Windley Key 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 Windley Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Club - Pool - Gym - Parking - Heart of Brickell

The Club - Pool - Gym - Parking - Heart of Brickell

4 out of 5
Brickell
Price was CA $2,693, price is now CA $1,394 per person
CA $1,394
per person
Jan 23 - Jan 30
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
No reviews

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was CA $48,281, price is now CA $23,323 per person
CA $23,323
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

District 225 - Rooftop Pool - Gym - Parking - Downtown Miami

District 225 - Rooftop Pool - Gym - Parking - Downtown Miami

4 out of 5
Downtown Miami
Price was CA $2,709, price is now CA $1,401 per person
CA $1,401
per person
Jan 23 - Jan 30
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
No reviews

Brickell Sea View 2BR Free Parking by Palermo Home

Brickell Sea View 2BR Free Parking by Palermo Home

2.5 out of 5
Brickell
Price was CA $3,466, price is now CA $1,878 per person
CA $1,878
per person
Jan 23 - Jan 30
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
10/10 Exceptional! (1 review)
Very nice stay

Reviewed on Mar 16, 2026

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
Price was CA $2,905, price is now CA $1,616 per person
CA $1,616
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.6/10 Excellent! (1,002 reviews)
I loved that it was an unique property & easily accessible to everything.

Reviewed on Nov 5, 2026

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Windley Key Hotel Deals

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $293 per night from Nov 29 to Nov 30
CA $293
CA $433 total
Nov 29 - Nov 30
includes taxes & fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $182 per night from Nov 29 to Nov 30
CA $182
CA $251 total
Nov 29 - Nov 30
includes taxes & fees
8.2/10 Very good! (1,002 reviews)
"Short term stay for fishing. Nice quiet two bed in one room with small bath. Ocean is always beautiful, close to bars, food and fishing. I would say from location and structure in the 3.5 area with 5 being a high end $$$$$."

Reviewed on Nov 7, 2026

Fisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
The price is CA $239 per night from Nov 15 to Nov 16
CA $239
CA $269 total
Nov 15 - Nov 16
includes taxes & fees
Coconut Cove Resort and Marina
See all 2,684 properties in Windley Key
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 Windley Key attractions

Windley Key Fossil Reef Geological State Park

8.8/10 (184 reviews)
Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails.
See properties

Frequently asked questions

How much does a Windley Key vacation package cost?
Custom make your Windley Key package from just CA $1,394. Choose from any combination of hotels, flights and rental cars to build the escape you've been dreaming about. Be sure to add on one or two experiences!
How do I get a cheap travel package to Windley Key?
Bundle your hotels and flights with Expedia to save big bucks on your next adventure. With more than 550 air carriers and 1,000,000 hotels across the globe, your Windley Key vacation package can be customized exactly to suit your travel style. With all that extra cash, why not include one or more exciting tours and experiences? It's an easy way to unlock even more savings. That vacation you've always dreamed of in Windley Key is closer than you thought!
How far in advance should I book my Windley Key vacation?
While prices change from time to time, we generally advise booking your flight as early as possible. Many international fares become available on Expedia up to a year in advance. If you're booking last minute, you might still be in luck. Discount prices to Windley Key sometimes appear just weeks before departure.
What does an Expedia Windley Key travel package include?
Expedia has everything you need to lock in Windley Key escape, but what your package looks like depends on you. Select from any combination of flights, rental cars and hotels. Looking for some tours or experiences to keep you on the move? Once you've made your booking, you can add them on too. No matter your style, there's a vacation package to meet your needs.
What should I know before booking a Windley Key travel package?
So many places to go, so many things to do. With a package, you can check more of them off your list. Bundle your flights, hotels and rental cars and see how much you save.
Can I choose my airline with a Windley Key Expedia vacation package?
With a vacation package, you're in charge. Whether you'd prefer to fly to Windley Key in business or coach, simply pick from the available airline options. Expedia has access to more than 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Windley Key vacation package?
It is possible to cancel your Windley Key booking if your plans have been upended. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.

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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.