Title: Book the Best Old Town Key West ALL INCLUSIVE Resorts and Hotels - All-inclusive Hotels in Old Town Key West, Key West | Expedia.ca [Flights to Key West](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)[Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)[Old Town Key West Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Key-West.d553248635976481920.Car-Rental-Guide)[Old Town Key West Vacations](https://expedia.ca/Old-Town-Key-West.d553248635976481920.Destination-Travel-Guides) ![Key West Lighthouse and Keeper\'s Quarters Museum featuring a lighthouse](https://images.trvl-media.com/place/501383/0a79f1bb-7c8b-43da-830f-8c77ccf8ffbb.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find All Inclusive Resorts and Hotels in Old Town Key West, Key West - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Old Town Key West All Inclusive Resorts and Hotels Tonight [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976481920&startDate=2025-12-14&endDate=2025-12-15&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 15 - Dec 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976481920&startDate=2025-12-15&endDate=2025-12-16&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976481920&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976481920&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Old Town Key West all-inclusive hotels ![Couples treatment rooms, facials, massages](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/546caf1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/3bfd19eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/70df70cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/1441613f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southernmost Beach Resort and Guesthouses [](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) Old Town Key West 8.8/10 Excellent (2928) "Great stay with an actual beach which is rare in Key West. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $259 CA $392 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/f2c5f58d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/360a1c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/841e73b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/0acd853b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Opal Key Resort & Marina, Key West [](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) Old Town Key West 9.2/10 Wonderful (1023) "Our stay was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $384 CA $487 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/45887e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/b0c5a846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/d7755f8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/799c47e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southwinds Motel [](https://www.expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.Hotel-Information) Old Town Key West 8.8/10 Excellent (1245) "Perfect little place, great location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hailey CA $212 CA $285 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/b5f8742c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Truman)](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/33f2b657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Train station shuttle](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/193f2662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 outdoor pools, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winslow's Bungalows - Key West Historic Inns [](https://www.expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) Old Town Key West 9.2/10 Wonderful (1073) "Beautiful property, nice clean bungalows and great staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $315 CA $424 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![Suite, 1 King Bed, Lanai, Oceanfront | View from room](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/14292c62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/7df2a82d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/1b169515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/bd916166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Marina Key West, Curio Collection by Hilton [](https://www.expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) Old Town Key West 8.4/10 Very good (470) "beautiful Hotel! " ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) iria CA $453 CA $592 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![Private beach, scuba diving, sailing, kayaking](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/bc3021c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/48229e5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/2fd2eeb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/123aeac4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Reach Key West, Curio Collection by Hilton [](https://www.expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) Old Town Key West 8.4/10 Very good (1002) "Great view, amazing room and friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristine CA $281 CA $399 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/e882a768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 2 Bedrooms (Royal Poinciana) | Living area](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/bab228c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/0047a3af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 2 Bedrooms (Royal Poinciana) | Living area](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/0da711be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paradise Inn Key West - Adults Only [](https://www.expedia.ca/Key-West-Hotels-Paradise-Inn-Key-West-Adults-Only.h3924835.Hotel-Information) Old Town Key West 9.2/10 Wonderful (1003) "Cozy place right near everything " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph [](https://www.expedia.ca/Key-West-Hotels-Paradise-Inn-Key-West-Adults-Only.h3924835.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/4000000/3840000/3830600/3830519/236726ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/4000000/3840000/3830600/3830519/f12b1e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3840000/3830600/3830519/00a251a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mansion Room #201 - Ocean View with private balcony - Adults Only | Living area](https://images.trvl-media.com/lodging/4000000/3840000/3830600/3830519/b9fdadbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southernmost House [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-House-Hotel.h3830519.Hotel-Information) Old Town Key West 9.4/10 Exceptional (1001) "Great place to stay. Staff was very friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacob CA $371 CA $545 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-House-Hotel.h3830519.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/3e2c6b2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/c435c8cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/e213aee6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/6eb12223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heron House - Adult Only [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) Old Town Key West 9.0/10 Wonderful (1135) "Loved the setup of the hotel and great location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel CA $176 CA $244 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/30000/20800/20796/a4035487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, wine bar](https://images.trvl-media.com/lodging/1000000/30000/20800/20796/3d82727e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/30000/20800/20796/a6d87cde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/30000/20800/20796/d484c05b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Gardens Hotel [](https://www.expedia.ca/Key-West-Hotels-The-Gardens-Hotel.h20796.Hotel-Information) Old Town Key West 9.8/10 Exceptional (1001) "Amazing hotel, the perfect Key West vibe. Clean rooms, delicious breakfast. We will come back again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Isis CA $355 CA $399 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-The-Gardens-Hotel.h20796.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.ca/Hotel-Search?startDate=2025-12-28&endDate=2025-12-29®ionId=553248635976481920&adults=2&mealPlan=ALL_INCLUSIVE&sort=RECOMMENDED&openPlayBack=true) ## Price trends for hotels in Old Town Key West | Less expensive | More expensive | This month | Next month | | -------------- | -------------- | ---------- | ---------- | | September | February | CA $472 | CA $581 | | Month | Price | | --------- | ------- | | January | CA $581 | | February | CA $645 | | March | CA $617 | | April | CA $561 | | May | CA $458 | | June | CA $400 | | July | CA $380 | | August | CA $310 | | September | CA $289 | | October | CA $358 | | November | CA $401 | | December | CA $472 | Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Old Town Key West. Select dates and complete search for nightly totals inclusive of taxes and fees. ## Top Old Town Key West Hotel Reviews ![Casa Marina Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450_y.jpg) ### Casa Marina Key West, Curio Collection by Hilton 10/10 Excellent "This resort is so beautiful, rooms where super clean and we stayed in the king room with beach access on the first floor. Had dinner at the restaurant that was actually very good." [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ## Frequently asked questions ### Looking for Old Town Key West all-inclusive resorts? ### What is there to do near my all-inclusive resort in Old Town Key West? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Cheap-Hotels.0-0-d553248635083902001-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Luxury-Hotel.0-0-d553248635083902001-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Downtown Key West ](https://www.expedia.ca/Downtown-Key-West-Key-West-Hotels-Adults-Only-Resorts.0-n553248635976470405-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Downtown Key West ](https://www.expedia.ca/Downtown-Key-West-Key-West-Hotels-Beach-Hotel.0-n553248635976470405-0-tBeachHotel.Travel-Guide-Filter-Hotels) - 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