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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.
  • Dec 22 - Dec 25

    Fisher Inn Resort & Marina + Flight

    Islamorada
    3 nights
    3.5 star property
    8.2/10 - Very good (1,005 reviews)
    Roundtrip • Toronto (YYZ) - Miami (MIA)
    YYZ - FLL • Nonstop FLL - YYZ • Nonstop
    CA $940
    per traveller
    found 1 day ago
    Fisher Inn Resort & Marina
  • Jan 29 - Feb 1

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

    Islamorada
    3 nights
    4.0 star property
    9.0/10 - Wonderful (312 reviews)
    "Great stay!"
    Reviewed November 11, 2026
    Roundtrip • Toronto (YYZ) - Miami (MIA)
    YYZ - FLL • Nonstop FLL - YYZ • Nonstop
    CA $2,105
    CA $1,555
    per traveller
    found 1 day ago
    Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
  • Dec 26 - Dec 31

    Drop Anchor + Flight

    Islamorada
    5 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 • Toronto (YYZ) - Miami (MIA)
    YYZ - MIA • 1 stop FLL - YYZ • 1 stop
    CA $2,450
    CA $2,018
    per traveller
    found 18 hours ago
    Drop Anchor
  • Dec 22 - Dec 25

    Coconut Cove Resort and Marina + Flight

    Islamorada
    3 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 • Toronto (YYZ) - Miami (MIA)
    YYZ - FLL • Nonstop FLL - YYZ • Nonstop
    CA $1,223
    CA $1,213
    per traveller
    found 1 day ago
    Coconut Cove Resort and Marina

Discover the most popular places to visit in Windley Key

What to do in Windley Key

Top Romantic Windley Key Hotels

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.

Plan unforgettable romantic Windley Key vacations

What are some of the benefits of booking a romantic Windley Key vacation?

When booking a romantic Windley Key vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in Islamorada.

How can I find the best vacation packages for couples?

If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the Windley Key destination, and you'll be met with an array of options for you and your partner to enjoy.

Can I find cheap romantic vacations for 2 in Windley Key?

Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $940 and can enjoy savings of up to when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first.

What do I need to consider when booking a romantic getaway in Windley Key?

Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout Windley Key certainly come in handy here.

What amenities should I look for in a luxury romantic vacation?

If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to Windley Key.

Can I book a romantic Windley Key vacation with a hot tub?

Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them.

How can I find romantic vacation getaways that are all-inclusive?

An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your Windley Key search.

Can I book a romantic trip to Windley Key that is fully refundable?

Several romantic Windley Key vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements.

Why should I book a romantic vacation with Expedia?

Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage.