Name: Chesapeake Beach Resort
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.

Henrosa Hotel

South Beach

Save 100% on your flight

per person

Sep 12 - Sep 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8.4/10 Very Good! (795 reviews)

Good location and friendly staff, Lois recently remodeled. My room door had plenty of sand in the floor.

Reviewed on Jun 28, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

per person

Sep 12 - Sep 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8/10 Very Good! (1 review)

Pelican Grand Beach Resort - A Noble House Resort

East Fort Lauderdale

Save 100% on your flight

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8.6/10 Excellent! (1,107 reviews)

Just amazing! We enjoyed every single minute - beautiful property and perfect location. Beach is wonderful - and the beach service was such a treat. Would love to return!

Reviewed on Jul 4, 2025

iCoconutGrove Vacation Rentals

Coconut Grove

per person

Sep 13 - Sep 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9.2/10 Wonderful! (1,003 reviews)

Very relaxing, & private. Loved it! Very easy to get ahold of management for any needs.

Reviewed on Jun 22, 2025

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

per person

Aug 21 - Aug 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8.4/10 Very Good! (1,000 reviews)

Perfectly located on Ocean Drive with an old-school Art Deco vibe that feels both historic and fresh. The room was spotless, the A/C was ice cold, and the bed was genuinely comfortable. Staff was friendly and helpful. You’re across from the beach, but it still feels like a quiet escape. Would absolutely stay here again.

Reviewed on Jul 1, 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

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

$50

per adult

92% of travellers recommend

See all activities in Florida Keys

Florida Keys Hotel Deals

Isla Bella Beach Resort & Spa

1 Knights Key Boulevard, MM 47, Marathon, FL

Fully refundableReserve now, pay when you stay

9/10 Wonderful! (1,000 reviews)

"Loved it and will be back"

Reviewed on Jun 28, 2025

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Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

9/10 Wonderful! (1,486 reviews)

"Very very good place."

Reviewed on Jul 2, 2025

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Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

8.8/10 Excellent! (1,219 reviews)

"Place was clean and the amenities are really nice. This is our third time in this hotel and we missed the store to buy essentials and souvenirs and we missed also the ice creams options, the ice cream fridge was empty."

Reviewed on Jun 30, 2025

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See all 8,106 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.