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Key West Vacation Packages

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Key West Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
24 North Hotel Key West - Newly Renovated

24 North Hotel Key West - Newly Renovated

4 out of 5
Save 100% on your flight
per person
Mar 25 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Smathers Beach and Duval Street are located nearby.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Save 100% on your flight
per person
Mar 25 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
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. Popular attractions Smathers Beach and Duval Street are located nearby.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
per person
Mar 25 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 4-star golf 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 attractions Smathers Beach and Southernmost Point are located nearby.
Douglas House

Douglas House

3 out of 5
Save 100% on your flight
per person
Mar 25 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star guesthouse in Key West. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Ernest Hemingway Home and Museum and Southernmost Point are located nearby.
The Gates Hotel Key West Newly Renovated

The Gates Hotel Key West Newly Renovated

4 out of 5
Save 100% on your flight
per person
Mar 25 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Smathers Beach and Duval Street are located nearby.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
per person
Mar 25 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Smathers Beach and Southernmost Point are located nearby.
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
Save 100% on your flight
per person
Mar 25 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3.5-star 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. Popular attractions Smathers Beach and Duval Street are located nearby.
Havana Cabana at Key West - Adults Only

Havana Cabana at Key West - Adults Only

4 out of 5
Save 100% on your flight
per person
Mar 25 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Smathers Beach and Duval Street are located nearby.

Key West Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
per person
Apr 6 - Apr 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Curry House

Curry House

2 out of 5
Key West Historic District
per person
Mar 26 - Mar 30
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
per person
Mar 27 - Mar 31
found 21 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony

2 out of 5
per person
Mar 26 - Mar 30
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Delta
Tue, Apr 22 - Wed, Apr 30
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$199 Roundtrip, found 4 days ago
$199
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Apr 22 from Baltimore Washington Intl. Thurgood Marshall to Key West Intl., returning Wed, Apr 30, priced at $199 found 4 days ago
United
Tue, Apr 22 - Wed, Apr 30
ORD
O'Hare Intl.
EYW
Key West Intl.
$201 Roundtrip, found 2 days ago
$201
Roundtrip
found 2 days ago
Select United flight, departing Tue, Apr 22 from O'Hare Intl. to Key West Intl., returning Wed, Apr 30, priced at $201 found 2 days ago
Delta
Tue, Feb 25 - Wed, Mar 5
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Feb 25 from Newark Liberty Intl. Airport to Key West Intl., returning Wed, Mar 5, priced at $224 found 1 day ago
United
Tue, Feb 18 - Wed, Feb 19
BOS
Logan Intl.
EYW
Key West Intl.
$227 Roundtrip, found 4 days ago
$227
Roundtrip
found 4 days ago
Select United flight, departing Tue, Feb 18 from Logan Intl. to Key West Intl., returning Wed, Feb 19, priced at $227 found 4 days ago