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Stock Island Vacation Packages

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Stock Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Grand Maloney Hotel

Grand Maloney Hotel

2 out of 5
Price was $1,741, price is now $1,357 per person
$1,357
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, laundry facilities, and premium bedding. Popular attractions Duval Street and Mallory Square are located nearby.
Excellent location in old town. Quiet room away from street.

Reviewed on Jan 1, 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $3,929, price is now $2,697 per person
$2,697
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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 Gardens Hotel

The Gardens Hotel

4 out of 5
Save 100% on your flight
Price was $2,672, price is now $1,972 per person
$1,972
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Key West (EYW)
Book a stay at this business-friendly B&B in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Price was $1,949, price is now $1,476 per person
$1,476
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, parking (surcharge), and a garden. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5
Save 100% on your flight
Price was $3,167, price is now $2,421 per person
$2,421
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
Stay at this cottage in Key West. Enjoy a beach locale, patios, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Loved it

Reviewed on Mar 20, 2026

Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
Price was $1,771, price is now $1,360 per person
$1,360
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Key West (EYW)
Book a stay at this historic guesthouse in Key West. Enjoy free WiFi, beach cabanas (surcharge), and a business center. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Save 100% on your flight
Price was $3,480, price is now $2,701 per person
$2,701
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3 out of 5
Save 100% on your flight
Price was $2,769, price is now $2,158 per person
$2,158
per person
Oct 26 - Oct 30
found 22 hours ago
Roundtrip flight included
Charlotte (CLT) to Key West (EYW)
Stay at this cottage in Key West. Enjoy a beach locale, patios, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Loved the closeness to Duval st and the privacy

Reviewed on Oct 17, 2025

Stock Island Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Old Town Key West
Price was $1,949, price is now $1,476 per person
$1,476
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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 $3,929, price is now $2,697 per person
$2,697
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Price was $2,257, price is now $1,715 per person
$1,715
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Key West (EYW)
Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5
Old Town Key West
Save 100% on your flight
Price was $3,167, price is now $2,421 per person
$2,421
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)

Stock Island Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
Key West Historic District
Price was $1,771, price is now $1,360 per person
$1,360
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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 $3,311, price is now $2,191 per person
$2,191
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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 $2,672, price is now $1,972 per person
$1,972
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Key West (EYW)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,837, price is now $2,131 per person
$2,131
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
$86 Roundtrip, found 1 day ago
$86
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Sun, Oct 18 from St. Petersburg-Clearwater Intl. to Key West Intl., returning Wed, Oct 28, priced at $86 found 1 day ago
Breeze Airways
Sat, Oct 17 - Tue, Oct 27
TPA
Tampa Intl.
EYW
Key West Intl.
$87 Roundtrip, found 1 day ago
$87
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Oct 17 from Tampa Intl. to Key West Intl., returning Tue, Oct 27, priced at $87 found 1 day ago
Bargain Flight
Mon, Nov 2 - Fri, Nov 6
BOS
Logan Intl.
EYW
Key West Intl.
$308 Roundtrip, found 9 hours ago
$308
Roundtrip
found 9 hours ago
Select Bargain Flight flight, departing Mon, Nov 2 from Logan Intl. to Key West Intl., returning Fri, Nov 6, priced at $308 found 9 hours ago
United
Mon, Nov 9 - Thu, Nov 26
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$344 Roundtrip, found 7 hours ago
$344
Roundtrip
found 7 hours ago
Select United flight, departing Mon, Nov 9 from Newark Liberty Intl. Airport to Key West Intl., returning Thu, Nov 26, priced at $344 found 7 hours ago