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.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $17,799
per person
Nov 18 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
Brickell Arch Apartment City Views & Free Parking by Palermo Home Miami
Brickell
CA $1,634
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
10/10 Exceptional! (4 reviews)
The room was very clean and organized with a wonderful city view. The building was relatively quiet. We especially loved how spacious the bathroom area is. Valet and concierge services are exceptional, the restaurant on the 25th floor is great, and it's in a great location in Miami.
However, we did encounter one issue that did cost us a decent amount of money. The water connection for the washer was not hooked up and no dryer was available. This meant instead of being able to do our laundry, we had to buy new clothing items.
There was also a feminine hygiene wrapper under the bed upon arrival. These things made me question if the bed sheets or towels were properly laundered.
Overall, we enjoyed the experience. We typically stay at the Icon, but due to the construction on that building we chose to try the Arch and will probably do that again.
Reviewed on Jul 6, 2026
The Penguin Hotel
South Beach
CA $994
per person
Nov 18 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.4/10 Very good! (1,963 reviews)
I stayed in room 401 as it showed a nice deck. What it didn’t say is there is no elevator to the 4th floor so you have to be able to haul your luggage up a flight of stairs. It was also very noisy because the room is directly under the air compressor units. I kept thing people were moving furniture. Great location though.
Reviewed on Sep 16, 2026
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
Rock Harbor
1 out of top 10 points of interest in this area
While Rock Harbor isn't home to many top sights, Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill are some notable places to visit nearby.
Silver Shores
If you're looking for some top things to see and do in Silver Shores and surrounding area, you can visit Bluefin Rock Harbor Marina and Harry Harris Park.
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 Jacob's Aquatic Center.
Key Largo Park
Though Key Largo Park might not have many top sights, you can venture to the surrounding area to see attractions like Jimmy Johnson's Big Chill and Jacob's Aquatic Center.
Winston Waterways
If you're looking for some top things to see and do in Winston Waterways and surrounding area, you can visit John Pennekamp Coral Reef State Park and MarineLab Undersea Laboratory.
Cross Key Waterways Hotel Deals
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
CA $205
CA $309 total
Sep 20 - Sep 21
includes taxes & fees
9.2/10 Wonderful! (1,775 reviews)
"Hotel is right on the ocean. Was a large room and shower. Plenty of pool towels. Had 2 pools. Could also bike and kayak. Breakfast was good. Great location for many activities and restaurants."
Reviewed on Sep 17, 2026
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
CA $332
CA $450 total
Sep 30 - Oct 1
includes taxes & fees
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
CA $306
CA $401 total
Sep 22 - Sep 23
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.
Frequently asked questions
How much does a Cross Key Waterways vacation package cost?
We make it simple for everyone to travel, with Cross Key Waterways vacation packages starting from just CA $920. You'll have the flexibility to bundle your preferred hotels, airlines and car rental. For the ultimate escape, why not add some experiences and tours to your travel itinerary?
How do I get a cheap travel package to Cross Key Waterways?
Just imagine all the amazing things you could do in Cross Key Waterways with a pile of extra cash in your pocket. Watch your savings stack up when you combine your flights, hotels and extras into a Cross Key Waterways vacation package. You have loads of choice when you book your trip with Expedia too. In fact, you can take your pick of more than 550 air carriers and 1,000,000 hotels throughout the world. Whether you're taking off with the entire family or surprising your special someone, organizing a getaway to Cross Key Waterways is better with a package.
Where should I stay in Cross Key Waterways?
It makes sense to stay near the action. Many travelers book hotels within easy reach of popular attractions, like Florida Keys Visitor Center, Caribbean Club Bar and MarineLab Undersea Laboratory.
What are the top hotels in Cross Key Waterways?
Get your escape off to a flying start by staying at Key Breeze Waterfront Home - Water View With Therapy Spa. It's one of most popular hotels in Cross Key Waterways. Another welcoming option is Modern Key Largo Waterfront Bayside Home.
How far in advance should I book my Cross Key Waterways vacation?
Travelers are normally able to browse international airfares on Expedia within 12 months of the departure date. Booking late? With a bit of luck, it's still possible to nab a cheap ticket only weeks before your flight.
What does an Expedia Cross Key Waterways travel package include?
With Expedia, you can select a combination of flights, hotels and car rentals to build your ideal Cross Key Waterways package. Once you've made your booking, you can add on fun stuff like sightseeing tours and activities. Don't forget, the more you bundle, the more discounts you'll get!
What should I know before booking a Cross Key Waterways travel package?
Bundling your bookings into a Cross Key Waterways vacation package is the most convenient way to organize your trip. Not only that, you'll save just for combining your hotels, flights and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a Cross Key Waterways Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines globally. Our vacation packages give you the freedom to pick from available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Cross Key Waterways vacation package?
Yes, you can cancel your Cross Key Waterways booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. It may be possible to cancel or change free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.
Things to do
Florida: Key West Overseas Highway App-Based Driving Audio Tour
CA $24
per traveller
88% of travellers recommend
Key Largo Coral Reef Glass Bottom Boat Adventure
CA $92
per adult
96% of travellers recommend
Florida's Must-See Sights: Self-Guided Driving Audio Tour Bundle
CA $55
per traveller
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.