Windley Key Romantic Vacations

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Top Romantic vacation packages in Windley Key

Price found within the past 48 hours. Click for updated prices.
  • A pool area with lounge chairs and a sign indicating a drop-off zone.
    Dec 16 - Dec 20

    Drop Anchor + Flight

    Islamorada
    4 nights
    3.0 star property
    8.6/10 - Excellent (1,003 reviews)
    "The futon in the living room should be replaced. Not comfortable at all as this was the main seating area. No TV was in the bedroom and the chairs on the patio felt like they were going to break"
    Reviewed November 9, 2026
    Roundtrip • New York (EWR) - Miami (MIA)
    EWR - MIA • Nonstop MIA - EWR • Nonstop
    $880
    $654
    per traveler
    found 1 day ago
    Drop Anchor
  • A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
    Jan 11 - Jan 16

    Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort + Flight

    Islamorada
    5 nights
    4.0 star property
    9.0/10 - Wonderful (312 reviews)
    "Great stay!"
    Reviewed November 11, 2026
    Roundtrip • Philadelphia (PHL) - Miami (MIA)
    PHL - MIA • Nonstop MIA - PHL • Nonstop
    Save 100% on your flight
    $1,823
    $1,105
    per traveler
    found 1 day ago
    Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
  • A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.
    Jan 16 - Jan 20

    Fisher Inn Resort & Marina + Flight

    Islamorada
    4 nights
    3.5 star property
    8.2/10 - Very good (1,005 reviews)
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop MIA - BOS • Nonstop
    $828
    $673
    per traveler
    found 1 hour ago
    Fisher Inn Resort & Marina
  • A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.
    Jan 16 - Jan 20

    Coconut Cove Resort and Marina + Flight

    Islamorada
    4 nights
    3.0 star property
    9.0/10 - Wonderful (307 reviews)
    "It was on the water, big plus. What a view from certain vantage points! Continental breakfast was not so hot. It served the purpose."
    Reviewed November 11, 2026
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop MIA - BOS • Nonstop
    $784
    $714
    per traveler
    found 1 hour ago
    Coconut Cove Resort and Marina

Discover the most popular places to visit in Windley Key

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

Top Romantic Windley Key Hotels

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
1.2 mi from Windley Key
9.0 out of 10, Wonderful, (312 reviews)
"Great stay!"
$272 nightly
The price is $306
Nov 29 - Nov 30
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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.
See all properties in Windley Key

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 $654. 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?