Luxury Vacations in Lower Florida Keys 2026

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Flight and Luxury hotel deals in Lower Florida Keys

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

The Gardens Hotel

Old Town Key West

Save 100% on your flight

CA $1,895

per person

Dec 13 - Dec 17

found 14 hours ago

Roundtrip flight included

Toronto (YTO) 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

The Marker Key West Harbor Resort

Key West Historic District

CA $1,958

per person

Oct 31 - Nov 4

found 12 hours ago

Roundtrip flight included

Buffalo (BUF) to Key West (EYW)

9.2/10 Wonderful! (1,016 reviews)

The hotel is in a great location for access to all that happens on Duval St with the majority of the destination points within a short, or reasonable, walking distance. The immediate surrounding area is fairly quiet, and since it IS Key West, laid-back. The room was comfortable with a nice balcony, effecient A/C and daily room service if you want / need it. While not "old", the room is a little dated and could use a refresh / update - particularly the bathroom. The hotel features 3 swimming pools with the 2 main pools being end to end to each other and sharing an outdoor bar / restaurant. The pools are a little on the small side and chairs get filled quickly. The live music each afternoon is a definate plus, although for the time we were there, the artists that performed did not offer much diversity or "something for everyone", sticking more to a tried and true style that while I'm sure it was comfortable for the performers, started to get a little monotonous. Overall, I recommend the Marker Key West primarily because of it's location because it is average to above average in just about every category. However, if your preferrence is luxury, you should probably look somewhere else.

Reviewed on Sep 29, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $3,267

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Key West (EYW)

8.6/10 Excellent! (3,560 reviews)

A+

Reviewed on Sep 28, 2026

Southernmost House - Adult Exclusive

Old Town Key West

CA $2,850

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Key West (EYW)

9.4/10 Exceptional! (1,004 reviews)

Blue Flamingo Resort Key West

New Town

CA $2,309

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Key West (EYW)

8.6/10 Excellent! (2,652 reviews)

Beautiful view,clean rooms nice staff

Reviewed on Sep 29, 2026

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3 Night Luxury holidays in Lower Florida Keys

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

Blue Flamingo Resort Key West

New Town

CA $1,693

per person

Nov 7 - Nov 10

found 18 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Key West (EYW)

8.6/10 Excellent! (2,652 reviews)

Beautiful view,clean rooms nice staff

Reviewed on Sep 29, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $2,447

per person

Nov 7 - Nov 10

found 18 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Key West (EYW)

8.6/10 Excellent! (3,560 reviews)

A+

Reviewed on Sep 28, 2026

Southernmost House - Adult Exclusive

Old Town Key West

CA $2,283

per person

Nov 7 - Nov 10

found 18 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Key West (EYW)

9.4/10 Exceptional! (1,004 reviews)

Don't see what you're looking for?

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4 Night Luxury holidays in Lower Florida Keys

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

The Marker Key West Harbor Resort

Key West Historic District

CA $1,958

per person

Oct 31 - Nov 4

found 12 hours ago

Roundtrip flight included

Buffalo (BUF) to Key West (EYW)

9.2/10 Wonderful! (1,016 reviews)

Reviewed on Sep 29, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

CA $3,908

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Key West (EYW)

9.2/10 Wonderful! (562 reviews)

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $3,267

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Key West (EYW)

8.6/10 Excellent! (3,560 reviews)

A+

Reviewed on Sep 28, 2026

Don't see what you're looking for?

See all available trips from Columbus to Lower Florida Keys

View all trips

What are some benefits when booking luxury Lower Florida Keys vacations?

When you book a luxury Lower Florida Keys vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Lower Florida Keys?

If you're looking for something luxurious in Lower Florida Keys, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $1,693, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 20. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Lower Florida Keys. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Lower Florida Keys?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Lower Florida Keys.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Lower Florida Keys. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Lower Florida Keys?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Lower Florida Keys or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Lower Florida Keys. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.