Windley Key Holidays

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Windley Key Flight & Hotel Packages

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 S$1,399, price is now S$988 per person
S$988
per person
18 Jul - 20 Jul
found 1 day ago
Return flight included
Mexico City (MEX) to Miami (MIA)
8.2/10 Very Good! (1,003 reviews)
Great service, very clean hotel.

Reviewed on 29 Apr, 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was S$1,723, price is now S$1,182 per person
S$1,182
per person
18 Jul - 20 Jul
found 1 day ago
Return flight included
Mexico City (MEX) to Miami (MIA)
8/10 Very Good! (1,142 reviews)
The staff was super friendly and accommodating. Loved the nice access to the pool. Our room was on the top floor and had an amazing view. Loved this place!

Reviewed on 20 Apr, 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was S$1,399, price is now S$989 per person
S$989
per person
18 Jul - 20 Jul
found 1 day ago
Return flight included
Mexico City (MEX) to Miami (MIA)
8.4/10 Very Good! (2,251 reviews)
The rooms were very very small compared to what pictures posted in website.

Reviewed on 30 Apr, 2026

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was S$1,348, price is now S$992 per person
S$992
per person
18 Jul - 20 Jul
found 1 day ago
Return flight included
Mexico City (MEX) to Miami (MIA)
8.2/10 Very Good! (1,807 reviews)
Hotel was at great location and staff was friendly. Towels an bedsheet was not very good. Thank you

Reviewed on 29 Apr, 2026

Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Price was S$1,598, price is now S$1,206 per person
S$1,206
per person
18 Jul - 20 Jul
found 1 day ago
Return flight included
Mexico City (MEX) to Miami (MIA)
9.2/10 Wonderful! (452 reviews)
Pros: Clean rooms, nice staff, close to the beach. Cons: resort fees per day, and hearing the noise outside my room (inside the hotel from staff or other guests). Overall, it was a nice and peaceful experience.

Reviewed on 29 Apr, 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 S$528 per night from 25 May to 26 May
S$528
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (192 reviews)
Clean updated room, great view and balcony! Loved the property and amenities.

Reviewed on 25 Apr, 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 S$286 per night from 3 May to 4 May
S$286
3 May - 4 May
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
Great place but needs new beds to noisy bother neighbor plus definitely needs a blender for making drinks 🍸

Reviewed on 29 Apr, 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$458 per night from 15 May to 16 May
S$458
15 May - 16 May
includes taxes & fees
9/10 Wonderful! (254 reviews)
The place rents out full time rooms the furniture is terrible the place is falling apart

Reviewed on 29 Apr, 2026

Coconut Cove Resort and Marina
See all 2,741 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

Explore Mangrove Creeks with an All Day SUP/single kayak Rental

Explore Mangrove Creeks with an All Day SUP/single kayak Rental

S$62
per adult
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
Sunset Kayak Adventure with Enchanting Underwater Lights

Sunset Kayak Adventure

S$99
per adult
Sunset Kayak Adventure
Mangrove Tunnels are a MUST...

1.5 Hour (20 miles) Waverunner Tour. See Mangrove Tunnels, 20 Islands & SandBar

S$330
per adult
100% of travellers recommend
1.5 Hour (20 miles) Waverunner Tour. See Mangrove Tunnels, 20 Islands & SandBar
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.