A sunset over a coastal landscape with a small island surrounded by water.

Stock Island Vacations from $996

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Stock Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Sep 24 - Sep 27

    Coconut Beach Resort + Flight

    Old Town Key West
    3 nights
    2.5 star property
    8.8/10 - Excellent (212 reviews)
    "Había sargazo y no se podía usar la picina por qué el olor era demasiado fuerte, el aire acondicionado de la habitación estaba dañado y solo tenían una unidad portátil dentro de el cuarto que se notaba que llevaba algún tiempo puesta por el tape y todo, la ducha no funcionaba bien, no hay elevador y hay mil escaleras… No me fui porque era solo por una noche y pagué un precio alto por ser 4 de Julio pero para quedarse por varios días no hubiera podido con tantas cosas mal. El personal muy..."
    Reviewed July 26, 2026
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    $1,397
    $996
    per traveler
    found 1 day ago
    Coconut Beach Resort
  • Oct 19 - Oct 23

    The Key West Hotel + Flight

    Key West Historic District
    4 nights
    3.0 star property
    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 July 27, 2026
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    Save 100% on your flight
    $3,934
    $2,471
    per traveler
    found 1 day ago
    The Key West Hotel
  • Oct 19 - Oct 23

    Southernmost House - Adult Exclusive + Flight

    Old Town Key West
    4 nights
    4.0 star property
    9.4/10 - Exceptional (1,002 reviews)
    "Great location and nice historic home"
    Reviewed August 1, 2026
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    Save 100% on your flight
    $2,676
    $1,929
    per traveler
    found 1 day ago
    Southernmost House - Adult Exclusive
  • Oct 9 - Oct 13

    Orchid Key Inn - Adults Only + Flight

    Old Town Key West
    4 nights
    3.5 star property
    9.8/10 - Exceptional (1,003 reviews)
    "Very nice"
    Reviewed August 3, 2026
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    Save 100% on your flight
    $1,576
    $1,149
    per traveler
    found 1 day ago
    Orchid Key Inn - Adults Only
  • Oct 19 - Oct 23

    The Gardens Hotel + Flight

    Old Town Key West
    4 nights
    4.0 star property
    9.8/10 - Exceptional (1,002 reviews)
    Roundtrip Atlanta (ATL) - Key West (EYW)
    ATL - EYWNonstop EYW - ATLNonstop
    Save 100% on your flight
    $2,148
    $1,601
    per traveler
    found 1 day ago
    The Gardens Hotel

Discover the most popular places to visit in Stock Island

What to do in Stock Island

Stock Island Hotel Deals

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.

Book with confidence

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.

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.

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.