Cheap flights from HPN to EYW (Westchester County to Key West Intl.)

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Cheap Flights from HPN to EYW starting at $327 One Way, $301 Round Trip

Prices starting at $301 for return flights and $327 for one-way flights to Key West Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Jan 5 - Sat, Jan 9
HPN
White Plains
EYW
Key West
$301 Roundtrip, found 4 days ago
$301
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jan 5 from White Plains to Key West, returning Sat, Jan 9, priced at $301 found 4 days ago
Tue, Jan 5 - Sat, Jan 9
HPN
White Plains
EYW
Key West
$351 Roundtrip, found 4 days ago
$351
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jan 5 from White Plains to Key West, returning Sat, Jan 9, priced at $351 found 4 days ago
Tue, Jan 5 - Sat, Jan 9
HPN
White Plains
EYW
Key West
$370 Roundtrip, found 4 days ago
$370
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jan 5 from White Plains to Key West, returning Sat, Jan 9, priced at $370 found 4 days ago
Fri, Sep 11 - Fri, Sep 18
HPN
White Plains
EYW
Key West
$375 Roundtrip, found 6 days ago
$375
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 11 from White Plains to Key West, returning Fri, Sep 18, priced at $375 found 6 days ago
Tue, Jan 5 - Sat, Jan 9
HPN
White Plains
EYW
Key West
$391 Roundtrip, found 4 days ago
$391
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jan 5 from White Plains to Key West, returning Sat, Jan 9, priced at $391 found 4 days ago

Hotel Ideas near Key West Intl.

Airport Hotels near Key West Intl.

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
3675 South Roosevelt Boulevard Key West FL
$213 nightly
The price is $240 total per night from Sep 16 to Sep 17
$240 total
Sep 16 - Sep 17
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular ...
Hyatt Vacation Club at Windward Pointe, Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd Key West FL
$139 nightly
The price is $156 total per night from Sep 20 to Sep 21
$156 total
Sep 20 - Sep 21
Total with taxes and fees
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 ...
Hampton Inn Key West FL
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
$141 nightly
The price is $159 total per night from Sep 27 to Sep 28
$159 total
Sep 27 - Sep 28
Total with taxes and fees
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! (1,083 reviews)
"My husband and I joined the hotel. I would definitely recommend this place. I felt like I was in a mini resort."

Reviewed on Aug 31, 2026

DoubleTree Resort by Hilton Grand Key - Key West
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.

Hotels In Key West

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
$195 nightly
The price is $219 total per night from Sep 7 to Sep 8
$219 total
Sep 7 - Sep 8
Total with taxes and fees
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. ...
Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$210 nightly
The price is $237 total per night from Sep 13 to Sep 14
$237 total
Sep 13 - Sep 14
Total with taxes and fees
Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Southernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
$234 nightly
The price is $263 total per night from Sep 16 to Sep 17
$263 total
Sep 16 - Sep 17
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
8.8/10 Excellent! (1,800 reviews)
"Outdoor pool and beach access are nice. A little far from old town, but you can use shuttle every hour."

Reviewed on Sep 2, 2026

Margaritaville Beach House Key West
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.

Key West Hotels With Airport Transportation

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
$141 nightly
The price is $159 total per night from Sep 27 to Sep 28
$159 total
Sep 27 - Sep 28
Total with taxes and fees
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! (1,083 reviews)
"My husband and I joined the hotel. I would definitely recommend this place. I felt like I was in a mini resort."

Reviewed on Aug 31, 2026

DoubleTree Resort by Hilton Grand Key - Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd Key West FL
$139 nightly
The price is $156 total per night from Sep 20 to Sep 21
$156 total
Sep 20 - Sep 21
Total with taxes and fees
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 ...
Hampton Inn Key West FL
Eden House

Eden House

4 out of 5
1015 Fleming St Key West FL
$142 nightly
The price is $160 total per night from Sep 8 to Sep 9
$160 total
Sep 8 - Sep 9
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free WiFi, in-room massages, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. ...
Eden House
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.

Low Priced Key West Hotels

Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$152 nightly
The price is $171 total per night from Sep 7 to Sep 8
$171 total
Sep 7 - Sep 8
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
8.6/10 Excellent! (1,373 reviews)
"Southwinds Motel has to be the absolute best spot I’ve stayed at when it comes to conveniences on site along with an awesome location and proximity to sites and activities. Perfectly located around the Southernmost part of Key West, Southwinds gives you fully stocked bar WITH a built-in liquor store. ..."

Reviewed on Sep 3, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$102 nightly
The price is $115 total per night from Sep 8 to Sep 9
$115 total
Sep 8 - Sep 9
Total with taxes and fees
Stay at this hostel in Key West. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (1,001 reviews)
"Maintenance was going on but still they were helpful and made out visit amazing."

Reviewed on Aug 29, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$119 nightly
The price is $131 total per night from Sep 16 to Sep 17
$131 total
Sep 16 - Sep 17
Total with taxes and fees
Stay at this B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular ...
Duval House
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.

Family Friendly Hotels in Key West

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$210 nightly
The price is $237 total per night from Sep 13 to Sep 14
$237 total
Sep 13 - Sep 14
Total with taxes and fees
Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Southernmost Beach Resort and Guesthouses
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$160 nightly
The price is $180 total per night from Sep 7 to Sep 8
$180 total
Sep 7 - Sep 8
Total with taxes and fees
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
8.6/10 Excellent! (2,649 reviews)

Families like: Outdoor pools, playground, miniature golf, game room

Travelers say...
"This was an adorable property! There were many things to do."

Reviewed on Sep 3, 2026

Blue Flamingo Resort Key West
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
$167 nightly
The price is $188 total per night from Sep 9 to Sep 10
$188 total
Sep 9 - Sep 10
Total with taxes and fees
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
9/10 Wonderful! (1,820 reviews)
"Liked everything but restaurant prices were extremely high for breakfast. Outrageous breakfast prices for simple breakfast. Cannot recommend restaurant."

Reviewed on Sep 3, 2026

Hilton Key West Resort & Marina
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.

HPN to EYW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
HPN Address & GPS
Address:
240 Airport Road, Suite 202
Westchester County NY, 10604
United States
IATA Code:
HPN
Longitude:
-73.703889
Latitude:
41.068674
Time Zone:
America/New_York
EYW Address & GPS
Address:
3491 South Roosevelt Boulevard
Key West FL, 33040-5260
United States
IATA Code:
EYW
Longitude:
-81.75501
Latitude:
24.553574
Time Zone:
America/New_York

Frequently asked questions

Are there non-stop flights from White Plains Airport to Key West Intl. Airport (EYW)?
While you can't fly straight from White Plains Airport to Key West Intl. Airport (EYW) at the moment, there are a number of airlines that service this route with just one stop. Why not check if the dates available with American Airlines or Delta Air Lines work with your travel plans? If not, take a look at JetBlue Airways.
What is the shortest flight from White Plains Airport to EYW?
Flying from Westchester County Airport (HPN) to Key West Intl. Airport (EYW) takes at least 4 hours and 38 minutes. Enjoy a wine and get stuck into that book — now's your chance to simply relax.
How many hours flight from White Plains Airport to Key West Intl. Airport (EYW)?
It typically takes about 4 hours and 42 minutes to jet from White Plains Airport to Key West Intl. Airport (EYW). You'll be in the air for a while, so bring your own entertainment, like a magazine or some movies.
What airlines have the most flights from White Plains Airport to Key West Intl. Airport?
You'll have to make one or more stopovers if you're traveling from White Plains to Key West. Right now, there are no airlines that advertise direct flights on this route.

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

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