s contemporary furnishings are a delightful contradiction to its historic façade. Minimalist platform beds are outfitted in the utmost comfort with silky fabrics, fine linens and a generous piling of plush pillows. Rattan accents and sleek glass shelves topped with bleached seashells are a decidedly upscale take on traditional island décor. And inspired works by local artists ensure the Key West scenery is never out of your line of sight – even inside the stylish comfort of your Santa Maria villa or suite. Santa Maria Suites Resort’s contemporary look continues inside the Ambrosia Restaurant, where Key West’s culinary masterminds have perfected the art of Asian cuisine and sushi presentation. Sip an exquisite glass of sake as you sample Ambrosia’s sashimi, tempura and other sea-faring treasures. Duval Street’s cafés and the Atlantic Ocean’s waters are both a block away, while Key West’s style hub – the upscale Clinton Market – offers a wide range of designer shops and boutiques just minutes from Santa Maria’s doors!

Related Onsite Offerings

Your Santa Mara Suites kitchen includes a Jenn-Air cooktop and stove, Sub-Zero refrigerator, Cuisinart cookware, wine chiller and more!

Highlights

Enjoy a Dove ice cream treat as you check in, plus turn-down service, fresh towels and a Dove chocolate placed upon your pillow each evening.

Getting there

From Miami International Airport, take LeJeune Road South to 836 West. Take the Florida Turnpike south toward Key West. The turnpike ends at U.S. 1 in Florida City. Follow U.S. 1 south as far as it goes and you will be in Key West. Proceed to the Santa Maria Suites Resort.

6 . Pier House Resort & Spa

Key West, Florida

CALL DIRECT: +1 (305) 296 - 4600

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Luxury, adventure and scenery await you in Key West. But as any traveler knows, a truly relaxing vacation requires a refreshing new perspective. Thankfully, a true Key West state of mind and an unprecedented level of luxury await you at our No. 6 spot, Pier House Resort and Spa.

If your Key West vacation wouldn’t be complete without a generous dose of Florida sun, the resort’s Lanai Rooms are just the accommodation you’ve been looking for. And if you’re torn between the upscale comfort of your Pier House suite and the lavish pampering of the onsite spa, we’ve found a solution! Inside the Caribbean Spa Rooms, French doors open to let the cool tropical breezes float over your four-poster bed, while a private whirlpool and the entrance to Key West’s only full-service spa are only a few steps away. Speaking of pampering, we found a Key West spa that promises to ease stress, sooth aching muscles and restore your sunny disposition – all within the span of a single spa treatment. The Pier House’s Caribbean Spa will even treat you to a sun-kissed Florida tan without the sun’s damaging effects. An invigorating sugar scrub, self tanning application and light dusting of shimmer powder will leave you with that coveted golden glow!

Highlights

Pier House Resort and Spa is located at the meeting point of two beloved Key West landmarks – vibrant Duval Street and the brilliant Gulf of Mexico.

Fun facts

Pier House Resort was the first to lay claim to Key West’s beloved sand beaches and premier oceanfront property.

Related Onsite Offerings

With four unique dining options all on site, the Pier House Resort and Spa offers you plenty of choices on your Key West vacation. Choose from the Beach Bar and Grille, the Chart Room Bar, the Harbour View Café or the Wine Galley Piano Bar.

7 . Marquesa Hotel

Key West, Florida

CALL DIRECT: +1 (305) 292 - 1919

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We’ve found a delightful turn-of-the-century accommodation that offers all the comforts of home – only better – on your Key West luxury vacation. Unless your daily life includes luxuries like turn-down service and exquisite Godiva chocolates perched atop a pile of plush pillows, we suggest making haste to our No. 7 pick, the Marquesa Hotel.

If daily maid service and custom chocolates aren’t enough to impress, perhaps a gourmet breakfast savored in the comfort of your suite is enough to tip the scales in Marquesa Hotel’s favor. This Florida luxury hotel even boasts a helpful concierge at your service, who can easily arrange everything from afternoon water sports to full-day Key West adventures at your whim. Snorkel trips, diving adventures and even sunset catamaran sails to the Dry Tortugas can all be arranged by Marquesa’s hospitable staff – all you have to do is choose and enjoy! From the Marquesa Hotel’s charming exterior to its suites’ lavish interiors, an exquisite level of luxury awaits you both inside and out at this Key West accommodation. Marble baths are the highlight of the Marquesa’s sunny rooms and suites, while lush tropical gardens frame the hotel’s two sparkling outdoor pools. From delightful crustaceans like conch and blue crabs to indulgent dishes like the macadamia-encrusted yellow snapper, the award-winning Café Marquesa serves up fresh fare with Key West flair!

Getting there

From Miami International Airport, exit MIA and follow the signs to Rt. 836 West. Take 836 West to the Florida Turnpike (Rt. 821) South until it ends at Florida City. You will then be on U.S. 1 South. Take U.S. 1 South approximately 120 miles. Key West is the last island on U.S. 1. The Marquesa Hotel is at 600 Fleming St., on the corner of Simonton and Fleming Streets.

Related Onsite Offerings

Looking for the luxury of the Marquesa paired with the seclusion of a private Floridian estate? Vacation rentals from Marquesa Cottages feature luxurious interiors, private pools and quiet Old Town locations.

Fun facts

The Marquesa Hotel was named to Conde Nast Traveler Magazine's 2009 Gold List of World's Best Places to Stay.

8 . The Gardens Hotel

Key West, Florida

CALL DIRECT: +1 (800) 526 - 2664

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Our No. 8 pick was named prettiest hotel in Key West by the New York Times. If you ask us, we think Key West luxury like this deserves to be experienced with the prettiest, handsomest and downright luckiest special someone in your life!

The historic Gardens Hotel boasts the intimacy of a Florida boutique hotel, the pulsing heartbeat and scenery of Key West and just a hint of Bahamian flair. Set in the heart of one of Florida’s most beloved and well-cared for botanical gardens, the Gardens was once the largest private estate in all of Key West. Winding brick pathways lead to intimate spaces for two, brightly-plumed tropical birds perch inside the hotel’s aviary and equally exquisite Japanese and Hawaiian orchids bloom on its expansive grounds. The Gardens Hotel offers a unique collection of Key West rooms, suites and cottages as diverse – and beautiful – as the tropical blooms that surround. For tropics-inspired romance on your Florida vacation, only the quirkily-named Eyebrow Cottage will do. Your eyes may widen in delight when you catch sight of this stand-alone suite’s authentic plantation style, complete with palm ceiling fans, exotic hardwoods and tropics-inspired fabrics. But we can think of something else worth raising inside this romantic Key West luxury retreat: your champagne flutes as you toast to each other!

Fun facts

The original Bahamian-style mansion at The Gardens Hotel Key West was built in the 1800s and is currently listed on the National Register of Historic Places.

Highlights

In July 2009, Travel and Leisure Magazine chose The Gardens Hotel as one of their top 21 favorite beachside hotels.

Related Onsite Offerings

Most rooms at the Garden Hotel feature outdoor verandahs, king beds dressed in European linens, crown moldings and marble baths with Jacuzzi tubs.

9 . Cheeca Lodge

Islamorada, Florida

CALL DIRECT: +1 (866) 264 - 0820

WEBSITE

So many resorts promise you the world, only to sorely disappoint upon arrival. Fortunately, our No. 9 pick is a far cry from such resorts. In fact, everything this Key West luxury resort promises, it delivers – and then some – in inimitable tropical style.

For a tropical getaway in the Florida Keys, Cheeca Lodge is our hands-down favorite. Palatial oceanfront suites – the largest in the Keys – serve as your oceanfront retreat complete with private lanais, open-air spa tubs and floor-to-ceiling windows that frame inspiring Atlantic Ocean views. Island-themed décor can bring to mind gaudy palm tree murals and cheesy mosquito netting, but Cheeca Lodge’s lavish interiors are anything but! Dark mahogany furnishings, oversized beds draped with luxurious fabrics and palm-leaf ceiling fans blend the beauty of Key West with the peak of Florida resort luxury. But it was what follows the “lodge” in Cheeca Lodge and Spa that truly captured our attention. Here on Islamadora, turquoise waters and fragrant tropical blooms set the stage for sheer rest and relaxation on your Key West vacation. Refreshing tropical breezes tickle your toes as you recline in a lacy hammock tied between to palm trees, while inside the Cheeca Spa, the soothing hands of a skilled masseuse lull you into a state of mind and body bliss.

Related activities

Set in the heart of the sport fishing capital of the world, Cheeca Lodge is an angler’s paradise. There’s even a kid-friendly Camp Cheeca for the littlest island-goers!

Related Onsite Offerings

Cheeca Lodge offers a wide range of Key West vacation packages, including the Islamadora Romance Package, the Heart of the Keys Valentine Package, the Family Snorkel Package and a Mind, Body and Soul spa package.

Highlights

Cheeca Lodge’s private, secluded Islamadora beaches are complemented by the addition of plushly-appointed cabanas and cascading waterfalls.

10 . The Westin Key West Resort

Key West, Florida

CALL DIRECT: +1 (877) 564 - 1277

WEBSITE

The final pick on our Top 10 Key West Luxury Resorts list may come with a typical Key West hotel address, but something unexpected awaits inside the Westin Key West Resort’s walls. Here, you’ll find all the luxury you’d expect from Starwood’s newest resort – but with a decidedly 19th century twist.

The Westin Key West Resort may boast hints of a bygone era, but the luxurious amenities harbored within its walls are straight out of the 21st century. Vaulted ceilings and expansive windows blend the inspiring Key West scenery with the décor featured in your stylish Westin suite, while down pillows and rich fabrics surround you in plush comfort throughout your stay. More exquisite treasures await you at nearby Duval Street, where you can easily spend a day perusing the boutiques, antique shops, artist galleries and more that line this famed lane. Westin Resorts are famous for the luxurious comfort of the Heavenly Bed – a Westin signature. But we found something even more ethereal outside the Westin Key West Resort’s walls – mainly, the breathtaking crimson and golden glows that paint the Gulf of Mexico horizon with every spectacular Key West sunrise and sunset. Even the private balcony attached to your Florida luxury hotel suite has been blessed with breathtaking Gulf of Mexico views!

Related Onsite Offerings

Valet parking with unlimited in and out privileges, 24-hour room service, concierge service, fitness and business centers.

Highlights

The Westin Key West Resort has been Key West’s only AAA Four-Diamond full-service resort for 10 consecutive years.

Fun facts

Florida residents save up to 10 percent off Westin Key West Resort’s best rates. Plan your getaway now and experience the beauty of Key West at a fraction of the regular rate.

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