Cross Key Waterways Holidays from NZ$1,014

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Top Holiday Package Deals in Cross Key Waterways

Price found within the past 48 hours. Click for updated prices.
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was NZ$1,889, price is now NZ$1,014 per person
NZ$1,014
per person
17 July - 20 July
found 4 hours ago
Return flight included
New York (JFK) to Miami (MIA)
8.2/10 Very Good! (1,830 reviews)
This hotel is very comfortable and welcoming, the service is excellent and the staff are very friendly. Highly recommended.

Reviewed on 7 May 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 NZ$31,684, price is now NZ$15,424 per person
NZ$15,424
per person
17 July - 20 July
found 4 hours ago
Return flight included
New York (JFK) to Miami (MIA)
8/10 Very Good! (1 review)
President Hotel

President Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was NZ$2,068, price is now NZ$1,085 per person
NZ$1,085
per person
17 July - 20 July
found 4 hours ago
Return flight included
New York (JFK) to Miami (MIA)
8.4/10 Very Good! (2,302 reviews)
Location is 10/10. 1 minute walk to beach. Staff is amazing, super kind and helpful. Overall, a great stay. Highly recommend.

Reviewed on 7 May 2026

Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Save 100% on your flight
Price was NZ$2,346, price is now NZ$1,359 per person
NZ$1,359
per person
17 July - 20 July
found 4 hours ago
Return flight included
New York (JFK) to Miami (MIA)
9.2/10 Wonderful! (457 reviews)
Loved the location in the middle of the art deco district. All staff were pleasant & helpful. Meals at restaurant were delicious.

Reviewed on 5 May 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Save 100% on your flight
Price was NZ$2,785, price is now NZ$1,642 per person
NZ$1,642
per person
17 July - 20 July
found 4 hours ago
Return flight included
New York (JFK) to Miami (MIA)
8/10 Very Good! (1,141 reviews)
Positives - Great food! Great amenities! Great section of the beach! Rooms were clean and modern! Negatives - Staff checking us in were not overly helpful - very transactional and seemed annoyed with any questions. - Beach had a lot of garbage - would be great if people would clean up after themselves, but if not, if there was staff to help pick up the garbage.

Reviewed on 4 May 2026

Our guide on 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 there might not be top attractions in Rock Harbor, you can explore the larger area and discover places like Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill.

Find hotels in Rock Harbor

Our pick of the best 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 NZ$417 per night from 28 May to 29 May
NZ$417
28 May - 29 May
includes taxes & fees
9.2/10 Wonderful! (1,723 reviews)
Chesapeake Beach Resort is overall a wonderful property that provided us with exactly the vacation we were hoping for. As some others have mentioned, the property is not impressive upon first viewing but once you arrive and begin to experience the facility you understand how nice it is. Many reviewers ...

Reviewed on 7 May 2026

Chesapeake Beach Resort
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 NZ$293 per night from 26 May to 27 May
NZ$293
26 May - 27 May
includes taxes & fees
9/10 Wonderful! (1,337 reviews)
Clean quiet room with quick harbor, restaurant and shopping access.

Reviewed on 7 May 2026

Waterside Suites & Marina
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 NZ$682 per night from 8 June to 9 June
NZ$682
8 June - 9 June
includes taxes & fees
8.6/10 Excellent! (1,066 reviews)
Great location. Plenty of beach chairs available.

Reviewed on 7 May 2026

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

Frequently asked questions

How much does a Cross Key Waterways holiday package cost?
We make it simple for everyone to travel, with Cross Key Waterways holiday packages starting from just NZ$1,014. 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 holiday 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, organising 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 travellers book hotels within easy reach of popular attractions, like Florida Keys Visitor Centre, 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 holiday?
Travellers 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 holiday package is the most convenient way to organise 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 holiday package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines globally. Our holiday 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 holiday 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.