Cheap flights from HVN to EYW (Tweed - New Haven Regional to Key West Intl.)

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Cheap Flights from HVN to EYW starting at $82 One Way, $163 Round Trip

Prices starting at $163 for return flights and $82 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.

Sat, Dec 19 - Wed, Dec 23
HVN
New Haven
EYW
Key West
$163 Roundtrip, just found
$163
Roundtrip
just found
Select Avelo Airlines flight, departing Sat, Dec 19 from New Haven to Key West, returning Wed, Dec 23, priced at $163 just found
Sat, Nov 21 - Wed, Nov 25
HVN
New Haven
EYW
Key West
$173 Roundtrip, found 3 days ago
$173
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Sat, Nov 21 from New Haven to Key West, returning Wed, Nov 25, priced at $173 found 3 days ago
Wed, Jan 13 - Sat, Jan 16
HVN
New Haven
EYW
Key West
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Wed, Jan 13 from New Haven to Key West, returning Sat, Jan 16, priced at $191 found 1 day ago
Wed, Nov 18 - Sat, Nov 21
HVN
New Haven
EYW
Key West
$198 Roundtrip, found 7 hours ago
$198
Roundtrip
found 7 hours ago
Select Avelo Airlines flight, departing Wed, Nov 18 from New Haven to Key West, returning Sat, Nov 21, priced at $198 found 7 hours ago
Wed, Nov 18 - Sat, Nov 21
HVN
New Haven
EYW
Key West
$208 Roundtrip, found 3 days ago
$208
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Wed, Nov 18 from New Haven to Key West, returning Sat, Nov 21, priced at $208 found 3 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
$240 nightly
The price is $270 total per night from Nov 29 to Nov 30
$270 total
Nov 29 - Nov 30
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! (1,338 reviews)
"The staff is very friendly and helpful. The resort is very clean and neat."

Reviewed on Nov 7, 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
$188 nightly
The price is $212 total per night from Nov 30 to Dec 1
$212 total
Nov 30 - Dec 1
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
$153 nightly
The price is $172 total per night from Nov 15 to Nov 16
$172 total
Nov 15 - Nov 16
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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
$285 nightly
The price is $321 total per night from Nov 18 to Nov 19
$321 total
Nov 18 - Nov 19
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the pool and the restaurant ...
8.8/10 Excellent! (1,810 reviews)
"Very well kept and staff was helpful and very friendly"

Reviewed on Nov 7, 2026

Margaritaville Beach House Key West
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
$200 nightly
The price is $225 total per night from Nov 29 to Nov 30
$225 total
Nov 29 - Nov 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
9/10 Wonderful! (1,902 reviews)
"Great hotel, great food, great staff, 5 stars, I am looking to book again now."

Reviewed on Nov 7, 2026

Havana Cabana at Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$175 nightly
The price is $197 total per night from Nov 15 to Nov 16
$197 total
Nov 15 - Nov 16
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 ...
Blue Flamingo Resort 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
$153 nightly
The price is $172 total per night from Nov 15 to Nov 16
$172 total
Nov 15 - Nov 16
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
$188 nightly
The price is $212 total per night from Nov 30 to Dec 1
$212 total
Nov 30 - Dec 1
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
$196 nightly
The price is $220 total per night from Nov 11 to Nov 12
$220 total
Nov 11 - Nov 12
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. ...
9/10 Wonderful! (1,001 reviews)
"Rooms are tiny, no room for anything"

Reviewed on Nov 7, 2026

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
$184 nightly
The price is $207 total per night from Dec 1 to Dec 2
$207 total
Dec 1 - Dec 2
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. ...
Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$193 nightly
The price is $217 total per night from Nov 22 to Nov 23
$217 total
Nov 22 - Nov 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 ...
Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$200 nightly
The price is $222 total per night from Nov 18 to Nov 19
$222 total
Nov 18 - Nov 19
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 ...
9.6/10 Exceptional! (1,135 reviews)
"Rooms were small, but quaint and clean."

Reviewed on Nov 6, 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
$268 nightly
The price is $302 total per night from Nov 30 to Dec 1
$302 total
Nov 30 - Dec 1
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
$175 nightly
The price is $197 total per night from Nov 15 to Nov 16
$197 total
Nov 15 - Nov 16
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 ...
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
$170 nightly
The price is $191 total per night from Nov 15 to Nov 16
$191 total
Nov 15 - Nov 16
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! (1,795 reviews)
"Fire alarm went off at 3 AM on Novembe 5th, but the siren could not be heard at all inside room 2306 due to the front vestibule. I only realized what was happening when I looked out the window and saw a crowd outside. There was absolutely zero communication or direction from hotel staff and no fire ..."

Reviewed on Nov 7, 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.

HVN to EYW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
HVN Address & GPS
Address:
155 Burr Street
New Haven CT, 06512
United States
IATA Code:
HVN
Longitude:
-72.888333
Latitude:
41.265278
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

What airlines have the most flights from HVN to Key West Intl. Airport (EYW)?
For now, you can't fly direct from Tweed - New Haven Regional Airport (HVN) to EYW. However, you will find flights with one or more stops. Look on the bright side — use the time to stretch your legs or sit down for a nice coffee!

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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