Stock Island Vacations from $569

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The Latest Stock Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

Old Town Key West
Save 100% on your flight
$569
per person
Oct 1 - Oct 5
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (985 reviews)
Great boutique hotel! The room was clean, the bed was very comfortable, and the location was perfect—just one block from Duval Street, with restaurants nearby. Breakfast was also better than I expected! Live music by the pool (afternoon and during breakfast) and at night was very quiet! Overall, a very pleasant stay!

Reviewed on Aug 30, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$1,826
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (562 reviews)
Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

Old Town Key West
Save 100% on your flight
$569
per person
Oct 1 - Oct 5
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,397 reviews)
Two concerns: 1) TV issue was not addressed by staff in a timely fashion. Note; the amenity fee was reduced as a result. 2) concern may be equal parts Winslow’s Bungalows and Expedia. There should be transparent pricing that includes the TOTAL AMOUNT. It’s distasteful to a customer amenity fees, etc. show up at check-in/out. Just quote the customer the true cost of their stay and avoid creating a frustration on behalf of the consumer.

Reviewed on Sep 1, 2026

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West
Save 100% on your flight
$966
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (414 reviews)
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

Old Town Key West
$892
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (494 reviews)
It is located in the heart of he old district snd everything was so accessible without having to use our car. The property is only 1 block off Duval so,we had the advantage of,accessibility without the noise. The property is protected by foliage which makes it feel private and protected. The complimentary breakfast is lovely, and there is wine by the pool daily. Dwight welcomes guests upon arrival,and made us feel,at home. The beds are so comfy, and each cottage has its own flavor. I hope to return and stay at Ella’s Cottages again, Expedia does a great job helping us narrow down our priorities, amenities, location, etc. That enabled us to find Ella’s Cottages, which was perfect for us.

Reviewed on Sep 1, 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 beautiful beaches or experience its lively festivals.
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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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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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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
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

$69
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
Miami to Key West Day Trip with Activity Options

Miami to Key West Day Trip with Activity Options

$39
per adult
84% of travellers recommend
Miami to Key West Day Trip with Activity Options
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
$199 nightly
$224 total
Sep 21 - Sep 22
Total with taxes and fees
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
$167 nightly
$188 total
Sep 8 - Sep 9
Total with taxes and fees
Hilton Key West Resort & Marina
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$210 nightly
$237 total
Sep 8 - Sep 9
Total with taxes and fees
Southernmost Beach Resort and Guesthouses
See all 3,072 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.