Florida Keys Adventure Vacations
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Flight and Adventure hotel deals in Florida Keys
Price found within the past 48 hours. Click for updated prices.
La Siesta Resort & Villas
Matecumbe
Price was CA $1,179, price is now CA $905 per person
CA $905
per person
Apr 26 - Apr 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.8/10 Excellent! (1,004 reviews)
The best I can say is that it was quiet, calm, and relaxing. Rooms were very good. Some showed sign of work - pencil marks from measuring for mirrors/paintings, and with beds right under a window that opened into the external hallway was a little noisy. Limited food options, no full bar (beer and wine only). The free use of kayaks and paddle boards was a plus.
Reviewed on Mar 27, 2026
Hawks Cay Resort
Price was CA $2,149, price is now CA $1,482 per person
CA $1,482
per person
May 27 - Jun 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8/10 Very Good! (1,015 reviews)
The water pressure is non existent. Had to use the wand to wash. LED bulbs burned out. The cleaning staff cleaned room 3 times in the 7 days!
Reviewed on Mar 26, 2026
Cheeca Lodge & Spa
Matecumbe
Price was CA $2,974, price is now CA $2,081 per person
CA $2,081
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
9.2/10 Wonderful! (1,308 reviews)
The staff was friendly and laid back. The resort was absolutely beautiful!
Reviewed on Mar 27, 2026
Tranquility Bay Beachfront Hotel and Resort
Price was CA $3,959, price is now CA $3,041 per person
CA $3,041
per person
Apr 26 - May 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.8/10 Excellent! (1,000 reviews)
All 3 pools were beautiful, I loved the surrounding landscape. The two bedroom / 2.5 bath villa was wonderful. I loved sitting on the villas deck each morning to drink my coffee and enjoy the palm tree ocean view. The kitchen had everything we needed to make our meals! I would definitely recommend.
Reviewed on Mar 21, 2026
Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Price was CA $4,750, price is now CA $3,770 per person
CA $3,770
per person
May 2 - May 9
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Key West (EYW)
8.4/10 Very Good! (572 reviews)
Outside building was great. Could improve with room maintenace. Our room was ocean view, but toilet fil valve was broken, and takes 30 minutes wait to flush. Window frame paint was peeling. Otherwise its a great place.
Reviewed on Mar 20, 2026
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View all trips5* Adventure holidays in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa
Matecumbe
Price was CA $2,974, price is now CA $2,081 per person
CA $2,081
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
9.2/10 Wonderful! (1,308 reviews)
The staff was friendly and laid back. The resort was absolutely beautiful!
Reviewed on Mar 27, 2026
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See all available trips from Columbus to Florida Keys
View all trips3 Night Adventure holidays in Florida Keys
Price found within the past 48 hours. Click for updated prices.
La Siesta Resort & Villas
Matecumbe
Price was CA $1,179, price is now CA $905 per person
CA $905
per person
Apr 26 - Apr 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.8/10 Excellent! (1,004 reviews)
The best I can say is that it was quiet, calm, and relaxing. Rooms were very good. Some showed sign of work - pencil marks from measuring for mirrors/paintings, and with beds right under a window that opened into the external hallway was a little noisy. Limited food options, no full bar (beer and wine only). The free use of kayaks and paddle boards was a plus.
Reviewed on Mar 27, 2026
Hawks Cay Resort
Price was CA $1,194, price is now CA $921 per person
CA $921
per person
Apr 27 - Apr 30
found 4 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
8/10 Very Good! (1,015 reviews)
The water pressure is non existent. Had to use the wand to wash. LED bulbs burned out. The cleaning staff cleaned room 3 times in the 7 days!
Reviewed on Mar 26, 2026
Cheeca Lodge & Spa
Matecumbe
Price was CA $2,068, price is now CA $1,672 per person
CA $1,672
per person
Apr 26 - Apr 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9.2/10 Wonderful! (1,308 reviews)
The staff was friendly and laid back. The resort was absolutely beautiful!
Reviewed on Mar 27, 2026
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See all available trips from Columbus to Florida Keys
View all trips4 Night Adventure holidays in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Hawks Cay Resort
Price was CA $1,895, price is now CA $1,371 per person
CA $1,371
per person
Jun 11 - Jun 15
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1,015 reviews)
The water pressure is non existent. Had to use the wand to wash. LED bulbs burned out. The cleaning staff cleaned room 3 times in the 7 days!
Reviewed on Mar 26, 2026
La Siesta Resort & Villas
Matecumbe
Price was CA $2,313, price is now CA $1,685 per person
CA $1,685
per person
Apr 30 - May 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.8/10 Excellent! (1,004 reviews)
The best I can say is that it was quiet, calm, and relaxing. Rooms were very good. Some showed sign of work - pencil marks from measuring for mirrors/paintings, and with beds right under a window that opened into the external hallway was a little noisy. Limited food options, no full bar (beer and wine only). The free use of kayaks and paddle boards was a plus.
Reviewed on Mar 27, 2026
Tranquility Bay Beachfront Hotel and Resort
Price was CA $2,098, price is now CA $1,607 per person
CA $1,607
per person
Apr 30 - May 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.8/10 Excellent! (1,000 reviews)
All 3 pools were beautiful, I loved the surrounding landscape. The two bedroom / 2.5 bath villa was wonderful. I loved sitting on the villas deck each morning to drink my coffee and enjoy the palm tree ocean view. The kitchen had everything we needed to make our meals! I would definitely recommend.
Reviewed on Mar 21, 2026
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See all available trips from Columbus to Florida Keys
View all tripsAdventure Hotels in Florida Keys
Hawks Cay Resort
61 Hawks Cay Blvd Marathon FL
Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8/10 Very Good! (1,000 reviews)
The water pressure is non existent. Had to use the wand to wash. LED bulbs burned out. The cleaning staff cleaned room 3 times in the 7 days!
Reviewed on Mar 26, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
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 ...
9.2/10 Wonderful! (1,299 reviews)
The staff was friendly and laid back. The resort was absolutely beautiful!
Reviewed on Mar 27, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (178 reviews)
Very, very good architectural design and construction. And a well-maintained facility.
Reviewed on Mar 23, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
