Stock Island Vacations from $827
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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 Beach House, Key West
Save 100% on your flight
Price was $1,411, price is now $827 per person
$827
per person
Nov 17 - Nov 23
found 2 days ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,025 reviews)
The 2 bedroom villa was great. It was spacious and comfortable. The master bathroom was a dream! I also enjoyed the screened in balcony with a view of the ocean and pool. I highly recommend this place!
Reviewed on Sep 30, 2025
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,605, price is now $1,468 per person
$1,468
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
We loved being the historic part of town. Our bungalow was beautifully appointed. The location offered access to restaurants and night life while being a quiet retreat when we were tired. The morning breakfast was good, but it didn't change from day to day. We stayed 7 nights and skipped the breakfast several mornings for its lack of variety. The morning coffee ran out before 10am on Sunday and was not replenished. The 24/7 coffee maker was stocked only with decaf.
Reviewed on Oct 9, 2025
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $2,414, price is now $1,410 per person
$1,410
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,722 reviews)
Staff was friendly and accommodating. The concierge booked trips for us and made some great recommendations for us.
Reviewed on Oct 8, 2025
Fitch Lodge - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was $2,053, price is now $1,209 per person
$1,209
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (484 reviews)
Property has a very cozy feel
Very nice lobby area breakfast was cute and fun. Parking is very limited. Flash flooding made it a tad bit difficult to reach out room.
Reviewed on Aug 24, 2025
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,490, price is now $898 per person
$898
per person
Nov 17 - Nov 23
found 2 days ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,016 reviews)
Family friendly.. amenities
Reviewed on Oct 6, 2025
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See all available trips from San Jose to Stock Island
View all tripsDiscover the most popular places to visit in Stock Island
Stock Island Yacht Club & Marina
4.5/5(2,254 reviews)
Explore the waterfront of Stock Island Yacht Club & Marina and enjoy activities such as boating in Key West. Discover the area's beautiful sunsets and lively bars.
Key West Golf Club
4/5(52 reviews)
Play a round of golf in Key West at Key West Golf Club, and enjoy other activities such as boating. Amble around the area's seaside or seek out the biking trails.
Key West Tropical Forest and Botanical Garden
4/5(5 reviews)
Enjoy the beautiful sunsets and explore Key West Tropical Forest and Botanical Garden, a lovely green space in Key West. Stroll along the area's seaside or experience its lively festivals.
What to do in Stock Island
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
$50
per adult
92% of travellers recommend
Key West Sunset Sail with Live Music, Drinks and Appetizers!
$80
per adult
92% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
$27
per adult
80% of travellers recommend
Stock Island Hotel Deals
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $213 total per night from Oct 14 to Oct 15
$213 total
Oct 14 - Oct 15
Total with taxes and fees
8.8/10 Excellent! (1,722 reviews)
"Overall just a good placecto saty whike yiur there"
Reviewed on Oct 3, 2025
The Perry Hotel & Marina Key West
7001 Shrimp Road, Key West, FL
Fully refundableReserve now, pay when you stay
$173 nightly
The price is $194 total per night from Oct 13 to Oct 14
$194 total
Oct 13 - Oct 14
Total with taxes and fees
9.4/10 Exceptional! (1,109 reviews)
"Very beautiful, clean, pet friendly resort definitely going back as soon as possible"
Reviewed on Oct 4, 2025
Aqua Lodges at Hurricane Hole Marina
5130 Overseas Hwy, Key West, FL
$238 nightly
The price is $268 total per night from Oct 12 to Oct 13
$268 total
Oct 12 - Oct 13
Total with taxes and fees
8.8/10 Excellent! (162 reviews)
"So fun staying on a houseboat. It was spacious, clean and comfortable. The view from the desk was beautiful."
Reviewed on Sep 3, 2025
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.
Stock Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
Population | 3,900 |
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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.