Name: Hawks Cay Resort
Price range: $356 total

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

$453

per person

Nov 11 - Nov 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (818 reviews)

Beach staff was rude.

Reviewed on Sep 8, 2025

Hotel Colonnade Coral Gables, Autograph Collection

Coral Gables Section

$488

per person

Nov 21 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,004 reviews)

The mattress is soft and old very difficult to get good sleep AC was noise it . The pool are and the pool needs an upgrade, as well as the pump of the water fountain by the pool does not work and we can hear the noise from the 5th flloor

Reviewed on Sep 8, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,696

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

President Villa

South Beach

$481

per person

Nov 11 - Nov 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,000 reviews)

Breakfast was tasty but the lady in the ams was a grump all 3 days she served us, lighten up girl you are servings Breakfast for guests . Room was clean and patio was great, not too much privacy but still enjoyed it. The bartender Michael, i believe was his name was awesome and very helpful and drinks were great ! Cons hardly had cold water which was a bit annoying and our tv was not working completely. Was a bit disappointed with the pool being out of service. When i booked room it stated pool would be ok on my day 2 of stay then it said 1 more day n then it said weeks to be repaired. Daily fee said it basically covered a few things including pool but we had no pool....

Reviewed on Sep 7, 2025

President Hotel

South Beach

Save 100% on your flight

$481

per person

Nov 11 - Nov 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,794 reviews)

Mold in room is very bad

Reviewed on Sep 11, 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

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

$40

per adult

92% of travellers recommend

12-Hours Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

$27

per adult

See all activities in Florida Keys

Florida Keys Hotel Deals

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$166 nightly

$187 total

Sep 14 - Sep 15

Total with taxes and fees

Cheeca Lodge & Spa

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

Fully refundableReserve now, pay when you stay

$165 nightly

$186 total

Sep 16 - Sep 17

Total with taxes and fees

Hawks Cay Resort

61 Hawks Cay Blvd, Marathon, FL

Fully refundableReserve now, pay when you stay

$317 nightly

$356 total

Sep 18 - Sep 19

Total with taxes and fees

See all 8,318 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.