Windley Key Trip

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Top Windley Key Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was ₹157,621, price is now ₹79,446 per person
₹79,446
per person
28 Mar - 3 Apr
found 16 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (997 reviews)
Room was clean only had a problem with the toilet it took them awhile to come fix it the breakfast was good and staff definitely did everything they could to make our stay comfortable even until check out they held our bags for us because we had a later flight from our check out.

Reviewed on 15 Feb 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 ₹2,349,859, price is now ₹1,085,870 per person
₹1,085,870
per person
28 Mar - 3 Apr
found 16 hours ago
Return flight included
Boston (BOS) 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 ₹190,925, price is now ₹90,275 per person
₹90,275
per person
28 Mar - 3 Apr
found 16 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Lets be clear, you stay here for the location and the art deco building. Amenities are just OK. Staff is friendly but rooms are dated. Sofa bed for my 2 daughters was broken (room 301). No common area (lounge to seat down and relax), it is all restaurant. So this is one of those “been there donde that” kind of places. Next time either a B&B or a large chain hotel.

Reviewed on 17 Feb 2026

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was ₹157,794, price is now ₹79,519 per person
₹79,519
per person
28 Mar - 3 Apr
found 16 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
The room was very clean and the staff was very friendly.

Reviewed on 16 Feb 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was ₹157,621, price is now ₹79,446 per person
₹79,446
per person
28 Mar - 3 Apr
found 16 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
Needs painting, and cleaning carpets.

Reviewed on 16 Feb 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 ₹40,757 per night from 8 Mar to 9 Mar
₹40,757
₹51,868 total
8 Mar - 9 Mar
includes taxes & fees
9/10 Wonderful! (148 reviews)
The was nice, clean and comfortable. All staff we encountered was extremely friendly and courteous. The amenities were excellent.

Reviewed on 13 Feb 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 ₹23,640 per night from 1 Mar to 2 Mar
₹23,640
₹29,553 total
1 Mar - 2 Mar
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
Clean room, great staff and location

Reviewed on 16 Feb 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 ₹28,244 per night from 19 Feb to 20 Feb
₹28,244
₹31,774 total
19 Feb - 20 Feb
includes taxes & fees
9/10 Wonderful! (192 reviews)
This place is one of the best places we have ever stayed. The host, Christie, was SO incredibly kind, helpful, friendly, gracious and her and her husband went so far out of their way to help us enjoy their stay. The property was beautiful and we enjoyed the property so much. It was quiet, peaceful, ...

Reviewed on 16 Feb 2026

Coconut Cove Resort and Marina
See all 2,747 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.

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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.