Name: Chesapeake Beach Resort
Price range: $208 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.

iCoconutGrove Vacation Rentals

Coconut Grove

per person

Sep 19 - Sep 22

found 13 hours ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9.2/10 Wonderful! (1,000 reviews)

The property was in a very populated area with lots of shops, restaurants and nightlife (if that’s your thing). The studio was very clean and there were no issues at all. Unlike hotel rooms, I could not hear what was happening right next door, so it was quiet as well. I would stay here again.

Reviewed on Jul 12, 2025

Casablanca Miami Beach

North Beach

per person

Oct 8 - Oct 15

found 1 day ago

Roundtrip flight included

New York (JFK) to Miami (MIA)

5.8/10 (303 reviews)

It was great for beach access. Nothing in our room worked. Coffee pot was broke. Stove was broke. We had to switch on and off the breakers to use it. Toilet would tflush half the time.

Reviewed on Jun 21, 2025

Barnacle Resort

Long Beach Estates

Save 100% on your flight

per person

Oct 10 - Oct 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8.2/10 Very Good! (39 reviews)

Perfect place for a quiet getaway.

Reviewed on May 24, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

per person

Sep 4 - Sep 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8/10 Very Good! (1 review)

PRAIA Hotel Boutique Miami Beach

North Beach

Save 100% on your flight

per person

Oct 8 - Oct 15

found 1 day ago

Roundtrip flight included

New York (JFK) to Miami (MIA)

7.4/10 Good! (21 reviews)

Perfect stay for a family!

Reviewed on Mar 10, 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

3 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

4.5/5(3,475 reviews)

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.

Southernmost Point

4.5/5(3,182 reviews)

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

Mallory Square

4.5/5(3,096 reviews)

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.

What to do in Florida Keys

12 hours Day at Key West With Boat Tour and Snorkeling

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

$27

per adult

78% of travellers recommend

12-Hours Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

$27

per adult

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

$45

per adult

92% of travellers recommend

See all activities in Florida Keys

Florida Keys Hotel Deals

Hawks Cay Resort

61 Hawks Cay Blvd, Marathon, FL

Fully refundableReserve now, pay when you stay

$291 nightly

$326 total

Aug 17 - Aug 18

Total includes taxes and fees

8/10 Very Good! (1,006 reviews)

"The people were friendly, property was well cared for. The resort was really nice. We enjoyed it all."

Reviewed on Jul 17, 2025

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL

Fully refundableReserve now, pay when you stay

$280 nightly

$316 total

Jul 20 - Jul 21

Total includes taxes and fees

9/10 Wonderful! (1,139 reviews)

"This is a really great property."

Reviewed on Jul 15, 2025

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$184 nightly

$208 total

Aug 13 - Aug 14

Total includes taxes and fees

9/10 Wonderful! (1,475 reviews)

"Absolutely liked everything about this hotel. From delicious breakfast options to cozy rooms with stunning views, everything exceeded my expectations."

Reviewed on Jul 16, 2025

See all 8,109 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.