Sunset Key Vacations from $623
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Your Sunset Key Vacation
Let our Sunset Key vacation packages take you to a destination where long-lasting memories are waiting to be made. While it's especially renowned for its coastal beaches, there's plenty to love about this neighborhood. Not sure where to go during your trip to Sunset Key? Nearby attractions like Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square are great places to start. No matter what your dream Sunset Key vacation may look like, you can turn it into reality with Expedia.
The Latest Sunset Key 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
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (1,668 reviews)
I really loved the whole experience from beginning to end! The receptionist are awesome and very pleasant to speak to all the staff are very pleasant and we really really enjoyed our stay
Reviewed on Jul 29, 2025
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Beautiful place ,the price incredible ,but the view from my balcony is the best , I fall in love with my apt/room .
Reviewed on Jul 30, 2025
Almond Tree Inn Hotel - Adults Only
Old Town Key West
Save 100% on your flight
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
10/10 Exceptional! (1,002 reviews)
It was just a all around grest place to stay. Clean, quiet, great staff snd walkable to nice restaurants and shopping.
Reviewed on Jul 31, 2025
Orchid Key Inn - Adults Only
Old Town Key West
Save 100% on your flight
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
great hotel in Key west ,friendly staff and old style 50's feel...rooms are on the small side ,however breakfast and water by the pool means rooms are for sleeping only
Reviewed on Aug 1, 2025
Where to stay in Sunset Key
Find the best Sunset Key areas and neighborhoods for the activities you enjoy most. Learn more about Sunset Key
Old Town Key West
3 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.
Sunset Key Hotel Deals
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $218 total per night from Aug 18 to Aug 19
$218 total
Aug 18 - Aug 19
Total includes taxes and fees
8.4/10 Very Good! (1,403 reviews)
"excellent"
Reviewed on Jul 30, 2025
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Fully refundable
$244 nightly
The price is $275 total per night from Aug 25 to Aug 26
$275 total
Aug 25 - Aug 26
Total includes taxes and fees
8.6/10 Excellent! (2,641 reviews)
"Location was perfect."
Reviewed on Jul 31, 2025
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$172 nightly
The price is $193 total per night from Sep 1 to Sep 2
$193 total
Sep 1 - Sep 2
Total includes taxes and fees
7.6/10 Good! (1,488 reviews)
"Good value for your money, convenient location and a friendly, welcoming staff. As a pet friendly resort, perhaps in the future have a couple of dog friendly entertainment areas on the resort so owners and their fur babies can spend time together."
Reviewed on Jul 29, 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.
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Key West Hotels
- All-inclusive Resorts in Key West
- Cheap Hotels in Key West
- Oceanfront Hotels in Key West
- Hotels near Duval Street
- Beach Hotels in Key West
- Adults Only Resorts & in Key West
- Hotels near Key West Historic District
- Hotels near Mallory Square
- Houseboats in Key West
- Hotels near Waterfront Playhouse
- Pet-friendly Hotels in Key West
- Hotels near Key West Shipwreck Museum
- Hotels near Mallory Dock
- Hotels near Museum of Art & History at the Custom House
- Hotels near Custom House Museum
- Hotels near Mel Fisher Maritime Museum
- Hotels near Audubon House and Tropical Gardens
- Hotels near Roy John-Karl Gallery
- Condo Rentals in Key West
- Hotels near Harry S. Truman Little White House
- Romantic Hotels in Key West
- Family Hotels in Key West
- Hotels near Observation Tower
- Hotels near Truman Annex
- Hotels near Curry Mansion Museum
- 4 Star Hotels in Key West
- Hilton Hotels in Key West
- Hotels near Historic Seaport
- Hotels near Red Barn Theater
- Hotels near Oldest House Museum and Garden
- Hotels near Key West Film Society
- 5 Star Hotels in Key West
- Honeymoon Resorts & in Key West
- Resorts in Key West
- Hotels near St. Paul's Episcopal Church
- Boutique Hotels in Key West
- Kimpton Hotels in Key West
- Hotels near Schooner Western Union
- Cabin Rentals in Key West
- Cottages in Key West
- B&B in Key West
- Luxury Hotels in Key West
- Gay friendly Hotels in Key West
- Historic Hotels in Key West
- Hotels near Donkey Milk House
- Hotels near Jackson Square
- Hotels with Kitchenettes in Key West
- Hotels with Free Airport Shuttle in Key West
- Guest Houses in Key West
- Best Western Hotels in Key West
- Wyndham Hotels in Key West
- Hotels near San Carlos Institute - Casa Cuba
- Hotels with smoking rooms in Key West
- Golf Hotels in Key West
- Key West Vacations
- All inclusive Vacation Packages Key West
- Ernest Hemingway Home and Museum
- Duval Street
- Custom House Museum
- Mallory Dock
- Mel Fisher Maritime Museum
- Key West Museum of Art and History
- Audubon House and Tropical Gardens
- Harry S. Truman Little White House
- Fort Zachary Taylor Historic State Park
- Roy John-Karl Gallery
- Curry Mansion Museum
- Oldest House Museum and Garden
- Red Barn Theater
- Donkey Milk House
- Schooner Western Union
- Jackson Square
- San Carlos Institute - Casa Cuba
- Visit Key West
- Florida Keys Eco - Discovery Center
- Sails To Rails Museum at Flagler Station
- Florida Keys National Marine Sanctuary
- The Kite House
- Key West Lighthouse and Keeper's Quarters Museum
- Key West Historic District Vacations
- Bahama Village Vacations
- Key West Cemetery
- Visit Historic Seaport
- Romantic Vacation Packages Key West
- Tennessee Williams Key West Exhibit
- Saint Mary Star of the Sea
- Key West Burlesque Theater
- Fleming Key Vacations
- South Beach
- Old Town Key West Vacations
- City Zoo Gallery
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.