Romantic Vacations in Florida Keys 2026

Plan, book, travel with confidence
Better together
Save up to CA $4,200 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Flight and Romantic hotel deals in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

CA $1,789

per person

Nov 14 - Nov 21

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Miami (MIA)

9.2/10 Wonderful! (1,422 reviews)

All the place is amazing but the rooms needs a little be of work to upgrade, and the beach was not as we imagined

Reviewed on Sep 29, 2026

The Gardens Hotel

Old Town Key West

Save 100% on your flight

CA $2,579

per person

Oct 31 - Nov 4

found 2 hours ago

Roundtrip flight included

Buffalo (BUF) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

It is a GREAT property in Key West, right in the center of the action.

Reviewed on Sep 28, 2026

Hawks Cay Resort

Save 100% on your flight

CA $1,831

per person

Dec 4 - Dec 9

found 5 hours ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8.2/10 Very good! (1,002 reviews)

Tranquility Bay Beachfront Hotel and Resort

CA $2,124

per person

Nov 8 - Nov 14

found 20 hours ago

Roundtrip non-stop flight included

Halifax (YHZ) to Miami (MIA)

8.8/10 Excellent! (1,003 reviews)

Great location and nice pool and beach! Daily tower replacement is also prompt and nice.

Reviewed on Sep 29, 2026

La Concha Key West, Autograph Collection

Key West Historic District

CA $1,996

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTT) to Key West (EYW)

9/10 Wonderful! (476 reviews)

Hotel is very conveniently located to old town Key West. The renovations that have been made to the hotel really make it a very fun place to stay.

Reviewed on Sep 28, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

5* Romantic holidays in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

CA $1,789

per person

Nov 14 - Nov 21

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Miami (MIA)

9.2/10 Wonderful! (1,422 reviews)

All the place is amazing but the rooms needs a little be of work to upgrade, and the beach was not as we imagined

Reviewed on Sep 29, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

3 Night Romantic holidays in Florida Keys

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

Hawks Cay Resort

CA $1,141

per person

Dec 14 - Dec 17

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Miami (MIA)

8.2/10 Very good! (1,002 reviews)

La Concha Key West, Autograph Collection

Key West Historic District

CA $1,996

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTT) to Key West (EYW)

9/10 Wonderful! (476 reviews)

Hotel is very conveniently located to old town Key West. The renovations that have been made to the hotel really make it a very fun place to stay.

Reviewed on Sep 28, 2026

Southernmost House - Adult Exclusive

Old Town Key West

CA $1,898

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTT) to Key West (EYW)

9.4/10 Exceptional! (1,004 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

4 Night Romantic holidays in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

CA $1,514

per person

Dec 11 - Dec 15

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

9.2/10 Wonderful! (1,422 reviews)

All the place is amazing but the rooms needs a little be of work to upgrade, and the beach was not as we imagined

Reviewed on Sep 29, 2026

The Gardens Hotel

Old Town Key West

Save 100% on your flight

CA $2,579

per person

Oct 31 - Nov 4

found 2 hours ago

Roundtrip flight included

Buffalo (BUF) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

It is a GREAT property in Key West, right in the center of the action.

Reviewed on Sep 28, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $1,656

per person

Oct 30 - Nov 3

found 2 hours ago

Roundtrip non-stop flight included

Buffalo (BUF) to Key West (EYW)

8.6/10 Excellent! (3,560 reviews)

Property was amazing, our second time here. Staff was very accommodating! Pools were clean and the atmosphere at the pools was perfect. We will definitely be returning.

Reviewed on Sep 29, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

What are some of the benefits of booking a romantic Florida Keys vacation?

When booking a romantic Florida Keys 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 United States of America.

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 Florida Keys 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 Florida Keys?

Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $1,141 and can enjoy savings of up to 28 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 Florida Keys?

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 Florida Keys 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 Florida Keys.

Can I book a romantic Florida Keys 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 Florida Keys search.

Can I book a romantic trip to Florida Keys that is fully refundable?

Several romantic Florida Keys 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.

Romantic Hotels in Florida Keys

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

10 min walk from Duval Street

Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...

8.6/10 Excellent! (3,637 reviews)

"Property was amazing, our second time here. Staff was very accommodating! Pools were clean and the atmosphere at the pools was perfect. We will definitely be returning."

Reviewed on Sep 29, 2026

Parrot Key Hotel & Villas

2801 N Roosevelt Blvd Key West FL

5 min drive from Duval Street

Book a stay at this beach hotel in Key West. Enjoy free WiFi, 4 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. ...

Pier House Resort & Spa

1 Duval St Key West FL

11 min walk from Duval Street

Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff ...

See all 8,221 properties in Florida Keys

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.