Stock Island Vacations from $971

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The Latest Stock Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

Northside Resort
$971
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.2/10 Very Good! (2,365 reviews)
The hotel is outside of town. The beach on the edge of the property is not very nice so it’s definitely not a pro. The restaurant and bar was closed for remodel when we went and being so far away from town we had to drive to find food. I feel like I over paid for the reservation. However, the rooms are nice and clean, the vending machines are stocked. There is plenty of parking and the pool seemed thumping.

Reviewed on Sep 28, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$2,516
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (562 reviews)
The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
$1,642
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
It is a GREAT property in Key West, right in the center of the action.

Reviewed on Sep 28, 2026

Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

Old Town Key West
$988
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

Old Town Key West
Save 100% on your flight
$2,695
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
10/10 Exceptional! (3 reviews)
Loved it

Reviewed on Mar 20, 2026

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Stay near popular Stock Island attractions

A serene landscape with a pond, palm trees, and a golf course.

Key West Golf Club

8.4/10 (163 reviews)
America's only Caribbean-style golf course features tropical landscapes and the infamous "Mangrove Hole" requiring a shot over dense mangroves. Enjoy the Rees Jones design amid palm-lined fairways.
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A stone pathway through a tropical forest with dense foliage and a stone wall.

Key West Tropical Forest and Botanical Garden

8.0/10 (9 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.
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Florida Keys Community College Library

After visiting Florida Keys Community College Library, make a plan to see the other sights and activities in Key West.
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Tennesse Williams Fine Art Center

You can get tickets for a performance at Tennesse Williams Fine Art Center on your trip to Key West.
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What to do in Stock Island

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

$59
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

$61
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
See all activities in Stock Island

Stock Island Hotel Deals

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

7001 Shrimp Road Key West FL
Fully refundableReserve now, pay when you stay
$193 nightly
$217 total
Oct 5 - Oct 6
Total with taxes and fees
9.4/10 Exceptional! (1,321 reviews)
"Good place to stay but watch out for the gratuity tax (it's a State of Florida thing). The property was well maintained, and we enjoyed the room. Overall, it was a good place to stay. Most of the staff were hospitable and management was amazing."

Reviewed on Sep 27, 2026

The Perry Hotel & Marina Key West
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$180 nightly
$202 total
Oct 6 - Oct 7
Total with taxes and fees
Hilton Key West Resort & Marina
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

5130 Overseas Hwy Key West FL
$242 nightly
$272 total
Oct 2 - Oct 3
Total with taxes and fees
8.8/10 Excellent! (198 reviews)
"Was a very nice accommodation. Was nice and clean"

Reviewed on Sep 27, 2026

Aqua Lodges at Hurricane Hole Marina
See all 3,062 properties in Stock Island
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.