Windley Key Vacation Packages

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Top Windley Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
A Perfect Stay on Ocean Drive I had a wonderful stay at this hotel right on Ocean Drive in South Beach. The location is unbeatable—just steps from the beach and in the heart of all the action. The customer service was attentive and friendly, always ready to help with a smile. The on-site restaurant was a pleasant surprise—great food, good vibes, and drinks. The decor throughout the hotel is stylish and inviting, with that classic South Beach charm. Highly recommend for anyone looking to soak up the Miami vibe in comfort and style!

Reviewed on Jul. 31, 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very Good! (906 reviews)
The property had just gone under new management, and things were a bit hectic. Unfortunately, we didn’t have TV service during our entire stay. However, the manager, Eric, went above and beyond to make up for the inconvenience—providing $15 food vouchers throughout our visit and waiving the resort fees. What a fantastic way to turn things around and keep a guest happy! Superb team and a perfect location. Be sure to go see Eric and his staff—they’re truly amazing individuals!

Reviewed on Jul. 31, 2025

Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (136 reviews)
Room was not fully equipped and bathroom was not clean

Reviewed on Aug. 1, 2025

Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (2,401 reviews)
Room very small. And garage situation is difficulty due to elevator upgrades. Hopefully it will be better soon.

Reviewed on Jul. 30, 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 13 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
Needs new sheets They felt like they had small balls from being super used Place need new bed with prosper new linen I stayed at a TownePlace for three nights that had better mattress and linen

Reviewed on Aug. 1, 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 $245 per night from Aug 19 to Aug 20
CA $245
CA $367 total
Aug 19 - Aug 20
includes taxes & fees
9/10 Wonderful! (53 reviews)
Three Waters is a beautiful place to vacation.
"Three Waters Resort was wonderful. We stayed in the Cove and it was very relaxing. The accommodations were spacious and clean."

Reviewed on Jul. 27, 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! (999 reviews)
"The property was prestine with a nice pool overlooking the water and a beautiful beach. I like the music they played on speaker in the recreational areas. They have dim lights at night the reflect on the water..so relaxing. The staff was excellent and manager, Thomas, was outstanding."

Reviewed on Jul. 27, 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 $178 per night from Sep 2 to Sep 3
CA $178
CA $201 total
Sep 2 - Sep 3
includes taxes & fees
7.6/10 Good! (809 reviews)
Very Relaxing
"Beautiful setting with nice pool as well! The staff is very friendly and helpful, especially Clancy!!"

Reviewed on Jul. 30, 2025

Coconut Cove Resort and Marina
See all 2,712 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

What to do in Windley Key

Explore the Mangrove Creeks with an All Day Kayak Rental

Explore Mangrove Creeks with an All Day SUP/single kayak Rental

CA $64
per adult
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
Ft. Lauderdale to Key West Bus Tour w/ 6 hours of free time in KW

Ft. Lauderdale to Key West Day Trip Quality Day Tours

CA $308
per adult
Ft. Lauderdale to Key West Day Trip Quality Day Tours
Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch

Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch

CA $341
per adult
Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch
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 $493. 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.