Stock Island Vacation Packages 2026 from $2,123

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The Latest Stock Island vacation packages

Price found within the past 48 hours. Click for updated prices.

Douglas House - Adults Only

Old Town Key West

Save 100% on your flight

$2,123

per person

Nov 24 - Nov 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.6/10 Exceptional! (542 reviews)

Loved our little private porch however the construction next door made it unbearable. Not the fault of the property. The room was spacious and the location was wonderful. The pool is well maintained and a nice oasis after a hot, busy day. Be aware parking is around the corner and very expensive. It cost us $100 for 3 days. The staff was friendly Overall an enjoyable stay and I would sty here again

Reviewed on Oct 11, 2026

The Key West Hotel

Key West Historic District

$2,987

per person

Dec 29 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (563 reviews)

Property was everything as described, clean, in the heart of the excitement that is Key West Pool was refreshing and close to tiki bar and local entertainment. The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer

Reviewed on Oct 6, 2026

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Old Town Key West

Save 100% on your flight

$5,558

per person

Dec 29 - Jan 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

10/10 Exceptional! (1 review)

Loved the closeness to Duval st and the privacy

Reviewed on Oct 17, 2025

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Key West Historic District

Save 100% on your flight

$2,344

per person

Dec 20 - Dec 27

found 1 day ago

Roundtrip flight included

New York (NYC) to Key West (EYW)

2/10 (1 review)

The listing says this property is “on beach property,” but it is not on the beach or even close to a beach, which was very misleading. While we were staying there, the pool was also resurfaced. We were told that it was a “last-minute” discovery that the pool needed to be closed, but this significantly affected our stay. We also had trouble getting ahold of anyone when we had questions or concerns. Calls to the management/maintenance contact went unanswered, and no one returned our calls. Another issue was the condition of the balconies. We were on one of the lower floors, and whenever the guests above us used their deck, dirt and sand would fall down onto ours while we were sitting outside. It made it very unpleasant to actually use the outdoor space. Overall, the property description was misleading, the unexpected pool closure was disappointing, communication was poor, and the balcony situation made the stay less enjoyable than expected.

Reviewed on Sep 12, 2026

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Save 100% on your flight

$2,680

per person

Dec 30 - Jan 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (3 reviews)

Key west is a vibe! My teenagers had a blast. No complaints. A lot of elders which is fine. I do have teens and they seems less than pleased while at he pool. We didn’t care though! We will be back, can not beat the location .

Reviewed on Mar 26, 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

Champagne and Sunsets: A Key West Catamaran Adventure

$59

per adult

94% of travellers recommend

Sunset Sail in Key West with Beverages Included

$79

per adult

98% of travellers recommend

See all activities in Stock Island

Stock Island Hotel Deals

Hilton Key West Resort & Marina

5950 Peninsular Avenue Key West FL

Fully refundableReserve now, pay when you stay

$175 nightly

$196 total

Oct 25 - Oct 26

Total with taxes and fees

9/10 Wonderful! (1,791 reviews)

"We went to Duval Street and Town Everyday, The Hilton KW Resort & Marina Shuttle Driver “Fausto” was a 15 Star!! He was so accommodating, professional, helpful people person, on time and just a Genuine Nice Guy! Wish everyone that we meant was like him!! Top Notch!!!!!👏👏🙌🙌 🌟🌟💫"

Reviewed on Oct 13, 2026

The Perry Hotel & Marina Key West

7001 Shrimp Road Key West FL

Fully refundableReserve now, pay when you stay

$188 nightly

$211 total

Oct 29 - Oct 30

Total with taxes and fees

9.4/10 Exceptional! (1,307 reviews)

"The Director of rooms, Chris, could not have been more of a help and a gentleman. Every staff member we ran into was delightful and more than willing to help with any questions or concerns. The hotel was wonderful in the pool, fantastic as well as the restaurants."

Reviewed on Oct 13, 2026

Aqua Lodges at Hurricane Hole Marina

5130 Overseas Hwy Key West FL

$259 nightly

$292 total

Oct 15 - Oct 16

Total with taxes and fees

8.8/10 Excellent! (199 reviews)

"Was a very nice accommodation. Was nice and clean"

Reviewed on Sep 27, 2026

See all 3,109 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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	71.1°F (21.7°C)	No Rain	Mostly Sunny	Slightly High	Average
February	72.1°F (22.3°C)	No Rain	Mostly Sunny	Slightly High	Slightly High
March	73.4°F (23.0°C)	No Rain	Mostly Sunny	Slightly High	Slightly High
April	76.8°F (24.9°C)	No Rain	Mostly Sunny	Average	Slightly High
May	79.3°F (26.3°C)	Light Rain	Mostly Sunny	Slightly Low	Average
June	82.6°F (28.1°C)	Light Rain	Mostly Sunny	Average	Average
July	84.0°F (28.9°C)	Light Rain	Mostly Sunny	Average	Average
August	84.4°F (29.1°C)	Light Rain	Mostly Sunny	Average	Slightly Low
September	83.7°F (28.7°C)	Light Rain	Mostly Sunny	Average	Slightly Low
October	80.8°F (27.1°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
November	76.6°F (24.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	73.9°F (23.3°C)	No Rain	Mostly Sunny	Average	Average

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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Frequently asked questions

How much does a Stock Island vacation package cost?

A Stock Island vacation package typically costs around $1,250 per adult for a week-long trip. Lower-priced options start around $800 per adult, while premium packages can reach up to $2,150.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

How can I save money on a Stock Island vacation package?

When you bundle, you can save up to 30%*. To save money on a Stock Island package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What's included in a Stock Island vacation package?

A Stock Island vacation package lets you combine flights, hotel stays, and rental cars. Most hotels here offer airport shuttle service to and from Key West, FL (EYW-Key West Intl.) airport.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

How do I find cheap Stock Island vacation package deals?

The cheapest Stock Island vacation package deals start around $670 per adult for weekend trips. Separately, September and October typically have the lowest average monthly prices, around $930 to $990 per adult, typically for a 4-day trip.Bundling flights and hotel together also typically saves money on a week-long trip — nearly all Stock Island packages include savings versus booking separately, typically around $220 per adult. Longer, two-week trips can save even more, often around $365 per adult.Browse cheap vacation packages in Stock Island on Expedia to compare current deals for your preferred dates.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

What is the best time to visit Stock Island?

The best time for a Stock Island vacation package is January through March, its most popular period for travelers. This peak season offers vibrant activity and pleasant conditions for exploring the area.Consider visiting in October for Fantasy Fest, a lively annual event, or in November for the Key West Offshore World Championship, which draws many visitors to the region. Event dates can change, so confirm the schedule before booking your Stock Island vacation.

What types of vacation packages are available in Stock Island?

Stock Island, known for its family-friendly attractions and beaches, offers several types of vacation packages:

Pet-friendly: The Perry Hotel & Marina Key West, a 4-star property rated 8.9 out of 10 by travelers, welcomes pets.
Beach: A Stock Island vacation package can include a stay at a beach-oriented property like Hilton Key West Resort & Marina, a 4-star hotel rated 8.5 out of 10 by travelers, which features an outdoor pool and free breakfast, with travelers often noting the well-kept pool.
Luxury: For a more upscale experience, about half of the priced hotels in Stock Island fall into the luxury tier, including The Perry Hotel & Marina Key West, a 4-star hotel rated 8.9 out of 10 by travelers, praised for its fantastic location and amazing rooms.

Is Stock Island better suited for a beach vacation or a cultural trip?

Stock Island is primarily a beach destination, ideal for travelers seeking coastal relaxation and water activities. Its location as a beach destination outside the city, combined with nearly all package hotels offering ocean views, makes it a strong choice for a beach-focused Stock Island vacation.While the area is known for its beaches like Smathers Beach, cultural trips are also accessible. Stock Island vacation packages can easily include excursions to nearby Key West, where you can explore attractions like the lively Duval Street. This allows for a blend of beach time with cultural experiences, making it versatile for different travel styles.

Which airport should I use for a Stock Island vacation?

For a Stock Island vacation, the primary gateway is Key West International Airport (EYW), which serves the area directly. This airport offers convenient access to Stock Island and the wider Key West region.An alternative option is Florida Keys Marathon Airport (MTH), located further north in the Florida Keys, which can also be used depending on your travel plans.

What are the top things to do in Stock Island?

A Stock Island vacation offers a mix of beach relaxation, water activities, and easy access to Key West's attractions:Browse and book things to do in Stock Island on Expedia.

What's included in a Stock Island beach vacation package?

A Stock Island beach vacation package typically bundles flights with a stay at a beach-oriented hotel. These packages offer a convenient way to experience the area's coastal charm. For example, The Perry Hotel & Marina Key West, a 4-star property rated 8.9 out of 10 by travelers, features an outdoor pool. Another option is Hilton Key West Resort & Marina, a 4-star hotel rated 8.5 out of 10 by travelers, which also provides an outdoor pool. While the package includes your flight and hotel, specific inclusions like water sports or excursions depend on the hotel and rate chosen.

What is the best time to book a Stock Island vacation package?

Book your Stock Island vacation package around 8 weeks in advance. It gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 4 and 14 weeks out.January, February, and March are the most popular months for Stock Island packages, so booking earlier is advisable if you're traveling during these times. If you're planning a spontaneous getaway, Expedia also offers last-minute Stock Island vacation packages.

How many days do you need for a Stock Island vacation?

Most Stock Island vacation packages last around 4 days. Stock Island is a beach destination known for its family-friendly attractions. This allows time to enjoy the area's highlights and explore local spots like the Key West Golf Club. While some travelers opt for weekend trips, week-long stays are also popular, and a select few choose extended two-week trips. Your Stock Island vacation package can be customized around these activities.

Can I change or cancel my Stock Island vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Stock Island vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Stock Island vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Stock Island vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Stock Island?

To find last-minute vacation packages to Stock Island, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Stock Island vacation packages?

Free cancellation on a Stock Island vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Stock Island vacation as a package or separately?

An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Stock Island getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Stock Island vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.

Stock Island Vacations from $2,123

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

The Latest Stock Island vacation packages

Douglas House - Adults Only

The Key West Hotel

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Stay near popular Stock Island attractions

Key West Golf Club

Key West Tropical Forest and Botanical Garden

Florida Keys Community College Library

Tennesse Williams Fine Art Center

What to do in Stock Island

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

Champagne and Sunsets: A Key West Catamaran Adventure

Sunset Sail in Key West with Beverages Included

Stock Island Hotel Deals

Hilton Key West Resort & Marina

The Perry Hotel & Marina Key West

Aqua Lodges at Hurricane Hole Marina

Find the Best Stock Island Vacation Packages

Things to do in and around Stock Island

Find the best attractions in and around Stock Island

Best time to go to Stock Island

Tips to save on your trip to Stock Island

Stock Island Essential Information

More vacations you might like

Frequently asked questions

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