Cross Key Waterways Vacation Packages

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Holiday Package Deals in Cross Key Waterways

Price found within the past 48 hours. Click for updated prices.
Creekside Inn

Creekside Inn

2.5 out of 5
Price was CA $2,232, price is now CA $1,096 per person
CA $1,096
per person
Mar 25 - Mar 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
Room was clean, spacious with a wonderful canal view.

Reviewed on Jan 27, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $9,440, price is now CA $4,649 per person
CA $4,649
per person
May 5 - May 10
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
5.8/10 (311 reviews)
I stood in the multiple bed 1 bedroom everything was good beach right there pool and security where very friendly

Reviewed on Nov 12, 2025

Broadmore Miami Beach

Broadmore Miami Beach

3.5 out of 5
North Beach
Price was CA $2,058, price is now CA $1,121 per person
CA $1,121
per person
Mar 20 - Mar 27
found 2 hours ago
Roundtrip flight included
Hamilton (YHM) to Miami (MIA)
5.6/10 (389 reviews)
The staff was amazing

Reviewed on Feb 12, 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 $39,704, price is now CA $21,903 per person
CA $21,903
per person
Mar 19 - Mar 26
found 14 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very Good! (1 review)
President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was CA $2,270, price is now CA $1,279 per person
CA $1,279
per person
Apr 27 - May 3
found 23 hours ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very Good! (997 reviews)
Clean room ! Excellent location. Nice amenities, free drinks, beach towels, nice buffet breakfast . Highly recommend for the overall value.

Reviewed on Feb 12, 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

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 $568 per night from Mar 12 to Mar 13
CA $568
CA $716 total
Mar 12 - Mar 13
includes taxes & fees
9.2/10 Wonderful! (1,675 reviews)
Nice stay

Reviewed on Feb 10, 2026

Chesapeake Beach Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

3.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
The price is CA $474 per night from Feb 23 to Feb 24
CA $474
CA $587 total
Feb 23 - Feb 24
includes taxes & fees
9.2/10 Wonderful! (1,354 reviews)
Staff were great and very helpful. This is a beautiful resort!

Reviewed on Feb 6, 2026

Reefhouse Resort & Marina
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

2.5 out of 5
527 Caribbean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
The price is CA $294 per night from Mar 4 to Mar 5
CA $294
CA $369 total
Mar 4 - Mar 5
includes taxes & fees
8.4/10 Very Good! (1,732 reviews)
Staff was wonderful and ver accommodating! Room was very clean and the grounds are beautiful. Breakfast by pool is wonderful!

Reviewed on Feb 10, 2026

Marina Del Mar Resort and Marina
See all 2,244 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
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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 $1,096. 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.