Florida Keys Trip

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Top Florida Keys Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was ₹156,678, price is now ₹109,195 per person
₹109,195
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
16.4/10 Exceptional! (1,491 reviews)
Front staff is nice and hotel is close to beach and everything

Reviewed on 18 Nov 2025

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Save 100% on your flight
Price was ₹309,690, price is now ₹177,925 per person
₹177,925
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
18.8/10 Exceptional! (56 reviews)
Staff super friendly and welcoming and helpful, room ready

Reviewed on 16 Nov 2025

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was ₹157,017, price is now ₹109,354 per person
₹109,354
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
16.8/10 Exceptional! (1,775 reviews)
Staff were all wonderful, especially Henry he was extremely helpful and had a great personality!

Reviewed on 18 Nov 2025

72 Park - Miami Beach by Nomada

72 Park - Miami Beach by Nomada

4.5 out of 5
North Beach
Price was ₹195,346, price is now ₹140,350 per person
₹140,350
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
18/10 Exceptional! (83 reviews)
Room was so well prepared VIEW WAS AMAZING, STAFF was COURTEOUS and ATTENTIVE

Reviewed on 16 Nov 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was ₹169,890, price is now ₹127,614 per person
₹127,614
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
17.2/10 Exceptional! (385 reviews)
Room was nice and big, clean and staff friendly. Just two issues - be prepared for loud music until midnight - upstairs neighbors very noisy in the early-hours.

Reviewed on 18 Nov 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
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Old Town Key West

2 out of top 10 points of interest in this area
5/5(6 area reviews)

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

Find hotels in Old Town Key West

Top hotels in Florida Keys

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 ₹17,639 per night from 1 Dec to 2 Dec
₹17,639
₹23,390 total
1 Dec - 2 Dec
includes taxes & fees
9.2/10 Wonderful! (1,318 reviews)
Rooms were clean big and had a great view. The staff was amazing.

Reviewed on 14 Nov 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 ₹8,506 per night from 20 Nov to 21 Nov
₹8,506
₹14,555 total
20 Nov - 21 Nov
includes taxes & fees
9.2/10 Wonderful! (1,570 reviews)
Room was clean, breakfast and staff were good

Reviewed on 14 Nov 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 ₹21,122 per night from 20 Nov to 21 Nov
₹21,122
₹29,745 total
20 Nov - 21 Nov
includes taxes & fees
9/10 Wonderful! (1,261 reviews)
Amazing!

Reviewed on 14 Nov 2025

Cheeca Lodge & Spa
See all 8,377 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.

Popular places to visit

Duval Street

Duval Street

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

Mallory Square

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

Southernmost Point

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

Southernmost Point

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 travellers 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 travelling 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 travelling 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.