Windley Key Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Windley Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The 27 Wynwood

The 27 Wynwood

4 out of 5
Wynwood Art District
Price was CA $2,446, price is now CA $1,495 per person
CA $1,495
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
10/10 Exceptional! (5 reviews)
Property is beautiful. The rooftop top pool is amazing. Everything is really close to the main street in wynwood. Will definitely be back.

Reviewed on Jun 5, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $3,869, price is now CA $2,037 per person
CA $2,037
per person
Jul 13 - Jul 20
found 2 hours ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
5.8/10 (324 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

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 $20,471, price is now CA $10,879 per person
CA $10,879
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8/10 Very Good! (1 review)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was CA $3,328, price is now CA $1,988 per person
CA $1,988
per person
Aug 16 - Aug 23
found 20 hours ago
Roundtrip flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very Good! (1,145 reviews)
The room was always super, super clean. All of the staff members were amazing, and always extremely kind&helpful. The beach view was beautiful, the breakfast was outstanding we were always excited to have breakfast, the buffet&food was delicious.

Reviewed on Jun 12, 2026

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

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

4 out of 5
Price was CA $2,784, price is now CA $1,701 per person
CA $1,701
per person
Aug 2 - Aug 9
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (202 reviews)
Nice! I thoroughly enjoyed the experience. enjoyed it.

Reviewed on Jun 13, 2026

Ready to book your vacation to Windley Key?

 

Choose your dates

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 $379 per night from Jul 7 to Jul 8
CA $379
CA $529 total
Jul 7 - Jul 8
includes taxes & fees
9/10 Wonderful! (207 reviews)
"Nice! I thoroughly enjoyed the experience. enjoyed it."

Reviewed on Jun 13, 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 $200 per night from Jun 15 to Jun 16
CA $200
CA $271 total
Jun 15 - Jun 16
includes taxes & fees
8.2/10 Very Good! (1,012 reviews)
"We had a wonderful stay! The staff were friendly and welcoming. Our room was clean, spacious, and very comfortable, with everything we needed for a relaxing visit. The hotel amenities were excellent and really added to the overall experience. We would definitely stay here again and highly recommend ..."

Reviewed on Jun 9, 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 $250 per night from Jun 16 to Jun 17
CA $250
CA $282 total
Jun 16 - Jun 17
includes taxes & fees
9/10 Wonderful! (266 reviews)
"The property was very beautiful and the staff was great. They have an ice machine on site and a large pool area. The tiki bar is a great spot in the evening to sit and have a drink"

Reviewed on May 25, 2026

Coconut Cove Resort and Marina
See all 2,714 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Windley Key attractions

Windley Key Fossil Reef Geological State Park

4.4/5 (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

Can I cancel my flight booking to Windley Key due to COVID-19?
Our handy Customer Service Portal has information about canceling your Windley Key flight due to COVID-19. Before booking your tickets, it's smart to check the terms and conditions of your preferred carrier too.
What's the best way to find cheap flights to Windley Key that have flexible change policies?
We get that travel schedules can change in a flash, so locking in a flexible ticket with Expedia is always a smart move. Just tick the "No change fee" box directly below the "Flexible change policies" filter. Your well-priced and flexible flight to Windley Key is only a few clicks away.
What are some of the general tips for travelers to Windley Key during the COVID-19 outbreak?
With strict COVID-19 precautions to adhere to, travel looks a lot different at the moment. These are some helpful things to know before you pack your bags for Windley Key:
  • Look into what rules and restrictions apply to both your origin and destination. It may not be possible to travel depending on local circumstances, so be sure to check in advance.
  • When you pass through airport checkpoints, do not remove your face mask. You will be asked to briefly lower it for ID purposes. Passengers who refuse to wear a face mask may face civil penalties and may also be denied boarding.
  • Rather than handing a TSA agent your boarding pass, position it straight on the scanner yourself. Then, hold it up for inspection.
  • One liquid hand sanitizer container is now permitted in your carry-on bag. It must not be larger than 12 oz (350 ml), and you'll need to take it out of your bag for scanning.
  • Place any personal items (phone, keys and wallet) in your carry-on rather than a bin to minimize handling during the screening process.
  • Separate any food you're carrying for screening. Placing it in a clear plastic bag and into a bin reduces the need for a TSA officer to handle and inspect your belongings.

Which airlines fly to Windley Key?
Book your fare with Delta and then begin planning your Windley Key itinerary. This leading airline provides 191 flights per month to Key West Intl. Airport (EYW), a central gateway.
How can I find cheap tickets to Windley Key?
You'll always find a fabulous deal with Expedia, but our "flexible dates" feature makes it that much easier. Enter your preferred flight date, then tick the flexible dates box above to reveal the cheapest prices for nearby days. was the best price for a flight to Windley Key in the last seven days.
How much is a flight to Windley Key?
You could have locked in a return air ticket to Windley Key from anywhere between and in the last seven days. For one-way journeys from (), the lowest amount paid during this time was .
What are the most popular airports to fly into in Windley Key?
The primary gateway to Windley Key, around 1119 flights taxi into Key West Intl. Airport (EYW) each month. Find a top deal, book your ticket and get ready to enjoy the best of this fantastic region.
When is the cheapest time to fly to Windley Key?
Try to jet off early on in the week to book a bargain airfare to Windley Key. Tuesday is routinely the most affordable day to depart, followed by Monday. Saturday typically has the highest prices. This is because lots of travelers like to begin their getaway on a weekend.
How much is a plane ticket to Windley Key?
In the last seven days, fares cost between and . Browse through our fantastic deals to Windley Key, make a booking and then get ready for your getaway!
Which airlines with flights to Windley Key employ COVID-19 cleanliness policies?
To help minimize contact between travelers and cabin crew during the ongoing pandemic, airlines have taken physical distancing and other precautionary measures to the skies. Just some of these are:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.