Key Haven Luxury Vacations

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Flight and Luxury hotel deals in Key Haven

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
Save 100% on your flight
CA $1,972
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (3,606 reviews)
We were looking for good value- we got it! Staff was friendly from start to finish. Rooms provided everything we wanted from a comfortable bed to a scenic ocean view.

Reviewed on Oct 1, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
Save 100% on your flight
CA $2,011
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
We arrived at Key West just after 12 noon on a Sunday. I was planning to just leave our luggage’s at the hotel since check in time was at 4pm. Catherine was the one that greeted us and help us out on our check in process. She was very professional and very friendly. We got our room ready right away and we didn’t have to wait until check in time at 4PM. Our room was right by the pool, it was clean, has a full size fridge and small microwave, some kitchen amenities (plates, cups, silverware’s) and a dehumidifier. The bathroom is clean and very spacious (shower area). We thought it will be loud since it’s close to the pool and the bar but the whole time we were there it was nice and quiet. There’s are near by restaurants, shops and coffee shops but I suggest to rent a scooter to get to the port area if you have any plans on going to any boating trips (it’s a good 20-30 mins walk from the hotel). We met dean on our 2nd day and he was very friendly and make sure to give us our parking pass for the scooter that we rented. Dean and Catherine definitely made our stay special. And we will definitely come back to stay at this facility on our next trip to Key West. I highly recommend this place if you want a relaxing, laidback stay at Key West.

Reviewed on Oct 1, 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
CA $2,579
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
It is a GREAT property in Key West, right in the center of the action.

Reviewed on Sep 28, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
Save 100% on your flight
CA $2,570
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,016 reviews)
Eden House

Eden House

Key West Historic District
CA $2,321
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9/10 Wonderful! (1,002 reviews)
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3 Night Luxury holidays in Key Haven

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

Eden House

Key West Historic District
CA $2,109
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (1,002 reviews)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
Save 100% on your flight
CA $2,690
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
We arrived at Key West just after 12 noon on a Sunday. I was planning to just leave our luggage’s at the hotel since check in time was at 4pm. Catherine was the one that greeted us and help us out on our check in process. She was very professional and very friendly. We got our room ready right away and we didn’t have to wait until check in time at 4PM. Our room was right by the pool, it was clean, has a full size fridge and small microwave, some kitchen amenities (plates, cups, silverware’s) and a dehumidifier. The bathroom is clean and very spacious (shower area). We thought it will be loud since it’s close to the pool and the bar but the whole time we were there it was nice and quiet. There’s are near by restaurants, shops and coffee shops but I suggest to rent a scooter to get to the port area if you have any plans on going to any boating trips (it’s a good 20-30 mins walk from the hotel). We met dean on our 2nd day and he was very friendly and make sure to give us our parking pass for the scooter that we rented. Dean and Catherine definitely made our stay special. And we will definitely come back to stay at this facility on our next trip to Key West. I highly recommend this place if you want a relaxing, laidback stay at Key West.

Reviewed on Oct 1, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
Save 100% on your flight
CA $2,285
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (3,606 reviews)
We were looking for good value- we got it! Staff was friendly from start to finish. Rooms provided everything we wanted from a comfortable bed to a scenic ocean view.

Reviewed on Oct 1, 2026

Don't see what you're looking for?
See all available trips from Columbus to Key Haven
View all trips

4 Night Luxury holidays in Key Haven

Price found within the past 48 hours. Click for updated prices.
Island City House Hotel

Island City House Hotel

Key West Historic District
CA $1,707
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.6/10 Exceptional! (1,003 reviews)
Absolutely stellar property - gorgeous in all respects. Our rooms, the spacious private porch, the grounds, pool, everything. Beds were comfy, staff was helpful, and we all enjoyed Bert's visits to our porch as well. As a former Key West resident, I loved the Old Town location and atmosphere of the Island City House Hotel. The staff were also friendly and helpful. We have every intention of staying here again in the future!

Reviewed on Sep 30, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
CA $2,108
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (563 reviews)
The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
CA $2,579
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
It is a GREAT property in Key West, right in the center of the action.

Reviewed on Sep 28, 2026

Don't see what you're looking for?
See all available trips from Columbus to Key Haven
View all trips

Plan the perfect luxury Key Haven vacation with Expedia

What are some benefits when booking luxury Key Haven vacations?

When you book a luxury Key Haven 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 Key Haven?

If you're looking for something luxurious in Key Haven, 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 $1,707, 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 24. 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 Key Haven. 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 Key Haven?

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 Key Haven.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Key Haven. 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 Key Haven?

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 Key Haven 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 Key Haven. 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.

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