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.

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

CA $4,291

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (1,432 reviews)

The Marker Key West Harbor Resort

Key West Historic District

Save 100% on your flight

CA $5,460

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (1,024 reviews)

Love this place!!!

Reviewed on Oct 24, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $5,056

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

8.6/10 Excellent! (3,636 reviews)

The room was perfectly clean and comfortable. However, our experience with the staff was a bit mixed. While some of the bartenders were incredibly friendly and welcoming, a few others could definitely use some training in hospitality and politeness. Additionally, it would be great if breakfast hours could be extended a bit later. When people are on vacation, they want to sleep in without worrying about missing the morning meal!

Reviewed on Oct 25, 2026

Southernmost House - Adult Exclusive

Old Town Key West

CA $4,940

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

staff was super friendly and accomodating

Reviewed on Oct 22, 2026

The Gardens Hotel

Old Town Key West

CA $5,649

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

Un hotel hermoso , limpio , con una localización insuperable . El servio de primera , volveré pronto

Reviewed on Oct 20, 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 $1,575

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

8.6/10 Excellent! (2,702 reviews)

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $1,902

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

8.6/10 Excellent! (3,636 reviews)

Reviewed on Oct 25, 2026

The Marker Key West Harbor Resort

Key West Historic District

CA $1,937

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (1,024 reviews)

Love this place!!!

Reviewed on Oct 24, 2026

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4 Night Luxury holidays in Lower Florida Keys

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

Orchid Key Inn - Adults Only

Old Town Key West

CA $2,058

per person

Nov 25 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

The Key West Hotel

Key West Historic District

CA $3,020

per person

Nov 25 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (564 reviews)

Property was everything as described, clean, in the heart of the excitement that is Key West Pool was refreshing and close to tiki bar and local entertainment. The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer

Reviewed on Oct 6, 2026

The Marker Key West Harbor Resort

Key West Historic District

CA $2,237

per person

Nov 25 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (1,024 reviews)

Love this place!!!

Reviewed on Oct 24, 2026

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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 $1,575, 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 18. 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.