Uptown - Upper Duval Vacation Packages
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- Hyatt Vacation Club at Windward Pointe, Key West
Aug 9 - Aug 15Hyatt Vacation Club at Windward Pointe, Key West + Flight
Key West6 nights9.4/10 - Exceptional (1,091 reviews)"Beautiful rooms. It has to be one of the nicest in the Keys."Reviewed May 19, 2026Roundtrip • Toronto (YYZ) - Fort Lauderdale (FLL)YYZ - FLL • Nonstop FLL - YYZ • NonstopCA $2,759CA $1,754found 16 hours agoper traveller - The Key West Hotel
Jul 6 - Jul 20The Key West Hotel + Flight
Key West Historic District14 nights9.2/10 - Wonderful (555 reviews)Roundtrip • Toronto (YYZ) - Miami (MIA)YYZ - MIA • 1 stop MIA - YYZ • 1 stopCA $7,349CA $4,752found 1 day agoper traveller - Hyatt Vacation Club at Sunset Harbor, Key West
Jul 31 - Aug 8Hyatt Vacation Club at Sunset Harbor, Key West + Flight
Old Town Key West8 nights8.6/10 - Excellent (371 reviews)"Wished we had paid more for a unit that at least had a window other than to a hallway. Room was clean but not spotless. Found at least 3 long hairs in the bathroom area. Staff at desk was quite abrupt and condescending. At check in AND check out. Gave 4 stars but 5 stars could easily be reached with just a little more attention to detail"Reviewed May 18, 2026Roundtrip • Montreal (YUL) - Key West (EYW)YUL - EYW • 1 stop EYW - YUL • 1 stopCA $4,847CA $3,165found 1 hour agoper traveller - The Perry Hotel & Marina Key West
Jul 6 - Jul 20The Perry Hotel & Marina Key West + Flight
Stock Island14 nights9.4/10 - Exceptional (1,271 reviews)"Hi. Love this place. Great location. Shuttle bus to Downtown Key West. So know need to drive. Pool is awesome. They have a good restaurant and happy hour. Fighter jets have their 'sorties' . Its pretty cool. Thanks"Reviewed May 18, 2026Roundtrip • Toronto (YYZ) - Miami (MIA)YYZ - MIA • 1 stop MIA - YYZ • 1 stopCA $3,714CA $2,626found 1 day agoper traveller - Southernmost Beach Resort and Guesthouses
Jul 6 - Jul 20Southernmost Beach Resort and Guesthouses + Flight
Old Town Key West14 nights8.8/10 - Excellent (3,337 reviews)"It was a large and fun property. The roosters will wake you up early! But everything is shut down by 9 pm, so it’s not a problem. Plemty of seating and four different bars. It’s comfortable and casual, but it’s not the kind of place where they are sorting on you necessarily (for the price). But for a long weekend it was great and close enough to a lot of great restaurants."Reviewed May 19, 2026Roundtrip • Toronto (YYZ) - Miami (MIA)YYZ - MIA • 1 stop MIA - YYZ • 1 stopCA $4,109CA $3,009found 1 day agoper traveller
Where to stay in Uptown - Upper Duval
Find the best Uptown - Upper Duval areas and neighborhoods for the activities you enjoy most. Learn more about Uptown - Upper Duval
Old Town Key West
3 out of top 10 points of interest in this area
3.5/5(8 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.
Uptown - Upper Duval Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
The price is CA $310 per night from Jun 7 to Jun 8
CA $310
CA $449 total
Jun 7 - Jun 8
includes taxes & fees
8.8/10 Excellent! (3,337 reviews)
"Our shower leaked all over the bathroom. Front desk staff was rude everyday. Very limited pool chairs. Pools were cloudy and could have used a good cleaning."
Reviewed on May 20, 2026
The Southernmost Inn - Adults Only
525 United Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from May 21 to May 22
CA $169
CA $252 total
May 21 - May 22
includes taxes & fees
8.4/10 Very Good! (1,365 reviews)
"Overall a solid option for the price and the location is right off Duvall!"
Reviewed on May 20, 2026
The Reach Key West, Curio Collection by Hilton
1435 Simonton Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $308 per night from Jun 1 to Jun 2
CA $308
CA $439 total
Jun 1 - Jun 2
includes taxes & fees
8.6/10 Excellent! (1,011 reviews)
"Beautiful private beach. Nice pool, beautiful grounds, nicely appointed rooms. A paradise witin a paradise."
Reviewed on May 19, 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.
Frequently asked questions
Discover the most popular places to visit in Uptown - Upper Duval
Southernmost Point
4/5(161 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
South Beach
4/5(54 reviews)
The southernmost beach in the continental United States is a convenient sandy enclave, just minutes from the center of town.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
CA $61
per adult
94% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $76
per adult
88% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
CA $75
per adult
86% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.