Stock Island Vacation Packages & Trips 2025 from CA $1,381

Top Stock Island Vacation Deals

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

The Perry Hotel & Marina Key West

Save 100% on your flight

per person

Jul. 18 - Jul. 25

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Key West (EYW)

9.4/10 Exceptional! (1,010 reviews)

A very nice place to stay. Grounds were lovely

Reviewed on Apr. 30, 2025

Ridley House - Key West Historic Inns

Key West Historic District

Save 100% on your flight

per person

Jul. 21 - Jul. 28

found 20 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Key West (EYW)

9.2/10 Wonderful! (762 reviews)

Really liked the location of the property and quiet area.

Reviewed on Apr. 29, 2025

The Gardens Hotel

Old Town Key West

Save 100% on your flight

per person

Jul. 21 - Jul. 28

found 20 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

We stayed at this hotel during our trip to Key West and overall had a great experience. The room had everything we needed and even more — it was clean, cozy, and thoughtfully prepared. The atmosphere was welcoming, and the service was excellent; the staff were friendly and always ready to help. The only downside was breakfast. I ordered avocado toast, but the bread was badly burnt, which really took away from the dish. Hopefully, it was just a one-time issue. Aside from that, it’s a lovely hotel, and I would happily stay here again!

Reviewed on Apr. 30, 2025

The Grand Guesthouse

Old Town Key West

Save 100% on your flight

per person

Jun. 13 - Jun. 18

found 8 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9.6/10 Exceptional! (1,001 reviews)

This is sooo cute, clean and convenient. Was able to bike to Mallory square at sunset. Then able to hit Duvall Street on the way home. Manager is so nice and incredibly helpful. Definitely will stay here again

Reviewed on Apr. 23, 2025

Southernmost Beach Resort

Old Town Key West

per person

Jul. 21 - Jul. 28

found 20 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Key West (EYW)

8.6/10 Excellent! (2,353 reviews)

Piscina the water ins’t clear

Reviewed on Apr. 30, 2025

Ready to book your vacation to Stock Island?

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Stock Island Hotel Deals

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue, Key West, FL

Fully refundableReserve now, pay when you stay

CA $266

CA $380 total

includes taxes & fees

May 22 - May 23

8.8/10 Excellent! (1,650 reviews)

"Great location for a quiet getaway. The resort has plenty of amenities, including restaurant and bar, 6 pools, and a gym. The rooms are clean, spacious, and thoughtfully designed, some including a terrace. There is also complimentary shuttle to Key West, 2hr bike and kayak rental. The only remark ..."

Reviewed on Apr. 28, 2025

The Perry Hotel & Marina Key West

7001 Shrimp Road, Key West, FL

Fully refundableReserve now, pay when you stay

CA $295

CA $413 total

includes taxes & fees

May 22 - May 23

9.4/10 Exceptional! (1,011 reviews)

"cozy and quiet. Nice marina view. Great food onsite."

Reviewed on Apr. 29, 2025

Aqua Lodges at Hurricane Hole Marina

5130 Overseas Hwy, Key West, FL

CA $191

CA $447 total

includes taxes & fees

May 31 - Jun 1

8.8/10 Excellent! (134 reviews)

Comfortable accommodation - need bug spray

"Got very timely and accurate communications from the property manager. No problem "checking in" with lockbox, etc. The space was just as advertised - beds were very comfortable and clean, plenty of towels in the bathroom, A/C kept the space at a comfortable temperature. The listing did give a heads ..."

Reviewed on Apr. 28, 2025

See all 3,254 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.

Frequently asked questions

How much does a Stock Island vacation package cost?

Our Stock Island packages, which start at just CA $1,381, are the easiest way to save. Pick and choose your preferred hotels, flights and rental car to create your dream itinerary.

How do I get a cheap travel package to Stock Island?

Crafting your own Stock Island vacation package with Expedia is a simple way to save. We offer more than 550 air carriers and 1,000,000 hotel options globally. With such a fantastic range to choose from, you’ll have no issues putting together your dream vacation.

Where should I stay in Stock Island?

With interesting attractions like Smathers Beach and Key West Art and Historical Society in this neighborhood, look for a hotel located near them. Key West Golf Club is another Stock Island hot spot that draws in the crowds.

What are the top hotels in Stock Island?

If it’s your first visit to Stock Island, book a room at Welcome Aboard or Oceanfront 3 Bedroom Condo - 6 Pools. Both offer comfortable beds and are favorites with lots of travelers.

How far in advance should I book my Stock Island vacation?

It’s always wise to book early. Air carriers usually advertise flights up to 12 months in advance, and this is a fantastic opportunity to pick up some rock-bottom prices. Boss just told you to take all your vacation days next month? That’s fine too — Expedia are never short of fantastic bargains to whisk you away on the getaway of your dreams, at a price you can afford.

What does an Expedia Stock Island travel package include?

Flights, hotels and rental cars — we have them covered. With Expedia, you can shape your Stock Island package however you want. All you have to do is work out what you need. Once you’ve made your booking, you can add on fun things like activities and tours. The more you bundle, the greater the savings!

What should I know before booking a Stock Island travel package?

So many places to go, so many things to see. With a package, you can tick more of them off your list. Bundle your hotels, flights and rental cars and make big savings.

Can I choose my airline with a Stock Island Expedia vacation package?

Yes, the choice is yours. Expedia has access to more than 550 partner airlines throughout the world, so you can tailor your Stock Island vacation according to your needs and budget.

If I'm not able to travel, can I cancel my Stock Island vacation package?

Because we understand life can be unpredictable, the answer is yes. To find out more, visit our Customer Service Portal. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to change or cancel it without penalty. Your airline, hotel or car rental company may impose a fee if you made your booking a while ago.