Luxury Florida Keys Vacation Packages 2026/2027

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Flight and Luxury hotel deals in Florida Keys

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

Hawks Cay Resort

CA $1,269

per person

Oct 20 - Oct 25

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Miami (MIA)

8.2/10 Very good! (1,009 reviews)

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

CA $1,451

per person

Oct 20 - Oct 25

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Miami (MIA)

9/10 Wonderful! (246 reviews)

Stayed in build 7 and it had a great view restaurant was good the bars where nice and most of all I booked a fishing trip with Whiskey Throttle guide service and Sean put me on a dinosaur of a tarpon and boy was it a beast. If the fishing is slow grab Whiskey Throttle for a great water adventures.

Reviewed on Aug 14, 2026

Southernmost House - Adult Exclusive

Old Town Key West

CA $3,529

per person

Oct 20 - Oct 25

found 8 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Excellent place to stay and will absolutely stay there again! The staff was so helpful and friendly! The restaurant on the property has delicious food! I highly recommend staying at he Southern Most House, great pool, great location, great vacation!

Reviewed on Aug 16, 2026

The Marker Key West Harbor Resort

Key West Historic District

CA $3,824

per person

Oct 20 - Oct 25

found 8 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9.2/10 Wonderful! (1,002 reviews)

Disappointed in room, we've stayed here many, many times and this was disappointing. Also, the amount of people that use the amenities that are not staying at resort OR paying resort fees.

Reviewed on Aug 14, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $3,098

per person

Oct 20 - Oct 25

found 8 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

8.8/10 Excellent! (3,469 reviews)

Great location , able to walk to restaurants on Duval Street . Nice pools , good services

Reviewed on Aug 16, 2026

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5* Luxury holidays in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe

CA $1,278

per person

Oct 1 - Oct 6

found 9 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Miami (MIA)

9.2/10 Wonderful! (1,360 reviews)

The pools and bars were great! Our room was dirty, our toilet base was broken, in room coffee pot was HORRIBLE! The food there is ok, I recommend eating out at least for dinners. The bar service while at the pool was the absolute best part. Butch was the best bartender!

Reviewed on Aug 17, 2026

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3 Night Luxury holidays in Florida Keys

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

Southernmost House - Adult Exclusive

Old Town Key West

CA $2,707

per person

Nov 5 - Nov 8

found 2 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Reviewed on Aug 16, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $2,829

per person

Nov 5 - Nov 8

found 2 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

8.8/10 Excellent! (3,469 reviews)

Great location , able to walk to restaurants on Duval Street . Nice pools , good services

Reviewed on Aug 16, 2026

La Concha Key West, Autograph Collection

Key West Historic District

CA $3,013

per person

Nov 5 - Nov 8

found 2 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9/10 Wonderful! (459 reviews)

Location is directly in old town area of Key West. Convenient walk to Mallory Square. Sunset Pier, Sloppy Joe's, Hogs Breath Salon and various other local hot spots and shops.

Reviewed on Aug 13, 2026

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4 Night Luxury holidays in Florida Keys

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

The Pelican Key Largo Cottages

CA $1,070

per person

Nov 3 - Nov 7

found 11 hours ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

9/10 Wonderful! (1,004 reviews)

Great place great price great location

Reviewed on Aug 16, 2026

Southernmost House - Adult Exclusive

Old Town Key West

CA $2,381

per person

Oct 23 - Oct 27

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Reviewed on Aug 16, 2026

The Marker Key West Harbor Resort

Key West Historic District

CA $2,472

per person

Oct 23 - Oct 27

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Key West (EYW)

9.2/10 Wonderful! (1,002 reviews)

Disappointed in room, we've stayed here many, many times and this was disappointing. Also, the amount of people that use the amenities that are not staying at resort OR paying resort fees.

Reviewed on Aug 14, 2026

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What are some benefits when booking luxury Florida Keys vacations?

When you book a luxury 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 Florida Keys?

If you're looking for something luxurious in 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 $1,070, 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 25. 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 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 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 Florida Keys.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in 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 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 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 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.

Luxury Hotels in Florida Keys

Hilton Key West Resort & Marina

5950 Peninsular Avenue Key West FL

10 min drive from Duval Street

Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...

The Marker Key West Harbor Resort

200 William Street Key West FL

10 min walk from Duval Street

Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful ...

9.2/10 Wonderful! (1,022 reviews)

"Disappointed in room, we've stayed here many, many times and this was disappointing. Also, the amount of people that use the amenities that are not staying at resort OR paying resort fees."

Reviewed on Aug 14, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

3 hours drive from Duval Street

Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...

9.2/10 Wonderful! (1,397 reviews)

"The pools and bars were great! Our room was dirty, our toilet base was broken, in room coffee pot was HORRIBLE! The food there is ok, I recommend eating out at least for dinners. The bar service while at the pool was the absolute best part. Butch was the best bartender!"

Reviewed on Aug 17, 2026

See all 8,271 properties in Florida Keys

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.