Search Deals onStock Island Vacation Packages
Stock Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Lighthouse Hotel - Key West Historic Inns
Save 100% on your flight
Price was $581, price is now $319 per person
$319
per person
Sep 9 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

Southernmost House - Adult Exclusive
Save 100% on your flight
Price was $3,206, price is now $2,139 per person
$2,139
per person
Oct 22 - Oct 26
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 free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Great location and nice historic home
Reviewed on Aug 1, 2026

Coconut Beach Resort
Save 100% on your flight
Price was $2,007, price is now $1,339 per person
$1,339
per person
Sep 22 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this beach resort in Key West. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Había sargazo y no se podía usar la picina por qué el olor era demasiado fuerte, el aire acondicionado de la habitación estaba dañado y solo tenían una unidad portátil dentro de el cuarto que se notaba que llevaba algún tiempo puesta por el tape y todo, la ducha no funcionaba bien, no hay elevador y hay mil escaleras… No me fui porque era solo por una noche y pagué un precio alto por ser 4 de Julio pero para quedarse por varios días no hubiera podido con tantas cosas mal. El personal muy chevere, la localización muy buena, la picina muy linda.
Reviewed on Jul 26, 2026

Winslow's Bungalows - Key West Historic Inns
Save 100% on your flight
Price was $590, price is now $398 per person
$398
per person
Sep 9 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). 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
Save 100% on your flight
Price was $3,160, price is now $2,156 per person
$2,156
per person
Oct 8 - Oct 13
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, room service, and daily housekeeping. Popular attractions Duval Street and Mallory Square are located nearby.
This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!
Reviewed on Jul 27, 2026

Pier House Resort & Spa
Save 100% on your flight
Price was $782, price is now $582 per person
$582
per person
Sep 9 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.

Kona Kai Oasis
Price was $987, price is now $745 per person
$745
per person
Oct 24 - Oct 26
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.
This room was disgustingly filthy. The front security did not work, you had to shove the door hard to get it to close. The carpets looked like someone poured oil on them. You could not walk in this room without shoes. Your socks or feet would turn black.
Reviewed on Aug 8, 2026

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool
Price was $2,182, price is now $1,650 per person
$1,650
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this beach cottage in Key West. Enjoy a beach locale, patios, and in-room washers/dryers. Popular attractions Duval Street and Ernest Hemingway Home and Museum 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.

Thu, Aug 20 - Sun, Aug 23
TPA
Tampa Intl.
EYW
Key West Intl.
$133 Roundtrip, found 1 day ago
$133
Roundtrip
found 1 day ago

Thu, Aug 20 - Sun, Aug 23
PIE
St. Petersburg-Clearwater Intl.
EYW
Key West Intl.
$144 Roundtrip, found 5 days ago
$144
Roundtrip
found 5 days ago

Sun, Sep 20 - Thu, Oct 1
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$263 Roundtrip, just found
$263
Roundtrip
just found

Tue, Sep 15 - Sat, Sep 19
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$323 Roundtrip, found 6 hours ago
$323
Roundtrip
found 6 hours ago
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