Key West Luxury Vacations

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Indulge in opulence and relaxation on your Key West retreat

Key West, Florida, is renowned for its stunning sunsets, vibrant bar scene, crystal-clear seas, lively music, and thrilling excursions. This tropical paradise offers a plethora of entertainment options, from festivals that celebrate the local culture to boating and biking adventures that allow visitors to explore its distinctive geographic landscapes. With live music filling the air and the inviting waters beckoning, Key West is the perfect destination for a luxurious getaway vacation. Whether you're looking for relaxation or excitement, this island oasis has something for everyone to enjoy.

Top Luxury vacation packages in Key West

Price found within the past 48 hours. Click for updated prices.
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Northside Resort
$605
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,455 reviews)
So spacious, perfect for groups. The room was very clean and the staff were helpful! 10/10 would stay again They were doing what seemed like a clorox cleaning of the common area sidewalks, which I thought would have been better scheduled during a week day when there werent many guests but other than that the stay was perfect

Reviewed on Aug 28, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
$879
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)
Super nice and clean, staff was wonderful w knowledge of the history of the mansion

Reviewed on Aug 24, 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
$1,176
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,003 reviews)
Worth it you should book

Reviewed on Aug 30, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
$793
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (3,534 reviews)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
$903
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,024 reviews)
The room was clean and had necessities like lotion, bath gel, shampoo and conditioner available for daily use and a blow dryer. We did have to call for extra bath clothes and towels, but they were delivered promptly. Several pools for our enjoyment with daily activities and live afternoon music performers. Also had a bar convenient to pool. Would recommend to others to stay at The Marker. Our room had a balcony, but no view of anything but trees and an alleyway. Don’t spend extra for a balcony, was not worth it!

Reviewed on Aug 28, 2026

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3 Night Luxury vacations in Key West

Price found within the past 48 hours. Click for updated prices.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
$936
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (3,534 reviews)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
$1,102
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,024 reviews)
The room was clean and had necessities like lotion, bath gel, shampoo and conditioner available for daily use and a blow dryer. We did have to call for extra bath clothes and towels, but they were delivered promptly. Several pools for our enjoyment with daily activities and live afternoon music performers. Also had a bar convenient to pool. Would recommend to others to stay at The Marker. Our room had a balcony, but no view of anything but trees and an alleyway. Don’t spend extra for a balcony, was not worth it!

Reviewed on Aug 28, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
$1,018
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)
Super nice and clean, staff was wonderful w knowledge of the history of the mansion

Reviewed on Aug 24, 2026

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See all available trips from Boydton to Key West
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4 Night Luxury vacations in Key West

Price found within the past 48 hours. Click for updated prices.
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

Old Town Key West
Save 100% on your flight
$735
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Key West (EYW)
9/10 Wonderful! (981 reviews)
Great stay 2nd year in a row! This time I enjoyed the bar and specialty drinks! Staff excellent as well!

Reviewed on Aug 28, 2026

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

Key West Historic District
Save 100% on your flight
$1,175
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Key West (EYW)
9.2/10 Wonderful! (951 reviews)
Pier House Resort & Spa

Pier House Resort & Spa

Key West Historic District
Save 100% on your flight
$1,168
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Key West (EYW)
9/10 Wonderful! (1,288 reviews)
We absolutely loved Pier House! The staff was wonderful, the outside bar and the Chart room were our favorite hang outs, and the private beach was absolutely amazing! The beds are not super comfortable and the walls are quite thin, so we did hear our loud neighbors one night, but I still give this place 5 stars, and we will definitely be staying there again!

Reviewed on Aug 29, 2026

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Top reasons for your vacation to Key West

  • Stunning Sunsets: Key West is renowned for its mesmerizing sunsets that create a breathtaking view.
  • Vibrant Bar Scene: The island offers a lively bar scene, where visitors can dance the night away to live music.
  • Crystal-Clear Seas: Key West is surrounded by crystal-clear seas, perfect for boating adventures and exploring the tropical islands.
  • Lively Music: The vibrant atmosphere is filled with live music, adding to the overall entertainment experience.
  • Thrilling Excursions: Key West offers exciting excursions, from boating adventures to leisurely bike rides, allowing visitors to explore the distinctive landscapes.

Book a Package and Save Money on Your Key West Vacation

A travel package combines flights with hotels or car rental, allowing you to conveniently book everything you need for your luxury getaway to Key West. It's a great idea because you can find everything in one place, saving you time and effort. Plus, it can help you save money by offering discounted prices and the ability to customize your package to fit your preferences and budget.

Indulge in the epitome of luxury by booking a package for your Key West getaway. With stunning sunsets, vibrant bars, and lively live music, you'll experience the perfect blend of relaxation and entertainment. Explore the sea with exciting excursions, enjoy the vibrant festivals, and indulge in boating and biking adventures. It's the ultimate luxury vacation destination.

How to Save Money on a Vacation to Key West

  • Utilize public transportation or rent a bike to explore Key West and save on transportation costs.
  • Take advantage of the Expedia OneKey Program to earn points and save money on accommodations, activities, and dining.
  • Visit the Key West Butterfly and Nature Conservatory for a budget-friendly and enchanting experience with beautiful butterflies and tropical plants.
  • Explore the Ernest Hemingway Home and Museum, where you can learn about the famous writer's life and see the six-toed cats roaming the property.
  • Enjoy the sunset at Mallory Square, a popular spot where you can watch street performers and witness the breathtaking view for free.

Where to Stay in Key West

When it comes to planning a luxury getaway in Key West, you'll find a variety of neighborhoods that cater to your desires. From the vibrant nightlife and live music scene in Duval Street, to the charming historic district of Old Town, or the upscale resorts and marinas in Stock Island, Key West offers something for everyone seeking a luxurious vacation.

  • Key West Historic District: This vibrant district is known for its lively festivals, bars, and breathtaking sunsets. Explore the area on a bike and indulge in the lively atmosphere with live music and entertainment. Take part in exciting excursions and enjoy the tropical beauty while boating.
  • Old Town Key West: Experience true luxury in Key West by staying in the charming and historic Old Town. Enjoy top-notch accommodations and immerse yourself in the rich history and culture of the area. With its beautiful architecture and quaint streets, Old Town is a perfect destination for a luxury vacation.
  • Historic Seaport: For a luxury vacation, the Historic Seaport offers a delightful atmosphere. Discover upscale dining options and enjoy waterfront views. Immerse yourself in the maritime history and indulge in the luxury amenities available in this charming area of Key West.

Explore the best places to visit in Key West

Key West, Florida is the ultimate destination for a luxury getaway vacation. With its stunning sunsets, vibrant bar scene, and breathtaking sea views, you'll feel like you're in paradise. Dance the night away to live music, indulge in exciting excursions, and be entertained by the lively festivals that take place throughout the year. Explore the crystal-clear waters on a boating adventure or take a leisurely bike ride around the island. Key West is the perfect place to relax, unwind, and experience the epitome of luxury.

  • Mallory Square: Experience the mesmerizing sunsets and enjoy the vibrant atmosphere of this modern square. Explore the beautiful beaches, go on exciting excursions, and indulge in delicious food and drinks at the festivals and bars. Take a boat or go sailing to discover the stunning islands, or rent a bike to explore the area's scenic beauty.
  • Stock Island Yacht Club & Marina: Immerse yourself in the stunning sunsets and relax on the serene beaches of this marina. Enjoy exciting excursions, vibrant festivals, and refreshing drinks at the bar. Experience the thrill of boating and explore the tropical islands. Embark on a biking adventure and soak in the beauty of the surroundings.
  • The Kite House: Be captivated by the picturesque sunsets and enjoy the tranquil beaches at this store. Join exciting excursions and immerse yourself in the festive atmosphere. Discover the beauty of the islands, unwind at the bar, and go biking or boating. Experience the tropical vibes and create lasting memories.

Best months to visit Key West

Key West boasts a year-around average temperature of 77.8°F, peaking at 84.6°F in July, August, its warmest month, and dipping to an average low of 69.3°F in January, the coolest. Rainfall averages at 84.3mm annually, with September seeing the heaviest showers and February being the driest month.

MonthTemperature (Fahrenheit)Rainfall (mm)
January69.351.8
February71.137.8
March73.252.1
April76.552.1
May80.476.2
June83.3104.4
July84.690.2
August84.6136.7
September83.1170.4
October80.2125.2
November75.758.4
December71.456.4

All you need to know about luxury vacations in Key West

What can I expect from a luxury Key West vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Key West vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Key West?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Key West luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $605. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Key West?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Key West with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Key West?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Key West with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Key West with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.

Top Luxury Key West Hotels

Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

5950 Peninsular Avenue Key West FL
  • 10 min drive from Duval Street
Pamper yourself with a luxury stay at Hilton Key West Resort & Marina, where you can enjoy amenities like Egyptian cotton sheets, plush bedding, and more. Deluxe ...
Hilton Key West Resort & Marina
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

200 William Street Key West FL
  • 10 min walk from Duval Street
Be treated to a grand stay at The Marker Key West Harbor Resort, where you'll find deep soaking bathtubs and premium bedding. The 3 outdoor pools, poolside bar, ...
9.2/10 Wonderful! (1,000 reviews)
"The room was clean and had necessities like lotion, bath gel, shampoo and conditioner available for daily use and a blow dryer. We did have to call for extra bath clothes and towels, but they were delivered promptly. Several pools for our enjoyment with daily activities and live afternoon music performers. ..."

Reviewed on Aug 28, 2026

The Marker Key West Harbor Resort
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL
  • 16 min walk from Duval Street
Casa Marina Key West, Curio Collection by Hilton is one of the Key West luxury 4-star beach properties where you can pamper yourself with designer toiletries, ...
Casa Marina Key West, Curio Collection by Hilton
See all 2,625 properties in Key West
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Things to do

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

$69
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$41
per adult
88% of travellers recommend
Key West Conch Tour Train
See all activities in Key West

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.