Stock Island Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Stock Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was CA $4,689, price is now CA $3,497 per person
CA $3,497
per person
Dec 9 - Dec 13
just found
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.2/10 Wonderful! (564 reviews)
Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!

Reviewed on Oct 29, 2026

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3 out of 5
Old Town Key West
Save 100% on your flight
Price was CA $9,365, price is now CA $6,547 per person
CA $6,547
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
10/10 Exceptional! (1 review)
Loved the closeness to Duval st and the privacy

Reviewed on Oct 17, 2025

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

3 out of 5
Old Town Key West
Save 100% on your flight
Price was CA $5,691, price is now CA $4,169 per person
CA $4,169
per person
Jan 20 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
10/10 Exceptional! (1 review)
Location, comfort and great customer service! A great place for a family to stay and share in some fun together!!

Reviewed on Jul 26, 2026

NEW The Rigby House - Pvt Pool Amazing Location

NEW The Rigby House - Pvt Pool Amazing Location

2.5 out of 5
Key West Historic District
Price was CA $29,319, price is now CA $22,230 per person
CA $22,230
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
No reviews

Brand New Build Larkshine House - Pool

Brand New Build Larkshine House - Pool

2 out of 5
Price was CA $24,972, price is now CA $18,979 per person
CA $18,979
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
No reviews

Ready to book your vacation to Stock Island?

 

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Stock Island Hotel Deals

Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Nov 15 to Nov 16
CA $177
CA $280 total
Nov 15 - Nov 16
includes taxes & fees
9/10 Wonderful! (1,803 reviews)
"unlike shawer floor"

Reviewed on Nov 3, 2026

Hilton Key West Resort & 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 $162 per night from Nov 30 to Dec 1
CA $162
CA $264 total
Nov 30 - Dec 1
includes taxes & fees
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 $221 per night from Nov 12 to Nov 13
CA $221
CA $490 total
Nov 12 - Nov 13
includes taxes & fees
Aqua Lodges at Hurricane Hole Marina
See all 3,097 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

Stay near popular Stock Island attractions

A marina with various boats docked, calm water, and a clear sky.

Stock Island Yacht Club & Marina

9.2/10 (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

What to do in Stock Island

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $63
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
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

CA $83
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
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 $3,497, 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.