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.
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

New Town
CA $893
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
8.6/10 Excellent! (2,652 reviews)
Friendly and helpful staff. Love the 2 pools. It's great that they have a complimentary shuttle to take you downtown.

Reviewed on Sep 22, 2026

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

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

CA $2,409
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Rouyn-Noranda (YUY) to Miami (MIA)
9/10 Wonderful! (258 reviews)
We stayed at the hotel for one night, and overall, it was an okay experience. The property is very new, especially The Cove, where we stayed. Our room was clean, modern, and well maintained. There were, however, a few disappointments. The air conditioning kept malfunctioning throughout our stay, and the room never reached the temperature we wanted. We repeatedly had to turn it off and back on to get it working properly. We were also told that complimentary bottled water would be available in the room, but none was provided. Another disappointment was related to my boyfriend's birthday. I contacted the hotel in advance by phone, email, and message and was told a birthday card and a voucher would be waiting for us. Unfortunately, neither was there upon arrival. I had to follow up at the front desk, and the voucher ended up being only for a dessert, which felt underwhelming. We also paid extra for an ocean-view room, but it did not feel worth the additional cost. The view was largely obstructed by palm trees and overlooked the pool more than the ocean. Overall, the hotel is nice, new, and has a lot of potential. Having three beaches is a great feature and not something commonly found in the Keys. While we enjoyed our stay, I felt the experience lacked attention to detail and follow-through on guest requests. I really value the small touches that make a stay feel special, and that is where the hotel fell short for me.

Reviewed on Sep 22, 2026

Hawks Cay Resort

Hawks Cay Resort

CA $2,393
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Rouyn-Noranda (YUY) to Miami (MIA)
8.2/10 Very good! (1,006 reviews)
The village we were assigned has roaches and the main bedroom has the pain from the felling peeling which could be a hazard. Also, the water park that was supposed to be completed on September has a delay and that was the main reason a reserve this hotel.

Reviewed on Sep 21, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
CA $2,490
per person
Oct 29 - Nov 4
found 24 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
Islander Resort

Islander Resort

Matecumbe
CA $2,566
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Rouyn-Noranda (YUY) to Miami (MIA)
9.4/10 Exceptional! (1,112 reviews)
Loved the property!!! So quiet and relaxing! Great bar, pools, beaches!!!! Would absolutely stay again!

Reviewed on Sep 22, 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 $1,621
per person
Oct 23 - Oct 30
found 23 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Miami (MIA)
9.2/10 Wonderful! (1,422 reviews)
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3 Night Beach holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

New Town
CA $893
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
8.6/10 Excellent! (2,652 reviews)
Friendly and helpful staff. Love the 2 pools. It's great that they have a complimentary shuttle to take you downtown.

Reviewed on Sep 22, 2026

Hawks Cay Resort

Hawks Cay Resort

CA $961
per person
Dec 16 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
8.2/10 Very good! (1,006 reviews)
The village we were assigned has roaches and the main bedroom has the pain from the felling peeling which could be a hazard. Also, the water park that was supposed to be completed on September has a delay and that was the main reason a reserve this hotel.

Reviewed on Sep 21, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
CA $2,347
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Moncton (YQM) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
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4 Night Beach holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Beachside Resort & Residences

Beachside Resort & Residences

CA $1,441
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Key West (EYW)
8.6/10 Excellent! (2,487 reviews)
Nice, spacious rooms. Nice Pool and fantastic bar tender! Maintenance speedy if needed. Nice to have the shuttle to/from downtown. Enjoyed our stay very much.

Reviewed on Sep 22, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
Save 100% on your flight
CA $2,860
per person
Dec 10 - Dec 14
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
CA $1,745
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
8.6/10 Excellent! (3,560 reviews)
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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 $893, 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 17.

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

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3675 South Roosevelt Boulevard Key West FL
  • 7 min drive from Duval Street
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 ...
Hyatt Vacation Club at Windward Pointe, Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
  • 10 min walk from Duval Street
Book a stay at this spa 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 ...
Southernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

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 ...
Margaritaville Beach House Key West
See all 8,221 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 $59
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 $77
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

CA $109
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
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.