Cross Key Waterways Vacation Packages 2026 from $651

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.

The Penguin Hotel

South Beach

Save 100% on your flight

$651

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,963 reviews)

Overall it was ok. It's perfect if you just need a place to sleep, great location just by the beach and lots of great restaurants around it. Service, however, was poor. When entering the receptionist doesn't greet or even acknowledge you. (Isn't that their job?) We had to ask several times for new towels and room cleaning.

Reviewed on Sep 22, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$8,794

per person

Oct 30 - Nov 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

President Hotel Villa

South Beach

Save 100% on your flight

$662

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,004 reviews)

I love the room. I would definitely stay again. The only thing I would say is the showers are definitely not hot enough for me. I don’t know if I just like it too hot but that’s the only issue I really had.

Reviewed on Sep 7, 2026

President Hotel

South Beach

Save 100% on your flight

$662

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (2,738 reviews)

Private Oasis at Arya

Coconut Grove

$1,102

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,034 reviews)

Disappointing experience with a third-party booking. Upon check-in, my assigned room was completely uncleaned from the previous occupants. Since this was booked via a private rental agent not the hotel, the front desk couldn't offer direct support. After waiting an hour in the lobby, I was moved to a clean but downgraded room. To make matters worse, the room's Wi-Fi failed to work (though the main Hotel guest network was strong enough to use), and the host completely ignored my multiple messages and emails. I like this area, but I will only book directly with the hotel in the future to avoid these communication gaps.

Reviewed on Sep 22, 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

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 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.

Silver Shores

If you're looking for some top things to see and do in Silver Shores and surrounding area, you can visit Bluefin Rock Harbor Marina and Harry Harris Park.

An aerial view of a coastal area with RVs parked along the shore, a small beach, and a clear view of the ocean.

Key Largo Park

Though Key Largo Park might not have many top sights, you can venture to the surrounding area to see attractions like Jacob's Aquatic Center and Jimmy Johnson's Big Chill.

A white speedboat on a blue ocean with a tropical island in the background.

Key Largo Village

While Key Largo Village might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Jacob's Aquatic Center and Jimmy Johnson's Big Chill.

Pirates Cove

While Pirates Cove might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill.

Cross Key Waterways Hotel Deals

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$199 nightly

$224 total

Oct 1 - Oct 2

Total with taxes and fees

9.2/10 Wonderful! (1,783 reviews)

"Great beach for the keys and great breakfast! The bar food is minimal and they don’t always open but Wahoo next door is amazing. Would definitely come back to this hotel."

Reviewed on Sep 22, 2026

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

97000 Overseas Hwy Key Largo FL

Fully refundableReserve now, pay when you stay

$315 nightly

$354 total

Oct 1 - Oct 2

Total with taxes and fees

8.6/10 Excellent! (1,191 reviews)

"All was great, we just had an issue with a food item we ordered twice and was incorrectly doubled charged in both occasions. It looked liked a POS system issue, and the staff quickly resolved it. Other than that, everyone and everything was great. The resort is paradise by the beach ⛱️ 💯"

Reviewed on Sep 22, 2026

Waterside Suites & Marina

201 Ocean Drive Key Largo FL

Fully refundableReserve now, pay when you stay

$140 nightly

$157 total

Oct 6 - Oct 7

Total with taxes and fees

9/10 Wonderful! (1,489 reviews)

"The room was fine but it had poor water pressure and a very old sliding door that didn’t lock. The grounds look neglected. A little work around the property would do it. I like the location."

Reviewed on Sep 21, 2026

See all 2,200 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.