Cross Key Waterways Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Cross Key Waterways

Price found within the past 48 hours. Click for updated prices.
Avi Lux Stay

Avi Lux Stay

4.5 out of 5
East Fort Lauderdale
Price was CA $1,598, price is now CA $857 per person
CA $857
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
7.6/10 Good! (10 reviews)
If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.

Reviewed on Aug 28, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was CA $18,234, price is now CA $9,620 per person
CA $9,620
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was CA $3,506, price is now CA $1,926 per person
CA $1,926
per person
Jan 17 - Jan 23
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.6/10 Excellent! (1,002 reviews)

Miami Vacation Rentals Downtown with Pool

Miami Vacation Rentals Downtown with Pool

2.5 out of 5
Downtown Miami
Price was CA $3,117, price is now CA $1,733 per person
CA $1,733
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
No reviews

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was CA $3,176, price is now CA $1,806 per person
CA $1,806
per person
Jan 17 - Jan 23
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very good! (1,220 reviews)

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
A wooden pier extending into calm waters, with a covered area at the end.

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.

Find hotels in Rock Harbor

Cross Key Waterways Hotel Deals

Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
The price is CA $306 per night from Nov 29 to Nov 30
CA $306
CA $400 total
Nov 29 - Nov 30
includes taxes & fees
9.2/10 Wonderful! (1,559 reviews)
"Very nice"

Reviewed on Nov 2, 2026

Reefhouse Resort & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from Nov 10 to Nov 11
CA $196
CA $299 total
Nov 10 - Nov 11
includes taxes & fees
Chesapeake Beach Resort
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4 out of 5
97000 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
The price is CA $348 per night from Nov 12 to Nov 13
CA $348
CA $468 total
Nov 12 - Nov 13
includes taxes & fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton
See all 2,211 properties in Cross Key Waterways
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $857. 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 Self-Driving Tour

Florida: Key West Overseas Highway App-Based Driving Audio Tour

CA $24
per traveller
88% of travellers recommend
Florida: Key West Overseas Highway App-Based Driving Audio Tour
Enjoying the view from the front topside

Key Largo Coral Reef Glass Bottom Boat Adventure

CA $94
per adult
96% of travellers recommend
Key Largo Coral Reef Glass Bottom Boat Adventure
Florida's Must-See Sights: Self-Guided Driving Audio Tour Bundle

Florida's Must-See Sights: Self-Guided Driving Audio Tour Bundle

CA $57
per traveller
100% of travellers recommend
Florida's Must-See Sights: Self-Guided Driving Audio Tour Bundle
See all activities in Key Largo
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.