Windley Key Holidays

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Windley Key Flight & Hotel Packages

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

The Penguin Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
5 Sept - 9 Sept
found 1 day ago
Return flight included
Chicago (CHI) to Miami (MIA)
8.2/10 Very Good! (1,329 reviews)
Great clean hotel and convenient location but very noisy and AC location blowing directly on bed ….

Reviewed on 23 Jul, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
5 Sept - 9 Sept
found 1 day ago
Return flight included
Chicago (CHI) to Miami (MIA)
9.4/10 Exceptional! (1,212 reviews)
Good stay, hotel was accommodating whenever I needed something. Great location in south beach. Will be back

Reviewed on 20 Jul, 2025

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
per person
5 Sept - 9 Sept
found 1 day ago
Return flight included
Chicago (CHI) to Miami (MIA)
8/10 Very Good! (6,535 reviews)
I have always liked this Hotel.

Reviewed on 23 Jul, 2025

Kimpton EPIC Hotel by IHG

Kimpton EPIC Hotel by IHG

5 out of 5
Downtown Miami
Save 100% on your flight
per person
5 Sept - 9 Sept
found 1 day ago
Return flight included
Chicago (CHI) to Miami (MIA)
8.8/10 Excellent! (1,881 reviews)
Everything about it was perfect

Reviewed on 23 Jul, 2025

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
Save 100% on your flight
per person
5 Sept - 9 Sept
found 1 day ago
Return flight included
Chicago (CHI) to Miami (MIA)
9.2/10 Wonderful! (3,202 reviews)
Loud construction noise is all you hear till 5:00

Reviewed on 22 Jul, 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 S$312 per night from 21 Aug to 22 Aug
S$312
21 Aug - 22 Aug
includes taxes & fees
9/10 Wonderful! (48 reviews)
Great, but eat off property
"Property and service were great. Food was not great. Very difficult to find options for a picky eater. Had to DoorDash Wendy’s several times."

Reviewed on 2 Jul, 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 S$215 per night from 12 Aug to 13 Aug
S$215
12 Aug - 13 Aug
includes taxes & fees
7.8/10 Good! (1,007 reviews)
"Spacious rooms. Beautiful view"

Reviewed on 21 Jul, 2025

Fisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

2.5 out of 5
84801 Overseas Highway, Islamorada, FL
The price is S$239 per night from 21 Aug to 22 Aug
S$239
21 Aug - 22 Aug
includes taxes & fees
7.6/10 Good! (804 reviews)
"Nice place great pool"

Reviewed on 20 Jul, 2025

Coconut Cove Resort and Marina
See all 2,708 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

S$640
per traveller
100% of travellers recommend
Private 3-Hour Islamorada Sandbar Tour
See all activities in Windley Key

Frequently asked questions

How much does a Windley Key holiday package cost?
Custom make your Windley Key package from just S$496. Choose from any combination of hotels, flights and rental cars to build the escape you've been dreaming about. Be sure to add on one or two experiences!
How do I get a cheap travel package to Windley Key?
Bundle your hotels and flights with Expedia to save big bucks on your next adventure. With more than 550 air carriers and 1,000,000 hotels across the globe, your Windley Key holiday package can be customized exactly to suit your travel style. With all that extra cash, why not include one or more exciting tours and experiences? It's an easy way to unlock even more savings. That holiday you've always dreamed of in Windley Key is closer than you thought!
How far in advance should I book my Windley Key holiday?
While prices change from time to time, we generally advise booking your flight as early as possible. Many international fares become available on Expedia up to a year in advance. If you're booking last minute, you might still be in luck. Discount prices to Windley Key sometimes appear just weeks before departure.
What does an Expedia Windley Key travel package include?
Expedia has everything you need to lock in Windley Key escape, but what your package looks like depends on you. Select from any combination of flights, rental cars and hotels. Looking for some tours or experiences to keep you on the move? Once you've made your booking, you can add them on too. No matter your style, there's a holiday package to meet your needs.
What should I know before booking a Windley Key travel package?
So many places to go, so many things to do. With a package, you can check more of them off your list. Bundle your flights, hotels and rental cars and see how much you save.
Can I choose my airline with a Windley Key Expedia holiday package?
With a holiday package, you're in charge. Whether you'd prefer to fly to Windley Key in business or coach, simply pick from the available airline options. Expedia has access to more than 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Windley Key holiday package?
It is possible to cancel your Windley Key booking if your plans have been upended. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.

* 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.