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The Latest Stock Island vacation packages
Price found within the past 48 hours. Click for updated prices.

Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
Price was $1,138, price is now $841 per person
$841
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (366 reviews)
Stayed in a one bedroom unit. Good size kitchen/living room, however bathroom was tiny. Bedroom was ok.. lots of closet/storage, however bed could have been bigger.
Location was awesome… just a couple blocks to everything!
Reviewed on May 6, 2026

Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,305, price is now $921 per person
$921
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,066 reviews)
The hidden resort fees were absolutely ridiculous! $40 a day, plus $5 a day plus $150 coverage without any explanation. This property is located directly next to the airport and they do not provide a shuttle service to pick you up. We used Uber for everything, another extra expense. ( The Hampton Inn next door had a shuttle that went everywhere)
Reviewed on May 5, 2026

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $1,632, price is now $1,151 per person
$1,151
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (552 reviews)
The staff at the hotel were excellent. Very friendly and helpful. Room was very clean and comfortable. We were right in the middle of the old district which had many many places to explore. Hotel had a wonderful hidden pool with live music/bar next to it in case we just wanted to relax after exploring all day.
Reviewed on Apr 21, 2026

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Save 100% on your flight
Price was $2,626, price is now $1,863 per person
$1,863
per person
Jun 10 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Key West (EYW)
9.4/10 Exceptional! (3 reviews)
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

Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,280, price is now $925 per person
$925
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,034 reviews)
Nice to have laundry in the apartment
Reviewed on May 7, 2026
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Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$251 nightly
The price is $283 total per night from Jun 3 to Jun 4
$283 total
Jun 3 - Jun 4
Total with taxes and fees
9/10 Wonderful! (1,868 reviews)
Downtown Key West is a great place to drink and party. But if you want that on some days, but want to combine with "just chilling," this is the place. Drop dead gorgeous views, watching private fishing boats come in and out, great restaurant food (wow!) etc. It is worth every penny! PS: concierge ...
Reviewed on May 9, 2026

The Perry Hotel & Marina Key West
7001 Shrimp Road Key West FL
Fully refundableReserve now, pay when you stay
$251 nightly
The price is $283 total per night from May 26 to May 27
$283 total
May 26 - May 27
Total with taxes and fees
9.4/10 Exceptional! (1,274 reviews)
Clean room and a free shuttle to downtown. The two restaurants were great and all of the staff was friendly and very helpful!
Reviewed on May 5, 2026

Aqua Lodges at Hurricane Hole Marina
5130 Overseas Hwy Key West FL
$283 nightly
The price is $319 total per night from May 27 to May 28
$319 total
May 27 - May 28
Total with taxes and fees
9/10 Wonderful! (183 reviews)
Dust was bad on back of tv’s, no staff on site bar and parking was good
Reviewed on Apr 29, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find the Best Stock Island Vacation Packages
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

















