
Fleming Key Vacations from $454
Book a Hotel + Flight or Car together to unlock savings
- 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 Fleming Key vacation packages
Price found within the past 48 hours. Click for updated prices.


Bay Breeze Premium Apartments By Eskape Collection
Price was $1,643, price is now $709 per person
$709
per person
Mar 17 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (189 reviews)
From the very efficient and effective check in, courteous customer service, and spotless room, our stay was great from the beginning. The place was spacious and modern. There was a big wrap around balcony (we had the two bedroom), and large kitchen. Even a washer and dryer. The only cons were the water pressure in the bathroom sink, and after a certain time, you cannot get more towels. House cleaning is "ask if you want", its not every day. For us we liked our privacy, so this worked for us. Another thing we loved was the quiet. The views were ok. Go ahead and book, you will not regret.
Reviewed on Dec 8, 2025

The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $1,970, price is now $875 per person
$875
per person
Feb 10 - Feb 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
Hotel was perfect to service to pool and beach to decor
Reviewed on Dec 24, 2025


Hawks Cay Resort
Price was $1,632, price is now $744 per person
$744
per person
Feb 1 - Feb 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,003 reviews)
We rented a villa, it was clean but a lot of things were broken and damaged. No outlets worked in the bedrooms to charge our phones. Bathroom had so much water damage, tiles popping up off floor and floor was bowing. Exhaust fan made crazy noises in bathroom downstairs. Kids kept getting locked in bathroom because doorknob was wonky. Sliding doors were messed up downstairs. Clean but not worth it for the price.
However could not beat backing up to the ocean where my son could fish all day. Lagoon was small and crowded, especially closer to weekend. Golf carts way overpriced to rent. The bikes were fun, but very hard to find more than one or two at a time.
Area was beautiful, staff was great, but felt hotel, food, amenities way overpriced for what it was. Had a great time, but villas and amenities need some work.
Reviewed on Dec 26, 2025
Don't see what you're looking for?
See all available trips from Columbus to Fleming Key
View all tripsFleming Key Hotel Deals

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$295 nightly
The price is $331 total per night from Jan 4 to Jan 5
$331 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (1,835 reviews)
Pool and hot tub were very nice,chicken walk was excellent! Great staff!!!!
Reviewed on Dec 26, 2025

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$283 nightly
The price is $318 total per night from Jan 8 to Jan 9
$318 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
8/10 Very Good! (1,791 reviews)
Room was nice and the vibe was good. Pool was excellent and staff are very friendly. Could do better with breakfast. There were limited options and it took 30+ minutes to take our order.overall we enjoyed our stay.
Reviewed on Dec 22, 2025

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$292 nightly
The price is $328 total per night from Jan 26 to Jan 27
$328 total
Jan 26 - Jan 27, 2026
Total with taxes and fees
8.8/10 Excellent! (1,757 reviews)
Great View
Reviewed on Dec 22, 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.
Find the Best Fleming Key Vacation Packages
Fleming Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Miami Intl. Airport (MIA) |
More vacations you might like
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
- Hotels near Key West Historic District
- Adults Only Resorts & in Key West
- Hotels near Sails To Rails Museum at Flagler Station
- Houseboats in Key West
- Pet-friendly Hotels in Key West
- Hotels near Schooner Western Union
- Hotels near Key West Burlesque Theater
- Hotels near Studios of Key West
- Condo Rentals in Key West
- Hotels near Mallory Square
- Romantic Hotels in Key West
- Family Hotels in Key West
- 4 Star Hotels in Key West
- Hotels near Meadows
- Hotels near Donkey Milk House
- Hotels near Historic Seaport
- Hotels near The Kite House
- Hilton Hotels in Key West
- Hotels near Curry Mansion Museum
- Hotels near Mallory Dock
- 5 Star Hotels in Key West
- Honeymoon Resorts & in Key West
- 4 Star Hotels in Key West Historic District
- Resorts in Key West
- Hotels near Waterfront Playhouse
- Hotels near Key West Cemetery
- Family Hotels in Key West Historic District
- Oceanfront Hotels in Key West Historic District
- Historic Hotels in Key West Historic District
- Gay friendly Hotels in Key West Historic District
- Pet-friendly Hotels in Key West Historic District
- Hotel Wedding Venues Hotels in Key West Historic District
- Hotels with Connecting Rooms in Key West Historic District
- Cheap Hotels in Key West Historic District
- Hotels with Free Airport Shuttle in Key West Historic District
- Hotels with Laundry Facilities in Key West Historic District
- Hotels with a Pool in Key West Historic District
- Hotels with Suites in Key West Historic District
- Adults Only Resorts & in Key West Historic District
- Hotels with Free Parking in Key West Historic District
- Luxury Hotels in Key West Historic District
- Romantic Hotels in Key West Historic District
- Boutique Hotels in Key West Historic District
- Hotels with Balconies in Key West Historic District
- Honeymoon Resorts & in Key West Historic District
- Beach Hotels in Key West Historic District
- Resorts & Hotels with Spas in Key West Historic District
- Hotels with Kitchenettes in Key West Historic District
- Non-Smoking Hotels in Key West Historic District
- Hotels with Free Breakfast in Key West Historic District
- Key West Vacations
- All inclusive Vacation Packages Key West
- Ernest Hemingway Home and Museum
- Sails To Rails Museum at Flagler Station
- Duval Street
- Schooner Western Union
- Key West Burlesque Theater
- Curry Mansion Museum
- Donkey Milk House
- The Kite House
- Key West Cemetery
- Mallory Dock
- Key West Historic District Vacations
- Custom House Museum
- Red Barn Theater
- Oldest House Museum and Garden
- Audubon House and Tropical Gardens
- Mel Fisher Maritime Museum
- Roy John-Karl Gallery
- Key West Museum of Art and History
- Saint Mary Star of the Sea
- San Carlos Institute - Casa Cuba
- Harry S. Truman Little White House
- Visit Key West
- Jackson Square
- Sunset Key Vacations
- Old Town Key West Vacations
- Fort Zachary Taylor Historic State Park
- Key West Lighthouse and Keeper's Quarters Museum
- Tennessee Williams Key West Exhibit
- Visit Historic Seaport
- South Beach
- Visit Key West Historic District
- Romantic Vacation Packages Key West
- City Zoo Gallery
- Bahama Village Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















