Florida Keys Holidays from NZ$2,741

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The Latest Florida Keys Holiday Deals

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
NZ$2,741
per person
24 Dec - 27 Dec
found 11 hours ago
Return direct flight included
Charlottesville (CHO) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
The resort was excellent. It was clean. The staff were very accommodating. The breakfast & dinners we had a The beach side Cafe were very good. The bars closed rather early on the resort by 9pm. We felt that one bar on the resort should open until 11pm to accommodate guests that want stay at the resort in the evening. Also a shuttle to and from the airport should be offered.

Reviewed on 13 Oct 2026

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

Old Town Key West
NZ$3,147
per person
24 Dec - 27 Dec
found 11 hours ago
Return direct flight included
Charlottesville (CHO) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
NZ$2,939
per person
24 Dec - 27 Dec
found 11 hours ago
Return direct flight included
Charlottesville (CHO) to Key West (EYW)
9.2/10 Wonderful! (1,024 reviews)
I didnt like this property at all

Reviewed on 13 Oct 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
NZ$2,886
per person
24 Dec - 27 Dec
found 11 hours ago
Return direct flight included
Charlottesville (CHO) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
Great stay. Older locations like this face many challenges so there is certainly more work to be done but everything worked like new and the staff was super helpful even offering an upgrade at no charge due to availability.

Reviewed on 11 Oct 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
NZ$3,548
per person
24 Dec - 27 Dec
found 11 hours ago
Return direct flight included
Charlottesville (CHO) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)

Our guide on where to stay in Florida Keys

Find the best Florida Keys areas and neighborhoods for the activities you enjoy most. Learn more about Florida Keys
A white building with shutters, palm trees, and a lawn.

Old Town Key West

2 out of top 10 points of interest in this area

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Florida Keys Beaches.

Find hotels in Old Town Key West
A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

Downtown Key West

While visiting Downtown Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

Find hotels in Downtown Key West
A two-story house with green shutters and a wooden balcony.

Key West Historic District

2 out of top 10 points of interest in this area

Travellers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to stop by Duval Street and Florida Keys Beaches.

Find hotels in Key West Historic District
A marina with yachts docked, a prominent red building, and a coastal cityscape in the background.

New Town

While there might not be top attractions in New Town, you can explore the larger area and discover places like Smathers Beach and Fort East Martello Museum and Gallery.

Find hotels in New Town
A sunset over the ocean with scattered clouds.

Uptown - Upper Duval

If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.

Find hotels in Uptown - Upper Duval

Florida Keys Holiday

Things to do near Florida Keys

Shopping

In the Florida Keys, visit The Kite House, a charming store located 11.3km from the heart of the keys, perfect for unique gifts. We Cycle Key West, situated 9.7km away, offers a selection of cycling gear and souvenirs for outdoor enthusiasts.

Recreation

At MLK Community Pool & Community Center, enjoy a refreshing swim amidst a family-friendly atmosphere. The Key West Golf Club offers a stunning outdoor golfing experience, while the Red Barn Theater combines romance and culture for an entertaining evening. Each venue promotes relaxation and fun.

Adventure

Explore the vibrant coral reefs of John Pennekamp Coral Reef State Park, renowned for snorkelling and diving. Experience the thrill of kayaking through tranquil mangroves at Florida Keys Kayak Tours, where you can spot diverse wildlife and enjoy the stunning coastal views.

Nightlife

The Florida Keys offer a vibrant nightlife with beach bars and live music. Visit the Green Parrot Bar for a lively atmosphere and enjoy local bands. For a laid-back vibe, check out the Sunset Pier, where you can sip cocktails while watching stunning sunsets and mingling with fellow travellers.

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

Find the best attractions near Florida Keys

The Florida Keys offer a fantastic getaway for beach lovers and families alike, featuring stunning beaches and vibrant coral reefs. With attractions ranging from modern squares and historic civic buildings to state parks, there's something for everyone. Adventurous travellers can explore key destinations and partake in various activities, while those seeking culture will find plenty of tourist attractions that highlight the region’s unique charm and natural beauty.

  • Mallory Square: Experience the vibrant atmosphere of Mallory Square, where you can enjoy street performances, local artisans, and breathtaking sunsets. This bustling square is perfect for soaking up the lively city vibes as you mingle with both locals and travellers alike.
  • Fort Zachary Taylor Historic State Park: Immerse yourself in the natural beauty and rich history at Fort Zachary Taylor Historic State Park. This scenic national park offers outdoor adventures such as swimming, picnicking, and exploring the historic fort, making it a great spot for nature lovers.
  • Mel Fisher Maritime Museum: Delve into the fascinating world of maritime history at the Mel Fisher Maritime Museum. With its impressive collection of shipwreck artefacts, this museum showcases the culture and stories of treasure hunting in the Florida Keys.

Best time to go to Florida Keys

The best time to visit Florida Keys can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Florida Keys falls in August, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature around Florida Keys falls in January, visitor numbers are average and weather is mostly sunny with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January70.9°F (21.6°C)No RainMostly SunnyAverageAverage
February72.1°F (22.3°C)No RainMostly SunnyAverageSlightly High
March73.2°F (22.9°C)No RainMostly SunnySlightly HighSlightly High
April76.8°F (24.9°C)No RainMostly SunnySlightly LowSlightly High
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.6°F (28.1°C)Light RainMostly SunnyAverageAverage
July84.0°F (28.9°C)Light RainMostly SunnySlightly HighAverage
August84.4°F (29.1°C)Light RainMostly SunnyAverageSlightly Low
September83.5°F (28.6°C)Light RainMostly SunnySlightly LowSlightly Low
October80.6°F (27.0°C)Light RainMostly SunnySlightly LowSlightly Low
November76.5°F (24.700000000000003°C)Light RainMostly SunnyAverageAverage
December73.6°F (23.1°C)No RainMostly SunnySlightly HighAverage

Tips to save on your trip to Florida Keys

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Florida Keys during the low season (August to October) for more affordable options.
  • 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.

Our pick of the best Florida Keys Hotel Deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
NZ$465
3 Nov - 4 Nov
includes taxes & fees
Cheeca Lodge & Spa
Waterside Suites & Marina

Waterside Suites & Marina

201 Ocean Drive Key Largo FL
NZ$269
20 Oct - 21 Oct
includes taxes & fees
Waterside Suites & Marina
Reefhouse Resort & Marina

Reefhouse Resort & Marina

103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
NZ$510
19 Oct - 20 Oct
includes taxes & fees
9.4/10 Exceptional! (1,549 reviews)
"The beach proximity was much better than most other hotels in the Keys. They have small walk-in sand beaches. Much better than coral or concrete barriers or rocks at other hotels along the Keys. This area has sea grass in the shallows. Not expecting to walk on grass, but it was fine. This location ..."

Reviewed on 13 Oct 2026

Reefhouse Resort & Marina
See all 8,242 properties in Florida Keys
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.

Stay near popular Florida Keys attractions

A street with a pharmacy, a theater, and a yellow building.

Duval Street

9.2/10 (20,928 reviews)
Stroll the vibrant heart of Key West where historic architecture meets lively entertainment. Evening visits offer the full experience of Duval Street's renowned music scene and spirited local culture.
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A wooden signpost with city names and distances, a beach with umbrellas, and lounge chairs.

Florida Keys Beaches

8.4/10 (858 reviews)
The Florida Keys' beaches showcase a coral island landscape with crystal-clear waters ideal for snorkelling. Relax under swaying palms at Bahia Honda State Park or explore marine life at Fort Zachary Taylor.
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A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.

Mallory Square

9.2/10 (15,939 reviews)
Mallory Square hosts Key West's legendary Sunset Celebration, where street performers and artisans gather nightly. Arrive early to secure a prime viewing spot for the breathtaking Gulf of Mexico sunset.
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A beach with clear turquoise water, white sand, and palm trees.

Sombrero Beach

9.0/10 (2,464 reviews)
Sombrero Beach offers a rare natural sandy shoreline in the Florida Keys with pristine white sands and turquoise waters. Watch for nesting loggerhead turtles while enjoying the peaceful palm-lined setting.
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A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.

Southernmost Point

8.8/10 (17,214 reviews)
This colourful buoy marks the continental United States' southernmost point, just 90 miles from Cuba. Arrive early to capture your photo at this iconic Key West landmark without the typical crowds.
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A beach with white sand, palm trees, and a building in the background.

Smathers Beach

8.4/10 (8,320 reviews)
Key West's largest beach boasts half a mile of soft white sand and calm, shallow waters ideal for swimming. Rent paddleboards or jet skis, or simply relax under swaying palms with panoramic ocean views.
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A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.

Ernest Hemingway Home and Museum

9.2/10 (8,543 reviews)
Step into the Spanish Colonial home where Hemingway wrote his classics, surrounded by descendants of his six-toed cats. Explore his writing studio and gardens for a glimpse into the legendary author's 1930s life.
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A coastal fortification with a staircase leading to a higher platform, overlooking the sea.

Fort Zachary Taylor Historic State Park

9.0/10 (4,544 reviews)
Explore a Civil War-era fortress housing the nation's largest collection of seacoast cannons. After touring the historic corridors, cool off at Key West's favourite beach with crystal-clear waters perfect for snorkelling.
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What to do in Florida Keys

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

NZ$74
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

NZ$57
per adult
82% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Discover Florida Keys: A Self-Guided Tour

Discover Florida Keys: A Self-Guided Tour

NZ$8
per adult
Discover Florida Keys: A Self-Guided Tour
See all activities in Florida Keys

Frequently asked questions

How much does a Florida Keys holiday package cost?
From just NZ$2,741, you can tailor your Florida Keys package. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Florida Keys?
Booking a hotel and flight together with Expedia won't just save valuable time — it'll save you dollars too. A Florida Keys holiday package makes it simple to arrange the perfect trip. With more than 550 airlines around the world to pick from, finding convenient flights that suit your busy schedule won't be an issue. On top of that, we've got over 1 000 000 hotel options globally to choose from. Now that's choice! Whatever your budget, Expedia can show you the world.
Where should I stay in Florida Keys?
If you want to explore popular attractions such as Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens, head for Key West. You might want to stay for a while to really get to know this buzzing city.
What are the top hotels in Florida Keys?
When it comes to properties in Key West, Margaritaville Beach House Key West and Southernmost Beach Resort are two fantastic options. If you're considering heading to Marathon, 24 North Hotel Key West and Faro Blanco Resort & Yacht Club will make you feel at home.
How far in advance should I book my Florida Keys holiday?
Travellers are normally able to browse international flights on Expedia within 12 months of departure. Booking at the last minute? With a little bit of luck, it's still possible to nab a cheaper ticket just weeks before your flight.
What does an Expedia Florida Keys travel package include?
That depends on what you're after. If you're travelling alone, you might decide to combine flights and hotels. Bringing the whole crew to Florida Keys? A travel package including rental cars, flights and hotels might be a better fit. Expedia gives you the freedom to customize your travel package.
What should I know before booking a Florida Keys travel package?
A package can be more affordable than separately booking everything you need for your trip. For example, bundle your flights, hotels and rental cars and save a tidy sum. No matter your holiday goals, you'll find a package that's right for you.
Can I choose my airline with a Florida Keys Expedia holiday package?
Yes, you can. We offer more than 550 partner airlines all over the world, so choose the carrier that's a good fit for your travel needs.
If I'm not able to travel, can I cancel my Florida Keys holiday package?
Don't worry if you're rethinking your Florida Keys holiday package — you can cancel or change your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We realise life can occasionally throw a spanner in the travel works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.