Key West Holidays

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Your Key West Holiday

Lock in a Key West holiday package and focus on what counts — enjoying yourself. There's no more travel planning headaches, just a lot more free time to savour what's special about this captivating city, such as its beaches and relaxed vibe. If a sightseeing tour is on the agenda during your trip to Key West, look around well-known attractions like Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Whoever you're taking a break with and whatever you plan to spend, your dream Key West holiday is just clicks away with Expedia.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

Our guide on where to stay in Key West

Find the best Key West areas and neighborhoods for the activities you enjoy most. Learn more about Key West

Key West Holiday

Key West Luxury Holiday Packages

Dabble in the finer things in life and get pampered with a luxury Key West package! Spoil yourself with our luxury Key West holiday packages and enjoy poolside cocktails, world-class dining and relaxing spa treatments. Dig your toes in the sand at Casa Marina Key West, Curio Collection by Hilton or go swimming in the year-round pool at Hyatt Centric Key West Resort & Spa.

Romantic Holiday Packages in Key West

Take your romantic Key West getaway to the next level with candlelit dinners, ocean views and couples massages. Expedia’s Key West romantic holiday packages are perfect for lovebirds looking to spice things up. Pop open a bottle of champagne in the hot tubs at Pier House Resort & Spa near Mallory Square or share a poolside cabana at Southernmost Beach Resort.

Take your romantic holidays in Key West to the next level with a photo shoot at your resort or the beach or a Key West marriage proposal package. Get inspired with our guide on things to do in Key West and add some loved-up activities to your Key West package deal today.

Where to Stay in Key West

When looking for Key West holiday packages, choosing the right place to stay is important. Whether you want a sun-packed stay or a history-packed holiday, this iconic island city has plenty of options on offer. Here’s a breakdown of where to stay for your Key West trip:

  •       Key West Historic District: You can enjoy the central location, buzzing streets and historical landmarks in this popular suburb. Topped with shopping, nightlife and restaurants, this is an ideal place to stay for those looking for convenience.
  •       Duval Street: Jam-packed with retail stores, nightlife, live music venues and restaurants, this is the ultimate spot to let loose on your Key West holiday.
  •       Historic Seaport: The picturesque marina is a top choice for art lovers, foodies and water sports fanatics.
  •       Bahama Village: This part of Key West is dotted with dazzling architecture, colourful homes and open-air restaurants.
  •       New Town: Laid-back New Town offers fewer crowds, making it one of the most tranquil holiday places in Key West.

Top Things to Do

Whether you’re into sightseeing, sunbathing or savouring flavour-packed cuisine, there are many things to do in Key West. Here’s a taste of what’s on offer:

Top Things to Do

Whether you’re into sightseeing, sunbathing or savouring flavour-packed cuisine, there are many things to do in Key West. Here’s a taste of what’s on offer:

How to Find Cheap Package Deals

Expedia’s cheap holiday packages to Key West allow you to see more, save more and stress less! You can save just by bundling your airfare and accommodation. Plus, by adding car rental, activities, tours and more, you can organise everything all in one place. Booking our Key West package deals is simple and straightforward. Simply enter your departure destination and desired travel dates. Then, use our filters to find cheap hotels in Key West.

*Prices and availability are subject to change. Additional terms apply.

**Savings based on all package bookings with Flight + Hotel made on Expedia from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

Where to Stay in Key West

When looking for Key West holiday packages, choosing the right place to stay is important. Whether you want a sun-packed stay or a history-packed holiday, this iconic island city has plenty of options on offer. Here’s a breakdown of where to stay for your Key West trip:

  •       Key West Historic District: You can enjoy the central location, buzzing streets and historical landmarks in this popular suburb. Topped with shopping, nightlife and restaurants, this is an ideal place to stay for those looking for convenience.
  •       Duval Street: Jam-packed with retail stores, nightlife, live music venues and restaurants, this is the ultimate spot to let loose on your Key West holiday.
  •       Historic Seaport: The picturesque marina is a top choice for art lovers, foodies and water sports fanatics.
  •       Bahama Village: This part of Key West is dotted with dazzling architecture, colourful homes and open-air restaurants.
  •       New Town: Laid-back New Town offers fewer crowds, making it one of the most tranquil holiday places in Key West.

Romantic Holiday Packages in Key West

Take your romantic Key West getaway to the next level with candlelit dinners, ocean views and couples massages. Expedia’s Key West romantic holiday packages are perfect for lovebirds looking to spice things up. Pop open a bottle of champagne in the hot tubs at Pier House Resort & Spa near Mallory Square or share a poolside cabana at Southernmost Beach Resort.

Take your romantic holidays in Key West to the next level with a photo shoot at your resort or the beach or a Key West marriage proposal package. Get inspired with our guide on things to do in Key West and add some loved-up activities to your Key West package deal today.

Key West Luxury Holiday Packages

Dabble in the finer things in life and get pampered with a luxury Key West package! Spoil yourself with our luxury Key West holiday packages and enjoy poolside cocktails, world-class dining and relaxing spa treatments. Dig your toes in the sand at Casa Marina Key West, Curio Collection by Hilton or go swimming in the year-round pool at Hyatt Centric Key West Resort & Spa.

How to Find Cheap Package Deals

Expedia’s cheap holiday packages to Key West allow you to see more, save more and stress less! You can save just by bundling your airfare and accommodation. Plus, by adding car rental, activities, tours and more, you can organise everything all in one place. Booking our Key West package deals is simple and straightforward. Simply enter your departure destination and desired travel dates. Then, use our filters to find cheap hotels in Key West.

*Prices and availability are subject to change. Additional terms apply.

**Savings based on all package bookings with Flight + Hotel made on Expedia from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

Things to do in and around Key West

Key West offers a delightful blend of family-friendly activities, shopping centres, and luxurious resorts, making it ideal for various vacation styles. Visitors can indulge in exciting attractions such as recreational tours, boat excursions, and thrilling snorkelling trips. Whether you're exploring the vibrant shopping areas or enjoying the local culture, Key West promises a memorable experience for all who visit.

Shopping

In Key West, visit The Kite House and We Cycle Key West for unique gifts and souvenirs. If you're up for a drive, the Big Pine Key Flea Market, located 46.7km away, offers a vibrant atmosphere with various stalls and local products to explore.

Recreation

The Key West Golf Club offers a serene golfing experience amidst lush landscapes, perfect for outdoor enthusiasts. At the Red Barn Theater, indulge in captivating performances that celebrate culture and family entertainment. For a refreshing family outing, the MLK Community Pool & Community Center provides a vibrant space for recreation and fun.

Adventure

Explore the vibrant coral reefs with a snorkelling tour, discovering colourful marine life and stunning underwater landscapes. For a thrilling experience, try parasailing to enjoy panoramic views of the island from above. Don’t miss the opportunity for a sunset kayak tour, paddling through serene waters while witnessing breathtaking sunsets.

Nightlife

In Key West, the nightlife is vibrant and eclectic, with Duval Street teeming with lively bars and live music venues. Enjoy sunset celebrations at Mallory Square, sip cocktails at rooftop bars, and dance the night away at local clubs, all set against the backdrop of stunning ocean views.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Key West

Key West, a charming destination in Florida, is ideal for family, city, and business vacations. Visitors can enjoy a variety of attractions, including beautiful beaches, historic houses, and national parks, catering to those seeking cultural experiences and outdoor adventures. Highlights include exploring local sights, visiting the Key West Museum, and staying in historic inns, making it a perfect getaway for diverse travellers.

  • Mallory Square: Experience the vibrant atmosphere of Mallory Square, where locals and tourists gather to enjoy street performances, artisan shops, and stunning sunset views over the Gulf of Mexico. This lively square embodies the spirit of Key West with its bustling energy and picturesque surroundings.
  • Southernmost Point: Stand at the iconic Southernmost Point buoy, a symbolic landmark representing the southern tip of the continental United States. This photo-worthy spot is steeped in local culture and offers a unique perspective on Key West's historical significance and maritime heritage.
  • Smathers Beach: Relax on the sandy shores of Smathers Beach, a popular destination for sunbathing, swimming, and water sports. With its palm-lined coastline and clear turquoise waters, it’s the perfect place to unwind and soak up the sun in a true beach paradise.

Tips to save on your trip to Key West

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Key West.
  • Consider traveling during the off-peak season (typically August to October) for more affordable package holidays to Key West.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Key West Beach Holiday

Unwind on the shore while you watch the sunlight glistening across the water during your Key West holiday. If you're hoping for an unforgettable beach experience, a trip to Key West will definitely deliver. There's a good chance you've heard of Smathers Beach (3 kilometres away). We suggest staying in accommodation close by. However, many sightseers also opt for Key West packages that are closer to South Beach or Boca Chica Nude Beach, two other excellent nearby options.

Things You Should Know About Key West

  • Escape the daily grind at one of our Key West beach hotels. The sweet sound of lapping water and seagulls cawing far above are just a couple of clicks away.
  • If you're searching for lots of room to spread out and relax, Key West private holiday homes are a great choice. After a much-needed family getaway or a few nights escape with that special someone? Grand Maloney Hotel and The Capitana Key West will fit the bill.
  • With a population of approximately 25,800 inches Key West, you're sure to find some friendly locals who are happy to share their sightseeing tips. For more handy hints, check out our Key West things to do page.

Key West Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Population
25,800
Max Temp Winter
24ºC
Max Temp Summer
29ºC
Top Sights
Smathers Beach, South Beach and Fort Zachary Taylor Historic State Park

Our pick of the best Key West Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
The price is AU$882 per night from 24 Mar to 25 Mar
AU$882
24 Mar - 25 Mar
includes taxes & fees
8.8/10 Excellent! (3,103 reviews)
This property has several different locations around Key West. Just make sure when you’re booking you are at the main resort. That’s where the pools and bars are

Reviewed on 2 Mar 2026

Southernmost Beach Resort and Guesthouses
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is AU$472 per night from 3 Mar to 4 Mar
AU$472
3 Mar - 4 Mar
includes taxes & fees
8/10 Very Good! (2,119 reviews)
Was able to get into the room early.

Reviewed on 2 Mar 2026

Ibis Bay Beach Resort
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is AU$722 per night from 25 Mar to 26 Mar
AU$722
25 Mar - 26 Mar
includes taxes & fees
8.8/10 Excellent! (1,785 reviews)
Staff was amazing!

Reviewed on 1 Mar 2026

Margaritaville Beach House 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.

Discover the most popular places to visit in Key West

What to do in Key West

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