Windley Key Holidays from £599

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to £335 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Packages with flights are ATOL protected

Top Windley Key Flight + Hotel Deals

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 £1,040, price is now £599 per person
£599
per person
22 Sept - 28 Sept
found 17 hours ago
Return flight included
London (LON) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Loved the Art Deco look of the rooms, lobby and hallway. Staff was very kind and helpful.

Reviewed on 16 Aug 2025

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 £15,480, price is now £7,030 per person
£7,030
per person
22 Sept - 28 Sept
found 16 hours ago
Return flight included
London (LON) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was £4,323, price is now £2,338 per person
£2,338
per person
27 Oct - 3 Nov
found 16 hours ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
9.4/10 Exceptional! (1,245 reviews)
Went for a family trip. Lots of healthy food options.

Reviewed on 17 Aug 2025

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
Price was £1,789, price is now £1,050 per person
£1,050
per person
20 Sept - 27 Sept
found 23 hours ago
Return flight included
Birmingham (BHX) to Miami (MIA)
8.8/10 Excellent! (1,156 reviews)
We had a wonderful time here. It was very family friendly with the lazy river, pool and easy beach access. They had fun events like a kids glow party with spelling bee and coconut race. My daughter had a blast. The staff were beyond accommodating, especially Andrew by the pool, Jean by the beach and Donte. I don’t have some of the names but everyone spoiled my daughter with fruit and ice cream any room she walked into and made her feel like a princess. We would definitely come back!

Reviewed on 20 Aug 2025

Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
Save 100% on your flight
Price was £1,833, price is now £1,120 per person
£1,120
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Miami (MIA)
9/10 Wonderful! (2,473 reviews)
First time there. Definitely will return.

Reviewed on 19 Aug 2025

Windley Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)

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 £204 per night from 27 Aug to 28 Aug
£204
27 Aug - 28 Aug
includes taxes & fees
9/10 Wonderful! (57 reviews)
"Great resort, excellent staff and customer service, I'll definitely coming back"

Reviewed on 7 Aug 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 £121 per night from 14 Sept to 15 Sept
£121
14 Sept - 15 Sept
includes taxes & fees
8/10 Very Good! (1,001 reviews)
Nice Resort But Best for Boat Owners
"We booked a waterfront king suite with a balcony and kitchenette, which was very spacious. The room was very clean and convenient. The "living room" had a sofa and tv and was located next to the balcony. The kitchenette was between the living area and bedroom, opposite the bathroom, which also had ..."

Reviewed on 11 Aug 2025

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 £108 per night from 8 Sept to 9 Sept
£108
8 Sept - 9 Sept
includes taxes & fees
7.6/10 Good! (814 reviews)
"Staff were very nice and welcoming. Nice pool and view. Room was nice clean and comfortable. Definitely would stay again"

Reviewed on 15 Aug 2025

Coconut Cove Resort and Marina
See all 2,711 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Windley Key travel package cost?
The most affordable Windley Key travel package is £599, so your dream holiday can become a reality — without spending a fortune. Combine flights, hotels and car rentals to tailor a package that suits your travel style.
If I'm not able to travel, can I cancel my Windley Key travel package?
It's impossible to predict what tomorrow might bring, so it's comforting to know that you can change or cancel your Windley Key travel package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal to learn more.
How do I get a cheap travel package to Windley Key?
Bundling your hotel and flight with Expedia won't just save you time — it'll save you cash too. A Windley Key travel package makes it a breeze to arrange the perfect trip. With more than 550 airlines worldwide to choose from, finding convenient flights that fit your schedule won't be hard. On top of that, we've got over 1,000,000 properties globally to select from. Now that's what you call choice. Whatever your budget, Expedia brings the world within your reach.
Does Expedia offer Book Now, Pay Later Windley Key holidays?
We certainly do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your holiday in instalments. Simply pick the payment plan that works for you during checkout and take away the stress of budgeting for your next trip. Be sure to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your travel buck. Consider these flexible payment options below:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that suit all budgets, so you can jet away on that well-deserved holiday now.
  • Pay in instalments holidays: If you want to pay for your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you come across an unbeatable deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock in your escape.

How far in advance should I book my Windley Key holiday?
Search Expedia to compare international airfares as soon as you know your travel dates. You can usually purchase a seat up to a year in advance. If you don't see your preferred air carrier, or you've left things to the last moment, fear not. Cheap fares to Windley Key occasionally appear just weeks before the date of departure.
What does an Expedia Windley Key travel package include?
Packages include hotels, flights and rental cars, but you can combine any of them to create your ideal Windley Key getaway. You can also add on tours and activities once you've made your booking. You're in the driver's seat! When you combine your bookings with Expedia, you'll score discounts you won't find anywhere else.
What should I know before booking a Windley Key travel package?
So many places to go, so many things to see and do. With a package, you can cross more of them off your list. Combine your flights, hotels and rental cars and make big savings.
Can I choose my airline with a Windley Key Expedia travel package?
Expedia has access to more than 550 airline partners globally, so you certainly can. Just select your preferred carrier and craft the perfect Windley Key escape.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.