Stock Island Vacation Packages

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Top Stock Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
New Town
Price was CA $2,258, price is now CA $1,533 per person
CA $1,533
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
8.8/10 Excellent! (1,749 reviews)
Clean room and the staff were very friendly.

Reviewed on Feb 8, 2026

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Price was CA $3,200, price is now CA $1,773 per person
CA $1,773
per person
Apr 26 - May 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
This place is amazing! The property is beautiful and quiet. The pool area was clean and well cared for. Our room was spacious, very clean and had everything we needed. The staff was kind and always helpful. We would definitely go back.

Reviewed on Feb 5, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was CA $6,545, price is now CA $4,348 per person
CA $4,348
per person
Mar 16 - Mar 20
found 20 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Everything was great. I couldn’t complain about anything if I wanted to. Thanks for a great stay!

Reviewed on Jan 28, 2026

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was CA $2,907, price is now CA $1,945 per person
CA $1,945
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Clean, nice and beautiful view

Reviewed on Feb 8, 2026

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was CA $2,445, price is now CA $1,646 per person
CA $1,646
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Said there was beach There is no beach Our initial flight was cancelled we re-rebooked for two days later The hotel would not refund the 2 nights We will reach out again to Expedia but hotel is. also very difficult to reach a live person

Reviewed on Feb 5, 2026

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Stock Island Hotel Deals

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $468 per night from Feb 9 to Feb 10
CA $468
per night
Feb 9 - Feb 10
8.8/10 Excellent! (1,801 reviews)
The room was very nice and homey feeling. The staff was very nice. We enjoyed breakfast lunch and diner at the restaurant the Waite staff was very friendly and food was good. We enjoyed the shuttle that is offered the drivers were knowledgeable about the island and history. Jeffery was the best. ...

Reviewed on Feb 3, 2026

Oceans Edge Key West Resort, Hotel & Marina
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
7001 Shrimp Road Key West FL
The price is CA $504 per night from Mar 5 to Mar 6
CA $504
per night
Mar 5 - Mar 6
9.4/10 Exceptional! (1,202 reviews)
The Perry Hotel was a great experience. Traveled with a friend and stayed in a Mangrove room. Rooms were clean and well cared for. Pool and outside area is clean too. Although outside of downtown, there is a free shuttle that takes you downtown. If you are planning a specific time to go into town, ...

Reviewed on Feb 1, 2026

The Perry Hotel & Marina Key West
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

2 out of 5
5130 Overseas Hwy Key West FL
The price is CA $303 per night from Mar 1 to Mar 2
CA $303
per night
Mar 1 - Mar 2
8.8/10 Excellent! (175 reviews)
Communication was quick and friendly, the houseboat was clean, and the location is wonderful. Great restaurant on site, and more good food and happy hours within easy walking distance. Highly recommended!

Reviewed on Jan 30, 2026

Aqua Lodges at Hurricane Hole Marina
See all 3,143 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.
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What to do in Stock Island

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $61
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Friends cheers with cocktails on Key West cruise

Key West Afternoon At The Reef Snorkeling Adventure with Open Bar!

CA $65
per adult
92% of travellers recommend
Key West Afternoon At The Reef Snorkeling Adventure with Open Bar!
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $79
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
See all activities in Stock Island

Frequently asked questions

Can I cancel my flight booking to Stock Island due to COVID-19?
Our convenient Customer Service Portal is where you can get information about changing or canceling your flight due to COVID-19. Before you reserve a seat, it's a good idea to read the terms and conditions of your preferred airline too.
What's the best way to find cheap flights to Stock Island that have flexible change policies?
When it comes to flying these days, flexibility is a must. That's why we've added a "No change fee" filter to help you find flexible, affordable fares to Stock Island. It's on the left of your screen just underneath the "Flexible change policies" heading.
What are some of the general tips for travelers to Stock Island during the COVID-19 outbreak?
The COVID-19 outbreak has affected how the world works in all kinds of ways, including how we can travel safely. These tips will help you navigate these new challenges and prepare you for your vacation in Stock Island:
  • Know what, if any, restrictions or rules apply to both your origin and destination. It may not be possible to travel depending on local circumstances, so don't forget to check government advisories before booking.
  • When you go through airport checkpoints, keep your face mask on. You will be asked to lower it briefly for identification purposes. Anyone refusing to wear a mask may be fined and denied boarding.
  • Do not hand your boarding pass (electronic or paper) directly to a TSA employee. Rather, you should position the pass on the reader and then hold it up so the agent can inspect it.
  • One container of liquid hand sanitizer is now permitted in your carry-on luggage. It must not be larger than 12 oz (350 ml), and you'll have to take it out of your bag for screening.
  • Remove personal items from your pockets, such as your phone, keys and wallet, and put them in your carry-on rather than the bins. This will minimize handling during the screening process.
  • Transport any food items in a clear plastic bag and also put them in a screening bin. Separating food from your carry-on makes it less likely that a TSA agent will need to open and touch your bag for inspection.

Which airlines fly to Stock Island?
Lock in your seat with Delta and then start planning your Stock Island must-do list. This leading carrier has 191 flights each month to Key West Intl. Airport (EYW), a key gateway.
How can I find cheap tickets to Stock Island?
One of the easiest ways to score cheap tickets to Stock Island is to be flexible with your travel dates. Search for your flights, then click "flexible dates" above the results. It will reveal the cheapest prices for nearby days. The lowest price for a flight to Stock Island in the last seven days was . Booking ahead of time will usually help you get an even bigger bargain.
How much is a flight to Stock Island?
You could have nabbed a return ticket to Stock Island from anywhere between and in the last seven days. For one-way trips departing from (), the lowest amount paid during this time was .
What are the most popular airports to fly into in Stock Island?
Start arranging your Stock Island escape by booking a ticket on one of the 1119 flights a month to Key West Intl. Airport (EYW). This is the region's main entryway.
When is the cheapest time to fly to Stock Island?
If you'd prefer to spend your hard-earned vacation money getting to know Stock Island rather than on getting there, leave early in the week. The most economical day to travel is normally Tuesday, with Monday coming in second. With many folks traveling on weekends, Saturday often has the costliest ticket prices.
How much is a plane ticket to Stock Island?
In the last seven days, fares to Stock Island cost between and . The early bird catches the worm, so snap up a cheap flight today.
Which airlines with flights to Stock Island employ COVID-19 cleanliness policies?
To help lessen the contact between passengers and aircrew during the ongoing pandemic, airlines have taken physical distancing and other measures to the skies. They include:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.