Florida Keys Vacation Packages 2026 from $542

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Your Florida Keys Vacation

When adventure calls, answer it with a tailor-made vacation package to Florida Keys. Wherever it is you're going and whatever you have planned, prepare to discover a destination with plenty to offer. A trip to Florida Keys wouldn't be complete without spending some time in its best cities, starting with Key West. Two of the top attractions here include Smathers Beach and Mallory Square. Key Largo is another favorite city with Florida Keys travelers. Visitors to this destination enjoy John Pennekamp Coral Reef State Park and Jimmy Johnson's Big Chill. Expedia has hotels, flights and whatever else you need to help you put together your very own customized Florida Keys vacation today.

The Latest Florida Keys vacation packages

Price found within the past 48 hours. Click for updated prices.

Hotel Victor

South Beach

Save 100% on your flight

$542

per person

Dec 17 - Dec 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (1,001 reviews)

Lovely stay, gave a free gift for my boyfriends 30th birthday which was very kind and appreciated. Beautiful room and probably the most comfortable bed I’ve ever slept in! Lovely hotel. Thank you for a wonderful and memorable stay!

Reviewed on Oct 11, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$13,699

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

The Penguin Hotel

South Beach

Save 100% on your flight

$911

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,996 reviews)

Hotel is showing some aging and the breakfast at the other / sister hotel was a zoo

Reviewed on Oct 12, 2026

President Hotel Villa

South Beach

Save 100% on your flight

$852

per person

Dec 1 - Dec 6

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,000 reviews)

Buen lugar excelente ubicación cerca de todo El único detalle es que las instalaciones son un poco antiguas, adicional no nos hicieron limpieza un dia en la habitación

Reviewed on Oct 11, 2026

President Hotel

South Beach

Save 100% on your flight

$848

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (2,812 reviews)

Sólo que no realizan limpieza en la habitación diaria, pero todo excelente , la ubicación, desayunos , personal muy atento, me encantó!

Reviewed on Oct 11, 2026

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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

Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.

A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

Downtown Key West

If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.

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

Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.

A marina with yachts docked, a prominent red building, and a coastal cityscape in the background.

New Town

Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Fort East Martello Museum and Gallery.

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.

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 snorkeling. Relax under swaying palms at Bahia Honda State Park or explore marine life at Fort Zachary Taylor.

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Southernmost Point

8.8/10 (17,214 reviews)

This colorful 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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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 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 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 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 favorite beach with crystal-clear waters perfect for snorkeling.

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What to do in Florida Keys

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

Champagne and Sunsets: A Key West Catamaran Adventure

$59

per adult

94% of travellers recommend

Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$41

per adult

88% of travellers recommend

See all activities in Florida Keys

Florida Keys Hotel Deals

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$248 nightly

$279 total

Oct 22 - Oct 23

Total with taxes and fees

Waterside Suites & Marina

201 Ocean Drive Key Largo FL

Fully refundableReserve now, pay when you stay

$136 nightly

$153 total

Oct 14 - Oct 15

Total with taxes and fees

9/10 Wonderful! (1,503 reviews)

"It was a good value for the cost of the rental! It was comfortable and close to all of the restaurants and things that we like to do! We would definitely rent again!"

Reviewed on Oct 11, 2026

Reefhouse Resort & Marina

103800 Overseas Hwy Key Largo FL

Fully refundableReserve now, pay when you stay

$259 nightly

$286 total

Oct 13 - Oct 14

Total with taxes and fees

9.4/10 Exceptional! (1,546 reviews)

"Spacious room and beautiful property."

Reviewed on Oct 10, 2026

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.

Find the Best Florida Keys Vacation Packages

Things to do near Florida Keys

The Florida Keys offer an ideal setting for beach and outdoor family vacations. Enjoy a variety of activities such as relaxing on stunning beaches, taking day trips, and indulging in the local shopping scene at various malls and centers. Don't miss the opportunity for a memorable Florida getaway, complete with scenic water taxi rides that showcase the beauty of the islands.

Shopping

The Kite House, located 7 miles from Florida Keys, offers a unique selection of gifts and souvenirs. For cycling enthusiasts, We Cycle Key West, just 6 miles away, provides great gear and local experiences. Both spots are perfect for memorable shopping during your visit.

Recreation

At Key West Golf Club, enjoy a picturesque golfing experience surrounded by lush landscapes and vibrant outdoor vibes. For a cultural evening, visit the Waterfront Playhouse, where captivating performances create a romantic atmosphere. Dive into family fun at the MLK Community Pool, perfect for relaxation and outdoor activities.

Adventure

In the Florida Keys, explore the vibrant coral reefs while snorkeling or scuba diving in the John Pennekamp Coral Reef State Park. Experience thrilling water sports like jet skiing and parasailing in Key West, or embark on a kayak adventure through the mangroves of Big Pine Key.

Nightlife

The Florida Keys nightlife is vibrant and diverse. Enjoy a cocktail at the lively Green Parrot Bar or dance the night away at the popular Hog's Breath Saloon. For a laid-back vibe, check out the Sunset Pier, offering stunning views and local music as the sun sets.

*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 is an ideal destination for beach lovers and outdoor enthusiasts, offering a variety of attractions such as modern squares, national parks, and historic buildings. Visitors can immerse themselves in culture and adventure while enjoying the stunning beaches and vibrant atmosphere. Key West is a must-visit for those seeking unique experiences, making the Florida Keys a perfect spot for family vacations and unforgettable memories.

Mallory Square: Experience the vibrant atmosphere of Mallory Square, known for its lively city vibes. Enjoy unique street performances, local vendors, and stunning views of the sunset over the Gulf of Mexico, making it a perfect spot for relaxation and entertainment.
Fort Zachary Taylor Historic State Park: Explore the historical significance and natural beauty of Fort Zachary Taylor Historic State Park. This park offers outdoor adventures, scenic trails, and a chance to swim at one of the best beaches in the Keys, all while immersing yourself in history.
Florida Keys National Marine Sanctuary: Discover the rich marine life at Florida Keys National Marine Sanctuary. Ideal for families and adventure seekers, you can snorkel, dive, or kayak through vibrant coral reefs and witness the incredible underwater ecosystem.

Best time to go to Florida Keys

The best time to visit Florida Keys is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with no rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	70.9°F (21.6°C)	No Rain	Mostly Sunny	Average	Average
February	72.1°F (22.3°C)	No Rain	Mostly Sunny	Average	Slightly High
March	73.2°F (22.9°C)	No Rain	Mostly Sunny	Slightly High	Slightly High
April	76.8°F (24.9°C)	No Rain	Mostly Sunny	Average	Slightly High
May	79.3°F (26.3°C)	Light Rain	Mostly Sunny	Average	Average
June	82.6°F (28.1°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	84.0°F (28.9°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	84.4°F (29.1°C)	Light Rain	Mostly Sunny	Average	Slightly Low
September	83.5°F (28.6°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
October	80.6°F (27.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
November	76.5°F (24.700000000000003°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	73.6°F (23.1°C)	No Rain	Mostly Sunny	Average	Average

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.

Florida Keys Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Miami Intl. Airport (MIA)

More vacations you might like

Frequently asked questions

How do vacation package prices compare across popular destinations in the Florida Keys?

Long Key has the lowest typical price for a week-long Florida Keys vacation package, while Islamorada runs higher, with typical prices ranging from around $1,150 to $1,550 per adult for a week-long trip.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

How can I save money on a Florida Keys vacation package?

When you bundle, you can save up to 30%*. To save money on a Florida Keys package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What's included in a Florida Keys vacation package?

A Florida Keys vacation package lets you combine flights, hotel stays, and rental cars, based in popular destinations like Key West, Key Largo, and Islamorada. In Key West, nearly all hotels offer airport shuttle service to and from Key West Intl. Airport (EYW), and most include free breakfast.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

Which destinations in the Florida Keys offer the best-value vacation package deals?

Summerland Key, Key Largo, Marathon, Islamorada, and Key West are some of the top destinations for cheap Florida Keys vacation package deals. For an affordable weekend getaway, Summerland Key is often among the most budget-friendly options, with package prices starting around $530 per adult. For notable bundle savings, Marathon is often among the best options, with flight-and-hotel bundles saving around $230 per adult.Browse cheap vacation packages in the Florida Keys on Expedia to compare current deals.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

When is the best time to visit the top destinations in the Florida Keys?

The best time to visit the Florida Keys for your vacation package depends on which destination you choose and your preference for crowds.Key West is busiest in December and March, when highs are around 75°F. February also sees high demand with the Key West Art and Craft Festival. If you'd prefer fewer visitors, September is quieter, with highs around 85°F.Marathon sees its peak demand in March and December, with highs around 75°F. March also hosts the 51st Original Marathon Seafood Festival. For a quieter trip, September is a good option, with highs around 85°F.Islamorada is busiest in March, June, and February, with highs around 75°F in March and December. The Islamorada Chamber of Commerce Holiday Festival takes place in December. If you'd prefer fewer crowds, January is quieter, with highs around 73°F.

What package types are available across the top destinations in the Florida Keys?

The Florida Keys, known for its beaches and outdoor activities, offer a variety of vacation package types across its popular destinations:

Budget: In Key West, the Weatherstation Inn, rated 8.9 out of 10 by travelers, offers free breakfast and an outdoor pool, making it a great value option.
Beach: Islamorada features beach-focused packages with stays at properties like the 5-star Cheeca Lodge & Spa, rated 8.4 out of 10 by travelers, which includes a kids club and hot tub.
Couples: In Marathon, the 4-star Hawks Cay Resort, rated 8.4 out of 10 by travelers, provides a hot tub and game room, with travelers often praising the beautiful rooms and great breakfast.
Family: Key Largo offers family-friendly packages with hotels such as the Holiday Inn Key Largo by IHG, rated 8.1 out of 10 by travelers, which features a game room and hot tub.
Pet-friendly: Summerland Key has options like Looe Key Reef Resort, where travelers can enjoy an outdoor pool and pet-friendly accommodations.

Which destinations should I consider for a Florida Keys vacation?

When planning a Florida Keys vacation, your ideal base depends on your preferred travel style and activities.

For a lively city experience: Key West is a popular package base known for its urban attractions, entertainment options, and family-friendly atmosphere.
For beach and outdoor adventures: Marathon is an excellent choice, offering plenty of beaches and outdoor activities, making it suitable for couples and families.
For water sports and nature: Key Largo is a top pick for those seeking adventure activities, beaches, and family-friendly attractions, with many options for couples.
For a blend of family fun and outdoor beauty: Islamorada provides a great mix of family-friendly attractions, outdoor activities, and beautiful beaches, also catering well to couples.

Is Florida Keys better suited for a beach vacation or a cultural trip?

The Florida Keys are primarily a beach and outdoor destination, offering a wealth of activities centered around its stunning coastal environment and natural beauty. Most of the Keys, including Marathon, Key Largo, Islamorada, Summerland Key, and Long Key, are known for their beaches, outdoor adventures, and family-friendly attractions.Travelers can enjoy activities like diving in John Pennekamp Coral Reef State Park in Key Largo or relaxing on Sombrero Beach in Marathon. The region's character is defined by its scenic views and opportunities for adventure.While the focus is on nature and the outdoors, Key West also provides a vibrant cultural and urban experience. Here, you can explore city attractions like Duval Street and historic sites such as the Ernest Hemingway Home and Museum, making a Florida Keys vacation package versatile for different travel styles.

Which airports serve the main destinations in the Florida Keys?

For a Florida Keys vacation, several airports provide convenient access to the region. Key West International Airport (EYW) serves the southernmost city of Key West, offering direct access to its vibrant attractions. Further north, Florida Keys Marathon Airport (MTH) serves the central Keys, including Marathon.Travelers can also consider flying into Homestead Air Reserve Base (HST) on the mainland, which provides another gateway to the upper Keys.

What are the top things to do across the destinations in the Florida Keys?

A Florida Keys vacation offers a diverse range of activities across its many islands, from vibrant city experiences to serene natural escapes.Here are some top things to do:Browse and book things to do in the Florida Keys on Expedia.

Are there family vacation packages in the Florida Keys with kid-friendly amenities?

Yes, family vacation packages in the Florida Keys offer a range of resorts with kid-friendly amenities across its destinations:Your Florida Keys vacation package can be customized around these activities.

What luxury vacation packages are available in the Florida Keys?

Luxury Florida Keys vacation packages are available across several destinations, offering high-end resorts with premium amenities:Most Florida Keys vacation packages pair the hotel with flights. Browse luxury vacation packages in the Florida Keys on Expedia to compare options.

Which destinations in the Florida Keys have adults-only resorts?

Key West is a destination in the Florida Keys that features several adults-only resorts, which can be part of your Florida Keys vacation package:Browse adults-only resorts in the Florida Keys on Expedia to compare.

When should I book vacation packages for the top destinations in the Florida Keys?

Booking times for a Florida Keys vacation package vary by destination, with most travelers booking around 5 to 7 weeks before departure.Travelers tend to book trips to these destinations most often in February, from March to April, from June to July, and in September. If you're planning a spontaneous getaway, Expedia also offers last-minute Florida Keys vacation packages.

How many days do you need for a Florida Keys vacation?

Most Florida Keys vacation packages last around 4 to 5 days, but the ideal trip length depends on where you're going and what you'd like to experience.Key West, known for its city and urban attractions and entertainment options, is often enjoyed over around 4 days. Weekend and week-long stays are popular here, with some travelers opting for longer visits to explore attractions like Duval Street.Key Largo, a destination for outdoor activities and adventure, also typically sees trips of around 4 days. Weekend and week-long stays are common, allowing time to experience places like John Pennekamp Coral Reef State Park.Islamorada, with its beaches and outdoor activities, is well-suited for a trip of around 5 days. Week-long stays are most common, though weekend trips are also popular, giving visitors time to enjoy unique experiences at places like Robbie's of Islamorada.

Can I change or cancel my Florida Keys vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Florida Keys vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Florida Keys vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Florida Keys vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Florida Keys?

To find last-minute vacation packages to Florida Keys, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Florida Keys vacation packages?

Free cancellation on a Florida Keys vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Florida Keys vacation as a package or separately?

An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Florida Keys getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Florida Keys vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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Flights to Florida Keys

Florida Keys Vacation Rentals

Things to do in Florida Keys

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

Florida Keys Vacations from $542

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Florida Keys Vacation

The Latest Florida Keys vacation packages

Hotel Victor

The Retreat Collection at 1 Hotel & Homes South Beach

The Penguin Hotel

President Hotel Villa

President Hotel

Where to stay in Florida Keys

Old Town Key West

Downtown Key West

Key West Historic District

New Town

Uptown - Upper Duval

Stay near popular Florida Keys attractions

Duval Street

Florida Keys Beaches

Southernmost Point

Mallory Square

Smathers Beach

Sombrero Beach

Ernest Hemingway Home and Museum

Fort Zachary Taylor Historic State Park

What to do in Florida Keys

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

Champagne and Sunsets: A Key West Catamaran Adventure

Key West Conch Tour Train

Florida Keys Hotel Deals

Cheeca Lodge & Spa

Waterside Suites & Marina

Reefhouse Resort & Marina

Find the Best Florida Keys Vacation Packages

Things to do near Florida Keys

Find the best attractions near Florida Keys

Best time to go to Florida Keys

Tips to save on your trip to Florida Keys

Florida Keys Essential Information

More vacations you might like

Frequently asked questions

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