Windley Key Vacation Packages

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Top Windley Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Avi Lux Stay

Avi Lux Stay

4.5 out of 5
East Fort Lauderdale
Save 100% on your flight
Price was CA $2,433, price is now CA $1,315 per person
CA $1,315
per person
Jan 4 - Jan 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
7.6/10 Good! (10 reviews)
If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.

Reviewed on Aug 28, 2025

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 $58,747, price is now CA $28,266 per person
CA $28,266
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Save 100% on your flight
Price was CA $3,736, price is now CA $2,194 per person
CA $2,194
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very good! (1,220 reviews)
The property is a great view but the toilet in my beachfront view room did not work, Elevator was not working, Staff member who was also waiting for elevator said the elevators has been a issue for months.Having to use stairs with travel luggage is bad

Reviewed on Oct 28, 2026

Miami Vacation Rentals - Downtown

Miami Vacation Rentals - Downtown

5 out of 5
Downtown Miami
Price was CA $4,854, price is now CA $2,917 per person
CA $2,917
per person
Jan 1 - Jan 8
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
9/10 Wonderful! (111 reviews)
Checkin and checkout process perfect Location perfect Apartment: rooms, kitchenette, balcony, … perfect Amenities perfect ViceVersa restaurant perfect Reception a bit too vibrant 🙃

Reviewed on Oct 23, 2026

Broadway Suites Downtown by RocketStay

Broadway Suites Downtown by RocketStay

3.5 out of 5
Coral Way
Price was CA $2,892, price is now CA $1,758 per person
CA $1,758
per person
Dec 28 - Jan 4
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8.6/10 Excellent! (230 reviews)
Muy bien ubicado, limpio, buena relación precio calidad

Reviewed on Aug 9, 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 $336 per night from Nov 18 to Nov 19
CA $336
CA $481 total
Nov 18 - Nov 19
includes taxes & fees
9.2/10 Wonderful! (303 reviews)
"This was by far the best hotel I have ever stayed in. It caters for all of your needs and you don’t have to leave the hotel at all if you don’t want to. They have thought about every little detail. I hope to come back one day"

Reviewed on Oct 28, 2026

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 $170 per night from Oct 29 to Oct 30
CA $170
CA $237 total
Oct 29 - Oct 30
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
"We were disappointed in a few things, one being the comfort- the couch in our room was so uncomfortable we couldn’t sit for long at all- it was also dirty with stains- fir the cost if the room, spending some money on a new, comfortable couch with washable cushion covers wouldn’t be too much to ask- ..."

Reviewed on Oct 28, 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 $237 per night from Nov 12 to Nov 13
CA $237
CA $266 total
Nov 12 - Nov 13
includes taxes & fees
9/10 Wonderful! (303 reviews)
"This is a family run resort. The grounds are beautiful and the pool is amazing. We will be back!"

Reviewed on Oct 25, 2026

Coconut Cove Resort and Marina
See all 2,682 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

What to do in Windley Key

Private 3-Hour Islamorada Sandbar Tour

Private 3-Hour Islamorada Sandbar Tour

CA $705
per traveller
100% of travellers recommend
Private 3-Hour Islamorada Sandbar Tour
See all activities in Windley Key

Frequently asked questions

How much does a Windley Key vacation package cost?
Custom make your Windley Key package from just CA $1,315. 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.