Windley Key Vacation Packages

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Top Windley Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
Price was CA $1,247, price is now CA $612 per person
CA $612
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Miami (MIA)
9/10 Wonderful! (2,473 reviews)
First time there. Definitely will return.

Reviewed on Aug. 19, 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 $22,592, price is now CA $10,212 per person
CA $10,212
per person
Oct 11 - Oct 16
found 2 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Miami (MIA)
8/10 Very Good! (1 review)
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Price was CA $1,355, price is now CA $677 per person
CA $677
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Miami (MIA)
8.8/10 Excellent! (1,156 reviews)
What a great experience, the whole staff was amazing I very recommend this place to stay

Reviewed on Aug. 19, 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was CA $1,715, price is now CA $888 per person
CA $888
per person
Nov 7 - Nov 11
found 5 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Miami (MIA)
8.2/10 Very Good! (911 reviews)
The property is welll located at the Ocean Drive on South Beach, though not on the beach itself. The staff was very friendly and thoroughly helpful. Food was great and tasty on the palate. The service and handling by Mr. Eric was superb and absolutely pleasing,

Reviewed on Aug. 19, 2025

EAST Miami Residences

EAST Miami Residences

5 out of 5
Downtown Miami
Price was CA $4,350, price is now CA $2,473 per person
CA $2,473
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9/10 Wonderful! (70 reviews)
This place is very beautiful, greats views with great customer service. This place just makes you feel very comfortable like your at home

Reviewed on Aug. 20, 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 $269 per night from Sep 18 to Sep 19
CA $269
CA $394 total
Sep 18 - Sep 19
includes taxes & fees
9/10 Wonderful! (57 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
The price is CA $160 per night from Aug 24 to Aug 25
CA $160
CA $225 total
Aug 24 - Aug 25
includes taxes & fees
8/10 Very Good! (1,003 reviews)
Nice Resort But Best for Boat Owners
"We booked a waterfront king suite with a balcony and kitchenette, which was very spacious. The room was very clean and convenient. The "living room" had a sofa and tv and was located next to the balcony. The kitchenette was between the living area and bedroom, opposite the bathroom, which also had ..."

Reviewed on Aug. 11, 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 $152 per night from Aug 21 to Aug 22
CA $152
CA $172 total
Aug 21 - Aug 22
includes taxes & fees
7.6/10 Good! (813 reviews)
"Staff were very nice and welcoming. Nice pool and view. Room was nice clean and comfortable. Definitely would stay again"

Reviewed on Aug. 15, 2025

Coconut Cove Resort and Marina
See all 2,696 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.
All Inclusive Vacations
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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 $612. 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.