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.

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $1,784

per person

Dec 8 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

8.6/10 Excellent! (3,606 reviews)

The resort itself was nice and most of the staff was super nice! But we paid way too much money for us not to be aware that the big pool was closed for the week and on top of it they ran a power washer for 3 days which sounded like it was inside of or room! It ran from 9-5 only turning off for about a hour for the rain! We couldn’t enjoy our balcony or even just relax in the room! We would have understood if they had to use it for a couple hours cuz they was just doing their job but not for 3 straight days!

Reviewed on Oct 4, 2026

The Gardens Hotel

Old Town Key West

Save 100% on your flight

CA $3,482

per person

Dec 21 - Dec 26

found 17 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

Very homey and luxurious at the same time

Reviewed on Oct 4, 2026

Southernmost House - Adult Exclusive

Old Town Key West

Save 100% on your flight

CA $5,432

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,001 reviews)

A very neat place to stay. Queen bungalow right next to the pool at the Southernmost house. Not a massive room. Has a microwave, medium fridge and small kitchen space. The outside patio is very appealing and chill.

Reviewed on Oct 3, 2026

The Marker Key West Harbor Resort

Key West Historic District

Save 100% on your flight

CA $2,069

per person

Dec 8 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (1,016 reviews)

Bathroom floor had hair all over the place. They decided to close the main pool and begin repairs which was loud and dusty. Basically we could not hang out at the pool. Staff was unapologetic. On the bright side the bartender was very nice and made great cocktails.

Reviewed on Oct 3, 2026

Eden House

Key West Historic District

CA $2,144

per person

Dec 8 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9/10 Wonderful! (1,002 reviews)

I feel like this is a hidden gem in key west. Its hidden in a neighborhood close to all the action. Beautiful pool, our room was clean and I mean it smelt clean that was nice. They also accommodated an early check in for me. It was a great experience I will definitely be back. I have zero complaints.

Reviewed on Oct 4, 2026

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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

Key West Historic District

CA $1,650

per person

Nov 26 - Nov 29

found 15 hours ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (1,016 reviews)

Reviewed on Oct 3, 2026

Southernmost House - Adult Exclusive

Old Town Key West

CA $1,904

per person

Nov 26 - Nov 29

found 15 hours ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,001 reviews)

Reviewed on Oct 3, 2026

The Gardens Hotel

Old Town Key West

CA $2,730

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! (1,000 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.

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

CA $1,899

per person

Dec 8 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,285 reviews)

The Key West Hotel

Key West Historic District

Save 100% on your flight

CA $2,435

per person

Dec 8 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (563 reviews)

The Marker Key West Harbor Resort

Key West Historic District

Save 100% on your flight

CA $2,069

per person

Dec 8 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (1,016 reviews)

Reviewed on Oct 3, 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 $1,650, 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.