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 Hotel

President Hotel

3.5 out of 5
South Beach
Price was CA $2,758, price is now CA $1,428 per person
CA $1,428
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.4/10 Very Good! (2,145 reviews)
It was average No repeat for me

Reviewed on Apr 10, 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 $31,482, price is now CA $15,134 per person
CA $15,134
per person
May 12 - May 18
found 2 days ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very Good! (1 review)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was CA $3,122, price is now CA $1,603 per person
CA $1,603
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.6/10 Excellent! (1,000 reviews)
Its my fourth time there and i loved it

Reviewed on Apr 6, 2026

President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was CA $2,758, price is now CA $1,428 per person
CA $1,428
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very Good! (1,001 reviews)
the breakfast was good, and so was the service!

Reviewed on Apr 10, 2026

Miami Downtown Condos

Miami Downtown Condos

5 out of 5
Downtown Miami
Price was CA $3,306, price is now CA $1,748 per person
CA $1,748
per person
Jul 2 - Jul 7
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very Good! (135 reviews)
Excellent Location and unit. Host was very communicative and responsive once my arrival date approached. Just a few negatives, but some “minor” maintenance needs to be I wouldn’t list them here, they know what has to be done. done. Also, I would place a TV in the main area, if possible as I don’t really watch tv in bed. In addition, a great touch was having coffee and raw sugar was an added touch, as I do drink coffee and only use sugar in the raw! So 1000 extra points for me! Overall I would stay and recommend this location again.

Reviewed on Apr 5, 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 $400 per night from May 4 to May 5
CA $400
CA $542 total
May 4 - May 5
includes taxes & fees
9/10 Wonderful! (181 reviews)
Pool staff great. Too windy to do beach activities our trip unfortunately. Hotel room was great. Beautiful views. Check in was an unfortunate process. We were hoping for an early check in, instead didn’t get checked in till after our guaranteed 4PM.

Reviewed on Apr 4, 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 $210 per night from May 6 to May 7
CA $210
CA $282 total
May 6 - May 7
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
Loved the location. View from our room was beautiful. We also loved Alfie at the front desk. She was a sweetheart. So helpful and wonderful personality. Great asset to the resort. We will definitely return.

Reviewed on Apr 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 $358 per night from Apr 13 to Apr 14
CA $358
CA $403 total
Apr 13 - Apr 14
includes taxes & fees
9/10 Wonderful! (235 reviews)
Worst breakfast ever! Everything thing else great!

Reviewed on Apr 10, 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
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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 Mangrove Creeks with an All Day SUP/single kayak Rental

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

CA $67
per adult
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
Islamorada Sunset Cruise with Champagne Toast and Snacks

Islamorada Sunset Cruise with Champagne Toast and Snacks

CA $94
per adult
Islamorada Sunset Cruise with Champagne Toast and Snacks
Islamorada Sandbar Escape Sightseeing Paddleboarding and Swimming

Islamorada Sandbar Escape Sightseeing Paddleboarding and Swimming

CA $100
per adult
Islamorada Sandbar Escape Sightseeing Paddleboarding and Swimming
See all activities in Windley Key

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.

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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.