Northside Resort Vacations from $1,239
Book a Hotel + Flight or Car together to unlock savings
Photo by Norwegian Girl
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Northside Resort Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $2,008, price is now $1,239 per person
$1,239
per person
Mar 20 - Mar 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Although not a lot of amenities you didn't need to pay for, we enjoyed the option to be away from the craziness of Key West and still be able to enjoy it via the very convenient shuttle. Gorgeous resort - we will be back!
Reviewed on Jan 13, 2026
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,155, price is now $1,268 per person
$1,268
per person
Mar 20 - Mar 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,044 reviews)
The place and staff were amazing!!!!
Reviewed on Jan 13, 2026
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,910, price is now $1,723 per person
$1,723
per person
Mar 20 - Mar 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Being right on Duval Street if city noise bothers you you might want to stay a block or two off Duval. But if you want all the action then this place is fantastic. Staff is great and the room was nicely appointed and very comfortable.
Reviewed on Dec 12, 2025
Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $2,146, price is now $1,408 per person
$1,408
per person
Mar 20 - Mar 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,844 reviews)
Very nice hotel to stay at. Had everything we needed
Reviewed on Jan 13, 2026
The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $1,880, price is now $1,271 per person
$1,271
per person
Mar 20 - Mar 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,151 reviews)
All staff were wonderful, especially the concierge. I also loved the ease of using the shuttle to get to the Old town. Everything was clean and comfortable. The room was actually spacious as well.
Reviewed on Jan 13, 2026
Where to stay in Northside Resort
Find the best Northside Resort areas and neighborhoods for the activities you enjoy most. Learn more about Northside Resort
Old Town Key West
5 out of top 10 points of interest in this area
4.5/5(226 area reviews)
Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.
Northside Resort Hotel Deals
Parrot Key Hotel & Villas
2801 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$305 nightly
The price is $343 total per night from Jan 21 to Jan 22
$343 total
Jan 21 - Jan 22
Total with taxes and fees
9/10 Wonderful! (1,228 reviews)
We had an amazing time and everyone was very friendly and professional.
Reviewed on Jan 11, 2026
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$413 nightly
The price is $465 total per night from Jan 15 to Jan 16
$465 total
Jan 15 - Jan 16
Total with taxes and fees
8/10 Very Good! (2,039 reviews)
The room was well maintained. There was a staff member on site 24/7 for the needs of the guests. The beach was a wonderful plus along with the turtles, shark feedin
Reviewed on Jan 11, 2026
Courtyard by Marriott Key West Waterfront
3031-41 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$329 nightly
The price is $370 total per night from Jan 22 to Jan 23
$370 total
Jan 22 - Jan 23
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
Great hotel
Reviewed on Jan 11, 2026
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.