Cross Key Waterways Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

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
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 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

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 NZ$512 per night from 29 Nov to 30 Nov
NZ$512
29 Nov - 30 Nov
includes taxes & fees
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 NZ$389 per night from 10 Nov to 11 Nov
NZ$389
10 Nov - 11 Nov
includes taxes & fees
9.4/10 Exceptional! (1,808 reviews)
"Amazingly great.can't wait to go back!!"

Reviewed on 7 Nov 2026

Chesapeake Beach Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$547 per night from 29 Nov to 30 Nov
NZ$547
29 Nov - 30 Nov
includes taxes & fees
9/10 Wonderful! (308 reviews)
"Rooms are too tiny. I was changed 3 times by my request. Finally i stayed in front of the beach with ocean view balcony it was only when i felt in a real hotel room, The Cove is like be on a Hialeah apartment. I was charged 5 different times on my credit card, and 4 days after checkout i still have ..."

Reviewed on 5 Nov 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
See all 2,210 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 . 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.

Activities

Florida: Key West Overseas Highway Self-Driving Tour

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

NZ$30
per traveller
88% of travellers recommend
Florida: Key West Overseas Highway App-Based Driving Audio Tour
Discover Florida Keys: A Self-Guided Tour

Discover Florida Keys: A Self-Guided Tour

NZ$2
per adult
Discover Florida Keys: A Self-Guided Tour
Enjoying the view from the front topside

Key Largo Coral Reef Glass Bottom Boat Adventure

NZ$117
per adult
96% of travellers recommend
Key Largo Coral Reef Glass Bottom Boat Adventure
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.