Cross Key Waterways Vacations from $499

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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.
Plunge Beach Resort

Plunge Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $914, price is now $499 per person
$499
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (1,192 reviews)
Clean room comfortable bed with plenty of pillows

Reviewed on Oct 7, 2025

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Price was $1,643, price is now $819 per person
$819
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (1,238 reviews)
Hotel was pretty and staff was great. During our 3 night stay we had to evacuate the hotel twice due to “an emergency” in the building. Both times, we were not given much information.

Reviewed on Oct 11, 2025

Soleado Hotel

Soleado Hotel

3 out of 5
East Fort Lauderdale
Save 100% on your flight
Price was $1,011, price is now $533 per person
$533
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (629 reviews)
First time staying here, I will definitely go back to this place , very clean and very short walk to beach also very nice pool area

Reviewed on Oct 6, 2025

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 $10,057, price is now $5,358 per person
$5,358
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was $1,642, price is now $880 per person
$880
per person
Dec 14 - Dec 17
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,307 reviews)
Great stay, well get back

Reviewed on Oct 10, 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
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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 Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park.

Find hotels in Key Largo Village

Cross Key Waterways Hotel Deals

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
$346 nightly
The price is $389 total per night from Oct 26 to Oct 27
$389 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (1,006 reviews)
"Excelent"

Reviewed on Oct 6, 2025

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

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$192 nightly
The price is $217 total per night from Oct 14 to Oct 15
$217 total
Oct 14 - Oct 15
Total with taxes and fees
9.2/10 Wonderful! (1,532 reviews)
"Quiet. Peaceful. Perfect getaway for couples. Excellent customer service. This was our second stay at Chesapeake. Chesapeake and Islamorada are our new favorite destinations in the Keys. Islamorada reminds us of the Key West we fell in love with 30 years ago. Low key and peaceful. Every day is perfect ..."

Reviewed on Oct 4, 2025

Chesapeake Beach Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

3.5 out of 5
103800 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $286 total per night from Oct 12 to Oct 13
$286 total
Oct 12 - Oct 13
Total with taxes and fees
9.2/10 Wonderful! (1,311 reviews)
"Bartender should be more helpful Saturday 10/4/25 Carlos was very helpful"

Reviewed on Oct 6, 2025

Reefhouse Resort & Marina
See all 2,231 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.