Windley Key Romantic Vacations
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Top Romantic vacation packages in Windley Key
- Drop Anchor
Sep 5 - Sep 7Drop Anchor + Flight
Islamorada2 nights3.0 star property8.8/10 - Excellent (1,006 reviews)Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop MIA - BOS • Nonstop$548$480found 1 day agoper traveler - Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Oct 8 - Oct 11Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort + Flight
Islamorada3 nights4.0 star property9.0/10 - Wonderful (246 reviews)Roundtrip • New York (NYC) - Miami (MIA)LGA - MIA • 1 stop MIA - EWR • 1 stop - Fisher Inn Resort & Marina
Oct 19 - Oct 23Fisher Inn Resort & Marina + Flight
Islamorada4 nights3.5 star property8.2/10 - Very Good (1,009 reviews)"Lo único malo q tenía muchas algas en el lado de la marina no pesqué nada pero la pasé bien"Reviewed August 5, 2026Roundtrip • New York (JFK) - Miami (MIA)JFK - MIA • Nonstop MIA - JFK • Nonstop$699$627found 1 day agoper traveler - Coconut Cove Resort and Marina
Oct 19 - Oct 23Coconut Cove Resort and Marina + Flight
Islamorada4 nights3.0 star property9.0/10 - Wonderful (279 reviews)"Wow! I stayed there for a week and I really felt like I was in my little slice of heaven! The resort is decorated beautifully. The room definitely has the Florida keys vibe and the staff were so awesome. I would have loved to stay there forever. I can't wait to go back!!!"Reviewed August 5, 2026Roundtrip • New York (JFK) - Miami (MIA)JFK - MIA • Nonstop MIA - JFK • Nonstop$703$679found 1 day agoper traveler
Top Romantic Windley Key Hotels
"Lo único malo q tenía muchas algas en el lado de la marina no pesqué nada pero la pasé bien"
"Drop Anchor was a nice experience. We stayed for two nights..no major issues except for the air-conditioning in our room wasn't covering the space inside enough, it was a small a/c unit and i think it's capacity wasn't enough to cool the room. So we were a bit uncomfortable based on that. But otherwise everything else was up to standard. I would consider visiting there again in the future tho. Staff very helpful and friendly, amenities nice and access to restaurants and other activities near by."
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Coconut Cove Resort and Marina
Coconut Cove Resort and Marina"Wow! I stayed there for a week and I really felt like I was in my little slice of heaven! The resort is decorated beautifully. The room definitely has the Florida keys vibe and the staff were so awesome. I would have loved to stay there forever. I can't wait to go back!!!"
"Food was excellent and the staff was delightful. Very accommodating"
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.
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 $480. 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.
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?