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.
Creekside Inn

Creekside Inn

2.5 out of 5
Price was CA $3,338, price is now CA $1,771 per person
CA $1,771
per person
May 14 - May 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
7.8/10 Good! (1,002 reviews)
This property is in a perfect location for walking to restaurants and bars. They have 2 very nice pools to choose from. The canal view room we had was very spacious and the balcony was very large to watch boats and nature pass by. The room fridge/freezer was just about full size which made it nice to keep leftovers and lots of drinks. Air conditioning was perfect temp and parking is included in your stay and ample. We also got to use the sister property's amenities which is called The Islander. All of the staff were very friendly and helpful. Jass the manager is wonderful! We will be back next season with our whole family! Thank you for a very memorable stay!

Reviewed on Apr 10, 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 $23,897, price is now CA $11,659 per person
CA $11,659
per person
May 16 - May 21
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very Good! (1 review)
Miami Downtown Condos

Miami Downtown Condos

5 out of 5
Downtown Miami
Price was CA $3,408, price is now CA $1,829 per person
CA $1,829
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very Good! (135 reviews)
Excellent Location and unit. Host was very communicative and responsive once my arrival date approached. Just a few negatives, but some “minor” maintenance needs to be I wouldn’t list them here, they know what has to be done. done. Also, I would place a TV in the main area, if possible as I don’t really watch tv in bed. In addition, a great touch was having coffee and raw sugar was an added touch, as I do drink coffee and only use sugar in the raw! So 1000 extra points for me! Overall I would stay and recommend this location again.

Reviewed on Apr 5, 2026

The Landon Bay Harbor - Miami Beach

The Landon Bay Harbor - Miami Beach

3.5 out of 5
Price was CA $6,622, price is now CA $3,697 per person
CA $3,697
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (1,002 reviews)
Property was nice, staff were great. Parking was kinda limited as there is a restaurant connected to the hotel. Our shower could have been cleaned better but overall our stay was good & the price wasn’t bad for the area & I booked it last minute! Beach was right down the street & shops nearby! Overall a wonderful stay!

Reviewed on Mar 27, 2026

Hyde Beach House Hollywood Pr Suites

Hyde Beach House Hollywood Pr Suites

4 out of 5
Hollywood Beach
Price was CA $5,228, price is now CA $3,109 per person
CA $3,109
per person
Jun 11 - Jun 16
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
6.8/10 (14 reviews)
My family had a perfect vacation. Beautiful hotel very spacious and comfortable for my family of 5. Also enjoyed the Beautiful pool and breathing view. Will definitely visit again.

Reviewed on Jun 28, 2024

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 $413 per night from Apr 19 to Apr 20
CA $413
CA $520 total
Apr 19 - Apr 20
includes taxes & fees
9.4/10 Exceptional! (1,406 reviews)
Ocean view is much nicer.

Reviewed on Apr 8, 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 $182 per night from May 11 to May 12
CA $182
CA $243 total
May 11 - May 12
includes taxes & fees
9/10 Wonderful! (1,277 reviews)
Having a balcony one looking the canal was really nice. And, having two bathrooms in the suite was great.

Reviewed on Apr 8, 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 $268 per night from May 4 to May 5
CA $268
CA $379 total
May 4 - May 5
includes taxes & fees
9.2/10 Wonderful! (1,693 reviews)
It was okay

Reviewed on Apr 10, 2026

Chesapeake Beach Resort
See all 2,215 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 $1,771. 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.