Cheap flights from SHD to EYW (Shenandoah Valley Regional to Key West Intl.)

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Cheap Flights from SHD to EYW starting at $310 One Way, $849 Round Trip

Prices starting at $849 for return flights and $310 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, May 31 - Wed, Jun 3
SHD
Weyers Cave
EYW
Key West
$849 Roundtrip, found 17 hours ago
$849
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sun, May 31 from Weyers Cave to Key West, returning Wed, Jun 3, priced at $849 found 17 hours ago
Sun, May 31 - Wed, Jun 3
SHD
Weyers Cave
EYW
Key West
$890 Roundtrip, found 17 hours ago
$890
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sun, May 31 from Weyers Cave to Key West, returning Wed, Jun 3, priced at $890 found 17 hours ago
Sun, May 31 - Wed, Jun 3
SHD
Weyers Cave
EYW
Key West
$959 Roundtrip, found 17 hours ago
$959
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sun, May 31 from Weyers Cave to Key West, returning Wed, Jun 3, priced at $959 found 17 hours ago
Sun, May 31 - Wed, Jun 3
SHD
Weyers Cave
EYW
Key West
$1,375 Roundtrip, found 17 hours ago
$1,375
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sun, May 31 from Weyers Cave to Key West, returning Wed, Jun 3, priced at $1,375 found 17 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
$411 nightly
The price is $463 total per night from May 5 to May 6
$463 total
May 5 - May 6
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! (1,015 reviews)
Rooms were clean and neat and everything we expected. Thank you so much for a wonderful honeymoon.

Reviewed on Apr 3, 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
$287 nightly
The price is $323 total per night from Apr 15 to Apr 16
$323 total
Apr 15 - Apr 16
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! (1,324 reviews)
This hotel is old and tired. The breakfast area is cramped and the offerings, particularly the cereal are boring.

Reviewed on Apr 2, 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
$265 nightly
The price is $298 total per night from Apr 26 to Apr 27
$298 total
Apr 26 - Apr 27
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 ...
8.2/10 Very Good! (1,000 reviews)
Yes

Reviewed on Mar 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

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$292 nightly
The price is $329 total per night from May 5 to May 6
$329 total
May 5 - May 6
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 ...
8.2/10 Very Good! (2,036 reviews)
Clen Room, Staff, Breakfast

Reviewed on Apr 4, 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
$407 nightly
The price is $458 total per night from May 4 to May 5
$458 total
May 4 - May 5
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! (3,167 reviews)
Nice location. Only big downfall was check in. The resort is huge and there wasn't a big enough front desk to accommodate check in. They had two-three people working but the process was slow and the line long. We gave them our bags and left to have something to eat. We returned about 90 minutes later ...

Reviewed on Apr 3, 2026

Southernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
$327 nightly
The price is $368 total per night from Apr 29 to Apr 30
$368 total
Apr 29 - Apr 30
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! (1,799 reviews)
Ideal for families with smaller children, and the pool was smaller than was indicated in the pictures overall good experience

Reviewed on Apr 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
$265 nightly
The price is $298 total per night from Apr 26 to Apr 27
$298 total
Apr 26 - Apr 27
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 ...
8.2/10 Very Good! (1,000 reviews)
Yes

Reviewed on Mar 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
$287 nightly
The price is $323 total per night from Apr 15 to Apr 16
$323 total
Apr 15 - Apr 16
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! (1,324 reviews)
This hotel is old and tired. The breakfast area is cramped and the offerings, particularly the cereal are boring.

Reviewed on Apr 2, 2026

Hampton Inn Key West FL
Eden House

Eden House

4 out of 5
1015 Fleming St Key West FL
$328 nightly
The price is $369 total per night from Apr 5 to Apr 6
$369 total
Apr 5 - Apr 6
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)
Second time staying here. We love it!!

Reviewed on Apr 3, 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
$272 nightly
The price is $305 total per night from Apr 12 to Apr 13
$305 total
Apr 12 - Apr 13
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! (1,295 reviews)
Yes yes

Reviewed on Apr 3, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$230 nightly
The price is $259 total per night from Apr 5 to Apr 6
$259 total
Apr 5 - Apr 6
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)
Yes

Reviewed on Apr 3, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$281 nightly
The price is $313 total per night from May 5 to May 6
$313 total
May 5 - May 6
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! (1,007 reviews)
Very accommodating. Very friendly. Excellent facilities, breakfast, pool. Will definitely stay again!!

Reviewed on Apr 1, 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
$407 nightly
The price is $458 total per night from May 4 to May 5
$458 total
May 4 - May 5
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! (3,167 reviews)
Nice location. Only big downfall was check in. The resort is huge and there wasn't a big enough front desk to accommodate check in. They had two-three people working but the process was slow and the line long. We gave them our bags and left to have something to eat. We returned about 90 minutes later ...

Reviewed on Apr 3, 2026

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
Book a stay at this beach hotel in Key West. Enjoy free parking, 2 restaurants, and breakfast (surcharge). Popular attractions Duval Street and Smathers Beach ...
8.4/10 Very Good! (999 reviews)

Families like: Outdoor pool, babysitting, close to beach, bicycle rentals

Travelers say...
Great visit

Reviewed on Feb 27, 2026

Get rates
Margaritaville Beach House Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$292 nightly
The price is $329 total per night from May 5 to May 6
$329 total
May 5 - May 6
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 ...
8.2/10 Very Good! (2,036 reviews)

Families like: Outdoor pools, miniature golf, game room, bicycle rentals

Travelers say...
Clen Room, Staff, Breakfast

Reviewed on Apr 4, 2026

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.

SHD to EYW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
SHD Address & GPS
Address:
77 Aviation Circle
Staunton VA, 24486
United States
IATA Code:
SHD
Longitude:
-78.896667
Latitude:
38.263889
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 Shenandoah Valley Regional Airport (SHD) to Key West Intl. Airport?
You'll need to make at least one stopover if you're traveling from SHD to EYW. Unfortunately, you won't find any 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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