Windley Key Beach Holidays 2026

Plan, book, travel with confidence
Better together
Save up to AU$703 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Top flight + Beach hotel deals in Windley Key

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

Hawks Cay Resort

AU$4,544

per person

9 Jan - 14 Jan

found 3 hours ago

Return direct flight included

Sydney (SYD) to Miami (MIA)

8/10 Very Good! (1,003 reviews)

Amazing for young families! Heading back again!

Reviewed on 29 Nov 2025

Isla Bella Beach Resort & Spa

AU$5,590

per person

9 Jan - 14 Jan

found 3 hours ago

Return direct flight included

Sydney (SYD) to Miami (MIA)

9.2/10 Wonderful! (1,055 reviews)

Beautiful property, stunning vistas, clean, spacious rooms, friendly staff.

Reviewed on 23 Nov 2025

Tranquility Bay Beachfront Hotel and Resort

AU$5,000

per person

9 Jan - 14 Jan

found 3 hours ago

Return direct flight included

Sydney (SYD) to Miami (MIA)

8.8/10 Excellent! (1,003 reviews)

The place was great and appropriately named because it was very tranquil and relaxing. The only disappointment was that there is no spa facility and breakfast available only in your room.

Reviewed on 27 Nov 2025

Pier House Resort & Spa

Key West Historic District

AU$5,644

per person

9 Jan - 14 Jan

found 3 hours ago

Return direct flight included

Sydney (SYD) to Key West (EYW)

9/10 Wonderful! (1,006 reviews)

Lovely hotel, great room and ideal location.

Reviewed on 30 Nov 2025

Oceans Edge Key West Resort, Hotel & Marina

AU$4,555

per person

9 Jan - 14 Jan

found 3 hours ago

Return direct flight included

Sydney (SYD) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

My stay at this hotel was absolutely outstanding! From the moment I arrived, I felt welcomed and well taken care of. The staff were incredibly professional, friendly, and always ready to help with anything I needed.

Reviewed on 1 Dec 2025

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

View all trips

5* Beach holidays in Windley Key

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

Kimpton EPIC Hotel by IHG

Downtown Miami

AU$857

per person

9 Jan - 11 Jan

found 13 hours ago

Return flight included

Dallas (DFW) to Miami (MIA)

9/10 Wonderful! (2,183 reviews)

No Bluetooth speakers

Reviewed on 2 Dec 2025

EAST Miami

Downtown Miami

Save 100% on your flight

AU$1,069

per person

9 Jan - 11 Jan

found 13 hours ago

Return flight included

Dallas (DFW) to Miami (MIA)

9.2/10 Wonderful! (3,553 reviews)

Outstanding location and outstanding service! Efficient and informative check in! Close to airport and has an adjoining mall. Wonderful city and water views. Walking distance to grocery stores, restaurants and shopping.

Reviewed on 1 Dec 2025

Isla Bella Beach Resort & Spa

AU$5,590

per person

9 Jan - 14 Jan

found 3 hours ago

Return direct flight included

Sydney (SYD) to Miami (MIA)

9.2/10 Wonderful! (1,055 reviews)

Beautiful property, stunning vistas, clean, spacious rooms, friendly staff.

Reviewed on 23 Nov 2025

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

View all trips

How can I book a Windley Key beach holiday package with Expedia?

Beach holidays to beach holidays on Expedia?

To find your ideal family-friendly Windley Key beach holiday package, simply use the site’s or the app’s search function to explore diverse packages tailored to your chosen destination. Refine your search with filters to narrow down options based on your favourite amenities.

How can I select the perfect beach holiday package for Windley Key?

Customise your quest for Windley Key beach holiday packages, including flights, with search filters and prioritise your preferred options. This way, you’ll uncover fantastic beach holidays, whether it’s a romantic beach escape, a luxurious beach package, or a surfers’ paradise in Windley Key.

How can I find the best Windley Key beach holiday deals?

Grab some of the best Windley Key beach holiday deals by being flexible with your destination and dates, ideally travelling outside of peak seasons. If you have specific seas in mind, enter the details and apply filters to uncover a budget-friendly trip.

How can I discover last-minute Windley Key beach holiday deals?

If you love a last-minute deal, you’ve come to the right place. Select our top picks or customise your beach getaway in Windley Key using date and destination filters. Bundle accommodation, airfare, and car rental for the best value. Tailor your search with filters covering amenities, price, star rating, and more.

How can I find pet-friendly Windley Key beach holiday packages?

Indulge yourself and your furry companion in Windley Key’s pet-friendly beach holiday options. Enhance your getaway with our filters, including doggy day care, divine pet-friendly beach apartments, and access to pet-friendly local beaches.

When are the best times to go for a Windley Key beach holiday?

For the ultimate Windley Key beach holiday, choose summer for vibrant energy. Alternatively, opt for winter to enjoy a tranquil, less crowded experience with ample alone time.