Name: Cheeca Lodge & Spa
Price range: $339 total
Rating: 9

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.

Solara Surfside

$547

per person

Jan 23 - Jan 29

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (44 reviews)

What I love about this hotel is the beach and the Location

Reviewed on Jul 18, 2025

Hawks Cay Resort

$2,106

per person

Dec 25 - Dec 31

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

16/10 Exceptional! (1,004 reviews)

Enjoyed a few days with the kids gere

Reviewed on Nov 15, 2025

The Shelborne By Proper, a Member of Design Hotels

South Beach

$1,946

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

18.8/10 Exceptional! (56 reviews)

Staff super friendly and welcoming and helpful, room ready

Reviewed on Nov 16, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$10,285

per person

Jan 28 - Feb 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

16/10 Exceptional! (1 review)

Villas At Hawks Cay Resort

$1,337

per person

Feb 1 - Feb 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (138 reviews)

great trip. Clean, easy to get around. Good amenities for a family trip.

Reviewed on Nov 16, 2025

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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

Old Town Key West

2 out of top 10 points of interest in this area

4.5/5(226 area reviews)

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.

Audubon House and Tropical Gardens featuring a house

Key West Historic District

2 out of top 10 points of interest in this area

4.5/5(4,033 area reviews)

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.

Discover the most popular places to visit in Florida Keys

Duval Street

Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.

Mallory Square

Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.

Southernmost Point

Snap a memorable photograph from the edge of North America at this monumental landmark.

What to do in Florida Keys

Miami to Key West Day Trip with Activity Options

$39

per adult

84% of travellers recommend

Entertainer in character at the Shipwreck Treasure Museum in Key West

Shipwreck Treasure Museum Tickets

$19

per adult

76% of travellers recommend

Lands End Sunset Cruise with Full Bar & Live Music

$75

per adult

90% of travellers recommend

See all activities in Florida Keys

Florida Keys Hotel Deals

Reefhouse Resort & Marina

103800 Overseas Hwy Key Largo FL

Fully refundableReserve now, pay when you stay

$239 nightly

$264 total

Dec 1 - Dec 2

Total with taxes and fees

9.2/10 Wonderful! (1,324 reviews)

The staff from the front desk to the grounds keepers were professional and polite. The grounds were so well maintained. We had a great time. Ken & Diane

Reviewed on Nov 16, 2025

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$143 nightly

$161 total

Nov 19 - Nov 20

Total with taxes and fees

9.2/10 Wonderful! (1,574 reviews)

Good spot.

Reviewed on Nov 15, 2025

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$301 nightly

$339 total

Nov 20 - Nov 21

Total with taxes and fees

9/10 Wonderful! (1,259 reviews)

Beautiful grounds, immaculate rooms, divine sushi and meals! The pier is nonstop entertainment for kids, especially if they fish. There are activities for everyone in your family. Highly recommend this resort!

Reviewed on Nov 13, 2025

See all 8,413 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.