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
Save 100% on your flight
per person
Sep 29 - Oct 6
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Key West (EYW)
8.8/10 Excellent! (1,744 reviews)
Amazing time. Clean, very nice staff

Reviewed on Jul. 15, 2025

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
10/10 Exceptional! (1,002 reviews)
This is my second stay at Almond Tree and since it was so nice the first time I’ll just keep going back. The hotel is great and the location can’t be beat.

Reviewed on Jul. 9, 2025

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
Very clean, relaxing, and the staff went above and beyond. Highly recommend!

Reviewed on Jul. 13, 2025

The Grand Guesthouse

The Grand Guesthouse

2.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Sep 22 - Sep 28
found 8 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Key West (EYW)
9.6/10 Exceptional! (1,000 reviews)
Great place, cousy and very clean. Well located

Reviewed on Jun. 29, 2025

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Great hotel! Lot of amenities!

Reviewed on Jul. 10, 2025

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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 Aug 10 to Aug 11
CA $255
CA $367 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,680 reviews)
"Very friendly family oriented place."

Reviewed on Jul. 15, 2025

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 $197 per night from Jul 17 to Jul 18
CA $197
CA $301 total
Jul 17 - Jul 18
includes taxes & fees
9.4/10 Exceptional! (1,024 reviews)
"Magnificent property on the marina! Beautiful hotel and rooms. Pools were clean. Bar outsude super!"

Reviewed on Jul. 14, 2025

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 $73 per night from Jul 25 to Jul 26
CA $73
CA $312 total
Jul 25 - Jul 26
includes taxes & fees
8.8/10 Excellent! (158 reviews)
"First time staying on a houseboat but will definitely not be the last. We loved sitting on the back porch watching the marine life."

Reviewed on Jun. 30, 2025

Aqua Lodges at Hurricane Hole Marina
See all 3,172 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

What to do in Stock Island

Half-Day Key West's Ultimate Sandbar Adventure with Mangrove Kayak Eco Tour

Half-Day Key West's Ultimate Sandbar Adventure with Mangrove Kayak Tour

CA $192
per adult
98% of travellers recommend
Half-Day Key West's Ultimate Sandbar Adventure with Mangrove Kayak Tour
Dry Tortugas National Park Day Trip by Axopar 37 XC

Dry Tortugas National Park Day Trip by Luxury Boat: Axopar 37 XC

CA $4,118
per adult
Dry Tortugas National Park Day Trip by Luxury Boat: Axopar 37 XC
Key West Back-Country Eco Tour with Snorkel

Key West Back-Country Tour with Snorkel - Drive Your Own Boat

CA $233
per adult
100% of travellers recommend
Key West Back-Country Tour with Snorkel - Drive Your Own Boat
See all activities in Stock Island

Frequently asked questions

How much does a Stock Island vacation package cost?
Our Stock Island packages, which start at just CA $1,098, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.