
Cross Key Waterways Vacation Packages
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Top Holiday Package Deals in Cross Key Waterways
Price found within the past 48 hours. Click for updated prices.

Pelican Grand Beach Resort - A Noble House Resort
East Fort Lauderdale
Price was CA $2,201, price is now CA $1,072 per person
CA $1,072
per person
Oct 22 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.8/10 Excellent! (1,224 reviews)
The pool was a bit small. The beach was fantastic. Hotel service staff and cleanliness superb. So was the room.
Reviewed on Sep 10, 2025


Ridley House - Key West Historic Inns
Key West Historic District
Price was CA $3,366, price is now CA $1,680 per person
CA $1,680
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (815 reviews)
The staff were wonderful and we loved the breakfast and sangria hour and how walkable the area was! We walked everywhere during our stay. The only downsides were it is very noisy, since you can hear everything outside from in the room, and the AC in our room took about 2 days to cool down enough to be comfortable after the previous guests apparently had left the AC off and the windows open during their stay.
Reviewed on Sep 3, 2025

Ella's Cottages - Key West Historic Inns
Old Town Key West
Price was CA $3,098, price is now CA $1,575 per person
CA $1,575
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (369 reviews)
This property is absolutely adorable! Room was clean and spacious. Front desk person was very nice and personable. The breakfast baskets that are delivered to your room are top notch! Will definitely be staying here again!
Reviewed on Aug 31, 2025

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Price was CA $2,796, price is now CA $1,454 per person
CA $1,454
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (781 reviews)
Pros: We loved the location. It's so easy to walk to any downtown place via Duval Street with tons of restaurant options. Since this is a hotel and no AirBnB, you gotta go eat somewhere.
You can also rent a golf cart or take an Uber to Fort Zachary Taylor Historic State Park Beach (best beach in Key West, except for overpriced bad food options).
A golf cart is the best mode of transportation with 2 kids in tow. Walking 30+min in this humid heat, including beach gear, snacks and etc..., is just no fun.
Parking around your hotel may be tricky and make sure you know the rules. We went off-season, so it was easy, but during high season-we have been told-it can be a challenge.
If you book a sunset, snorkeling, sandbar or fishing trip on a boat, which I highly recommend, it only takes 20min to walk to the harbor or you simply book a cab/Uber/Lyft.
The housekeepers were amazing and always made sure that we had enough clean towels.
Beach towels are never in shortage and available to pick up by the pool area 24/7.
Cons: The pool is very small, but then we didn't go to Key West to spend time at a pool. We prefer the beach and what nature has to offer. The marine life is just too amazing to dwell in a pool for us.
Reviewed on Sep 8, 2025
Where to stay in Cross Key Waterways
Find the best Cross Key Waterways areas and neighborhoods for the activities you enjoy most. Learn more about Cross Key Waterways

Key Largo Village
While Key Largo Village might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park.
Cross Key Waterways Hotel Deals

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Sep 11 to Sep 12
CA $169
CA $268 total
Sep 11 - Sep 12
includes taxes & fees

Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is CA $351 per night from Sep 16 to Sep 17
CA $351
CA $471 total
Sep 16 - Sep 17
includes taxes & fees

Waterside Suites & Marina
201 Ocean Drive, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Sep 28 to Sep 29
CA $137
CA $193 total
Sep 28 - Sep 29
includes taxes & fees
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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