Florida Keys Vacations from ￥237,596

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Florida Keys Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was ￥310,124, price is now ￥237,596 per person
￥237,596
per person
Feb 7 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Key West (EYW)
18.8/10 Exceptional! (390 reviews)
I absolutely loved my stay at Ella’s Cottage. The location was perfect, the rooms and outdoor areas were stunning. Really great service with breakfast baskets and super friendly staff. The only downside was that my room was located very close to the maintenance staff office/storage so unfortunately in the morning I was woken up and could hear everything going on. Side note beware that the roosters will wake you up at sunrise!

Reviewed on Nov 16, 2025

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was ￥448,807, price is now ￥321,734 per person
￥321,734
per person
Feb 7 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Key West (EYW)
18.4/10 Exceptional! (505 reviews)
Everything was awesome at the Key West Hotel. My girlfriend and I enjoyed the our stay very much. Booked a room for a birthday trip for her, first time stay and we will definitely be back. I would have to say that we may have found our forever Key West hotel. Close to everything easy to walk and the staff is top notch. We could not have asked for a better stay. I would highly recommend this hotel, especially if it’s an adult trip. All the places you want to go are within walking distance.

Reviewed on Nov 21, 2025

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was ￥320,185, price is now ￥248,714 per person
￥248,714
per person
Feb 7 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Key West (EYW)
18.4/10 Exceptional! (845 reviews)
Everything was awesome - Staff, property itself, breakfast. Only issue is that building is old and next to main roads so you will hear loud noises if your room is next to a road.

Reviewed on Nov 16, 2025

The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Price was ￥399,842, price is now ￥315,154 per person
￥315,154
per person
Feb 7 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Key West (EYW)
19.6/10 Exceptional! (1,000 reviews)
Great breakfast, convenient location. Staff is very friendly. Rooms are nice and the garden area is pretty. I read all of the reviews and the hype around the place so it fell short of my expectations. If I had just gone there and not read the reviews I may have enjoyed it more. I would go back but I had stayed at places as nice or nice for my needs for what I believe to be better value. That being said I am glad I stayed there

Reviewed on Nov 20, 2025

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was ￥300,151, price is now ￥238,240 per person
￥238,240
per person
Feb 7 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Key West (EYW)
18/10 Exceptional! (831 reviews)
The staff was outstanding especially Laura at the front desk. Such a beautiful lady. I have stayed in many places but the Light House was beyond my expectations. Loved everything about it

Reviewed on Nov 15, 2025

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
Key West Historic District

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.

Find hotels in Old Town Key West

Find the Best Florida Keys Vacation Packages

Florida Keys Hotel Deals

Reefhouse Resort & Marina

Reefhouse Resort & Marina

3.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
The price is ￥31,325 per night from Dec 1 to Dec 2
￥31,325
￥41,537 total
Dec 1 - Dec 2
includes taxes & fees
9.2/10 Wonderful! (1,324 reviews)
The staff from the front desk to the grounds keepers were professional and polite. The grounds were so well maintained. We had a great time. Ken & Diane

Reviewed on Nov 16, 2025

Reefhouse Resort & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ￥19,032 per night from Dec 1 to Dec 2
￥19,032
￥30,244 total
Dec 1 - Dec 2
includes taxes & fees
9.2/10 Wonderful! (1,574 reviews)
Good spot.

Reviewed on Nov 15, 2025

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ￥37,507 per night from Dec 1 to Dec 2
￥37,507
￥52,821 total
Dec 1 - Dec 2
includes taxes & fees
9/10 Wonderful! (1,270 reviews)
Everything about our stay was amazing and exceeded our expectations in every way!!

Reviewed on Nov 17, 2025

Cheeca Lodge & Spa
See all 8,417 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.

Discover the most popular places to visit in Florida Keys

Duval Street featuring signage

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.

Duval Street
Mallory Square which includes a sunset and a bay or harbor as well as a large group of people

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.

Mallory Square
Southernmost Point featuring signage as well as a large group of people

Southernmost Point

4.5/5(3,182 reviews)

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

Southernmost Point

What to do in Florida Keys

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

￥7,625
per adult
92% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Key Largo Coral Reef Glass Bottom Boat Adventure

Key Largo Coral Reef Glass Bottom Boat Adventure

￥6,870
per adult
88% of travellers recommend
Key Largo Coral Reef Glass Bottom Boat Adventure
Family navigating the sea on the glass bottom boat in Key West

Key West Sunset Cruise & Glass Bottom Eco Tour

￥9,758
per adult
74% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
See all activities in Florida Keys

Frequently asked questions

Can I cancel my flight booking to Florida Keys due to COVID-19?
If you've yet to book your tickets, read the terms and conditions of the airfare you're considering. If you've already reserved your flight to Florida Keys, make use of our Customer Service Portal. The information here will help determine which COVID-19 policies apply to your booking and guide you with the next steps.
What's the best way to find cheap flights to Florida Keys that have flexible change policies?
We understand that things can change from one minute to the next, so booking a flexible ticket with Expedia is a sensible idea. Just tick the "No change fee" box directly under the "Flexible change policies" filter. Your low-cost, flexible flight to Florida Keys is just a few clicks away.
What are some of the general tips for travelers to Florida Keys during the COVID-19 outbreak?
The COVID-19 pandemic has brought about dramatic changes to the way we travel. If you're planning an escape to Florida Keys, the following tips will help you navigate these new rules and challenges:
  • Research what, if any, rules or restrictions apply to both your origin and destination. It may not be possible to travel depending on local circumstances, so be sure to check before you lock something in.
  • When you pass through airport screening, keep your face mask on. You will be asked to briefly lower it for identification purposes. Anyone refusing to wear a mask may be fined and denied entry.
  • Avoid handing your boarding pass directly to a TSA employee. Instead, position the pass on the reader and then hold it up to allow the agent to visually inspect it.
  • TSA is now permitting passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on luggage. This will have to be removed from your bag for screening.
  • Put any personal items (phone, wallet and keys) in your carry-on rather than a bin to minimize handling during screening.
  • Separate any food you have for X-ray screening. Placing it in a clear plastic bag and into a bin reduces the need for a TSA employee to touch and inspect your belongings.

Which airlines fly to Florida Keys?
Delta is a leading airline servicing Florida Keys. Search for airfares to Key West Intl. Airport (EYW) and you'll have 191 Delta flights each month to pick from.
How can I find cheap tickets to Florida Keys?
An effective strategy for scoring cheap airfares is to be flexible with your travel dates. Begin with searching for your flight to Florida Keys, then click on the "flexible dates" box to see prices for nearby days. Another helpful hint? Book well in advance. To give you an idea of fares, was the best price for a flight to Florida Keys in the last seven days.
How much is a flight to Florida Keys?
The cost of a round-trip journey to Florida Keys in the last seven days ranged between and . If you were traveling one way from (), you could have gotten a great deal from only .
What are the most popular airports to fly into in Florida Keys?
Start planning your Florida Keys escape by securing one of the 1119 flights each month to Key West Intl. Airport (EYW). This is the region's main entry point.
When is the cheapest time to fly to Florida Keys?
Jet off on a Tuesday to boost your odds of picking up the cheapest deal to Florida Keys. Mondays are usually the second most affordable day to depart. Saturday is normally the most expensive day to fly anywhere.
How much is a plane ticket to Florida Keys?
In the last seven days, ticket prices to Florida Keys varied from to .
Which airlines with flights to Florida Keys employ COVID-19 cleanliness policies?
As passengers begin traveling once again, most reputable airlines have introduced social distancing and other important measures to help lessen the spread of COVID-19. Here are some of them:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • Frontier Airlines - this airline is known for electrostatic cleaning and conducting passenger temperature checks.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.