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 Hotel
South Beach
CA $785
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
9.2/10 Wonderful! (506 reviews)
Resort Fee is something that we did not notice when we booked online through Expedia. We paid $45+tax extra per night.
Also, there is Service fee $3 per person for Breakfast that is included.
Reviewed on Sep 22, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $12,917
per person
Nov 26 - Nov 30
found 9 hours ago
Roundtrip 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
Shore View Hotel
Hollywood Beach
CA $1,193
per person
Nov 26 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
9.4/10 Exceptional! (49 reviews)
Room was not clean- kitchen sink in particular was filthy. Check in was terrible- no one at the office, stood outside for 45 mins waiting for someone to answer the phone. Would not stay here again.
Reviewed on Apr 27, 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 Park
Though Key Largo Park might not have many top sights, you can venture to the surrounding area to see attractions like Jacob's Aquatic Center and Jimmy Johnson's Big Chill.
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 Jacob's Aquatic Center and Jimmy Johnson's Big Chill.
Pirates Cove
While Pirates Cove might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill.
Cross Key Waterways Hotel Deals
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
CA $201
CA $305 total
Sep 24 - Sep 25
includes taxes & fees
9.2/10 Wonderful! (1,786 reviews)
"We had a wonderful stay at this hotel. I stayed with my mom, sister, and niece, and we truly loved the property. The location is great, the hotel is beautiful, and we really enjoyed the amenities and our time together. Overall, it was a very nice experience. The only area I feel could use some improvement ..."
Reviewed on Sep 23, 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 $374
CA $498 total
Oct 1 - Oct 2
includes taxes & fees
8.6/10 Excellent! (1,180 reviews)
"This place feels like paradise! It is so calm and relaxing yet vibrant and fun. We had amazing weather all weekend. The ocean was so nice. The poolside trivia, scavenger hunt, smores and silent disco were so fun. The live music was a hit! We cannot WAIT to come back soon!"
Reviewed on Sep 22, 2026
Waterside Suites & Marina
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
CA $160
CA $219 total
Oct 5 - Oct 6
includes taxes & fees
9/10 Wonderful! (1,488 reviews)
"The room was fine but it had poor water pressure and a very old sliding door that didn’t lock. The grounds look neglected. A little work around the property would do it. I like the location."
Reviewed on Sep 21, 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.
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 $785. 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.