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

President Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
14 Jun - 18 Jun
found 24 hours ago
Return direct flight included
Philadelphia (PHL) to Miami (MIA)
8.2/10 Very Good! (1,331 reviews)
Hotel was excellent and great spot within walking distance to everything. The only item for us was the bathroom not enough counter space for your toiletries. Staff was very friendly and always there to answer your questions

Reviewed on 24 Apr 2025

Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
14 Jun - 18 Jun
found 24 hours ago
Return direct flight included
Philadelphia (PHL) to Miami (MIA)
8.4/10 Very Good! (768 reviews)
Very nice hotel a block off the beach in an art deco type building.front desk staff were very friendly and helpful.Cozy comfortable lobby lobby with a small outside patio at the front of the hotel. Very clean room , spacious bathroom and considerate staff maintaining the floors, in that they were pretty quiet for those that were sleeping in. This was very much appreciated. No restaurant at the hotel but not necessary considering how many options are very close by.

Reviewed on 8 Apr 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
14 Jun - 18 Jun
found 24 hours ago
Return direct flight included
Philadelphia (PHL) to Miami (MIA)
9.2/10 Wonderful! (1,097 reviews)
Amazing experience. Explore everything. It’s all amazing and well worth the money

Reviewed on 24 Apr 2025

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
14 Jun - 18 Jun
found 24 hours ago
Return direct flight included
Philadelphia (PHL) to Miami (MIA)
8/10 Very Good! (1,143 reviews)
Nice Stay, however the hotel states that resort fee inc breakfast when I asked they stated it was before a certain date booked. Nice welcome drink at the next door bar. Hotel room was perfect for 2 nights stay. Great location.

Reviewed on 24 Apr 2025

President Villa

President Villa

3.5 out of 5
South Beach
Save 100% on your flight
per person
14 Jun - 18 Jun
found 20 hours ago
Return direct flight included
Philadelphia (PHL) to Miami (MIA)
8.2/10 Very Good! (1,002 reviews)
good location, nice base

Reviewed on 23 Apr 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 ₹23,163 per night from 27 Apr to 28 Apr
₹23,163
₹31,729 total
includes taxes & fees
27 Apr - 28 Apr
9/10 Wonderful! (16 reviews)
"We loved the hotel. Perfect weekend getaway with our dog. It really is pet friendly and everyone is super nice. Loved all the dinning options as well as the amount of different spaces to be at. Definitely will be coming back!"

Reviewed on 19 Apr 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 ₹16,453 per night from 1 May to 2 May
₹16,453
₹21,297 total
includes taxes & fees
1 May - 2 May
7.8/10 Good! (999 reviews)
"EVERYTHING WAS GREAT"

Reviewed on 22 Apr 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 ₹14,410 per night from 6 May to 7 May
₹14,410
₹16,212 total
includes taxes & fees
6 May - 7 May
7.4/10 Good! (768 reviews)
"We really enjoyed our stay. The staff treated us like family and went the extra mile to ensure that our daughter had a great time. The pool & beach area were great & incredibly clean. The staff were all so friendly and even lent me a large cooler to use for our family fishing trip."

Reviewed on 20 Apr 2025

Coconut Cove Resort and Marina
See all 2,717 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

How much does a Windley Key holiday package cost?
Custom make your Windley Key package from just ₹41,190. 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.