Windley Key Holidays from £1,275
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top Windley Key Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
£10,747
per person
26 Sept - 3 Oct
found 1 day ago
Return direct flight included
London (LON) 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
South Beach
£2,734
per person
2 Nov - 9 Nov
found 1 day ago
Return direct flight included
London (LGW) to Miami (MIA)
9.4/10 Exceptional! (1,613 reviews)
I cannot say enough great things about this last experience. The staff were all so caring and incredible, and sooo attentive to all questions and help needed.
Reviewed on 23 Aug 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
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
£224
30 Aug - 31 Aug
includes taxes & fees
9/10 Wonderful! (255 reviews)
"I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff."
Reviewed on 23 Aug 2026
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
£107
20 Sept - 21 Sept
includes taxes & fees
8.2/10 Very good! (1,015 reviews)
"Was Great! Everyone was super nice and helpful!"
Reviewed on 23 Aug 2026
Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
£115
25 Aug - 26 Aug
includes taxes & fees
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.
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.
Hog Heaven
After visiting Hog Heaven, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this relaxing area or enjoy its fishing spots.
Frequently asked questions
How much does a Windley Key travel package cost?
The most affordable Windley Key travel package is £1,275, 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
- 5 Star Hotels in Islamorada
- 5 Star Hotels in Key Largo
- Hotels near Harry Harris Park
- Beach Resorts & in Islamorada
- Beautiful Home in a Great Neighborhood with Ocean Access and Boat Ramp on Property
- Cheap Hotels in Islamorada
- Family-Friendly Hotels in Islamorada
- Sleeps 8
- Hotels Suites in Islamorada
- Hotels with a Bar in Islamorada
- Hotels with Connecting Rooms in Islamorada
- Hotels with Hot Tubs in Islamorada
- Isla Honeydew
- Isla Lychee
- Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
- Bayside Villas by Islander Resort
- Luxury Hotels in Islamorada
- Three Waters Resort and Marina
- Islamorada Hotels
- Hotels near Jimmy Johnson's Big Chill
- 124 Mariners Club
- 200ft of Waterfront with Tiki & Heated Pool
- Spectacular Oceanfront Views 3 bed/bath Villa with Amazing Views!
- 3bed vacation ocean side townhome 2pools
- 403 Mariners Club
- All-Inclusive Hotels in Key Largo
- Beach Resorts & in Key Largo
- Mariners Club Townhouse
- Cheap Hotels in Key Largo
- Family-Friendly Hotels in Key Largo
- Florida Keys canal front Vacation Home
- Gay-Friendly Hotels in Key Largo
- Island Paradise with private beach & private bay sunset views.
- Kawama Yacht Club
- Key Largo 3 Bedroom Penthouse Condo with Boat Slip and Bay View
- Pennekamp Hideaway
- Full TIME LIC MGR
- Mariner's Club Key Largo by KeysCaribbean
- Oceanfront 2BR/2.5BA Mariner's Club Villa 512 with Oasis Pool
- Paradise Cove-1stFloor- Key Largo
- Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.
- Private Beach Bayside 6 Bedroom Resort Home with Pool
- Reefhouse Resort & Marina
- Marina Vista Gem • Modern 2BR/2BA • Steps to Pickleball
- Sunrise Escape
- New! CASA AZUL OCEANSIDE
- Key Largo Hotels
- Layton Hotels
- Matecumbe Hotels
- Key Largo Baha Penthouse Ocean Pointe 1416
- Modern and Coastal Ocean Pointe 2307
- Ocean Oasis at Ocean Pointe Key Largo Pool Jacuzzi Beach in a Safe Gated Resort
- New Ocean Pearl • Beach • Restaurant • Pickleball • Marina
- Whispering Palms
- Tavernier Hotels
- Big Pine Key Holidays
- Bill Baggs Cape Florida State Park
- Calusa Beach
- Coconut Grove Holidays
- Curry Hammock State Park
- Dadeland Mall
- Everglades National Park
- Florida City Holidays
- Homestead Air Force Base
- Homestead Holidays
- Islamorada Holidays
- Visit Islamorada
- Jimmy Johnson's Big Chill
- Kendall Holidays
- Key Biscayne Holidays
- Key Largo Holidays
- Visit Key Largo
- Visit Long Key
- Marathon Holidays
- Matheson Hammock Park
- National Hurricane Center
- Old Cutler Trail
- Visit Plantation Key
- Sombrero Beach
- Visit Tavernier
- Visit Upper Matecumbe Key
- Vaca Key
- Zoo Miami
* 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.
