Search Cheap Flights to
Florida Keys

Name: Chesapeake Beach Resort
Rating: 9.2

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Florida Keys Flights as Low as $85

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

All deals

One way

Roundtrip

Tue, Oct 20 - Sun, Oct 25

ATL

Hartsfield-Jackson Atlanta Intl.

MIA

Miami Intl.

$85

Roundtrip

found 2 hours ago

Sun, Aug 23 - Sun, Sep 6

ATL

Hartsfield-Jackson Atlanta Intl.

MIA

Miami Intl.

$87

Roundtrip

found 19 hours ago

Sun, Oct 25 - Mon, Oct 26

ATL

Hartsfield-Jackson Atlanta Intl.

MIA

Miami Intl.

$90

Roundtrip

found 5 hours ago

Tue, Oct 20 - Sun, Oct 25

ATL

Hartsfield-Jackson Atlanta Intl.

MIA

Miami Intl.

$159

Roundtrip

found 2 hours ago

Tue, Sep 8 - Sat, Sep 26

JFK

John F. Kennedy Intl.

MIA

Miami Intl.

$167

Roundtrip

found 1 day ago

Fri, Aug 28 - Tue, Sep 1

ATL

Hartsfield-Jackson Atlanta Intl.

MIA

Miami Intl.

$167

Roundtrip

found 20 hours ago

Tue, Aug 25 - Sat, Aug 29

MSP

Minneapolis - St. Paul Intl.

MIA

Miami Intl.

$199

Roundtrip

found 23 hours ago

Fri, Aug 28 - Tue, Sep 1

ATL

Hartsfield-Jackson Atlanta Intl.

MIA

Miami Intl.

$218

Roundtrip

found 20 hours ago

Mon, Aug 24 - Fri, Aug 28

ATL

Hartsfield-Jackson Atlanta Intl.

EKW

Miami Central Brightline Train Station

$272

Roundtrip

found 2 days ago

Fri, Aug 28 - Tue, Sep 1

ATL

Hartsfield-Jackson Atlanta Intl.

AVT

Aventura Brightline Train Station

$293

Roundtrip

found 20 hours ago

Sat, Sep 19 - Tue, Sep 29

ATL

Hartsfield-Jackson Atlanta Intl.

EYW

Key West Intl.

$299

Roundtrip

found 20 hours ago

Thu, Nov 26 - Tue, Dec 1

JFK

John F. Kennedy Intl.

EYW

Key West Intl.

$329

Roundtrip

found 2 days ago

Mon, Aug 24 - Fri, Aug 28

JFK

John F. Kennedy Intl.

EKW

Miami Central Brightline Train Station

$351

Roundtrip

found 3 days ago

Tue, Sep 8 - Sat, Sep 26

JFK

John F. Kennedy Intl.

AVT

Aventura Brightline Train Station

$362

Roundtrip

found 1 day ago

Wed, Jul 1 - Wed, Jul 8

MSP

Minneapolis - St. Paul Intl.

EYW

Key West Intl.

$473

Roundtrip

found 2 days ago

Sun, Sep 27 - Sun, Oct 4

MSP

Minneapolis - St. Paul Intl.

MIA

Miami Intl.

$728

Roundtrip

found 23 hours ago

Cheap Flights to Florida Keys

Fall in love at first flight with your vacation to Florida Keys by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Florida Keys on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Florida Keys, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Florida Keys

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Florida Keys with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the MIA airport.

What is the cheapest month to fly to Florida Keys?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Florida Keys are in October, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Florida Keys?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Florida Keys.

What airport is best to fly into Florida Keys?

When you’re planning your trip to Florida Keys, convenience is the name of the game. Luckily, Florida Keys Florida Keys Marathon Airport is nearby so you can deplane and get going on checking off everything on your Florida Keys must-do list.

How much are flights to Florida Keys?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Florida Keys on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $85, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Florida Keys?

The trick to saving a stack of cash on your flight to Florida Keys? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $85 right now, why wait?

Florida Keys Flight Information
Destination airport	Miami Intl.
Destination airport IATA code	MIA
Roundtrip price	$85

Last Minute Hotel Deals in Florida Keys

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL

Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...

8.2/10 Very Good! (1,001 reviews)

"The property is good but the rooms need to be upkept better. We rented three rooms and one of them smelled pretty bad like a wet smell the other room drain was not working too good. We found the breakfast extremely bad, expensive and with little offerings. The pool area bar and lobby were nice and ..."

Reviewed on Jun 26, 2026

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Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...

9.2/10 Wonderful! (1,326 reviews)

"Perfect for families"

Reviewed on Jun 26, 2026

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Reefhouse Resort & Marina

103800 Overseas Hwy Key Largo FL

Book a stay at this luxury hotel in Key Largo. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the pool and the helpful staff in ...

9.4/10 Exceptional! (1,472 reviews)

"My new favorite place!!"

Reviewed on Jun 26, 2026

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Isla Bella Beach Resort & Spa

1 Knights Key Boulevard Marathon FL

Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...

9.2/10 Wonderful! (1,175 reviews)

"The grounds were lush and serene with 5 beautiful pools, white sand and colorful flowers. The rooms were impeccable with an amazing view from the balcony. 20/10 recommendation!"

Reviewed on Jun 26, 2026

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Baker's Cay Resort Key Largo, Curio Collection by Hilton

97000 Overseas Hwy Key Largo FL

Book a stay at this beach resort in Key Largo. Enjoy 2 outdoor pools, 2 restaurants, and a private beach. Our guests praise the helpful staff and the clean rooms ...

8.6/10 Excellent! (1,116 reviews)

"A beautiful property and everyone is so nice . Probably the nicest property on Key largo. Staff is very nice."

Reviewed on Jun 26, 2026

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Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ...

8.8/10 Excellent! (1,285 reviews)

"The first room is the room we reserved and paid for, a ground level with king, beach front, and water view. We asked to be moved because of the strong smell of mildew. My family and I very allergic and did not feel safe in that room. We tried using the phone to ask to be moved but it wasn’t working ..."

Reviewed on Jun 26, 2026

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Lime Tree Bay Resort

68500 Overseas Hwy Long Key FL

Book a stay at this beach resort in Long Key. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...

9.2/10 Wonderful! (1,340 reviews)

"."

Reviewed on Jun 26, 2026

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Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...

9.2/10 Wonderful! (1,736 reviews)

"Room was clean and the air conditioning was great. The breakfast was a bonus with personal omelets made to order. Plenty of lounge chairs throughout the property. Restaurants next door were also a plus. Tiki bar available and friendly staff. Bikes, paddle boards and kayaks were there just had to ..."

Reviewed on Jun 26, 2026

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See all 8,289 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.

Top Hotels With Free Airport Shuttle

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...

9/10 Wonderful! (1,402 reviews)

"Everything was great. Clean room, great breakfast and pool"

Reviewed on Jun 26, 2026

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DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd Key West FL

Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...

8.4/10 Very Good! (1,044 reviews)

"We loved staying in New Town and enjoyed the shuttle service back and forth to Old Town"

Reviewed on Jun 26, 2026

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The Garden House

329 Elizabeth Street Key West FL

Stay at this B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...

9.2/10 Wonderful! (712 reviews)

"Everything was great including the location as I could walk to everything. I was able to find free parking on the street. I will return to this property."

Reviewed on Jun 24, 2026

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Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...

8.6/10 Excellent! (2,310 reviews)

"The elevator was broken my whole stay and the beach it’s dirty and very small. The pool was good and the food at the pool area was excellent."

Reviewed on Jun 26, 2026

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Key West Sailing Adventure

201 Williams Street; Historic Seaport Key West FL

Stay at this houseboat in Key West. Enjoy free WiFi, 2 beach bars, and parking (surcharge). Popular attractions Duval Street and Southernmost Point are located ...

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Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Book a stay at this beach hotel in Key West. Enjoy free parking, 2 restaurants, and breakfast (surcharge). Popular attractions Southernmost Point and Duval Street ...

8.4/10 Very Good! (999 reviews)

"This is a beautiful resort full of amenities! Margaritas when you arrive, smoothies at the pool each day around noon, free airport and old town shuttles so we didn’t need to Uber anywhere, also coffee/water/cookies in the lobby daily. The beach is an easy walk across the street. The hotel is super ..."

Reviewed on Apr 19, 2026

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See all 8,289 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.

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Florida Keys

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