Key Haven Beach Vacations

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Flight and Beach hotel deals in Key Haven

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

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

CA $1,654

per person

Nov 10 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Key West (EYW)

9.2/10 Wonderful! (1,397 reviews)

Two concerns: 1) TV issue was not addressed by staff in a timely fashion. Note; the amenity fee was reduced as a result. 2) concern may be equal parts Winslow’s Bungalows and Expedia. There should be transparent pricing that includes the TOTAL AMOUNT. It’s distasteful to a customer amenity fees, etc. show up at check-in/out. Just quote the customer the true cost of their stay and avoid creating a frustration on behalf of the consumer.

Reviewed on Sep 1, 2026

The Gardens Hotel

Old Town Key West

CA $3,429

per person

Nov 13 - Nov 20

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $3,122

per person

Nov 10 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Key West (EYW)

8.8/10 Excellent! (3,534 reviews)

The resort fee is very expensive for what the resort has to offer for the guests. I will not rebook this resort the next time we are in Keywest. No shuttle services are offered. Nothing complimentary but two welcome drinks.

Reviewed on Sep 1, 2026

The Marker Key West Harbor Resort

Key West Historic District

CA $2,801

per person

Nov 10 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Key West (EYW)

9.2/10 Wonderful! (1,027 reviews)

Beautiful stay

Reviewed on Aug 31, 2026

Southernmost House - Adult Exclusive

Old Town Key West

CA $2,584

per person

Nov 10 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Key West (EYW)

9.4/10 Exceptional! (1,004 reviews)

We were on the top floor. Lots of stairs. Make sure you can do stairs when booking or request a lower floor. It's beautiful, great location and would go back again.

Reviewed on Sep 1, 2026

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3 Night Beach holidays in Key Haven

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

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

CA $671

per person

Nov 9 - Nov 12

found 14 hours ago

Roundtrip flight included

Toronto (YYZ) to Key West (EYW)

9.2/10 Wonderful! (1,397 reviews)

Reviewed on Sep 1, 2026

The Marker Key West Harbor Resort

Key West Historic District

CA $1,221

per person

Nov 9 - Nov 12

found 14 hours ago

Roundtrip flight included

Toronto (YYZ) to Key West (EYW)

9.2/10 Wonderful! (1,027 reviews)

Beautiful stay

Reviewed on Aug 31, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $1,055

per person

Nov 9 - Nov 12

found 14 hours ago

Roundtrip flight included

Toronto (YYZ) to Key West (EYW)

8.8/10 Excellent! (3,534 reviews)

Reviewed on Sep 1, 2026

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See all available trips from Columbus to Key Haven

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4 Night Beach holidays in Key Haven

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

Ella's Cottages - Key West Historic Inns

Old Town Key West

CA $1,473

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9.4/10 Exceptional! (494 reviews)

It is located in the heart of he old district snd everything was so accessible without having to use our car. The property is only 1 block off Duval so,we had the advantage of,accessibility without the noise. The property is protected by foliage which makes it feel private and protected. The complimentary breakfast is lovely, and there is wine by the pool daily. Dwight welcomes guests upon arrival,and made us feel,at home. The beds are so comfy, and each cottage has its own flavor. I hope to return and stay at Ella’s Cottages again, Expedia does a great job helping us narrow down our priorities, amenities, location, etc. That enabled us to find Ella’s Cottages, which was perfect for us.

Reviewed on Sep 1, 2026

Southernmost House - Adult Exclusive

Old Town Key West

CA $2,307

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! (1,004 reviews)

We were on the top floor. Lots of stairs. Make sure you can do stairs when booking or request a lower floor. It's beautiful, great location and would go back again.

Reviewed on Sep 1, 2026

The Key West Hotel

Key West Historic District

CA $4,698

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! (562 reviews)

Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

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What are some benefits when booking beach vacations in Key Haven?

When you travel to the beach in Key Haven, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip.

How can I book the best beach vacations in Key Haven?

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Key Haven trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit.

Can I book cheap beach vacations in Key Haven?

There are quite a few things you can do to get cheap beach vacations in Key Haven. Prices range from CA $671, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out.

Can I book beach packages?

Yes, and you'll find quite a few beach packages available in Key Haven. These package deals let you save by booking your accommodation and your flight together with savings of up to 33.

Why should I book family beach vacations?

When you're travelling with the family to Key Haven, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room.

How can I find a beachfront vacation in Key Haven?

It's easy to find a beachfront vacation accommodation in Key Haven using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

How can I book last-minute beach vacations?

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Key Haven as your destination and see what's available.

Can I find all-inclusive beach vacations ?

Yes, all you have to do to find all-inclusive beach vacations in Key Haven is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance.

Can I book a beach trip that's fully refundable?

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Key West. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

Why should I book beach vacations with Expedia?

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.

Beach Hotels in Key Haven

Floralee House in Key West

Key West FL

11 min drive from Duval Street

Stay at this vacation home in Key West. Enjoy free parking and a garden. Popular attractions Duval Street and Smathers Beach are located nearby.

Private & Haven-ly - Pool Home on Boating Canal

Key Haven FL

11 min drive from Duval Street

Stay at this vacation home in Key West. Enjoy laundry facilities, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Duval Street and ...

See all 3,114 properties in Key Haven

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.