Stock Island Vacations from $769

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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 Windward Pointe, Key West
The Key West Hotel
Oceans Edge Key West Resort, Hotel & Marina
Winslow's Bungalows - Key West Historic Inns
Southernmost Beach Resort and Guesthouses
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Discover the most popular places to visit in Stock Island

What to do in Stock Island

Stock Island Hotel Deals

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$308 nightly
The price is $346 total per night from Jan 13 to Jan 14
$346 total
Jan 13 - Jan 14
Total with taxes and fees
8.8/10 Excellent! (1,778 reviews)
The staff was outstanding, rooms were clean and beautiful and food was excellent. All around a great hotel!

Reviewed on Jan 11, 2026

Oceans Edge Key West Resort, Hotel & Marina
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
7001 Shrimp Road Key West FL
Fully refundableReserve now, pay when you stay
$383 nightly
The price is $431 total per night from Jan 14 to Jan 15
$431 total
Jan 14 - Jan 15
Total with taxes and fees
9.4/10 Exceptional! (1,187 reviews)
really liked the shuttle especially for New Years Eve. Room is okay - could use some more decorations or touches. Excellent pool and grounds and welcoming staff. will stay again.

Reviewed on Jan 8, 2026

The Perry Hotel & Marina Key West
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

2 out of 5
5130 Overseas Hwy Key West FL
$346 nightly
The price is $389 total per night from Jan 19 to Jan 20
$389 total
Jan 19 - Jan 20
Total with taxes and fees
8.8/10 Excellent! (172 reviews)
Unique Stay. Fun for my kids who love fishing. This is a working fishing marina so we got to see the fish being loaded to the pier and processed by the fishermen. The house boat was clean and had everything we needed, and worked out great for our short stay. The marina itself is cute and we saw plenty ...

Reviewed on Jan 6, 2026

Aqua Lodges at Hurricane Hole Marina
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

Things to do in and around Stock Island

Stock Island offers a variety of activities suitable for families and business travelers alike. Enjoy a day trip exploring the vibrant shopping areas and malls, or unwind at a nearby golf course. Don’t miss out on the unique Keys experiences and popular attractions that highlight the charm of this tropical paradise. Stock Island is the perfect destination for a memorable vacation filled with fun and relaxation.

Shopping

Experience shopping in Stock Island at The Kite House and We Cycle Key West, both located 4 miles away. For a unique vibe, visit the Big Pine Key Flea Market, 25 miles from Stock Island, where you can find a variety of local goods and souvenirs.

Recreation

At Key West Golf Club, enjoy a refreshing day on the greens surrounded by lush landscapes. Nearby, the Key West Burlesque Theater offers a captivating mix of culture and entertainment. For family fun, visit the MLK Community Pool & Community Center, where you can unwind and swim in a welcoming atmosphere.

Adventure

In Stock Island, explore the vibrant waters through thrilling kayaking adventures, or embark on a fishing charter to reel in local catches. Experience the excitement of jet skiing along the coast, and discover the underwater world while snorkeling in the beautiful reefs nearby.

Nightlife

For an exciting nightlife experience in Stock Island, check out local hotspots like The Perry Hotel and Hogfish Bar & Grill, where you can enjoy live music, delicious seafood, and vibrant bars. The atmosphere is laid-back yet lively, perfect for unwinding after a day of exploring the Florida Keys.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Stock Island

Stock Island, Florida, is an ideal destination for family, city, and business-themed vacations. Visitors can explore beautiful beaches, marinas, and the island's unique charm, catering to those seeking outdoor adventures and cultural experiences. Key attractions include the Stock Island Marina and various local points of interest, offering a perfect blend of relaxation and exploration for every type of traveler.

  • Smathers Beach: Located 3 miles from Stock Island, Smathers Beach offers a quintessential beach experience with its soft sand, clear waters, and vibrant atmosphere. Enjoy sunbathing, swimming, and various water sports while soaking up the laid-back beach vibes.
  • Stock Island Yacht Club & Marina: Situated within Stock Island, this marina is perfect for adventure seekers. Experience outdoor activities like boating and fishing, all while enjoying the refreshing coastal breeze and beach vibes surrounding the club.
  • Key West Tropical Forest and Botanical Garden: This serene botanical garden, also located in Stock Island, is ideal for families and couples. Stroll through lush landscapes and discover diverse plant species, making it a romantic and peaceful outdoor retreat.

Best time to go to Stock Island

The best time to visit Stock Island, Key West can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Stock Island, Key West falls in August, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature around Stock Island, Key West falls in January, visitor numbers are slightly high and weather is mostly sunny with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January71.1°F (21.7°C)No RainMostly SunnySlightly HighAverage
February72.1°F (22.3°C)No RainMostly SunnySlightly HighSlightly High
March73.4°F (23.0°C)No RainMostly SunnySlightly HighSlightly High
April76.8°F (24.9°C)No RainMostly SunnyAverageSlightly High
May79.3°F (26.3°C)Light RainMostly SunnySlightly LowAverage
June82.6°F (28.1°C)Light RainMostly SunnyAverageAverage
July84.0°F (28.9°C)Light RainMostly SunnyAverageAverage
August84.4°F (29.1°C)Light RainMostly SunnyAverageSlightly Low
September83.7°F (28.7°C)Light RainMostly SunnyAverageSlightly Low
October80.8°F (27.1°C)Light RainMostly SunnySlightly LowSlightly Low
November76.6°F (24.8°C)Light RainMostly SunnySlightly LowAverage
December73.9°F (23.3°C)No RainMostly SunnyAverageAverage

Tips to save on your trip to Stock Island

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically August to October) for more affordable package holidays to Stock Island.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Stock Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Population
3,900

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