Stock Island Vacations from $911

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The Latest Stock Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

Old Town Key West
Save 100% on your flight
$911
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,371 reviews)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
$976
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
Excellent place to stay and will absolutely stay there again! The staff was so helpful and friendly! The restaurant on the property has delicious food! I highly recommend staying at he Southern Most House, great pool, great location, great vacation!

Reviewed on Aug 16, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$1,907
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (561 reviews)
This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!

Reviewed on Jul 27, 2026

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

Old Town Key West
Save 100% on your flight
$924
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (971 reviews)
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

Key West Historic District
Save 100% on your flight
$952
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (946 reviews)
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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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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
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
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$45
per adult
88% of travellers recommend
Key West Conch Tour Train
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
$181 nightly
$203 total
Sep 2 - Sep 3
Total with taxes and fees
9.4/10 Exceptional! (1,329 reviews)
"Great Staff and nice environment, rooms, and amenities. The only shortcoming is that the hotel is about a 15-minute drive from where all the attractions are, but the staff and food were amazing"

Reviewed on Aug 17, 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
$188 nightly
$211 total
Aug 25 - Aug 26
Total with taxes and fees
9/10 Wonderful! (1,838 reviews)
"The room was clean and smells clean. Staffs are very helpful and greeted me enthusiastically. It was a place that I was expecting to be in and relax after a long drive. The pool was nice, heated and relaxing. Highly recommended."

Reviewed on Aug 17, 2026

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
$203 nightly
$228 total
Sep 1 - Sep 2
Total with taxes and fees
8.8/10 Excellent! (3,535 reviews)
"Everyone was pleasant. The resort offered things to do and kept you informed via email. Check in went smooth if you read all the information you will be prepared for the added expenses. The resort is in a great locale. I recommend not having a car rather rent bikes, use bus, trolley or uber. Yes, ..."

Reviewed on Aug 18, 2026

Southernmost Beach Resort and Guesthouses
See all 3,081 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.