Raccoon Key Romantic Vacations

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Flight and Romantic hotel deals in Raccoon Key

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

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

CA $1,359

per person

Oct 29 - Nov 4

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (1,398 reviews)

This property was the perfect spot for seeing all of Key West. We had a brief problem with our door and the team was so responsive and apologetic and offered things to make it right. Have already recommended to friends and family in the 24hrs of being home.

Reviewed on Sep 23, 2026

The Gardens Hotel

Old Town Key West

Save 100% on your flight

CA $2,736

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.8/10 Exceptional! (1,003 reviews)

We loved the location of this hotel. The breakfast was so good and the staff were really kind.

Reviewed on Sep 22, 2026

Eden House

Key West Historic District

Save 100% on your flight

CA $1,905

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9/10 Wonderful! (1,003 reviews)

The Marker Key West Harbor Resort

Key West Historic District

Save 100% on your flight

CA $2,271

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (1,003 reviews)

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $1,948

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

8.6/10 Excellent! (3,560 reviews)

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3 Night Romantic holidays in Raccoon Key

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

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

CA $1,234

per person

Nov 20 - Nov 23

found 16 hours ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (1,398 reviews)

Reviewed on Sep 23, 2026

The Gardens Hotel

Old Town Key West

CA $2,087

per person

Nov 28 - Dec 1

found 15 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.8/10 Exceptional! (1,003 reviews)

We loved the location of this hotel. The breakfast was so good and the staff were really kind.

Reviewed on Sep 22, 2026

The Marker Key West Harbor Resort

Key West Historic District

CA $1,690

per person

Nov 28 - Dec 1

found 15 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (1,003 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Raccoon Key

View all trips

4 Night Romantic holidays in Raccoon Key

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

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

CA $1,802

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,255 reviews)

The Key West Hotel

Key West Historic District

Save 100% on your flight

CA $2,696

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (562 reviews)

Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

The Gardens Hotel

Old Town Key West

Save 100% on your flight

CA $2,736

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.8/10 Exceptional! (1,003 reviews)

We loved the location of this hotel. The breakfast was so good and the staff were really kind.

Reviewed on Sep 22, 2026

Don't see what you're looking for?

See all available trips from Columbus to Raccoon Key

View all trips

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

When booking a romantic Raccoon 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 Key West.

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 Raccoon 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 Raccoon 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 $1,234 and can enjoy savings of up to 21 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 Raccoon 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 Raccoon 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 Raccoon Key.

Can I book a romantic Raccoon 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 Raccoon Key search.

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

Several romantic Raccoon 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.