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 $31,030
per person
Dec 28 - Jan 2
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
Private Oasis at Arya
Coconut Grove
CA $1,711
per person
Nov 11 - Nov 18
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.6/10 Excellent! (1,050 reviews)
Communication from the host via hotels.com was unusable. At check in they photographed my DL (which I don’t care for) and required a large deposit be placed on my credit card or pay a smaller non-refundable amount up front. I don’t care for hidden charges.
Prior to checkout I received an email that stated that if not out by 11AM they would charge an additional substantial amount.
Their communication is couched in friendliness, but I didn’t get that impression in reality.
Reviewed on Oct 5, 2026
Miami Vacation Rentals - Downtown
Downtown Miami
CA $3,344
per person
Dec 25 - Jan 1
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (92 reviews)
Beware! The parking is not as advertised and cost a fortune. The room was noisy at night making sleep difficult due to noisy air conditioner. The staff at the hotel was quite unfriendly and was quite unhelpful. And most of all getting in touch with Expedia was impossible to achieve, even as I write this review they have not responded to my claims.
Reviewed on Oct 4, 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
Waterside Suites & Marina
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
CA $157
CA $216 total
Oct 18 - Oct 19
includes taxes & fees
9/10 Wonderful! (1,497 reviews)
"Great place. We stay here every year"
Reviewed on Oct 6, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
CA $200
CA $305 total
Oct 18 - Oct 19
includes taxes & fees
9.2/10 Wonderful! (1,798 reviews)
"Absolutely beautiful property. The front desk staff is friendly and as helpful as you could ask for. The breakfast provided was excellent. We definitely took the opportunity to use all the activity options we could in a one-night stay. I will recommend this place to anyone and everyone."
Reviewed on Oct 7, 2026
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
CA $311
CA $407 total
Oct 8 - Oct 9
includes taxes & fees
9.2/10 Wonderful! (1,548 reviews)
"Excellent place"
Reviewed on Oct 5, 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 $1,406. 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 $93
per adult
96% of travellers recommend
Florida's Must-See Sights: Self-Guided Driving Audio Tour Bundle
CA $56
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.