Florida Keys Beach Vacations

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Flight and Beach hotel deals in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Northside Resort
CA $1,156
per person
Oct 8 - Oct 12
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (1,433 reviews)
Hotel was a welcome relief after a long hot day on the island. Seemed like a hidden paradise.

Reviewed on Aug 8, 2026

Hawks Cay Resort

Hawks Cay Resort

CA $1,658
per person
Oct 8 - Oct 12
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very good! (1,017 reviews)
Half of the amenities where closed. Could get a hold of front desk most of the time. Service was never right when you did get someone. Even met a guy waiting on a mattress for his kid standing in the lobby. Never stay here. Overpriced. Not enough for kids. Website list activity’s that aren’t available, consider anywhere but here.

Reviewed on Aug 7, 2026

Pier House Resort & Spa

Pier House Resort & Spa

Key West Historic District
CA $1,430
per person
Oct 8 - Oct 12
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (1,253 reviews)
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

CA $1,813
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
9/10 Wonderful! (238 reviews)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
CA $1,412
per person
Oct 8 - Oct 12
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (3,487 reviews)
Disappointing Stay — Not What We Expected From a “Beach Resort” Unfortunately, our stay at Southernmost Beach Resort was very disappointing and did not live up to our expectations, particularly considering the price and how the property is marketed. The rooms were not up to the standard we expected from a resort in this price range. Overall, the property and amenities also felt underwhelming and did not provide the resort experience we anticipated. Even more disappointing was the service. We did not find the staff particularly friendly or welcoming, which makes a significant difference when you are spending your vacation—and your money—at a resort. Our biggest frustration, however, was the beach. The beach was essentially unusable because of the amount of seaweed. Obviously, the resort cannot control Mother Nature or the seaweed conditions, and I would never fault them for that. What I do fault them for is the lack of transparency. When a property specifically markets itself as a beach resort, guests should be made aware prior to arrival when the beach is currently in a condition that makes it practically unusable. Had we known, it absolutely would have factored into our decision about where to stay. We travel often and understand that not every hotel or resort will be perfect, but this stay simply did not meet the level of quality, hospitality, or overall experience we expected. I would strongly encourage future guests to check the current beach conditions

Reviewed on Aug 8, 2026

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5* Beach holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
CA $1,680
per person
Oct 9 - Oct 12
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
9.2/10 Wonderful! (1,360 reviews)
Don't see what you're looking for?
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3 Night Beach holidays in Florida Keys

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

Hawks Cay Resort

CA $900
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
8.2/10 Very good! (1,017 reviews)
Half of the amenities where closed. Could get a hold of front desk most of the time. Service was never right when you did get someone. Even met a guy waiting on a mattress for his kid standing in the lobby. Never stay here. Overpriced. Not enough for kids. Website list activity’s that aren’t available, consider anywhere but here.

Reviewed on Aug 7, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
CA $2,832
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
Pier House Resort & Spa

Pier House Resort & Spa

Key West Historic District
CA $1,426
per person
Oct 9 - Oct 12
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9/10 Wonderful! (1,253 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Florida Keys
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4 Night Beach holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Northside Resort
CA $1,156
per person
Oct 8 - Oct 12
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (1,433 reviews)
Hotel was a welcome relief after a long hot day on the island. Seemed like a hidden paradise.

Reviewed on Aug 8, 2026

Hawks Cay Resort

Hawks Cay Resort

CA $1,658
per person
Oct 8 - Oct 12
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very good! (1,017 reviews)
Half of the amenities where closed. Could get a hold of front desk most of the time. Service was never right when you did get someone. Even met a guy waiting on a mattress for his kid standing in the lobby. Never stay here. Overpriced. Not enough for kids. Website list activity’s that aren’t available, consider anywhere but here.

Reviewed on Aug 7, 2026

Pier House Resort & Spa

Pier House Resort & Spa

Key West Historic District
CA $1,430
per person
Oct 8 - Oct 12
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (1,253 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Florida Keys
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Find the best beach vacations in Florida Keys

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 $900, 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 23.

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

Beachside Resort & Residences

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL
  • 29 min drive from Florida Keys Beaches
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
  • 36 min drive from Florida Keys Beaches
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (3,489 reviews)
"Disappointing Stay — Not What We Expected From a “Beach Resort” Unfortunately, our stay at Southernmost Beach Resort was very disappointing and did not live up to our expectations, particularly considering the price and how the property is marketed. The rooms were not up to the standard we expected ..."

Reviewed on Aug 8, 2026

Southernmost Beach Resort and Guesthouses
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3675 South Roosevelt Boulevard Key West FL
  • 30 min drive from Florida Keys Beaches
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (1,219 reviews)
"The property is absolutely STUNNING. Balconies with rocking chairs, table and telescope. Gas grills, lovely infinity pool and hot tub. Close to the airport, over 4 days I heard the planes like 5 or 6 times and that was it. Need to Uber or Cab down to Old Town. Maria was AWESOME, she showed us to ..."

Reviewed on Aug 6, 2026

Hyatt Vacation Club at Windward Pointe, Key West
See all 8,280 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.

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $63
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $78
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Snorkler waving underwater in Key West

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

CA $85
per adult
86% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
See all activities in Florida Keys

More vacations you might like

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