Windley Key Holidays

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Top Flight + Hotel Deals in Windley Key

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
Price was €1,909, price is now €1,101 per person
€1,101
per person
7 Mar - 13 Mar
found 1 day ago
Return flight included
Shannon (SNN) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Main road in front of hotel was closed. When we arrived, the concierge had no idea where to tell us to park. If they were transparent about it, ok. I would be ok. Then they said they are out of the 'free' wine, but could charge me $8 for a Heineken. Then couldn't get the elevator to work (we were on the 2nd floor thank God) The room was in good shape. The parking is what set off the chain for me. It's not hard to update a website. Or at least tell your staff what to say. Ended up parking in the City parking garage. I'd give it like a 75/100.

Reviewed on 6 Jan 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 €22,455, price is now €10,575 per person
€10,575
per person
7 Mar - 13 Mar
found 1 day ago
Return flight included
Shannon (SNN) to Miami (MIA)
8/10 Very Good! (1 review)
Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Save 100% on your flight
Price was €4,483, price is now €2,511 per person
€2,511
per person
7 Mar - 13 Mar
found 1 day ago
Return flight included
Shannon (SNN) to Miami (MIA)
8.6/10 Excellent! (385 reviews)
Great time , wish I could have stayed longer .

Reviewed on 10 Jan 2026

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was €5,586, price is now €3,213 per person
€3,213
per person
7 Mar - 13 Mar
found 1 day ago
Return flight included
Shannon (SNN) to Miami (MIA)
9.4/10 Exceptional! (1,365 reviews)
The best hotel hands down in south Miami.

Reviewed on 8 Jan 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Save 100% on your flight
Price was €2,213, price is now €1,391 per person
€1,391
per person
7 Mar - 13 Mar
found 1 day ago
Return flight included
Shannon (SNN) to Miami (MIA)
8/10 Very Good! (1,120 reviews)
The water: beach and swimming pool are wonderful! Staff in both areas were attentive and friendly

Reviewed on 10 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 €344 per night from 21 Jan to 22 Jan
€344
21 Jan - 22 Jan
includes taxes & fees
8.8/10 Excellent! (124 reviews)
Amazing place - so much variety

Reviewed on 6 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 €193 per night from 19 Jan to 20 Jan
€193
19 Jan - 20 Jan
includes taxes & fees
8.2/10 Very Good! (1,009 reviews)
Todo ok

Reviewed on 4 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 €208 per night from 12 Jan to 13 Jan
€208
12 Jan - 13 Jan
includes taxes & fees
9/10 Wonderful! (164 reviews)
Staff was amazing! Two couples manage this property, and they go above and beyond to make sure you enjoy this cute, old style Florida resort. Upon check in Crystal seemed like an old friend.

Reviewed on 2 Jan 2026

Coconut Cove Resort and Marina
See all 2,745 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

€426
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.

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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.