Windley Key Trip

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Top Windley Key Flight + Hotel Deals

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

The Penguin Hotel

3.5 out of 5
South Beach
Price was ₹156,678, price is now ₹109,195 per person
₹109,195
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
16.4/10 Exceptional! (1,491 reviews)
The area was very colourful and convenient to be around.

Reviewed on 17 Nov 2025

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Save 100% on your flight
Price was ₹309,690, price is now ₹177,925 per person
₹177,925
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
18.8/10 Exceptional! (56 reviews)
Staff super friendly and welcoming and helpful, room ready

Reviewed on 16 Nov 2025

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was ₹157,017, price is now ₹109,354 per person
₹109,354
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
16.8/10 Exceptional! (1,775 reviews)
Very clean and updated. Good price. Great location!!! Other than the bed there was only a small desk and desk chair and one luggage rack. No other places to put suitcases to open them other than the bed. There was also no comfy chair to sit in to read. If you wanted to sit down there was only the small desk chair and the bed. The elevator was also very small (3 person) so during busy times it took forever to get a lift to room or to lobby. The breakfast was really good but area was very crowded. Coffee should have been out in lobby so you could get a cup before breakfast. That would also remove it from adding to the crowding in the small diningroom. The outside dining area in back had pigeons. Not real sanitary for eating in.

Reviewed on 16 Nov 2025

72 Park - Miami Beach by Nomada

72 Park - Miami Beach by Nomada

4.5 out of 5
North Beach
Price was ₹195,346, price is now ₹140,350 per person
₹140,350
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
8.8/10 Excellent! (64 reviews)
Room was so well prepared VIEW WAS AMAZING, STAFF was COURTEOUS and ATTENTIVE

Reviewed on 16 Nov 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was ₹169,890, price is now ₹127,614 per person
₹127,614
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
17.2/10 Exceptional! (385 reviews)
Wonderful Stay every time I come to Miami I will be there just to stay at this hotel.

Reviewed on 18 Nov 2025

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 ₹15,747 per night from 14 Dec to 15 Dec
₹15,747
₹23,599 total
14 Dec - 15 Dec
includes taxes & fees
8.8/10 Excellent! (109 reviews)
We had the best family stay at this resort in the Keys. The rooms were spotless, comfortable, and perfect for winding down after a day in the sun. The pool was the real star for us… our kiddo didn’t want to get out. The whole place felt relaxed and welcoming, Truly one of our favorite family trips. ...

Reviewed on 10 Nov 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 refundable
The price is ₹7,144 per night from 4 Dec to 5 Dec
₹7,144
₹10,930 total
4 Dec - 5 Dec
includes taxes & fees
8/10 Very Good! (1,001 reviews)
We stay here about 3-4 times a year. Always great. Nice rooms. Parking is easy and right in front of the rooms. Comp breakfast. Can fish from anywhere on the property and spot to clean your catch, hands and rods. Dog friendly! We love this spot.

Reviewed on 11 Nov 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 ₹11,886 per night from 20 Nov to 21 Nov
₹11,886
₹13,372 total
20 Nov - 21 Nov
includes taxes & fees
9/10 Wonderful! (140 reviews)
I just got back from spending a week at the Coconut Cove Resort & Marina and it was seriously the best vacation ever! I was so impressed with everything. Our room was super clean, which was awesome, and the whole resort looked amazing the entire time we were there. Mandy at the front desk was so ...

Reviewed on 16 Nov 2025

Coconut Cove Resort and Marina
See all 2,785 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.

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.

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