Stock Island Vacation Packages

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Top Stock Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Old Town Key West
Price was CA $2,269, price is now CA $1,825 per person
CA $1,825
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
8.6/10 Excellent! (380 reviews)
Great location, wonderful room, great pool, and great views. Lacking services: no shuttle, no restaurant, you pay resort fees per night but no amenities? We feel like they used the bait and switch on us, great reservation price on room but hit you with nightly fees once you get there. That was our only real negative

Reviewed on Jun 16, 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was CA $2,894, price is now CA $2,239 per person
CA $2,239
per person
Aug 27 - Aug 31
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (558 reviews)
We loved staying here and highly recommended it. Only thing that people might not like is the solo musicians play till 11pm every night. We didn’t mind it since we are not early birds.

Reviewed on Jun 7, 2026

Caribbean House

Caribbean House

3 out of 5
Old Town Key West
Price was CA $2,401, price is now CA $1,900 per person
CA $1,900
per person
Aug 28 - Sep 4
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9/10 Wonderful! (367 reviews)
Awesome affordable spot. Perfect spot for spending the day out and about and coming back to sleep for the night.

Reviewed on Jun 17, 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 $2,448, price is now CA $1,942 per person
CA $1,942
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
9.4/10 Exceptional! (1,094 reviews)
A later checkout time would be ideal. 10:00am is too early.

Reviewed on Jun 17, 2026

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

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

3 out of 5
Key West Historic District
Price was CA $3,056, price is now CA $2,485 per person
CA $2,485
per person
Aug 28 - Sep 4
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
No reviews

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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 $239 per night from Jul 8 to Jul 9
CA $239
CA $354 total
Jul 8 - Jul 9
includes taxes & fees
9/10 Wonderful! (1,860 reviews)
"The property was well maintained and the house keeping was excellent."

Reviewed on Jun 14, 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 $234 per night from Jun 23 to Jun 24
CA $234
CA $348 total
Jun 23 - Jun 24
includes taxes & fees
9.4/10 Exceptional! (1,278 reviews)
"Not a package deal on Expedia then had to spend more money on hidden fees. If I buy a package I want everything included with no surprise fees."

Reviewed on Jun 16, 2026

The Perry Hotel & Marina Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Jun 21 to Jun 22
CA $176
CA $278 total
Jun 21 - Jun 22
includes taxes & fees
8.4/10 Very Good! (2,407 reviews)
"Blue Flamingo was a wonderful hotel and I will go back. The pools were lovely, but it would have been nice if one pool was designated to children and the other for adults. The room was lovely as well. Our only problem was with housekeeping. Upon cleaning our room, they took all the dirty towels but ..."

Reviewed on Jun 17, 2026

Blue Flamingo Resort Key West
See all 3,091 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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Stay near popular Stock Island attractions

S2KBYX

Stock Island Yacht Club & Marina

9.2/5 (8,513 reviews)
Explore the waterfront of Stock Island Yacht Club & Marina and enjoy activities such as boating in Key West. Discover the area's beautiful sunsets and lively bars.
See properties

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.