Cross Key Waterways Vacations from $381
Book a Hotel + Flight or Car together to unlock savings
Your Cross Key Waterways Vacation
Cross Key Waterways is beckoning! Whatever type of break you're organizing, you can experience and see more of this neighborhood with a Cross Key Waterways vacation package. Not sure where to go during your trip to Cross Key Waterways? Nearby attractions such as John Pennekamp Coral Reef State Park, Caribbean Club Bar and MarineLab Undersea Laboratory are good places to begin. Expedia is here to put your plans into action. Book your ultimate Cross Key Waterways vacation now.
The Latest Cross Key Waterways Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Pelican Hotel
South Beach
Price was $886, price is now $381 per person
$381
per person
Feb 25 - Feb 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (394 reviews)
Staff was friendly, room was clean, bed was comfortable, and everything looked as pictured, but down-rated slightly because a couple of little wall fixtures were broken in the room and the chairs in the room were uncomfortable. BEWARE there is a daily resort fee hiding in the fine print that increases the cost of the room and there was no major amenity like a swimming pool or spa that seemed to justify this. Breakfast was not included in the price of stay.
Reviewed on Dec 8, 2025
The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $1,796, price is now $824 per person
$824
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
Everything was clean and well maintained
Reviewed on Dec 12, 2025
Bay Breeze Premium Apartments By Eskape Collection
Price was $1,065, price is now $492 per person
$492
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (189 reviews)
From the very efficient and effective check in, courteous customer service, and spotless room, our stay was great from the beginning. The place was spacious and modern. There was a big wrap around balcony (we had the two bedroom), and large kitchen. Even a washer and dryer. The only cons were the water pressure in the bathroom sink, and after a certain time, you cannot get more towels. House cleaning is "ask if you want", its not every day. For us we liked our privacy, so this worked for us. Another thing we loved was the quiet. The views were ok. Go ahead and book, you will not regret.
Reviewed on Dec 8, 2025
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
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.
Cross Key Waterways Hotel Deals
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$221 nightly
The price is $249 total per night from Jan 5 to Jan 6
$249 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
9.2/10 Wonderful! (1,588 reviews)
Room was great. Staff was awesome views amazing !!!!!
Reviewed on Dec 11, 2025
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
$269 nightly
The price is $298 total per night from Dec 14 to Dec 15
$298 total
Dec 14 - Dec 15
Total with taxes and fees
9.2/10 Wonderful! (1,332 reviews)
Staff was amazing and food was excellent
Reviewed on Dec 2, 2025
Waterside Suites & Marina
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $175 total per night from Dec 18 to Dec 19
$175 total
Dec 18 - Dec 19
Total with taxes and fees
8.8/10 Excellent! (1,149 reviews)
Love the area
Reviewed on Dec 8, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.