Florida Keys Vacations from $496

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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.
Luxuri Suites

Luxuri Suites

South Beach
Save 100% on your flight
$496
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
6.8/10 (57 reviews)
Ok the fact we had no desk for check was terrible. I could not check in due to a code for door and room acess never being sent to my email resulted in me not checking for 3hours until I was told about a sister property 3 blocks from where I was stay had to walk in the rain to the siater property for thwm to grant me acess codes to get into my room now at 3am. I wouls likw to be reemburst for that night and day. My TV had no working batteries and once I go batteries the TV volum did not work.

Reviewed on Jul 9, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach
$12,074
per person
Oct 24 - Oct 31
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

Sea Glass Cove

Sea Glass Cove

$2,724
per person
Sep 27 - Oct 4
found 24 hours ago
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
No reviews
Pelican Hotel

Pelican Hotel

South Beach
Save 100% on your flight
$759
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (492 reviews)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

South Beach
Save 100% on your flight
$577
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,014 reviews)
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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 Key West Tropical Forest and Botanical Garden.

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 beach with a pier extending into the ocean during sunset.

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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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 sailboat named 'Soundwave' docked at a calm harbor with clear blue water, surrounded by a sandy beach and lush greenery.

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 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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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 brick corridor with arched ceilings and benches.

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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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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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
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

$45
per adult
88% of travellers recommend
Key West Conch Tour Train
See all activities in Florida Keys

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
$195 nightly
$219 total
Sep 1 - Sep 2
Total with taxes and fees
Cheeca Lodge & Spa
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

1 Knights Key Boulevard Marathon FL
Fully refundableReserve now, pay when you stay
$262 nightly
$294 total
Aug 18 - Aug 19
Total with taxes and fees
9.2/10 Wonderful! (1,238 reviews)
"Honestly expected more. Not all the hype that surrounded this property met expectations. Yes, property has five pools, but big main pool is really where you’re spending most of your time. None of the pools are heated & no jacuzzi, which was a major disappointment. We brought a speaker and provided ..."

Reviewed on Aug 17, 2026

Isla Bella Beach Resort & Spa
Hawks Cay Resort

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL
Fully refundableReserve now, pay when you stay
$258 nightly
$288 total
Aug 30 - Aug 31
Total with taxes and fees
Hawks Cay Resort
See all 8,271 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.

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 SunnyAverageSlightly High
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.6°F (28.1°C)Light RainMostly SunnySlightly HighAverage
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 SunnySlightly LowAverage
December73.6°F (23.1°C)No RainMostly SunnyAverageAverage

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)

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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.