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.
President Hotel

President Hotel

3.5 out of 5
South Beach
Price was CA $1,683, price is now CA $943 per person
CA $943
per person
Apr 13 - Apr 17
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Miami (MIA)
8.4/10 Very Good! (2,048 reviews)
Great Customer Service by Mike and the team.

Reviewed on Mar 10, 2026

Creekside Inn

Creekside Inn

2.5 out of 5
Price was CA $2,305, price is now CA $1,047 per person
CA $1,047
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
7.8/10 Good! (1,013 reviews)
It’s totally sufficient for the type of hotel. Older but clean. Great location

Reviewed on Mar 9, 2026

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 $20,675, price is now CA $11,317 per person
CA $11,317
per person
Apr 13 - Apr 17
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very Good! (1 review)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was CA $1,921, price is now CA $1,090 per person
CA $1,090
per person
May 23 - May 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.6/10 Excellent! (1,002 reviews)
The Cavalier is a quirky, fun hotel in the art deco district. It’s near the quieter end, so it’s perfect for adults, they provide beach access and free chairs, the restaurant is great- a mix of American and Italian. The employees are nice, Philip checked us in and Lester was our wonderful bar tender and server and had our drinks waiting! We should be back in six months for our bi annual girls trip! The rooms are quirky and cute and really loved the stylized feel with the older touches they preserved! Room was super clean, breakfast cost less than Starbucks and was so much better! Loved the original elevator- a must try- and just the whole vibe! This is old Miami at its best!

Reviewed on Mar 5, 2026

President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was CA $2,123, price is now CA $1,226 per person
CA $1,226
per person
Apr 16 - Apr 21
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (1,007 reviews)
I love it there, it’s definitely a nice hotel.

Reviewed on Mar 9, 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
Safety Harbor, Florida

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 $542 per night from Mar 15 to Mar 16
CA $542
CA $664 total
Mar 15 - Mar 16
includes taxes & fees
9.4/10 Exceptional! (1,405 reviews)
Excellent we love it

Reviewed on Mar 9, 2026

Reefhouse Resort & Marina
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
The price is CA $253 per night from Mar 11 to Mar 12
CA $253
CA $323 total
Mar 11 - Mar 12
includes taxes & fees
9/10 Wonderful! (1,232 reviews)
I made a last minute reservation to stay just one night and found the room ready for me and staff very welcoming. All rooms are second floor level and there is no lift or elevator, but an excellent ramp makes it possible to wheel suitcases or a wheelchair to the room. The bedroom in my one-bed unit ...

Reviewed on Mar 10, 2026

Waterside Suites & 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 $424 per night from Apr 8 to Apr 9
CA $424
CA $554 total
Apr 8 - Apr 9
includes taxes & fees
9.2/10 Wonderful! (1,678 reviews)
little dated in the rooms but nice

Reviewed on Mar 10, 2026

Chesapeake Beach Resort
See all 2,224 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.
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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 $943. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.