Search Deals onStock Island Vacation Packages
Stock Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West
Price was $1,287, price is now $949 per person
$949
per person
Feb 1 - Feb 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, parking (surcharge), and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Beautiful property, loved the drinks from tiki bar and Suzy Q was awesome and makes fabulous drinks.
Reviewed on Nov 15, 2026
The Key West Hotel
Price was $4,173, price is now $2,703 per person
$2,703
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!
Reviewed on Oct 29, 2026
Orchid Key Inn - Adults Only
Price was $2,423, price is now $1,678 per person
$1,678
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Always enjoy our stay here. The drink selection at the bar are fantastic and the drinks themselves are delicious. Very clean property. A lot of attention to detail here
Reviewed on Nov 12, 2026
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Price was $4,716, price is now $3,344 per person
$3,344
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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
Grand Maloney Hotel
Price was $1,872, price is now $1,368 per person
$1,368
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool
Save 100% on your flight
Price was $3,932, price is now $2,883 per person
$2,883
per person
Jan 30 - Feb 6
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
This was the worst stay we have had in years,washer was broken price was upwards of 2 thousand and the hole had 1998 ceiling fans, ac and furniture, neighbors kept us up till 2am. Downstairs toilet was clogged and back doors didn't even shut all the way. This place is no way ready to rent out. Carpet was filthy, I can go on and on. DO NOT STAY HERE!
Reviewed on Jun 10, 2026
The Marker Key West Harbor Resort
Price was $1,974, price is now $1,451 per person
$1,451
per person
Feb 1 - Feb 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Southernmost Beach Resort and Guesthouses
Price was $1,701, price is now $1,253 per person
$1,253
per person
Feb 1 - Feb 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Book a stay at this spa 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 reviews. Popular attractions Duval Street and South Beach are located nearby.
Stock Island Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Stock Island Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Dec 7 - Sat, Dec 12
PIE
St. Petersburg-Clearwater Intl.
EYW
Key West Intl.
$89 Roundtrip, found 15 hours ago
$89
Roundtrip
found 15 hours ago
Mon, Dec 7 - Sat, Dec 12
TPA
Tampa Intl.
EYW
Key West Intl.
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Sun, Dec 6 - Fri, Dec 18
BOS
Logan Intl.
EYW
Key West Intl.
$311 Roundtrip, found 2 hours ago
$311
Roundtrip
found 2 hours ago
Mon, Jan 25 - Tue, Feb 2
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$379 Roundtrip, found 6 hours ago
$379
Roundtrip
found 6 hours ago
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