--- title: "Fleming Key Vacation Packages 2026 from $800 | Expedia" description: "Bundle Fleming Key flight + hotel & save up to 100% off your flight with Expedia. FREE cancellation on select hotels :white_check_mark:" canonical: "https://www.expedia.com/Fleming-Key.d180162.Destination-Travel-Guides" language: en-US market: US currency: USD prices_as_of: 2026-11-13T09:24:01Z --- # Fleming Key Vacations from $800 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $2,000 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 ## The Latest Fleming Key Vacation Packages Price found within the past 48 hours. Click for updated prices. Trip length 3 nights4 nights5 nights6-7 nights Stars 5 star4 star & up3 star & up2 star & up Flight class EconomyPremium economyBusinessFirst class Remove all filters - ![A modern living room with a large window, a flat-screen TV, a potted plant, a candle, and a view of a city skyline.](https://images.trvl-media.com/lodging/137000000/136010000/136001300/136001274/74a0856c.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern living room with a sofa, two round tables, a floor lamp, and a large mirror.](https://images.trvl-media.com/lodging/137000000/136010000/136001300/136001274/ef617444.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 16 - Jan 21** ### [501 First Studio Balcony by Palermo Home + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-16/2027-01-21/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=136001274&dealMarker=&paandie=true&cabinClass=e) Downtown Miami 5 nights Roundtrip • Boston (BOS) - Miami (MIA) BOS - MIA • Nonstop FLL - BOS • Nonstop [~~$1,612~~](https://www.expedia.com/) **$800** per traveler found 1 day ago - ![A poolside area with lounge chairs, a table with a beverage, and a view of the ocean.](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A spacious living room with a large window overlooking the beach, a comfortable sofa, a wooden coffee table, and a wicker chair.](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/39c5dd42.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Dec 27 - Jan 2** ### [The Retreat Collection at 1 Hotel & Homes South Beach + Flight](https://www.expedia.com/go/package/search/FlightHotel/2026-12-27/2027-01-02/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&dealMarker=&paandie=true&cabinClass=e) South Beach 6 nights **8.0/10** \- Very good (1 review) "Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay...." Reviewed June 22, 2016 Roundtrip • Boston (BOS) - Miami (MIA) BOS - FLL • Nonstop MIA - BOS • 1 stop [~~$49,695~~](https://www.expedia.com/) **$24,399** per traveler found 1 day ago - ![A balcony with a city view, a table with a champagne bottle, and a chair.](https://images.trvl-media.com/lodging/133000000/132830000/132825000/132824939/w1024h767x0y1-2187af23.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A swimming pool with a view of a historic tower and palm trees.](https://images.trvl-media.com/lodging/133000000/132830000/132825000/132824939/w1024h767x0y1-674aec04.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 1 - Feb 6** ### [Miami Vacation Rentals Downtown with Pool + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-02-01/2027-02-06/?FromAirport=EWR&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=132824939&dealMarker=&paandie=true&cabinClass=e) Downtown Miami 5 nights Roundtrip • New York (EWR) - Miami (MIA) EWR - MIA • Nonstop MIA - EWR • Nonstop [~~$2,237~~](https://www.expedia.com/) **$1,198** per traveler found 16 hours ago - ![A modern living room with a sofa, a coffee table, and a TV. There are large windows with a city view.](https://images.trvl-media.com/lodging/136000000/135380000/135372100/135372016/da7bd00a.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern kitchen with wooden cabinets, a marble countertop, and a city view through large windows.](https://images.trvl-media.com/lodging/136000000/135380000/135372100/135372016/1fc8d276.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 16 - Jan 21** ### [The Crosby Worldcenter 2BR Palermo Home + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-16/2027-01-21/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=135372016&dealMarker=&paandie=true&cabinClass=e) Downtown Miami 5 nights Roundtrip • Boston (BOS) - Miami (MIA) BOS - MIA • Nonstop FLL - BOS • Nonstop [~~$2,059~~](https://www.expedia.com/) **$1,113** per traveler found 1 day ago - ![A multi-story building with balconies, a street view, and a clear sky.](https://images.trvl-media.com/lodging/135000000/134330000/134322500/134322401/c6417f08.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern lounge area with a curved white sofa, a round gold table, and a bar area in the background.](https://images.trvl-media.com/lodging/135000000/134330000/134322500/134322401/756ddac7.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 16 - Jan 21** ### [The Crosby Balcony 1BR by Palermo Home + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-16/2027-01-21/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=134322401&dealMarker=&paandie=true&cabinClass=e) Downtown Miami 5 nights Roundtrip • Boston (BOS) - Miami (MIA) BOS - MIA • Nonstop FLL - BOS • Nonstop [~~$1,953~~](https://www.expedia.com/) **$1,056** per traveler found 1 day ago ## Fleming Key Hotel Deals ### [Opal Key Resort & Marina, Key West](https://www.expedia.com/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) ![A covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/360a1c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 245 Front Street, Key West, FL, 33040, US - Location: Old Town Key West, 1.6 mi from Fleming Key - Star rating: 5/5 - Guest rating: 9.2/10 (Wonderful, 1224 reviews) - Price: $294 nightly, $331 total, Nov 29 - Nov 30, Total with taxes and fees ### [Fairfield by Marriott Inn & Suites Key West at The Keys Collection](https://www.expedia.com/Key-West-Hotels-Fairfield-Inn-Suites-Key-West-At-The-Keys-Collection.h21871.Hotel-Information) ![A pool area with lounge chairs and umbrellas, surrounded by palm trees.](https://images.trvl-media.com/lodging/1000000/30000/21900/21871/ca442072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 3852 North Roosevelt Boulevard, Key West, FL, 33040, US - Location: New Town, 2.9 mi from Fleming Key - Star rating: 3.5/5 - Guest rating: 8.8/10 (Excellent, 1203 reviews) - Price: $159 nightly, $179 total, Nov 29 - Nov 30, Total with taxes and fees ### [Hyatt Centric Key West Resort and Spa](https://www.expedia.com/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ![A hotel with a swimming pool, balconies, and a view of the sea.](https://images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 601 Front St, Key West, FL, 33040, US - Location: Historic Seaport, 1.4 mi from Fleming Key - Star rating: 4/5 - Guest rating: 9.2/10 (Wonderful, 1005 reviews) - Price: $306 nightly, $345 total, Nov 29 - Nov 30, Total with taxes and fees - Review: Best location and it’s beautiful..great food on site! It was the best choice ### [Hampton Inn Key West FL](https://www.expedia.com/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.Hotel-Information) ![A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.](https://images.trvl-media.com/lodging/1000000/20000/15800/15720/046434c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 3755 S Roosevelt Blvd, Key West, FL, 33040, US - Location: 3.4 mi from Fleming Key - Star rating: 2.5/5 - Guest rating: 9/10 (Wonderful, 1581 reviews) - Price: $154 nightly, $173 total, Nov 17 - Nov 18, Total with taxes and fees - Review: The view from our room was wonderful. The pool was clean and staff was friendly. ### [Courtyard by Marriott Key West Waterfront](https://www.expedia.com/Key-West-Hotels-Courtyard-By-Marriott-Key-West-Waterfront.h663132.Hotel-Information) ![A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.](https://images.trvl-media.com/lodging/1000000/670000/663200/663132/f56e20a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 3031-41 N Roosevelt Blvd, Key West, FL, 33040, US - Location: Northside Resort, 1.9 mi from Fleming Key - Star rating: 3/5 - Guest rating: 8.8/10 (Excellent, 1000 reviews) - Price: $169 nightly, $190 total, Nov 29 - Nov 30, Total with taxes and fees ### [Silver Palms Inn & Historic Homes](https://www.expedia.com/Key-West-Hotels-Silver-Palms-Inn.h894030.Hotel-Information) ![A swimming pool with water splashing, surrounded by palm trees and a building in the background.](https://images.trvl-media.com/lodging/1000000/900000/894100/894030/dc763054.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 830 Truman Ave, Key West, FL, 33040, US - Location: Old Town Key West, 1.8 mi from Fleming Key - Star rating: 3.5/5 - Guest rating: 9.4/10 (Exceptional, 1040 reviews) - Price: $229 nightly, $258 total, Dec 2 - Dec 3, Total with taxes and fees - Review: Very central location ### [The Perry Hotel & Marina Key West](https://www.expedia.com/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/deb8b21f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 7001 Shrimp Road, Key West, FL, 33040, US - Location: Stock Island, 3.7 mi from Fleming Key - Star rating: 4/5 - Guest rating: 9.4/10 (Exceptional, 1317 reviews) - Price: $175 nightly, $197 total, Nov 30 - Dec 1, Total with taxes and fees ### [The Reach Key West, Curio Collection by Hilton](https://www.expedia.com/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) ![A beach with a wooden pier, palm trees, and beach umbrellas.](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/w5759h3835x0y5-5cf80996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1435 Simonton Street, Key West, FL, 33040, US - Location: Uptown - Upper Duval, 2.3 mi from Fleming Key - Star rating: 4/5 - Guest rating: 8.6/10 (Excellent, 1068 reviews) - Price: $289 nightly, $325 total, Dec 13 - Dec 14, Total with taxes and fees 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. 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[Key West National Wildlife Refuge](https://www.expedia.com/Key-West-National-Wildlife-Refuge-Key-West.d6177705.Vacation-Attraction) - [Key West Historic District Vacations](https://www.expedia.com/Key-West-Historic-District.d6281809.Destination-Travel-Guides) - [Museum of Art & History at the Custom House](https://www.expedia.com/Museum-Of-Art-History-At-The-Custom-House-Old-Town-Key-West.d553248621533115796.Vacation-Attraction) - [Mallory Dock](https://www.expedia.com/Mallory-Dock-Key-West-Historic-District.d553248621563220296.Vacation-Attraction) - [Visit Downtown Key West](https://www.expedia.com/Key-West-Downtown-Key-West.dx553248635976470405) - [Ernest Hemingway Home and Museum](https://www.expedia.com/Ernest-Hemingway-Home-And-Museum-Old-Town-Key-West.d501376.Vacation-Attraction) - [South Beach](https://www.expedia.com/South-Beach-Old-Town-Key-West.d6246827.Vacation-Attraction) - [Duval Street](https://www.expedia.com/Duval-Street-Key-West-Historic-District.d6068616.Vacation-Attraction) - [Waterfront Playhouse](https://www.expedia.com/Waterfront-Playhouse-Key-West-Historic-District.d553248621532652609.Vacation-Attraction) - [Southernmost Point](https://www.expedia.com/Southernmost-Point-Old-Town-Key-West.d501380.Vacation-Attraction) - [Key West Museum of Art and History](https://www.expedia.com/Key-West-Museum-Of-Art-And-History-Old-Town-Key-West.d6069279.Vacation-Attraction) - [Key West Butterfly and Nature Conservatory](https://www.expedia.com/Key-West-Butterfly-And-Nature-Conservatory-Old-Town-Key-West.d6068597.Vacation-Attraction) - [Sunset Key Vacations](https://www.expedia.com/Sunset-Key.d553248635976481798.Destination-Travel-Guides) - [Sails To Rails Museum at Flagler Station](https://www.expedia.com/Sails-To-Rails-Museum-At-Flagler-Station-Key-West-Historic-District.d553248621532652635.Vacation-Attraction) - [Red Barn Theater](https://www.expedia.com/Red-Barn-Theater-Key-West-Historic-District.d6069271.Vacation-Attraction) - [Key West Shipwreck Museum](https://www.expedia.com/Key-West-Shipwreck-Museum-Key-West-Historic-District.d6063545.Vacation-Attraction) - [Key West Lighthouse and Keeper's Quarters Museum](https://www.expedia.com/Key-West-Lighthouse-And-Keepers-Quarters-Museum-Old-Town-Key-West.d501383.Vacation-Attraction) - [Key West Burlesque Theater](https://www.expedia.com/Key-West-Burlesque-Theater-Old-Town-Key-West.d553248621532652629.Vacation-Attraction) - [Visit Key West](https://www.expedia.com/Key-West.dx1187) - [Smathers Beach](https://www.expedia.com/Smathers-Beach-Beachside.d6069255.Vacation-Attraction) - [The Kite House](https://www.expedia.com/The-Kite-House-Old-Town-Key-West.d553248621532652628.Vacation-Attraction) - [Curry Mansion Museum](https://www.expedia.com/Curry-Mansion-Museum-Key-West-Historic-District.d553248621532652631.Vacation-Attraction) - [San Carlos Institute - Casa Cuba](https://www.expedia.com/San-Carlos-Institute-Casa-Cuba-Old-Town-Key-West.d6068607.Vacation-Attraction) - [Mallory Square](https://www.expedia.com/Mallory-Square-Key-West-Historic-District.d501385.Vacation-Attraction) - [Clarence S. Higgs Memorial Beach Park](https://www.expedia.com/Clarence-S-Higgs-Memorial-Beach-Park-Old-Town-Key-West.d6246822.Vacation-Attraction) - [Harry S. Truman Little White House](https://www.expedia.com/Harry-S-Truman-Little-White-House-Old-Town-Key-West.d6068605.Vacation-Attraction) - [Car rental Key West](https://www.expedia.com/Car-Rentals-In-Key-West.d1187.Car-Rental-Guide) - [Rental cars Key West Intl. airport](https://www.expedia.com/Car-Rentals-In-Key-West-Intl.d5724485.Car-Rental-Guide) - [Key West Vacation Rentals](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals) - [Things to do in Key West](https://www.expedia.com/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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