Lower Florida Keys Luxury Vacations

Book a Hotel + Flight or Car together to unlock savings

  • 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 Luxury hotel deals in Lower Florida Keys

Price found within the past 48 hours. Click for updated prices.
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Northside Resort
CA $1,526
per person
Nov 19 - Nov 23
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (1,460 reviews)
Wonderful stay with my family. Fantastic location. Friendly staff. Large, clean rooms.

Reviewed on Sep 11, 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
CA $2,232
per person
Nov 19 - Nov 23
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.8/10 Exceptional! (1,003 reviews)
Wonderful property and staff! Annette, Luna and George, our pool bartenders and breakfast staff were outstanding. Front desk staff very helpful and pleasant as well. Beautiful gardens and grounds, clean rooms, love that the pool is open all night for swimming. Live music every afternoon. Great location centrally located in old town, convenient to everything! Will definitely book here again!

Reviewed on Sep 12, 2026

Lighthouse Suites Collection

Lighthouse Suites Collection

Old Town Key West
CA $3,006
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
No reviews
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
CA $2,172
per person
Nov 19 - Nov 23
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
CA $2,085
per person
Nov 19 - Nov 23
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Lower Florida Keys
View all trips

3 Night Luxury holidays in Lower Florida Keys

Price found within the past 48 hours. Click for updated prices.
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
CA $2,307
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
Lighthouse Suites Collection

Lighthouse Suites Collection

Old Town Key West
CA $2,418
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
No reviews
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Northside Resort
CA $2,665
per person
Oct 22 - Oct 25
found 5 hours ago
Roundtrip flight included
Ottawa (YOW) to Key West (EYW)
9/10 Wonderful! (1,460 reviews)
Wonderful stay with my family. Fantastic location. Friendly staff. Large, clean rooms.

Reviewed on Sep 11, 2026

Don't see what you're looking for?
See all available trips from Columbus to Lower Florida Keys
View all trips

4 Night Luxury holidays in Lower Florida Keys

Price found within the past 48 hours. Click for updated prices.
Heron House - Adult Only

Heron House - Adult Only

Old Town Key West
CA $1,678
per person
Oct 26 - Oct 30
found 11 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Key West (EYW)
9.2/10 Wonderful! (1,158 reviews)
The Key West Hotel

The Key West Hotel

Key West Historic District
CA $2,359
per person
Nov 19 - Nov 23
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (562 reviews)
Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
CA $2,232
per person
Nov 19 - Nov 23
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.8/10 Exceptional! (1,003 reviews)
Wonderful property and staff! Annette, Luna and George, our pool bartenders and breakfast staff were outstanding. Front desk staff very helpful and pleasant as well. Beautiful gardens and grounds, clean rooms, love that the pool is open all night for swimming. Live music every afternoon. Great location centrally located in old town, convenient to everything! Will definitely book here again!

Reviewed on Sep 12, 2026

Don't see what you're looking for?
See all available trips from Columbus to Lower Florida Keys
View all trips

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 $1,526, 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 22. 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 $77
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Parasailing Downtown

Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides

CA $94
per traveller
92% of travellers recommend
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
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.