Beach Vacations in Florida Keys 2026

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Flight and Beach hotel deals in Florida Keys

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

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

CA $1,350

per person

Nov 13 - Nov 16

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Miami (MIA)

9/10 Wonderful! (281 reviews)

this was the nicest place i have ever stayed. the staff was so incredibly helpful and the amenities they provide are amazing. will definitely stay here again. 10/10

Reviewed on Oct 12, 2026

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

CA $1,891

per person

Nov 13 - Nov 18

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

9.2/10 Wonderful! (1,471 reviews)

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $1,585

per person

Nov 13 - Nov 16

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

8.6/10 Excellent! (3,636 reviews)

We went with 2 other couples 2nd year in a row at Southern Most, that should tell you how much we enjoyed it! Great location, food rooms were always cleaned.

Reviewed on Oct 12, 2026

Islander Resort

Matecumbe

CA $1,500

per person

Nov 13 - Nov 16

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Miami (MIA)

9.4/10 Exceptional! (1,132 reviews)

Fabulous bedroom cozy bed and awesome hot shower. Couch was sorta cheap and no fridge but we loved the ice maker and kitchenette. We loved the pool and the staff. Weak drinks but good food. The feeling there is soooo great. Will 100% come back.

Reviewed on Oct 13, 2026

Hawks Cay Resort

CA $2,203

per person

Dec 18 - Dec 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Miami (MIA)

8.2/10 Very good! (1,006 reviews)

Loved every moment

Reviewed on Oct 12, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

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5* Beach holidays in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

CA $1,891

per person

Nov 13 - Nov 18

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

9.2/10 Wonderful! (1,471 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

3 Night Beach holidays in Florida Keys

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

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

CA $1,350

per person

Nov 13 - Nov 16

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Miami (MIA)

9/10 Wonderful! (281 reviews)

this was the nicest place i have ever stayed. the staff was so incredibly helpful and the amenities they provide are amazing. will definitely stay here again. 10/10

Reviewed on Oct 12, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $1,585

per person

Nov 13 - Nov 16

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

8.6/10 Excellent! (3,636 reviews)

We went with 2 other couples 2nd year in a row at Southern Most, that should tell you how much we enjoyed it! Great location, food rooms were always cleaned.

Reviewed on Oct 12, 2026

Islander Resort

Matecumbe

CA $1,500

per person

Nov 13 - Nov 16

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Miami (MIA)

9.4/10 Exceptional! (1,132 reviews)

Reviewed on Oct 13, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

4 Night Beach holidays in Florida Keys

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

Southernmost House - Adult Exclusive

Old Town Key West

CA $2,194

per person

Nov 26 - Nov 30

found 19 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,001 reviews)

Great stay. Older locations like this face many challenges so there is certainly more work to be done but everything worked like new and the staff was super helpful even offering an upgrade at no charge due to availability.

Reviewed on Oct 11, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $3,706

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Key West (EYW)

8.6/10 Excellent! (3,636 reviews)

We went with 2 other couples 2nd year in a row at Southern Most, that should tell you how much we enjoyed it! Great location, food rooms were always cleaned.

Reviewed on Oct 12, 2026

Blue Flamingo Resort Key West

New Town

CA $3,148

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Key West (EYW)

8.6/10 Excellent! (2,702 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

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What are some benefits when booking beach vacations in Florida Keys?

When you travel to the beach in Florida Keys, 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 Florida Keys?

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 Florida Keys 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 Florida Keys?

There are quite a few things you can do to get cheap beach vacations in Florida Keys. Prices range from CA $1,350, 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 Florida Keys. These package deals let you save by booking your accommodation and your flight together with savings of up to 25.

Why should I book family beach vacations?

When you're travelling with the family to Florida Keys, 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 Florida Keys?

It's easy to find a beachfront vacation accommodation in Florida Keys 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 Florida Keys 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 Florida Keys 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 United States of America. 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 Florida Keys

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

4 min drive from Duval Street

Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the pool and the restaurant ...

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

16 min walk from Duval Street

Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and Southernmost ...

8.4/10 Very good! (966 reviews)

"Will not return again poor service room was dirty"

Reviewed on Oct 13, 2026

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd Key West FL

7 min drive from Duval Street

Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...

8.4/10 Very good! (1,116 reviews)

"Staff was great"

Reviewed on Oct 13, 2026

See all 8,208 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.