
Fleming Key Vacations from $418
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.


Hollywood by the Sea Hotel
Hollywood Beach
Price was $1,502, price is now $555 per person
$555
per person
Jan 8 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
7.6/10 Good! (349 reviews)
Pictures were a bit deceiving. Floors were sticky and felt a little unclean. We arrived at night and it felt a little unsafe. And we were charged extra $19 that we are refuting. But the proximity to the beach can’t be beat! The sunrise was beautiful!
Reviewed on Oct 25, 2025


Cavalier Hotel South Beach
South Beach
Price was $1,361, price is now $592 per person
$592
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Wonderful stay for it being our first time in Miami. The hotel was clean and perfectly sized for a nice short trip. Location was incredible being on Ocean drive. Pricing was extremely fair for it being a holiday week and the service was incredible. Thank you for a good time and a pleasant stay!
Reviewed on Nov 28, 2025

Iberostar Waves Berkeley Shore
South Beach
Price was $1,679, price is now $733 per person
$733
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (1,449 reviews)
Is a very good hotel. Location is excellent and the staff is very kind. Recommended.
Reviewed on Dec 2, 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
$202 nightly
The price is $228 total per night from Dec 16 to Dec 17
$228 total
Dec 16 - Dec 17
Total with taxes and fees
8.6/10 Excellent! (1,734 reviews)
Staff very courteous! We arrived very early- hoping we could at least chk our bags before going to lunch ( 2 couples- booking two rooms). Our friends' room was already available .We were told ours would be ready soon. We had a lovely, long, leisurely lunch at Chicken Walk. Our room still wasnt ready ...
Reviewed on Dec 3, 2025

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $197 total per night from Dec 4 to Dec 5
$197 total
Dec 4 - Dec 5
Total with taxes and fees
8/10 Very Good! (1,750 reviews)
Yes
Reviewed on Dec 1, 2025

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $218 total per night from Dec 4 to Dec 5
$218 total
Dec 4 - Dec 5
Total with taxes and fees
8.8/10 Excellent! (1,760 reviews)
My stay at this hotel was absolutely outstanding! From the moment I arrived, I felt welcomed and well taken care of. The staff were incredibly professional, friendly, and always ready to help with anything I needed.
Reviewed on Dec 1, 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.




















