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

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights from HPN to EYW starting at $308 One Way, $728 Round Trip

Prices starting at $728 for return flights and $308 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.

Thu, Aug 20 - Sun, Aug 23
HPN
White Plains
EYW
Key West
$728 Roundtrip, found 4 days ago
$728
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Aug 20 from White Plains to Key West, returning Sun, Aug 23, priced at $728 found 4 days ago
Thu, Aug 20 - Sun, Aug 23
HPN
White Plains
EYW
Key West
$738 Roundtrip, found 4 days ago
$738
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Aug 20 from White Plains to Key West, returning Sun, Aug 23, priced at $738 found 4 days ago
Thu, Aug 20 - Sun, Aug 23
HPN
White Plains
EYW
Key West
$753 Roundtrip, found 4 days ago
$753
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Aug 20 from White Plains to Key West, returning Sun, Aug 23, priced at $753 found 4 days ago
Fri, Aug 7 - Mon, Aug 10
HPN
White Plains
EYW
Key West
$779 Roundtrip, found 3 days ago
$779
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Aug 7 from White Plains to Key West, returning Mon, Aug 10, priced at $779 found 3 days ago
Thu, Feb 18 - Sun, Feb 21
HPN
White Plains
EYW
Key West
$795 Roundtrip, found 5 hours ago
$795
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Thu, Feb 18 from White Plains to Key West, returning Sun, Feb 21, priced at $795 found 5 hours 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
$295 nightly
The price is $332 total per night from Aug 13 to Aug 14
$332 total
Aug 13 - Aug 14
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 ...
9.4/10 Exceptional! (1,201 reviews)
"Excellent place very clean and excellent location"

Reviewed on Jul 19, 2026

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
$161 nightly
The price is $181 total per night from Aug 11 to Aug 12
$181 total
Aug 11 - Aug 12
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
$165 nightly
The price is $186 total per night from Aug 9 to Aug 10
$186 total
Aug 9 - Aug 10
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 ...
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
$202 nightly
The price is $227 total per night from Aug 17 to Aug 18
$227 total
Aug 17 - Aug 18
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 Aug 18 to Aug 19
$237 total
Aug 18 - Aug 19
Total with taxes and fees
Book a stay at this beach 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
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
$156 nightly
The price is $175 total per night from Aug 18 to Aug 19
$175 total
Aug 18 - Aug 19
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ...
Hilton Garden Inn Key West / The Keys Collection
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
$165 nightly
The price is $186 total per night from Aug 9 to Aug 10
$186 total
Aug 9 - Aug 10
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 ...
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
$161 nightly
The price is $181 total per night from Aug 11 to Aug 12
$181 total
Aug 11 - Aug 12
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
$173 nightly
The price is $195 total per night from Aug 17 to Aug 18
$195 total
Aug 17 - Aug 18
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
$155 nightly
The price is $175 total per night from Aug 16 to Aug 17
$175 total
Aug 16 - Aug 17
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! (1,361 reviews)
"Room was clean, pool was cool. Breakfast was appreciated!"

Reviewed on Jul 20, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$109 nightly
The price is $123 total per night from Jul 22 to Jul 23
$123 total
Jul 22 - Jul 23
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! (1,000 reviews)
"Affordable"

Reviewed on Jul 10, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$123 nightly
The price is $136 total per night from Jul 30 to Jul 31
$136 total
Jul 30 - Jul 31
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 ...
9.4/10 Exceptional! (1,053 reviews)
"Love it"

Reviewed on Jul 20, 2026

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 Aug 18 to Aug 19
$237 total
Aug 18 - Aug 19
Total with taxes and fees
Book a stay at this beach 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
$171 nightly
The price is $192 total per night from Aug 19 to Aug 20
$192 total
Aug 19 - Aug 20
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 ...
8.4/10 Very Good! (2,562 reviews)

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

Travelers say...
"Had a great time."

Reviewed on Jul 20, 2026

Blue Flamingo Resort Key West
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
$190 nightly
The price is $214 total per night from Aug 3 to Aug 4
$214 total
Aug 3 - Aug 4
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! (1,851 reviews)
"very nice place to go on family vacation, totally recommend"

Reviewed on Jul 19, 2026

Oceans Edge Key West Resort, Hotel & 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.

More to Explore