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 ₹103,243, price is now ₹66,570 per person
₹66,570
per person
27 Jun - 30 Jun
found 22 hours ago
Return flight included
Port of Spain (POS) to Miami (MIA)
8.2/10 Very Good! (1,830 reviews)
Very good location, the staff is really nice. The pool and the breakfast area is at a different property, that was really inconvenient and uncomfortable. The breakfast is not that good and there is not enough tables to sit around.

Reviewed on 17 May 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was ₹106,241, price is now ₹77,489 per person
₹77,489
per person
25 Jun - 27 Jun
found 10 hours ago
Return flight included
Jacksonville (JAX) to Miami (MIA)
8.4/10 Very Good! (2,302 reviews)
Front desk attendant Henry was very helpful and professional trying to help everyone and also bellman very helpful with luggage and also breakfast we like this place also because it is close to the beach and social life in evenings! Next time we also will come here and will tell all our friends about this affordable hotel!

Reviewed on 18 May 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was ₹140,271, price is now ₹102,633 per person
₹102,633
per person
25 Jun - 27 Jun
found 10 hours ago
Return flight included
Jacksonville (JAX) to Miami (MIA)
8/10 Very Good! (1,139 reviews)
Breakfast and dinner buffets were excellent. Felt like a resort. We had a partial ocean view room and the balcony view was amazing, as was the room. The staff was wonderful. However the person who assisted with checkout at the desk was not very friendly. It felt a little like he thought I didn’t belong there. I would definitely stay there again. Valet parking only, for $50 a day but the booking info said onsite parking options include a garage.

Reviewed on 14 May 2026

Kimpton EPIC Hotel by IHG

Kimpton EPIC Hotel by IHG

5 out of 5
Downtown Miami
Price was ₹145,638, price is now ₹107,974 per person
₹107,974
per person
25 Jun - 27 Jun
found 10 hours ago
Return flight included
Jacksonville (JAX) to Miami (MIA)
9/10 Wonderful! (2,461 reviews)
Everything was excellent just wish they would’ve had a microwave, available to heat up leftovers from restaurants. Location was amazing. The staff was very friendly and helpful. We had an amazing time. Can’t wait to go back.

Reviewed on 17 May 2026

EAST Miami

EAST Miami

5 out of 5
Brickell
Price was ₹152,036, price is now ₹116,078 per person
₹116,078
per person
25 Jun - 27 Jun
found 10 hours ago
Return flight included
Jacksonville (JAX) to Miami (MIA)
9.2/10 Wonderful! (3,779 reviews)
it was walking distance to many of the most popular restaurants and right next to the mall

Reviewed on 18 May 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

4 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ₹24,391 per night from 1 Jun to 2 Jun
₹24,391
₹34,458 total
1 Jun - 2 Jun
includes taxes & fees
9/10 Wonderful! (198 reviews)
"My only suggestion is to clean the garbage littered in the beach-lounging area. There’s also litter in the ocean (under Little Limon deck) that we picked up and a strong smell of sewage that hits the nostrils as soon as we exit our room or walk towards the Tiki bar. The ice cream place also needs ..."

Reviewed on 16 May 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 ₹12,970 per night from 3 Jun to 4 Jun
₹12,970
₹17,723 total
3 Jun - 4 Jun
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"Beautiful scenery and well-maintained."

Reviewed on 18 May 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 ₹15,895 per night from 21 May to 22 May
₹15,895
₹17,881 total
21 May - 22 May
includes taxes & fees
9/10 Wonderful! (262 reviews)
"The property is beautiful. The pool is amazing. It's a walk in pool that gradually gets deeper to a tall rock formation with a waterfall cascading down with cool refreshing water. You can relax in the pool with a picturesque ocean view. The property is owner operated, so much love goes into the care ..."

Reviewed on 12 May 2026

Coconut Cove Resort and Marina
See all 2,698 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.