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 $1,303
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9/10 Wonderful! (1,438 reviews)
The rooms was spacious and immaculate. Check in was very pleasant, we were greeted with mimosas by the staff. The pool and restaurant were amazing as well. Centralized location just minutes form restaurants and activities.

Reviewed on Aug 23, 2026

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

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

CA $1,692
per person
Oct 17 - Oct 24
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9/10 Wonderful! (246 reviews)
I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff.

Reviewed on Aug 23, 2026

Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
CA $1,764
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
9.2/10 Wonderful! (1,360 reviews)
I didnt have a great stay here, but I am scouting a place for family reunion. I think I will give it another shot. Could have just been a fluke. The grounds were impeccably maintained. The dock was great. Wish they had more than one class for Teaching kids to fish. Most of the Staff was great. Food was good. For some reason I really felt like we did not belong. Glared at by employees, bad room way in the back, terrible metal scrapping noise that started at 11pm each night. Weird barn type door between bathroom and bedroom, kids loved playing on it. Adults not so much. I think I will try it again, not on a holiday and maybe in the main part of hotel.

Reviewed on Aug 23, 2026

Hawks Cay Resort

Hawks Cay Resort

CA $1,652
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
8.2/10 Very good! (1,009 reviews)
Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

CA $2,073
per person
Nov 9 - Nov 14
just found
Roundtrip flight included
Edmonton (YEA) to Miami (MIA)
8.8/10 Excellent! (1,006 reviews)
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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 $1,764
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
9.2/10 Wonderful! (1,360 reviews)
I didnt have a great stay here, but I am scouting a place for family reunion. I think I will give it another shot. Could have just been a fluke. The grounds were impeccably maintained. The dock was great. Wish they had more than one class for Teaching kids to fish. Most of the Staff was great. Food was good. For some reason I really felt like we did not belong. Glared at by employees, bad room way in the back, terrible metal scrapping noise that started at 11pm each night. Weird barn type door between bathroom and bedroom, kids loved playing on it. Adults not so much. I think I will try it again, not on a holiday and maybe in the main part of hotel.

Reviewed on Aug 23, 2026

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3 Night Beach holidays in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe
CA $895
per person
Oct 1 - Oct 4
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (1,360 reviews)
I didnt have a great stay here, but I am scouting a place for family reunion. I think I will give it another shot. Could have just been a fluke. The grounds were impeccably maintained. The dock was great. Wish they had more than one class for Teaching kids to fish. Most of the Staff was great. Food was good. For some reason I really felt like we did not belong. Glared at by employees, bad room way in the back, terrible metal scrapping noise that started at 11pm each night. Weird barn type door between bathroom and bedroom, kids loved playing on it. Adults not so much. I think I will try it again, not on a holiday and maybe in the main part of hotel.

Reviewed on Aug 23, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
CA $1,518
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
We had a great time at the Southernmost House. The staff was extremely kind, helpful, and friendly. The food at the bar that we had for breakfast and lunch was fantastic. The house was charming, and while it needs some updating, the staff is actively working to improve the property. We always had a place to park our golf cart and any issue we had was solved quickly. The location was great and we would definitely stay there again.

Reviewed on Aug 20, 2026

Hawks Cay Resort

Hawks Cay Resort

CA $1,652
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
8.2/10 Very good! (1,009 reviews)
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4 Night Beach holidays in Florida Keys

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
CA $1,774
per person
Oct 8 - Oct 12
found 1 hour ago
Roundtrip non-stop flight included
Halifax (YHZ) to Key West (EYW)
8.8/10 Excellent! (3,469 reviews)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
CA $2,767
per person
Nov 5 - Nov 9
found 2 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
We had a great time at the Southernmost House. The staff was extremely kind, helpful, and friendly. The food at the bar that we had for breakfast and lunch was fantastic. The house was charming, and while it needs some updating, the staff is actively working to improve the property. We always had a place to park our golf cart and any issue we had was solved quickly. The location was great and we would definitely stay there again.

Reviewed on Aug 20, 2026

Pier House Resort & Spa

Pier House Resort & Spa

Key West Historic District
CA $2,199
per person
Oct 8 - Oct 12
found 1 hour ago
Roundtrip non-stop flight included
Halifax (YHZ) to Key West (EYW)
9/10 Wonderful! (1,258 reviews)
We loved our stay! Within walking distance to so much, the grounds felt tropical and the private beach was a definite plus. Good food and drink options too.

Reviewed on Aug 23, 2026

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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 $895, 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 19.

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

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
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 ...
9.4/10 Exceptional! (1,246 reviews)
"So we have stayed here both times coming to Key West. The staff is outstanding and very nice from check in.. to check out. I will say that when you purchase through Expedia make sure you still have enough to pay for the resort fees and tax... they are NOT included."

Reviewed on Aug 23, 2026

Hyatt Vacation Club at Windward Pointe, Key West
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), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
Margaritaville Beach House Key West
See all 8,253 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.