Windley Key Holidays from £1,055

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    Save up to £750 when you book a flight and hotel together*

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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
Price was £1,558, price is now £1,055 per person
£1,055
per person
11 Aug - 18 Aug
found 10 hours ago
Return direct flight included
London (LHR) to Miami (MIA)
8.6/10 Excellent! (1,009 reviews)
This was a very unique hotel compared to where we usually stay. May not be unique to Miami but this was our first trip to Miami. Staff was very courteous. Enjoyed staying there and will stay again.

Reviewed on 7 Jul 2026

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 £18,973, price is now £9,799 per person
£9,799
per person
13 Sept - 20 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on 22 Jun 2016

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was £2,990, price is now £1,997 per person
£1,997
per person
11 Sept - 18 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Miami (MIA)
9.4/10 Exceptional! (1,577 reviews)
Hotel is beautiful and charming. Very well located. The night manager that check us in - Matt- was incredibly helpful, smart and nice, going beyond to make us feel welcome and comfortable. We were truly impressed. Food at rooftop was very good. Definitely would stay again.

Reviewed on 9 Jul 2026

Nobu Hotel Miami Beach

Nobu Hotel Miami Beach

5 out of 5
Mid Beach
Price was £1,934, price is now £1,345 per person
£1,345
per person
11 Aug - 18 Aug
found 10 hours ago
Return direct flight included
London (LHR) to Miami (MIA)
8.6/10 Excellent! (1,415 reviews)
Our room was not ready when we arrived due to water issues at the hotel. We were relocated to a room at the hotel next door, which was in poor condition. The room was dirty, and the sink was clogged with standing water. We had to stay there for approximately four days, which was a very disappointing experience. We received only $200 in compensation, which did not come close to covering the difference in value or the inconvenience we experienced. We paid significantly more for our stay at Nobu than what we received in return, and the hotel was unwilling to adjust the rate to reflect the accommodations at the neighboring hotel. Overall, we were very disappointed with how the situation was handled and with the level of customer service. Unfortunately, we will not be returning.

Reviewed on 8 Jul 2026

EAST Miami Residences

EAST Miami Residences

5 out of 5
Brickell
Save 100% on your flight
Price was £2,581, price is now £1,813 per person
£1,813
per person
13 Sept - 20 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Miami (MIA)
9.2/10 Wonderful! (138 reviews)
Great property

Reviewed on 23 Jun 2026

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

4 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is £268 per night from 9 Aug to 10 Aug
£268
9 Aug - 10 Aug
includes taxes & fees
9/10 Wonderful! (225 reviews)
"Beautiful place I had a great t"

Reviewed on 8 Jul 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 £137 per night from 9 Aug to 10 Aug
£137
9 Aug - 10 Aug
includes taxes & fees
8.2/10 Very good! (1,004 reviews)
"I arrived to find that my room was overbooked and already taken . I was offered two other rooms that were not acceptable. One without a sofa and one with no view. After traveling to the keys from Ft. Lauderdale it was most disappointing. They offered a refund and it took me three hours to find somewhere ..."

Reviewed on 1 Jul 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 £159 per night from 13 Jul to 14 Jul
£159
13 Jul - 14 Jul
includes taxes & fees
9/10 Wonderful! (272 reviews)
"We had a great day here and I would recommend it to anybody and everybody. We got a little Casita really nice and quaint close to the beach. They’re close to a number of different hangout spots and just a nice spot to stay."

Reviewed on 4 Jul 2026

Coconut Cove Resort and Marina
See all 2,702 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.
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Stay near popular Windley Key attractions

Windley Key Fossil Reef Geological State Park

8.8/10 (184 reviews)
Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails.
See properties

Frequently asked questions

How much does a Windley Key travel package cost?
The most affordable Windley Key travel package is £1,055, 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.

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. Flight-inclusive packages are ATOL protected.