Title: Fleming Key, FL Cottage Rentals from $505 | Expedia.com [Fleming Key Travel Guide](https://expedia.com/Fleming-Key.dx180162)[Hotels in Fleming Key](https://expedia.com/Fleming-Key-Hotels.d180162.Travel-Guide-Hotels)[Vacation Rentals in Fleming Key](https://expedia.com/Fleming-Key-Vacation-Rentals.d180162.Travel-Guide-VacationRentals)[Flights to Fleming Key](https://expedia.com/Cheap-Flights-To-Fleming-Key.d180162.Travel-Guide-Flights)[Car Rentals in Fleming Key](https://expedia.com/Car-Rentals-In-Fleming-Key.d180162.Car-Rental-Guide)[Fleming Key Vacation Packages](https://expedia.com/Fleming-Key.d180162.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=180162&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=180162&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=180162&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=180162&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Fleming Key cottages ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161428/5f2bb115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161428/14f6d7b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161428/2a965799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161428/fff32e8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Osprey Suite | Charming Hideaway, Hot Tubs! [](https://www.expedia.com/Key-West-Hotels-Osprey-Suite-Charming-Hideaway.h110161428.Hotel-Information) Old Town Key West 9.8/10 Exceptional (35 reviews) "Loved this little place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles N. $455 nightly $505 total Mar 24 - Mar 25 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Osprey-Suite-Charming-Hideaway.h110161428.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106290000/106285400/106285346/8c527034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106290000/106285400/106285346/7046c018.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106290000/106285400/106285346/6813018e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/107000000/106290000/106285400/106285346/1bf65662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### OSPREY STUDIO @ The Colony-Sleeps up to 4 [](https://www.expedia.com/Key-West-Hotels-OSPREY-STUDIO-The-Colony-Sleeps-Up-To-4.h106285346.Hotel-Information) Old Town Key West 9.6/10 Exceptional (55 reviews) "We loved our stay here. It was calm and quiet--such a nice place to lounge and enjoy a morning coffee when you're not hanging out on Duval or exploring the island! We loved it!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dean H. $733 nightly $805 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-OSPREY-STUDIO-The-Colony-Sleeps-Up-To-4.h106285346.Hotel-Information) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161435/fc057fec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161435/80e4040d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161435/31ef68a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161435/bd32f18f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pelican Suite | Cozy Cottage, Hot Tubs, Close to D [](https://www.expedia.com/Key-West-Hotels-Pelican-Suite-Cozy-Cottage.h110161435.Hotel-Information) Old Town Key West 10/10 Exceptional (33 reviews) "Very clean and host was available and helpful.The beds were extremely comfortable. Only issue was the height of the beds. We are short people so climbing into bed was more difficult. We would book again!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia C. $510 nightly $566 total Mar 28 - Mar 29 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Pelican-Suite-Cozy-Cottage.h110161435.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/22000000/21720000/21717500/21717498/fff2c2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/22000000/21720000/21717500/21717498/5a10f17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/22000000/21720000/21717500/21717498/54ad7b38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/22000000/21720000/21717500/21717498/27d1327b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable Cottage with Private Pool & Lovely Garden - Great Location [](https://www.expedia.com/Key-West-Hotels-Comfortable-Cottage-With-Private-Pool-Lovely-Garden-Great-Location.h21717498.Hotel-Information) Old Town Key West 8.8/10 Excellent (122 reviews) "Great location and a great pool " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) J C. $1,020 nightly $1,131 total Mar 20 - Mar 21 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Comfortable-Cottage-With-Private-Pool-Lovely-Garden-Great-Location.h21717498.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106170000/106161400/106161399/88ffbc64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106170000/106161400/106161399/12e38f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/107000000/106170000/106161400/106161399/w1600h1197x0y3-686d442a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/107000000/106170000/106161400/106161399/6feb29f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HIDDEN OASIS 3 blocks from Duval [](https://www.expedia.com/Key-West-Hotels-HIDDEN-OASIS-3-Blocks-From-Duval.h106161399.Hotel-Information) Old Town Key West 9.6/10 Exceptional (100 reviews) "Loved the location of the cottage " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Betty B. $836 nightly $919 total Mar 14 - Mar 15 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-HIDDEN-OASIS-3-Blocks-From-Duval.h106161399.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106170000/106161500/106161404/w2499h1667x1y0-498f0aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/107000000/106170000/106161500/106161404/w2499h1666x1y1-41f4071b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106170000/106161500/106161404/w2499h1666x1y1-309d168f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/107000000/106170000/106161500/106161404/w2499h1666x1y1-cebdca02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Find your zen at HIDDEN TREASURE [](https://www.expedia.com/Key-West-Hotels-Find-Your-Zen-At-HIDDEN-TREASURE.h106161404.Hotel-Information) Old Town Key West 9.0/10 Wonderful (14 reviews) "Great place to stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sarah R. $1,000 nightly $1,100 total Apr 2 - Apr 3 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Find-Your-Zen-At-HIDDEN-TREASURE.h106161404.Hotel-Information) 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. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-25&endDate=2026-03-26®ionId=180162&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AA_SPRING_PROMO_180162) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America®ionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=CABIN) Villas [](https://www.expedia.com/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America®ionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=VILLA) Cottages [](https://www.expedia.com/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America®ionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=COTTAGE) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America®ionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America®ionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=APART_HOTEL) Condos [](https://www.expedia.com/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America®ionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=CONDO) Houseboats [](https://www.expedia.com/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America®ionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=HOUSE_BOAT) Apartments [](https://www.expedia.com/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America®ionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=APARTMENT) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FFleming-Key-Cottages.d180162-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FFleming-Key-Cottages.d180162-aaCottages.Travel-Guide-Accommodation) ## Top Fleming Key Hotel Reviews ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/a1e6ec60_y.jpg) ### Beachside Resort & Residences 6/10 Okay "Property was a bit dated and not the “resort” experience. Room had a single window looking at adjacent building wall and elevators did not work. Technically it had a“beach” as advertised, but I would not have called it that. With no breakfast or beneficial location, I would have been better off at a lower end chain hotel. The best perk is a shuttle running most the day to downtown. While no airport pick up, this saves on uber or trying to self park. Great communication from the property from pre-arrival through checkout. " [](https://expedia.com/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg) ### Pier House Resort & Spa 10/10 Excellent "Wonderful location and very nice hotel!!" [](https://expedia.com/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1_y.jpg) ### Blue Flamingo Resort Key West 2/10 Terrible "Was an act of god to get fresh towels and general housekeeping. When they did get around to housekeeping, it always seemed like an inconvenience. Key card wristbands generally stopped working each time we left the room. Became usual practice to go to front desk to get wristbands reactivated. Waiters/waitresses were rude. Every interaction always seemed like we were bothering them. Became uncomfortable to ask for anything to the point where we just went to Publix to get groceries/snacks instead of bothering the staff. My son asked for a smoothy or Shirley temple at the bar. He is 6\. It became an issue because the pina colada mix or strawberry daiquiri mix is “Reserved for alcoholic drinks, not kids” And no, it wasn’t pre made with alcohol. One elevator worked. Plan on taking the steps like we did. Or set aside 15 minutes every trip up or down waiting on the elevator. ESPECIALLY when the staff is using the elevator. They made it very clearly known that they take precedence of the elevator over the GUESTS. Everything in our room clogged at least three times. Sink clogged, bathroom drain clogged, and toilet clogged multiple times. And no, we didn’t clog it. We actually showed up to the room with a clogged toilet and clogged sink. Will all of the issues stated above, the staff made ZERO EFFORT to make these issues right. Management wasn’t willing to meet at the front desk. Their idea of making things right, was refunding the $25 nightly resort fee for one night. " [](https://expedia.com/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Parrot Key Hotel & Villas](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/cf132c1e_y.jpg) ### Parrot Key Hotel & Villas 10/10 Excellent "We enjoyed the multiple pools with friends. Our room was amazing and had a beautiful view of the water with lounge chairs and hammocks for relaxing!" [](https://expedia.com/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) ![Ibis Bay Beach Resort](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/7ea6251e_y.jpg) ### Ibis Bay Beach Resort 10/10 Excellent "Great area and nice outdoor area to hang out at." [](https://expedia.com/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.Hotel-Information) ![The Reach Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/bc3021c3_y.jpg) ### The Reach Key West, Curio Collection by Hilton 6/10 Okay "Resort Room was fine. Balcony small with other balcony to left and right akward" [](https://expedia.com/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/546caf1e_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "we stayed in a standard room but it was lovely and close to the pools with a wonderful side patio. pretty property. would definitely stay there again." [](https://expedia.com/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Havana Cabana at Key West ](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/62539afb_y.jpg) ### Havana Cabana at Key West 10/10 Excellent "The pool was just like the pictures. They had decorated well for the closest holiday. The staff was very fun! No outside food or drinks at the pool were allowed, which was a little disappointing because my group was planning on purchasing outside drinks from a grocery store to save money. The shuttle from the hotel was very helpful. The hotel was very close to the airport, which was convenient. The condition of the room was great!" [](https://expedia.com/Key-West-Hotels-Havana-Cabana-At-Key-West.h21241090.Hotel-Information) ![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/af5a58cd_y.jpg) ### Hyatt Vacation Club at Windward Pointe, Key West 8/10 Good "The property shares a fence with the airport. At check in we were greeted by idling jets and jet fuel in air. The noise level inside the unit and on our veranda was much more tolerable. The property was exceptional and we enjoyed our stay despite the occasional plane taking off." [](https://expedia.com/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ## Find out more about Fleming Key ## Fleming Key Cottages information | Number of reviews | 359 | | ----------------- | ----------- | | Accommodation | 87 Cottages | | Lowest Price | $505 | | Highest Price | $1,131 | ## Frequently asked questions ### Why book your cottage in Fleming Key with Expedia? ### How can I find cheap cottages in Fleming Key? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Key West Hotels ](https://www.expedia.com/Key-West-Hotels.d1187.Travel-Guide-Hotels) - [All-Inclusive Resorts in Key West ](https://www.expedia.com/Key-West-Hotels-All-Inclusive-Hotel.0-0-d1187-tAllinclusiveHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Key West ](https://www.expedia.com/Key-West-Hotels-Cheap-Hotels.0-0-d1187-tCheapHotels.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Key West ](https://www.expedia.com/Key-West-Hotels-Oceanfront-Hotels.0-0-d1187-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - 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