Lower Florida Keys Luxury Vacations

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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

Winslow's Bungalows - Key West Historic Inns

Old Town Key West
CA $1,267
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,432 reviews)
The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
CA $4,784
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
Very homey and luxurious at the same time

Reviewed on Oct 4, 2026

Lighthouse Suites Collection

Lighthouse Suites Collection

Old Town Key West
Save 100% on your flight
CA $5,770
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
10/10 Exceptional! (1 review)
My favorite place now. Won’t stay anywhere else. Lost track of the amount of my Key West stays, but this place has been the the most memorable.

Reviewed on Sep 13, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
CA $1,934
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
CA $1,874
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,024 reviews)
Very nice room with lots of space. Comfortable bed. Nice pool area with an outdoor bar and live music/entertainment. Good food. Friendly, helpful staff. Great location next to the historic seaport and 3 blocks from Duval Street. Lots of shops, restaurants, and bars within easy walking distance. Would definitely stay here again.

Reviewed on Oct 6, 2026

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3 Night Luxury holidays in Lower Florida Keys

Price found within the past 48 hours. Click for updated prices.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
CA $1,443
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
Onsite parking was $50 a day. We were given a room with the view of the dumpster and construction area. The beach was mostly non-existent and had sea grass that smelled heavily like cow manure. Onsite restaurant prices were ridiculous $123 dollars for two appetizers, two Pepsi's, and a Mahi plate all eaten while enduring the cow manure smell. We had our do not disturb on our room, housecleaning waited till the last day after their work hours to let us know they would like to clean the room. The very small room had the window air conditioner vent propped with a hotel brochure and blowed directly across the bed and was very noisy.

Reviewed on Oct 6, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
CA $2,355
per person
Dec 9 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
The Gardens Hotel

The Gardens Hotel

Old Town Key West
CA $2,677
per person
Dec 9 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
Very homey and luxurious at the same time

Reviewed on Oct 4, 2026

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4 Night Luxury holidays in Lower Florida Keys

Price found within the past 48 hours. Click for updated prices.
The Key West Hotel

The Key West Hotel

Key West Historic District
CA $2,508
per person
Nov 27 - Dec 1
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (563 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

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

Old Town Key West
CA $3,636
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Key West (EYW)
9.8/10 Exceptional! (1,001 reviews)
Brand New Build Larkshine House - Pool

Brand New Build Larkshine House - Pool

Save 100% on your flight
CA $24,349
per person
Dec 28 - Jan 1
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
No reviews
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Plan the perfect luxury Lower Florida Keys vacation with Expedia

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 $1,267, 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 14. 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.

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $59
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $78
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

CA $82
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
See all activities in Lower Florida Keys

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.