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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.
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
Price was $1,322, price is now $933 per person
$933
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the pool and the restaurant in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.

Kona Kai Oasis

Kona Kai Oasis

3 out of 5
Price was $1,727, price is now $1,115 per person
$1,115
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Great location for a night or 2. Was quiet and served it's purpose. The pool could use a little tlc. And the property is contactless. No front desk. 7/10

Reviewed on Sep 16, 2026

Lighthouse Suites Collection

Lighthouse Suites Collection

4 out of 5
Save 100% on your flight
Price was $3,044, price is now $2,059 per person
$2,059
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this aparthotel in Key West. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
My favorite place now. Won’t stay anywhere else. Lost track of the amount of my Key West stays, but this place has been the the most memorable.

Reviewed on Sep 13, 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $3,091, price is now $2,108 per person
$2,108
per person
Dec 1 - Dec 5
found 13 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

The Mermaid & Alligator

The Mermaid & Alligator

3.5 out of 5
Price was $1,592, price is now $1,092 per person
$1,092
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Clean room beautiful home. A little confusing on what to do at breakfast (sit at table or wait in kitchen for meal). Not overly friendly staff but they get the job done.

Reviewed on Sep 15, 2026

Douglas House - Adults Only

Douglas House - Adults Only

3 out of 5
Price was $1,641, price is now $1,203 per person
$1,203
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, daily housekeeping, and a garden. 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
Save 100% on your flight
Price was $3,170, price is now $2,332 per person
$2,332
per person
Nov 9 - Nov 16
found 13 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Key West (EYW)
Book a stay at this beach cottage in Key West. Enjoy a beach locale, balconies, and in-room washers/dryers. Popular attractions Duval Street and Smathers Beach are located nearby.
Key west is a vibe! My teenagers had a blast. No complaints. A lot of elders which is fine. I do have teens and they seems less than pleased while at he pool. We didn’t care though! We will be back, can not beat the location .

Reviewed on Mar 26, 2026

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

3.5 out of 5
Price was $1,887, price is now $1,392 per person
$1,392
per person
Nov 9 - Nov 12
found 3 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this cottage in Key West. Enjoy free parking, a beach locale, and concierge services. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The location to the things we wanted to do was perfect

Reviewed on May 1, 2026

Key West Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Mermaid & Alligator

The Mermaid & Alligator

3.5 out of 5
Old Town Key West
Price was $1,592, price is now $1,092 per person
$1,092
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Kona Kai Oasis

Kona Kai Oasis

3 out of 5
Old Town Key West
Price was $1,727, price is now $1,115 per person
$1,115
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Lighthouse Suites Collection

Lighthouse Suites Collection

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $3,044, price is now $2,059 per person
$2,059
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $3,091, price is now $2,108 per person
$2,108
per person
Dec 1 - Dec 5
found 13 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)

Key West Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $1,525, price is now $1,097 per person
$1,097
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,704, price is now $1,753 per person
$1,753
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,344, price is now $1,663 per person
$1,663
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Key West (EYW)
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,606, price is now $1,146 per person
$1,146
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Key West (EYW)

Top Flight Deals

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

Allegiant Air
Sun, Oct 18 - Wed, Oct 28
PIE
St. Petersburg-Clearwater Intl.
EYW
Key West Intl.
$92 Roundtrip, found 6 hours ago
$92
Roundtrip
found 6 hours ago
Select Allegiant Air flight, departing Sun, Oct 18 from St. Petersburg-Clearwater Intl. to Key West Intl., returning Wed, Oct 28, priced at $92 found 6 hours ago
Breeze Airways
Sun, Oct 18 - Wed, Oct 28
TPA
Tampa Intl.
EYW
Key West Intl.
$113 Roundtrip, found 12 hours ago
$113
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Sun, Oct 18 from Tampa Intl. to Key West Intl., returning Wed, Oct 28, priced at $113 found 12 hours ago
United
Sun, Nov 8 - Wed, Nov 25
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$344 Roundtrip, found 12 hours ago
$344
Roundtrip
found 12 hours ago
Select United flight, departing Sun, Nov 8 from Newark Liberty Intl. Airport to Key West Intl., returning Wed, Nov 25, priced at $344 found 12 hours ago
Delta
Wed, Nov 18 - Thu, Nov 26
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$349 Roundtrip, found 13 hours ago
$349
Roundtrip
found 13 hours ago
Select Delta flight, departing Wed, Nov 18 from Baltimore Washington Intl. Thurgood Marshall to Key West Intl., returning Thu, Nov 26, priced at $349 found 13 hours ago