Windley Key Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 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

Windley Key Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was S$1,704, price is now S$1,370 per person
S$1,370
per person
10 Mar - 13 Mar
found 1 day ago
Return flight included
Chicago (ORD) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Good... The carpet needs deep cleaned. Stayed here before and room was newer/cleaner.

Reviewed on 26 Jan, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was S$2,984, price is now S$2,038 per person
S$2,038
per person
10 Mar - 13 Mar
found 1 day ago
Return flight included
Chicago (ORD) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Everything was great. I couldn’t complain about anything if I wanted to. Thanks for a great stay!

Reviewed on 28 Jan, 2026

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was S$2,306, price is now S$1,812 per person
S$1,812
per person
10 Mar - 13 Mar
found 1 day ago
Return flight included
Chicago (ORD) to Key West (EYW)
9.4/10 Exceptional! (390 reviews)
The room was good but very small. It wasn’t a major thing because we were not in it most of the day. Everything was clean and cleaning services were provided daily. The breakfast wasn’t what I was expecting, but it was a true continental breakfast I guess. Front desk help was great. We didn’t use the pool because it was cold weather when we were there.

Reviewed on 26 Jan, 2026

Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
New Town
Price was S$1,714, price is now S$1,383 per person
S$1,383
per person
10 Mar - 13 Mar
found 1 day ago
Return flight included
Chicago (ORD) to Key West (EYW)
8.8/10 Excellent! (1,749 reviews)
Great room and bathroom. Loved the amenities.The shuttle was awesome. Wish we could have stayed longer.

Reviewed on 29 Jan, 2026

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was S$1,716, price is now S$1,403 per person
S$1,403
per person
10 Mar - 13 Mar
found 1 day ago
Return flight included
Chicago (ORD) to Key West (EYW)
9.4/10 Exceptional! (1,151 reviews)
Loved the hotel, the balcony over the marina, the restaurants. However, having to pay a premium (much higher than any other hotel) for our dog for a dirty dog run without cleanup bags was not acceptable.

Reviewed on 29 Jan, 2026

Top hotels in Windley Key

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 S$580 per night from 3 Feb to 4 Feb
S$580
3 Feb - 4 Feb
includes taxes & fees
9/10 Wonderful! (137 reviews)
Hotel/room was very clean and well care for. Staff very professional. Breakfast that was provided very good.

Reviewed on 27 Jan, 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 refundable
The price is S$365 per night from 3 Feb to 4 Feb
S$365
3 Feb - 4 Feb
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
Clean and comfortable. Room 210 was spacious with a great waterfront balcony. Outdoor furniture and fire pit were awesome. Staff, especially Riley and Barbara and the entire staffbwas so courteous and helpful in every way. But they should wear a name tag and tell guests their names.. I had to ...

Reviewed on 25 Jan, 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 S$338 per night from 1 Feb to 2 Feb
S$338
1 Feb - 2 Feb
includes taxes & fees
9/10 Wonderful! (176 reviews)
Kristi and Crystal were amazing! Small old school Florida vibe that truly immersed you in that island experience. Rooms are not fancy but very comfortable with great views. Location is fantastic, Islamorada is our favorite of the Key Islands!

Reviewed on 28 Jan, 2026

Coconut Cove Resort and Marina
See all 2,772 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.

What to do in Windley Key

Private 3-Hour Islamorada Sandbar Tour

Private 3-Hour Islamorada Sandbar Tour

S$644
per traveller
100% of travellers recommend
Private 3-Hour Islamorada Sandbar Tour
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 cancelling 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 travellers 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 travellers 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 travellers 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.