Stock Island Vacation Packages
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Top Stock Island vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Hyatt Vacation Club at Windward Pointe, Key West
9.4/10 Exceptional! (1,255 reviews)
Nov 16 - Nov 20
4 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,555, price is now $1,115 per person
$1,115
per person
found 1 day ago
They have a great outdoor space with pool and hot tub. There is a poolside bar with food for purchase. The suites are large and great to share with 2 couples.It is a vacation club so they are going to offer you to go to a sales presentation.
Reviewed on Sep 29, 2026
4.0-star property
The Gardens Hotel
Old Town Key West
9.8/10 Exceptional! (1,000 reviews)
Nov 16 - Nov 20
4 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Price was $1,506, price is now $1,121 per person
$1,121
per person
found 1 day ago
It is a GREAT property in Key West, right in the center of the action.
Reviewed on Sep 28, 2026
3.0-star property
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Old Town Key West
10/10 Exceptional! (1 review)
Nov 10 - Nov 14
4 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,586, price is now $2,722 per person
$2,722
per person
found 1 day ago
Loved the closeness to Duval st and the privacy
Reviewed on Oct 17, 2025
Top rated hotels for your Stock Island vacation package
The Perry Hotel & Marina Key West
7001 Shrimp Road Key West FL
Free Cancellation
Reserve now, pay when you stay
0.54 mi from city center
$191 nightly
The price is $215 total per night
$215 total
Oct 6 - Oct 7
Total with taxes and fees
Guests of The Perry Hotel & Marina Key West have access to a marina, 2 outdoor pools, and a 24-hour gym. If you drive, self parking is USD 30.38 per night, and there's also an area shuttle. The front desk has multilingual staff on hand 24/7 to help with securing valuables, concierge services, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls and an off-leash area. Additional amenities include free WiFi in public areas, conference space, and a microwave in a common area.
Pool
Pet friendly
Hilton Key West Resort & Marina
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
1 mi from city center
$180 nightly
The price is $202 total per night
$202 total
Oct 6 - Oct 7
Total with taxes and fees
Guests of Hilton Key West Resort & Marina have access to a marina, 6 outdoor pools, and a 24-hour gym. If you drive, self parking is USD 32.63 per night, and there's also an area shuttle. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include free WiFi in public areas, meeting rooms, and free use of bicycles.
Pool
Pet friendly
Aqua Lodges at Hurricane Hole Marina
5130 Overseas Hwy Key West FL
0.41 mi from city center
$242 nightly
The price is $272 total per night
$272 total
Oct 7 - Oct 8
Total with taxes and fees
Guests staying at this houseboat enjoy features like a marina and free WiFi in public areas. You can put free parking to good use if you drive.
Parking included
Free WiFi
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.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
$42
per adult
94% of travellers recommend
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
$68
per traveler
92% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travellers recommend
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- Southernmost Point
- Coupon Bight Aquatic Preserve
- Donkey Milk House
- National Key Deer Refuge Visitor Center
- Ernest Hemingway Home and Museum
- Crane Point Museum and Nature Center
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- Key West Butterfly and Nature Conservatory
- Sails To Rails Museum at Flagler Station
- Ramrod Key Vacations
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- All inclusive Vacation Packages Key West
- Blue Hole
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- Fleming Key Vacations
- Florida Keys Eco - Discovery Center
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- Smathers Beach
- Bahia Honda Key Vacations
- Key West Tropical Forest and Botanical Garden
- The Kite House
- Marathon Vacations
- Mlk Community Pool & Community Center
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- Fort East Martello Museum and Gallery
- Fort Zachary Taylor Historic State Park
- Duval Street
