Florida Keys Vacations from $351

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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.
Modern Icon Brickell By Palermo Home
Flow Miami Hotel
Pelican Grand Beach Resort - A Noble House Resort
Barnacle Resort
EAST Miami
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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

Discover the most popular places to visit in Florida Keys

What to do in Florida Keys

Florida Keys Hotel Deals

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$166 nightly
The price is $187 total per night from Aug 20 to Aug 21
$187 total
Aug 20 - Aug 21
Total includes taxes and fees
9/10 Wonderful! (1,495 reviews)
"Overall it was a great resort that offered activities and a free continental breakfast. Omelette station was a pleasant surprise."

Reviewed on Aug 15, 2025

Chesapeake Beach Resort
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
1 Knights Key Boulevard, MM 47, Marathon, FL
Fully refundableReserve now, pay when you stay
$286 nightly
The price is $322 total per night from Sep 17 to Sep 18
$322 total
Sep 17 - Sep 18
Total includes taxes and fees
9/10 Wonderful! (1,027 reviews)
"The resort was beautiful. Only complaint was the beds were very uncomfortable and the pillows were thin."

Reviewed on Aug 17, 2025

Isla Bella Beach Resort & Spa
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
$211 nightly
The price is $238 total per night from Aug 20 to Aug 21
$238 total
Aug 20 - Aug 21
Total includes taxes and fees
9/10 Wonderful! (1,149 reviews)
"Great place. Best way to relax and enjoy the keys."

Reviewed on Aug 17, 2025

Cheeca Lodge & Spa
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.

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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.