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 $1,990, price is now CA $1,511 per person
CA $1,511
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (1,230 reviews)
Winslow’s Bungalows offers a delightful stay for guests. It is centrally located for exploring Key West. The staff were very helpful.

Reviewed on Apr 10, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was CA $4,530, price is now CA $2,862 per person
CA $2,862
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (542 reviews)
Great location! We were very impressed with Chris! He told us where to park and was very welcoming when we arrived. The loft room setup was perfect for us and the Bali Bar did not disappoint! We will be back!!

Reviewed on Apr 5, 2026

Duval s Duet on Duval by Brightwild

Duval s Duet on Duval by Brightwild

2 out of 5
Old Town Key West
Price was CA $13,392, price is now CA $10,102 per person
CA $10,102
per person
Jul 4 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
No reviews
Sky Suites Retreat by Brightwild 2 Stunning Condos

Sky Suites Retreat by Brightwild 2 Stunning Condos

2 out of 5
Old Town Key West
Price was CA $12,862, price is now CA $9,710 per person
CA $9,710
per person
Jul 4 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
No reviews
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
Old Town Key West
Price was CA $2,357, price is now CA $1,782 per person
CA $1,782
per person
Jun 13 - Jun 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
8.4/10 Very Good! (595 reviews)
We had a great time. The hotel is beautiful and in a great location. The beach and two pools are perfectly located. A easy walk to Duval st. The rooms are nice but not much storage or closet space for clothing. The showers could use some shelving for personal shower products. The food and drinks are outrageously expensive, so you may wa t to think about dinner and drinks elsewhere. Overall we really loved the place. The staff was amazing. We will come back next year.

Reviewed on Apr 11, 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 $364 per night from May 4 to May 5
CA $364
CA $495 total
May 4 - May 5
includes taxes & fees
9/10 Wonderful! (1,862 reviews)
Our once-in-a-lifetime family trip was deeply disappointing because of our experience with the restaurant staff at Oceans Edge Resort & Marina Key West. Their rude and unprofessional behavior had a major negative impact on what should have been a special vacation. We chose to eat most of our meals ...

Reviewed on Apr 11, 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 $326 per night from May 11 to May 12
CA $326
CA $451 total
May 11 - May 12
includes taxes & fees
9.4/10 Exceptional! (1,245 reviews)
Property overall was amazing. Quiet, and very clean. Staff was great!

Reviewed on Apr 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 $228 per night from May 4 to May 5
CA $228
CA $489 total
May 4 - May 5
includes taxes & fees
9/10 Wonderful! (182 reviews)
Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again.

Reviewed on Apr 3, 2026

Aqua Lodges at Hurricane Hole Marina
See all 3,106 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 $58
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 $79
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

CA $75
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
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.