Windley Key Vacation Packages

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Top Windley Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
President Villa

President Villa

3.5 out of 5
South Beach
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
Hospitable staff, clean, location ideal to walking distance to beach and shopping. Safe place!

Reviewed on Aug. 8, 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
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8/10 Very Good! (1 review)
Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
per person
Oct 25 - Nov 1
found 19 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9/10 Wonderful! (2,473 reviews)
Food at the restaurant is good service good

Reviewed on Aug. 9, 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
per person
Oct 25 - Nov 1
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (911 reviews)
Perfectly situated. Right on the strip. Walking distance to the beach and night life. We had an ocean view room, but even with windows closed, it could get pretty noisy in the evening.

Reviewed on Aug. 11, 2025

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
per person
Oct 25 - Nov 1
found 19 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.8/10 Excellent! (1,156 reviews)
It's a very quaint hotel. The rooms are spacious with a living area. The pool is small, but it's a good thing there were not too many people. Great happy hours even during the weekend. I didn't like that they only have valet parking. Albert was the best server at Ocean 2000. And Jennifer and Melissa at the O2K Lounge.

Reviewed on Aug. 10, 2025

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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

3.5 out of 5
84001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $268 per night from Sep 8 to Sep 9
CA $268
CA $393 total
Sep 8 - Sep 9
includes taxes & fees
8.8/10 Excellent! (56 reviews)
"Great resort, excellent staff and customer service, I'll definitely coming back"

Reviewed on Aug. 7, 2025

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 $141 per night from Aug 12 to Aug 13
CA $141
CA $204 total
Aug 12 - Aug 13
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Great vibe. Very helpful. Great scenery and location!"

Reviewed on Aug. 10, 2025

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 $173 per night from Sep 8 to Sep 9
CA $173
CA $195 total
Sep 8 - Sep 9
includes taxes & fees
7.6/10 Good! (812 reviews)
The most relaxing night
"Amazing group of people works in this hotel ! Super friendly can’t wait to come back again"

Reviewed on Aug. 1, 2025

Coconut Cove Resort and Marina
See all 2,711 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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Discover the most popular places to visit in Windley Key

Windley Key Fossil Reef Geological State Park

Windley Key Fossil Reef Geological State Park

Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails.

Windley Key Fossil Reef Geological State Park

Frequently asked questions

How much does a Windley Key vacation package cost?
Custom make your Windley Key package from just CA $754. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.