
Stock Island Cheap Vacations
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Flight and Cheap hotel deals in Stock Island
Price found within the past 48 hours. Click for updated prices.

Southernmost Beach Resort and Guesthouses
Old Town Key West
CA $1,972
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (3,606 reviews)
We were looking for good value- we got it! Staff was friendly from start to finish. Rooms provided everything we wanted from a comfortable bed to a scenic ocean view.
Reviewed on Oct 1, 2026

Southernmost House - Adult Exclusive
Old Town Key West
CA $2,011
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
We arrived at Key West just after 12 noon on a Sunday. I was planning to just leave our luggage’s at the hotel since check in time was at 4pm. Catherine was the one that greeted us and help us out on our check in process. She was very professional and very friendly. We got our room ready right away and we didn’t have to wait until check in time at 4PM.
Our room was right by the pool, it was clean, has a full size fridge and small microwave, some kitchen amenities (plates, cups, silverware’s) and a dehumidifier.
The bathroom is clean and very spacious (shower area). We thought it will be loud since it’s close to the pool and the bar but the whole time we were there it was nice and quiet.
There’s are near by restaurants, shops and coffee shops but I suggest to rent a scooter to get to the port area if you have any plans on going to any boating trips (it’s a good 20-30 mins walk from the hotel).
We met dean on our 2nd day and he was very friendly and make sure to give us our parking pass for the scooter that we rented. Dean and Catherine definitely made our stay special. And we will definitely come back to stay at this facility on our next trip to Key West. I highly recommend this place if you want a relaxing, laidback stay at Key West.
Reviewed on Oct 1, 2026



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View all trips3 Night Cheap holidays in Stock Island
Price found within the past 48 hours. Click for updated prices.


Southernmost House - Adult Exclusive
Old Town Key West
CA $2,690
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
We arrived at Key West just after 12 noon on a Sunday. I was planning to just leave our luggage’s at the hotel since check in time was at 4pm. Catherine was the one that greeted us and help us out on our check in process. She was very professional and very friendly. We got our room ready right away and we didn’t have to wait until check in time at 4PM.
Our room was right by the pool, it was clean, has a full size fridge and small microwave, some kitchen amenities (plates, cups, silverware’s) and a dehumidifier.
The bathroom is clean and very spacious (shower area). We thought it will be loud since it’s close to the pool and the bar but the whole time we were there it was nice and quiet.
There’s are near by restaurants, shops and coffee shops but I suggest to rent a scooter to get to the port area if you have any plans on going to any boating trips (it’s a good 20-30 mins walk from the hotel).
We met dean on our 2nd day and he was very friendly and make sure to give us our parking pass for the scooter that we rented. Dean and Catherine definitely made our stay special. And we will definitely come back to stay at this facility on our next trip to Key West. I highly recommend this place if you want a relaxing, laidback stay at Key West.
Reviewed on Oct 1, 2026

Southernmost Beach Resort and Guesthouses
Old Town Key West
CA $2,285
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (3,606 reviews)
We were looking for good value- we got it! Staff was friendly from start to finish. Rooms provided everything we wanted from a comfortable bed to a scenic ocean view.
Reviewed on Oct 1, 2026
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View all trips4 Night Cheap holidays in Stock Island
Price found within the past 48 hours. Click for updated prices.

Island City House Hotel
Key West Historic District
CA $1,707
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.6/10 Exceptional! (1,003 reviews)
Absolutely stellar property - gorgeous in all respects. Our rooms, the spacious private porch, the grounds, pool, everything. Beds were comfy, staff was helpful, and we all enjoyed Bert's visits to our porch as well. As a former Key West resident, I loved the Old Town location and atmosphere of the Island City House Hotel. The staff were also friendly and helpful. We have every intention of staying here again in the future!
Reviewed on Sep 30, 2026


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View all tripsThings to do

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
CA $59
per adult
94% of travellers recommend

Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $78
per adult
88% of travellers recommend

Champagne and Sunsets: A Key West Catamaran Adventure
CA $82
per adult
94% of travellers recommend
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