
Windley Key Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 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 easyPlan, book, and manage your trip all in one place
Top Romantic vacation packages in Windley Key

Nomada Residences
Reviewed on Feb 1, 2026


Park Central South Beach
Reviewed on Feb 4, 2026

Oceans Edge Key West Resort, Hotel & Marina
Reviewed on Feb 4, 2026

Waterfront House with Boat Dock
Reviewed on Jan 9, 2026
5* Romantic vacations in Windley Key

Isla Bella Beach Resort & Spa
Reviewed on Jan 31, 2026


Waterfront House with Boat Dock
Reviewed on Jan 9, 2026
3 Night Romantic vacations in Windley Key

Solé Miami, A Noble House Resort
Reviewed on Feb 4, 2026


The Shelborne By Proper, a Member of Design Hotels
Reviewed on Feb 1, 2026
4 Night Romantic vacations in Windley Key

Broadmore Miami Beach
Reviewed on Jan 31, 2026

Casablanca Miami Beach
Reviewed on Nov 12, 2025

How to find a romantic Windley Key vacation
How can I find the best Windley Key vacation packages for couples?
To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.
How can I find cheap Windley Key romantic packages for two?
For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering and visiting outside busy months of .
How can I plan a great romantic trip to Windley Key?
Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.
How much is a trip for two to Windley Key?
Put a price on love with stunning deals for duos starting at just $283. Stay during the quiet season, in , for breaks to make your bank balance smile. Prices and availability are subject to change. Additional terms may apply.
Can I book Windley Key spa packages for couples?
Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.
What’s the best time of year for a romantic vacation in Windley Key?
Book your romantic getaway during the quieter months of when you can have the place to yourself, pretty much. To show your partner off to the world, provide a more abundant audience.
How can I book romantic weekend getaway packages in Windley Key?
To book a loved-up break in Windley Key, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).
Can I book a romantic trip to Windley Key with free cancellation and/or flexible dates?
The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.
Why should I book my Windley Key romantic holiday with Expedia?
If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?



















