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 $134 One Way, $261 Round Trip

Prices starting at $261 for return flights and $134 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, Jan 2 - Wed, Jan 6
HVN
New Haven
EYW
Key West
$261 Roundtrip, found 1 hour ago
$261
Roundtrip
found 1 hour ago
Select Avelo Airlines flight, departing Sat, Jan 2 from New Haven to Key West, returning Wed, Jan 6, priced at $261 found 1 hour ago
Wed, Jan 6 - Wed, Jan 13
HVN
New Haven
EYW
Key West
$277 Roundtrip, found 1 hour ago
$277
Roundtrip
found 1 hour ago
Select Avelo Airlines flight, departing Wed, Jan 6 from New Haven to Key West, returning Wed, Jan 13, priced at $277 found 1 hour ago
Sat, Nov 21 - Wed, Nov 25
HVN
New Haven
EYW
Key West
$288 Roundtrip, found 1 hour ago
$288
Roundtrip
found 1 hour ago
Select Avelo Airlines flight, departing Sat, Nov 21 from New Haven to Key West, returning Wed, Nov 25, priced at $288 found 1 hour ago
Wed, Nov 18 - Wed, Nov 25
HVN
New Haven
EYW
Key West
$323 Roundtrip, found 4 days ago
$323
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Wed, Nov 18 from New Haven to Key West, returning Wed, Nov 25, priced at $323 found 4 days ago
Wed, Jan 13 - Sat, Jan 16
HVN
New Haven
EYW
Key West
$358 Roundtrip, found 1 hour ago
$358
Roundtrip
found 1 hour ago
Select Avelo Airlines flight, departing Wed, Jan 13 from New Haven to Key West, returning Sat, Jan 16, priced at $358 found 1 hour ago
Thu, Dec 10 - Sun, Dec 13
HVN
New Haven
EYW
Key West
$407 Roundtrip, found 1 hour ago
$407
Roundtrip
found 1 hour ago
Select Avelo Airlines flight, departing Thu, Dec 10 from New Haven to Key West, returning Sun, Dec 13, priced at $407 found 1 hour ago
Sat, Dec 26 - Sat, Jan 2
HVN
New Haven
EYW
Key West
$939 Roundtrip, found 6 hours ago
$939
Roundtrip
found 6 hours ago
Select Avelo Airlines flight, departing Sat, Dec 26 from New Haven to Key West, returning Sat, Jan 2, priced at $939 found 6 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
$407 nightly
The price is $458 total per night from Jul 27 to Jul 28
$458 total
Jul 27 - Jul 28
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! (1,172 reviews)
"This resort was excellent and surpassed my expectations, worth the money. The rooms were great, with a comfortable balcony that oversees the beautiful courtyard, pool, to the ocean. The staff was ver nice, professional and friendly. Everything was perfect at this place. You must reserve at least ..."

Reviewed on Jul 4, 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
$189 nightly
The price is $213 total per night from Jul 6 to Jul 7
$213 total
Jul 6 - Jul 7
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! (1,417 reviews)
"Excellent"

Reviewed on Jul 5, 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
$169 nightly
The price is $190 total per night from Jul 15 to Jul 16
$190 total
Jul 15 - Jul 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 ...
8.4/10 Very Good! (1,046 reviews)
"We were pleasantly impressed with this hotel. Staff were excellent, everything was clean and well run. Great value for money in this part of the US."

Reviewed on Jul 2, 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
$193 nightly
The price is $217 total per night from Jul 6 to Jul 7
$217 total
Jul 6 - Jul 7
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. ...
8.6/10 Excellent! (2,325 reviews)
"The house keeping and towels could be more clean. The beds are not great and the ac did not work well in the room."

Reviewed on Jul 5, 2026

Beachside Resort & Residences
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 Jul 6 to Jul 7
$197 total
Jul 6 - Jul 7
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! (2,493 reviews)
"Staff is very friendly, professional, and helpful. The room was comfortable and clean. Could use more pool seatings. Overall excellent stay. Would stay again."

Reviewed on Jul 5, 2026

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$232 nightly
The price is $261 total per night from Jul 14 to Jul 15
$261 total
Jul 14 - Jul 15
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 ...
8.8/10 Excellent! (3,425 reviews)
"Management was horrible! Wayyyy over priced and wayyy under delivered. Dirty rooms, ants, cracks in the door, false advertisement! Horrible rotten egg smell all over. Couldn’t use the beach! Don’t stay here!!! Complete rip off and they only wanted to reimburse about less than 10% for a $$$$ stay!!! ..."

Reviewed on Jul 5, 2026

Southernmost Beach Resort and Guesthouses
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
$169 nightly
The price is $190 total per night from Jul 15 to Jul 16
$190 total
Jul 15 - Jul 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 ...
8.4/10 Very Good! (1,046 reviews)
"We were pleasantly impressed with this hotel. Staff were excellent, everything was clean and well run. Great value for money in this part of the US."

Reviewed on Jul 2, 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
$189 nightly
The price is $213 total per night from Jul 6 to Jul 7
$213 total
Jul 6 - Jul 7
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! (1,417 reviews)
"Excellent"

Reviewed on Jul 5, 2026

Hampton Inn Key West FL
Eden House

Eden House

4 out of 5
1015 Fleming St Key West FL
$159 nightly
The price is $179 total per night from Jul 8 to Jul 9
$179 total
Jul 8 - Jul 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. ...
9/10 Wonderful! (1,005 reviews)
"Everything was excellent"

Reviewed on Jul 5, 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
$165 nightly
The price is $185 total per night from Aug 2 to Aug 3
$185 total
Aug 2 - Aug 3
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! (1,350 reviews)
"Excellent staff and a fun place to stay."

Reviewed on Jul 5, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$131 nightly
The price is $147 total per night from Jul 6 to Jul 7
$147 total
Jul 6 - Jul 7
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)
"Loved the close proximity to walk to the popular Duvall street for shopping and dining. The bathroom was huge!! Upgraded bathroom fixtures and tile. Great water pressure. Adjustable temperature A/C unit which was cold that I chose to turn up. Comfortable plush mattress, though the bed squeaked a ..."

Reviewed on Jun 8, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$125 nightly
The price is $138 total per night from Jul 6 to Jul 7
$138 total
Jul 6 - Jul 7
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! (1,041 reviews)
"The Duval house is quiet and quaint with a beatful outside area. It's adults only which was nice but the pool closes at sunset. As an adult only place the pool should at least be home until midnight. The breakfast has zero meats. Parking is expensive and not guaranteed a spot."

Reviewed on Jul 2, 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
$232 nightly
The price is $261 total per night from Jul 14 to Jul 15
$261 total
Jul 14 - Jul 15
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 ...
8.8/10 Excellent! (3,425 reviews)
"Management was horrible! Wayyyy over priced and wayyy under delivered. Dirty rooms, ants, cracks in the door, false advertisement! Horrible rotten egg smell all over. Couldn’t use the beach! Don’t stay here!!! Complete rip off and they only wanted to reimburse about less than 10% for a $$$$ stay!!! ..."

Reviewed on Jul 5, 2026

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 Jul 6 to Jul 7
$197 total
Jul 6 - Jul 7
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! (2,493 reviews)

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

Travelers say...
"Staff is very friendly, professional, and helpful. The room was comfortable and clean. Could use more pool seatings. Overall excellent stay. Would stay again."

Reviewed on Jul 5, 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
$245 nightly
The price is $276 total per night from Jul 13 to Jul 14
$276 total
Jul 13 - Jul 14
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! (1,859 reviews)
"It was a good experience. Thank you!"

Reviewed on Jul 5, 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.

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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