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 $132 One Way, $243 Round Trip

Prices starting at $243 for return flights and $132 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.

Sun, Dec 13 - Wed, Dec 16
HVN
New Haven
EYW
Key West
$243 Roundtrip, found 4 days ago
$243
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Sun, Dec 13 from New Haven to Key West, returning Wed, Dec 16, priced at $243 found 4 days ago
Wed, Nov 25 - Thu, Dec 3
HVN
New Haven
EYW
Key West
$259 Roundtrip, found 1 day ago
$259
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Wed, Nov 25 from New Haven to Key West, returning Thu, Dec 3, priced at $259 found 1 day ago
Sun, Dec 6 - Thu, Dec 10
HVN
New Haven
EYW
Key West
$263 Roundtrip, found 4 days ago
$263
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Sun, Dec 6 from New Haven to Key West, returning Thu, Dec 10, priced at $263 found 4 days ago
Sat, Dec 19 - Wed, Dec 23
HVN
New Haven
EYW
Key West
$317 Roundtrip, found 8 hours ago
$317
Roundtrip
found 8 hours ago
Select Avelo Airlines flight, departing Sat, Dec 19 from New Haven to Key West, returning Wed, Dec 23, priced at $317 found 8 hours ago
Sat, Feb 20 - Wed, Feb 24
HVN
New Haven
EYW
Key West
$376 Roundtrip, found 6 days ago
$376
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Sat, Feb 20 from New Haven to Key West, returning Wed, Feb 24, priced at $376 found 6 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
$209 nightly
The price is $235 total per night from Aug 30 to Aug 31
$235 total
Aug 30 - Aug 31
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
$118 nightly
The price is $133 total per night from Aug 30 to Aug 31
$133 total
Aug 30 - Aug 31
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 ...
9/10 Wonderful! (1,480 reviews)
"Great place to stay. They offer a shuttle that drops you off five minutes from duval st and goes back to the hotel!"

Reviewed on Aug 23, 2026

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
$144 nightly
The price is $162 total per night from Sep 1 to Sep 2
$162 total
Sep 1 - Sep 2
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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$203 nightly
The price is $228 total per night from Sep 1 to Sep 2
$228 total
Sep 1 - Sep 2
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
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
$136 nightly
The price is $153 total per night from Aug 24 to Aug 25
$153 total
Aug 24 - Aug 25
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (2,357 reviews)
"I always stay here. It's nice and clean. Rooms are pretty tight, but they are nice."

Reviewed on Aug 22, 2026

Ibis Bay Beach Resort
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 Sep 7 to Sep 8
$225 total
Sep 7 - Sep 8
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! (1,863 reviews)
"It was so relaxing and shuttles was awesome to and from downtown and airport."

Reviewed on Aug 21, 2026

Havana Cabana at 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
$144 nightly
The price is $162 total per night from Sep 1 to Sep 2
$162 total
Sep 1 - Sep 2
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
$118 nightly
The price is $133 total per night from Aug 30 to Aug 31
$133 total
Aug 30 - Aug 31
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 ...
9/10 Wonderful! (1,480 reviews)
"Great place to stay. They offer a shuttle that drops you off five minutes from duval st and goes back to the hotel!"

Reviewed on Aug 23, 2026

Hampton Inn Key West FL
Eden House

Eden House

4 out of 5
1015 Fleming St Key West FL
$133 nightly
The price is $149 total per night from Aug 26 to Aug 27
$149 total
Aug 26 - Aug 27
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! (1,389 reviews)
"This was day 16 of a US road trip and this was BY FAR my favorite stay. 1 block away from Duval St. Free drink tickets. Great bed and pillows. Microwave, fridge. Everything was GREAT! Only downside was we went to bed at 10 and the nearby bar was still playing loud live music, however the loud AC ..."

Reviewed on Aug 20, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$87 nightly
The price is $98 total per night from Aug 24 to Aug 25
$98 total
Aug 24 - Aug 25
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)
"The room itself was very nice, clean, and comfortable, and the location was great because it was very close to everything. My main disappointment was that the listing mentioned a shared area, but when we arrived, it was under construction. There appeared to be a new pool that was already filled with ..."

Reviewed on Aug 13, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$124 nightly
The price is $136 total per night from Aug 31 to Sep 1
$136 total
Aug 31 - Sep 1
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! (1,093 reviews)
"Staff was attentive and friendly"

Reviewed on Aug 22, 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
$203 nightly
The price is $228 total per night from Sep 1 to Sep 2
$228 total
Sep 1 - Sep 2
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
$166 nightly
The price is $187 total per night from Aug 24 to Aug 25
$187 total
Aug 24 - Aug 25
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
$167 nightly
The price is $188 total per night from Sep 7 to Sep 8
$188 total
Sep 7 - Sep 8
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! (1,846 reviews)
"Friendly concierge. Was able to help me get my friend a birthday massage in the room"

Reviewed on Aug 23, 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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