Name: Chesapeake Beach Resort
Price range: $251 total
Rating: 9.2

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.

Beach Place Hotel

North Beach

$295

per person

Jan 21 - Jan 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1,007 reviews)

The staff are super friendly! I wasn't expecting to come to such a dilapidated place, but served the purpose.

Reviewed on Nov 5, 2025

The Shelborne By Proper, a Member of Design Hotels

South Beach

$858

per person

Jan 26 - Jan 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.8/10 Exceptional! (39 reviews)

Fantastic experience. One of the best hotels we have stayed at. Shout out to Jenny, Marta , Shane and Louis, William and Josh and all of the other wonderful staff. Definitely recommend it and will certainly go back !

Reviewed on Nov 1, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,504

per person

Jan 26 - Jan 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

President Hotel

South Beach

Save 100% on your flight

$397

per person

Jan 26 - Jan 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,905 reviews)

The staff is very helpful with information specially Henry and the lady who works at the same desk when he is off duty. Even the guy who is parking cars offered a usufull information about the area.

Reviewed on Oct 29, 2025

Bentley Hotel South Beach

South Beach

$664

per person

Jan 26 - Jan 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (390 reviews)

Great staff, location, super helpful, knowledgable, kind and friendly. Room upgrade was superb and staff were so prompt and professional.

Reviewed on Nov 3, 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

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

$50

per adult

92% of travellers recommend

Key Largo Coral Reef Glass Bottom Boat Adventure

$45

per adult

88% of travellers recommend

Key West Sunset Sail with Live Music, Drinks and Appetizers!

$80

per adult

92% 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

$269 nightly

$298 total

Nov 6 - Nov 7

Total with taxes and fees

9.2/10 Wonderful! (1,316 reviews)

Very nice

Reviewed on Nov 2, 2025

Cheeca Lodge & Spa

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

Fully refundableReserve now, pay when you stay

$259 nightly

$291 total

Nov 20 - Nov 21

Total with taxes and fees

9/10 Wonderful! (1,265 reviews)

Always a great stay at Cheeca. Lovely property, great restaurants, clean rooms and wonderful service by the staff.

Reviewed on Oct 30, 2025

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$223 nightly

$251 total

Dec 4 - Dec 5

Total with taxes and fees

9.2/10 Wonderful! (1,552 reviews)

Friendly staff

Reviewed on Nov 2, 2025

See all 8,381 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.