
Key West Cheap Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Flight and Cheap hotel deals in Key West
Price found within the past 48 hours. Click for updated prices.

Pier House Resort & Spa
Key West Historic District
Price was CA $1,824, price is now CA $1,518 per person
CA $1,518
per person
Jul 15 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9/10 Wonderful! (1,094 reviews)
We really enjoyed our stay at the Pier House and will definitely come back. We are not big spa people so we would like to try an oceanfront room next time. But our room was great. The beds were very comfortable. We had a fun time visiting the Chart Room and sitting on the beach at night. Perfect location to all the activities!
Reviewed on May 10, 2026

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Price was CA $2,771, price is now CA $2,219 per person
CA $2,219
per person
Jul 25 - Aug 1
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.4/10 Very Good! (635 reviews)
The hotel is beautiful, but honestly I expected a bit more. I would definitely recommend booking a partial or direct ocean view room, it makes a huge difference to the experience.
Reviewed on May 10, 2026

Southernmost Beach Resort and Guesthouses
Old Town Key West
Price was CA $2,431, price is now CA $2,001 per person
CA $2,001
per person
Jun 12 - Jun 17
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
8.8/10 Excellent! (3,248 reviews)
The ocean view was good. The beach was full of sea weed , and was only cleaned one day, the smell was bad when the wind shifted.
Reviewed on May 11, 2026

Parrot Key Hotel & Villas
Northside Resort
Price was CA $2,044, price is now CA $1,831 per person
CA $1,831
per person
Jun 12 - Jun 17
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9/10 Wonderful! (1,382 reviews)
Everything was wonderful except having some mosquitoes in room.
Reviewed on May 7, 2026

Eden House
Key West Historic District
Price was CA $2,418, price is now CA $2,180 per person
CA $2,180
per person
Jun 12 - Jun 17
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9/10 Wonderful! (1,008 reviews)
Hot tub out of order, and the room was a bit cramped, but that's on me I should have paid for a larger room. The staff on Mother's Day weekend was excellent.
Reviewed on May 11, 2026
3 Night Cheap holidays in Key West
Price found within the past 48 hours. Click for updated prices.

Pier House Resort & Spa
Key West Historic District
Price was CA $1,824, price is now CA $1,518 per person
CA $1,518
per person
Jul 15 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9/10 Wonderful! (1,094 reviews)
We really enjoyed our stay at the Pier House and will definitely come back. We are not big spa people so we would like to try an oceanfront room next time. But our room was great. The beds were very comfortable. We had a fun time visiting the Chart Room and sitting on the beach at night. Perfect location to all the activities!
Reviewed on May 10, 2026

Southernmost Beach Resort and Guesthouses
Old Town Key West
Price was CA $1,858, price is now CA $1,556 per person
CA $1,556
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (3,248 reviews)
The ocean view was good. The beach was full of sea weed , and was only cleaned one day, the smell was bad when the wind shifted.
Reviewed on May 11, 2026

Santa Maria Suites
Old Town Key West
Price was CA $2,189, price is now CA $1,971 per person
CA $1,971
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.6/10 Exceptional! (1,000 reviews)
I prefer bottom line pricing, without added fees. Companies are all about making money on everything they can. This is a fabulous property, but would be much better to have ALL costs included in the bottom line.
Reviewed on May 11, 2026
4 Night Cheap holidays in Key West
Price found within the past 48 hours. Click for updated prices.

Almond Tree Inn Hotel - Adults Only
Old Town Key West
Price was CA $1,448, price is now CA $1,195 per person
CA $1,195
per person
Jun 13 - Jun 17
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
10/10 Exceptional! (1,002 reviews)
Wonderful staff. Very clean and comfortable. Great breakfast and nice happy hour.
Reviewed on May 12, 2026

Southernmost Beach Resort and Guesthouses
Old Town Key West
Price was CA $1,525, price is now CA $1,214 per person
CA $1,214
per person
Jun 13 - Jun 17
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (3,248 reviews)
The ocean view was good. The beach was full of sea weed , and was only cleaned one day, the smell was bad when the wind shifted.
Reviewed on May 11, 2026

Ibis Bay Beach Resort
Northside Resort
Price was CA $1,797, price is now CA $1,527 per person
CA $1,527
per person
Jun 24 - Jun 28
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
8/10 Very Good! (2,242 reviews)
What a delightful stay !!! The decore was very "beachie" and had a hammock out back. It was an end room on the bay and in the morning iguana's would come up out of the trees to see us. Very memorable [:-)
Reviewed on May 10, 2026
Cheap Hotels in Key West

Seashell Motel
718 South Street Key West FL
Stay at this hostel in Key West. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (1,006 reviews)
Great location with very nice renovated rooms.
Reviewed on May 8, 2026

Southwinds Motel
1321 Simonton Street Key West FL
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
8.6/10 Excellent! (1,338 reviews)
This hotel is very old but well maintained. The location was 1 block from Duval with many restaurants choices. Very close to the Henningway home and tour. They offer a private beach access providing a chair and towel. The breakfast was ok however the muffins were delicious. There is a very nice outside ...
Reviewed on May 11, 2026

Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. ...
8/10 Very Good! (2,264 reviews)
Loved the view.
Reviewed on May 11, 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.
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.







