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 25 - Sep 28

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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

Pelican Grand Beach Resort - A Noble House Resort

East Fort Lauderdale

per person

Sep 16 - Sep 19

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

8.6/10 Excellent! (1,119 reviews)

Lazy river was great along with the pool and great beach access. GG the lady server that brings you food and drinks at the pool was one of the nicest and kindest people I’ve ever met at a hotel. She truly deserves a big raise. If GG isn’t making a little less than the manager then the management doesn’t know how to manage. GG literally went out of her way to try to make your pool day unforgettable. The only place I would ever be staying at when I return to Fort Lauderdale would be Pelican and reason being is the staff.

Reviewed on Jul 12, 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

Dallas (DFW) to Miami (MIA)

8/10 Very Good! (1 review)

iCoconutGrove Vacation Rentals

Coconut Grove

Save 100% on your flight

per person

Sep 12 - Sep 16

found 18 hours ago

Roundtrip flight included

Philadelphia (PHL) to Miami (MIA)

9.2/10 Wonderful! (1,003 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

1 Hotel South Beach

South Beach

Save 100% on your flight

per person

Sep 22 - Sep 25

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Miami (MIA)

9.4/10 Exceptional! (1,212 reviews)

The property was beautiful. The overall esthetics of the One Hotel was intoxicating and welcoming at the same time. My only complaint was with the hotel service in terms of house cleaning; they could use some improvement.

Reviewed on Jul 9, 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

Hawks Cay Resort

61 Hawks Cay Blvd, Marathon, FL

Fully refundableReserve now, pay when you stay

8/10 Very Good! (1,011 reviews)

"Great vacation. We will be returning soon!"

Reviewed on Jul 9, 2025

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Cheeca Lodge & Spa

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

Fully refundableReserve now, pay when you stay

9/10 Wonderful! (1,128 reviews)

"Resort has a lot of rentals and plenty to do there. Staff is awesome."

Reviewed on Jul 10, 2025

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Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

9/10 Wonderful! (1,484 reviews)

"Amenities were great"

Reviewed on Jul 9, 2025

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See all 8,146 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.