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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.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Price was $1,565, price is now $1,131 per person
$1,131
per person
Feb 26 - Feb 28
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and 3 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $3,480, price is now $2,094 per person
$2,094
per person
Mar 28 - Apr 2
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Duval Street and Mallory Square 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
Price was $2,684, price is now $1,792 per person
$1,792
per person
Mar 28 - Apr 2
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
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 attractions Duval Street and Smathers Beach are located nearby.
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
Save 100% on your flight
Price was $1,960, price is now $1,400 per person
$1,400
per person
Mar 17 - Mar 21
found 15 hours ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
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 staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Save 100% on your flight
Price was $3,099, price is now $2,221 per person
$2,221
per person
Mar 28 - Apr 2
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $2,292, price is now $1,667 per person
$1,667
per person
Mar 28 - Apr 2
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
Book a stay at this 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 Duval Street and Smathers Beach are located nearby.
Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

3 out of 5
Price was $4,786, price is now $3,507 per person
$3,507
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Key West (EYW)
Stay at this cottage in Key West. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

3 out of 5
Price was $4,190, price is now $3,103 per person
$3,103
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Key West (EYW)
Stay at this cottage in Key West. Enjoy balconies, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Smathers Beach 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
Price was $1,380, price is now $902 per person
$902
per person
Feb 22 - Feb 26
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,782, price is now $1,654 per person
$1,654
per person
Mar 6 - Mar 10
found 24 hours ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Price was $1,925, price is now $1,374 per person
$1,374
per person
Apr 2 - Apr 6
found 15 hours ago
Roundtrip non-stop flight included
Washington (DCA) to Key West (EYW)
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
New Town
Save 100% on your flight
Price was $1,960, price is now $1,400 per person
$1,400
per person
Mar 17 - Mar 21
found 15 hours ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)

Key West Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,188, price is now $1,303 per person
$1,303
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $3,480, price is now $2,094 per person
$2,094
per person
Mar 28 - Apr 2
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was $2,106, price is now $1,318 per person
$1,318
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Save 100% on your flight
Price was $3,099, price is now $2,221 per person
$2,221
per person
Mar 28 - Apr 2
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)

Top Flight Deals

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

Breeze Airways
Fri, Jan 30 - Fri, Feb 6
TPA
Tampa Intl.
EYW
Key West Intl.
$116 Roundtrip, just found
$116
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Jan 30 from Tampa Intl. to Key West Intl., returning Fri, Feb 6, priced at $116 just found
United
Mon, Feb 9 - Fri, Feb 13
BOS
Logan Intl.
EYW
Key West Intl.
$199 Roundtrip, found 2 days ago
$199
Roundtrip
found 2 days ago
Select United flight, departing Mon, Feb 9 from Logan Intl. to Key West Intl., returning Fri, Feb 13, priced at $199 found 2 days ago
United
Tue, Sep 15 - Sat, Sep 19
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 15 from Newark Liberty Intl. Airport to Key West Intl., returning Sat, Sep 19, priced at $229 found 1 day ago
Spirit Airlines
Mon, Feb 16 - Thu, Feb 19
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$230 Roundtrip, found 1 day ago
$230
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Feb 16 from Baltimore Washington Intl. Thurgood Marshall to Key West Intl., returning Thu, Feb 19, priced at $230 found 1 day ago