Stock Island Vacation Packages

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Top Stock Island Vacation Deals

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

4 out of 5
Old Town Key West
Price was CA $1,470, price is now CA $1,036 per person
CA $1,036
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,267 reviews)
Great stay. Little gem that feels like home. Casual accommodations that fit perfectly for a trip to paradise. Two free drinks when you check in, SOLD. Will definitely return.

Reviewed on May 12, 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was CA $4,677, price is now CA $3,136 per person
CA $3,136
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (552 reviews)
The staff at the hotel were excellent. Very friendly and helpful. Room was very clean and comfortable. We were right in the middle of the old district which had many many places to explore. Hotel had a wonderful hidden pool with live music/bar next to it in case we just wanted to relax after exploring all day.

Reviewed on Apr 21, 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 $2,269, price is now CA $1,716 per person
CA $1,716
per person
Jul 16 - Jul 19
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,066 reviews)
The property staff wasn’t as attentive as I would have hoped at a resort like this. The rooms were spacious and clean.

Reviewed on May 12, 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 $2,180, price is now CA $1,662 per person
CA $1,662
per person
Jul 16 - Jul 19
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,034 reviews)
The 2 bedroom suite was space clean and every comfortable for our group of 5. When we needed more towels they came very fast with them. Will stay here again.

Reviewed on May 10, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Price was CA $1,495, price is now CA $1,153 per person
CA $1,153
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (3,272 reviews)
This is a very nice property that has great amenities. The two big pools each have nice bars with them and you can charge what you get to your room so you don't have to take your wallet. They also give you your key card on a wristband so you don't have to worry about taking anything when you go to the or the ocean. I also really enjoyed that it's on the bottom of Duval Street, so you can get to a lot of the bars and restaurants but you're not right beside them

Reviewed on May 13, 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 $255 per night from May 25 to May 26
CA $255
CA $370 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (1,857 reviews)
Everything about oceans edge was wonderful! The rooms were beautiful! The beds and pillows do comfortable! The view was beautiful! The property and pool lovely. Loved the marina view! The shuttle to downtown was great and the drivers - esp Jeffrey! And the food and drinks at Yellowfin Restaurant ...

Reviewed on May 12, 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
Fully refundableReserve now, pay when you stay
The price is CA $268 per night from May 26 to May 27
CA $268
CA $384 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (1,268 reviews)
Love the pool and marina, but Marina needs to have floating garbage removed.

Reviewed on May 12, 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 $171 per night from May 17 to May 18
CA $171
CA $423 total
May 17 - May 18
includes taxes & fees
9/10 Wonderful! (185 reviews)
My stay at Aqua Lodges at Hurricane Hole Marina was not terrible, but it definitely was not what I expected. The location has potential and the area is nice, however, on the day we were leaving I noticed bed bugs in the room. After discovering them, I immediately contacted the host. They told me ...

Reviewed on May 13, 2026

Aqua Lodges at Hurricane Hole Marina
See all 3,126 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 $59
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

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

CA $77
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Snorkler waving underwater in Key West

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

CA $75
per adult
86% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
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.