Florida Keys Adventure Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Flight and Adventure hotel deals in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

CA $1,565
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Miami (MIA)
8.8/10 Excellent! (1,009 reviews)
The room was clean and the pools were excellent! But everything else was just average, and I don't know that I'd say it was worth a $50/day resort fee (what does this cover? Why not just put it in the room rate?) We stayed 4 nights and by the third night we had to ask to have someone come by and bring fresh towels. I'm used to seeing signs at hotels that state for environmental reasons they may only clean rooms every so often, but there was no such indication. Our room was off at the edge of the resort, by the fitness room which meant every time someone came in the building, the whole building shook when the door slammed behind them. So much for getting a nice sleep-in on vacation because this started at 5 or 6 am. I can definitely see the benefit to staying here with a larger group, families and friends staying in one of the villas. But as a couple, I probably wouldn't come back.

Reviewed on Sep 15, 2026

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

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

CA $1,781
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Miami (MIA)
9/10 Wonderful! (258 reviews)
We had an excellent stay at Three Waters Resort in Islamorada. Everything about the property was great from start to finish. Our room was very clean, comfortable, and well maintained, and the entire resort was beautiful and inviting. One of the things we really enjoyed was all of the included amenities. We took advantage of the complimentary kayaks, and they also had bikes available for guests to use at no additional charge. It was a great way to get out, explore, and enjoy the area. The fire pits at night were another highlight. Sitting outside by the fire was the perfect way to end the day and really added to the relaxing Keys atmosphere. Overall, we had a fantastic experience. The property was clean, the amenities were excellent, and there honestly wasn’t anything we could complain about. We would absolutely stay at Three Waters again and highly recommend it to anyone visiting Islamorada!

Reviewed on Sep 15, 2026

Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
CA $3,861
per person
Nov 19 - Nov 26
found 12 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Miami (MIA)
9.2/10 Wonderful! (1,422 reviews)
Hawks Cay Resort

Hawks Cay Resort

CA $1,571
per person
Nov 18 - Nov 22
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.2/10 Very good! (1,006 reviews)
Beautiful resort

Reviewed on Sep 15, 2026

La Siesta Resort & Villas

La Siesta Resort & Villas

Matecumbe
CA $1,682
per person
Nov 19 - Nov 26
found 12 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Miami (MIA)
8.8/10 Excellent! (1,005 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Florida Keys
View all trips

5* Adventure holidays in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe
CA $3,861
per person
Nov 19 - Nov 26
found 12 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Miami (MIA)
9.2/10 Wonderful! (1,422 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Florida Keys
View all trips

4 Night Adventure holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Heron House - Adult Only

Heron House - Adult Only

Old Town Key West
CA $1,533
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.2/10 Wonderful! (1,158 reviews)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
CA $2,147
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
Eden House

Eden House

Key West Historic District
CA $1,771
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Key West (EYW)
9/10 Wonderful! (1,003 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Florida Keys
View all trips

Adventure 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 ...
8.6/10 Excellent! (3,605 reviews)
"The property should have advertised that it was off season and there were amenities closed. The beach was closed the pool was closed. Those were two reasons we chose this resort. We also had a noise issue with the room and the front desk staff tried to give us ear plugs instead of trying to find ..."

Reviewed on Sep 16, 2026

Southernmost Beach Resort and Guesthouses
Hawks Cay Resort

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL
  • 2 hours drive from Duval Street
Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.2/10 Very good! (1,011 reviews)
"Beautiful resort"

Reviewed on Sep 15, 2026

Hawks Cay Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
  • 3 hours drive from Duval Street
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
Cheeca Lodge & Spa
See all 8,273 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.