Title: Key West Vacation Home Rentals from CA $411: Search Top Private Vacation Homes for Rent | Expedia.ca [Key West Travel Guide](https://expedia.ca/Key-West.dx1187)[Hotels in Key West](https://expedia.ca/Key-West-Hotels.d1187.Travel-Guide-Hotels)[Vacation Rentals in Key West](https://expedia.ca/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals)[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)[Key West Car Rentals](https://expedia.ca/Car-Rentals-In-Key-West.d1187.Car-Rental-Guide)[Key West Vacation Packages](https://expedia.ca/Key-West.d1187.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/1187/a7c3fad3-5f12-4d91-8996-ed0e1b61b0a3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Key West Vacation Rentals - ![](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 prices for these dates In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=1187&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=1187&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=1187&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=1187&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Key West Vacation Homes ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/53dba367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/w3000h1999x0y1-09a4d9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/w3000h1999x0y1-e258b195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books, video library](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/w3000h1999x0y1-215da3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Key West 9.8/10 Exceptional (53) "Perfect for our family! Recommend 10/10!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa F. CA $230 CA $411 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-411.h76584886.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/d7a848f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/w4000h2998x0y2-2789293b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/w4000h2998x0y2-ffef9e21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/8590cf39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Key West 9.2/10 Wonderful (28) "The property and our place was really nice. Would definitely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah M. CA $280 CA $484 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-412.h76568286.Hotel-Information) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110280000/110270700/110270651/2167d440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110280000/110270700/110270651/f02f370b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker](https://images.trvl-media.com/lodging/111000000/110280000/110270700/110270651/b1b917f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110280000/110270700/110270651/8aad29ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Old Town Key West 9.0/10 Wonderful (18) "Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Easy walks to everything!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Don N. CA $227 CA $511 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Key-West-Hotels-Wahoo-Way-Charming-Hideaway-On-Duval-Street.h110270651.Hotel-Information) ![House](https://images.trvl-media.com/lodging/110000000/109120000/109115500/109115482/a2623807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109120000/109115500/109115482/506c248d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109120000/109115500/109115482/75e7846c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109120000/109115500/109115482/55508c9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key CA $1,693 CA $3,164 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Key-West-Hotels-Palmgale-House-In-Key-West.h109115482.Hotel-Information) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122930000/122927400/122927397/70cb0b88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122930000/122927400/122927397/3d2276d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/123000000/122930000/122927400/122927397/d65fb01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/123000000/122930000/122927400/122927397/8339cd21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Stock Island CA $253 CA $628 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Key-West-Hotels-Spacious-3-Bedroom-Townhome-On-Stock-Island-With-Resort-Style-Pool.h122927397.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/9d11031b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/4dc70db6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/d6954c4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/f7bd180e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Stock Island 9.8/10 Exceptional (115) "Great location, close to everything family had a great time." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) rafael m. CA $373 CA $819 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/19354712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/0255f9e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/538d3495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/0ce6f815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key CA $1,795 CA $3,676 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Key-West-Hotels-Parking.h115994655.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/97000000/96050000/96041800/96041709/ea3f582f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/97000000/96050000/96041800/96041709/338d7cb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96050000/96041800/96041709/82590615.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96050000/96041800/96041709/15f319d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Stock Island 9.8/10 Exceptional (19) "Great little place with covered parking and comfortable beds. Very clean! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean CA $496 CA $951 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Key-West-Hotels-Gone-Coastal.h96041709.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/fb618b03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/7cb43e96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/9608f8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/6584f86b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key 9.8/10 Exceptional (28) "The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $1,035 CA $2,275 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Key-West-Hotels-Waterfront.h74132652.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/b05798e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/3e9dc28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/a4bc633c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/e6a3d753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key 10/10 Exceptional (18) "The perfect House , everything was good " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CARLOS G. CA $1,035 CA $2,204 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Key-West-Hotels-Parking.h74132624.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96960000/96960000/96959915/029d384c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96960000/96960000/96959915/06da87e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96960000/96960000/96959915/e02baa0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96960000/96960000/96959915/1ee4261d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key 10/10 Exceptional (1) "The house and property was perfect for 4 adults and 4 kids. Gourmet kitchen for great breakfasts to start the day. Grill for cookouts and swimming in the early evenings. Good proximity to downtown key west, but far enough away for quiet time. Would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vicki L. CA $1,380 CA $3,063 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Key-West-Hotels-New-The-Crestwood-House-Heated-Pool-Parking.h96959915.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107980000/107978800/107978707/fd1ec856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107980000/107978800/107978707/16db7f83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107980000/107978800/107978707/ac674f5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107980000/107978800/107978707/ca30f8b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key 9.8/10 Exceptional (6) "Awesome place definitely recommend if going to key west " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon M. CA $1,380 CA $3,063 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Key-West-Hotels-Brand-New-Catchlight-House-With-Private-Pool.h107978707.Hotel-Information) ![TV, stereo, offices](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994681/641278c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, stereo, offices](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994681/db01ac81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994681/8609440e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994681/18e38456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key CA $1,795 CA $3,676 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Key-West-Hotels-Waterfront.h115994681.Hotel-Information) ![House](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/3886ab1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/eafa7da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/cb76905e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/977525fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key CA $2,156 CA $3,769 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Key-West-Hotels-The-Fairhaven-House-At-Solaire-Lunara-Bay.h120239529.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106550000/106542300/106542217/a0cce2f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/107000000/106550000/106542300/106542217/c5daa077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/107000000/106550000/106542300/106542217/2b2fa112.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106550000/106542300/106542217/8d3caaff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Old Town Key West 8.8/10 Excellent (9) "Wonderful stay. Easy in , easy out. Definitely will stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patti R. CA $363 CA $888 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Key-West-Hotels-Tropical-Utopia-By-RENT-KEY-WEST-VACATIONS-QuietGatedPoolBalconyPet-Friendl.h106542217.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/393ef519.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/f5bed563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/680217a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/44f43dc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key 9.8/10 Exceptional (43) "It was great. House was amazing" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ernest H. CA $1,035 CA $2,275 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Key-West-Hotels-Parking.h74132637.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132659/83acafdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132659/7dbae7b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132659/5505546a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132659/8cc2a42b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key 10/10 Exceptional (28) "The BrightWild team is very professional and responsive. Always a great stay every year!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris S. CA $1,035 CA $2,226 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Key-West-Hotels-Parking.h74132659.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115050000/115046900/115046813/b8059d68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/116000000/115050000/115046900/115046813/766170f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![8 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115050000/115046900/115046813/9aa2f02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115050000/115046900/115046813/feca8770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key CA $1,795 CA $3,676 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Key-West-Hotels-Parking.h115046813.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/118000000/118000000/117997000/117996915/5c412777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/118000000/117997000/117996915/22d360af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![8 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/118000000/117997000/117996915/79b8a22d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/118000000/118000000/117997000/117996915/9c855c0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key 10/10 Exceptional (1) "This was a beautiful property and was everything I expected. Staff took great care making sure it was ready for us." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tony H. CA $1,795 CA $3,605 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Key-West-Hotels-New-Waterfront-Home-Dreamside-House.h117996915.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/98e970a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/58396c65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/383e9ae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/46f398f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key 10/10 Exceptional (11) "Great house. Large space, everything you need is there. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CRIMSON A. CA $1,380 CA $3,063 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Key-West-Hotels-Altair-House-At-Lunara-Bay.h97538167.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=2025-12-22&endDate=2025-12-23®ionId=1187&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Key+West%2C+Florida%2C+United+States+of+America®ionId=1187&latLong=24.554807%2C-81.802079&adults=2&startDate=2026-03-08&d1=2026-03-08&endDate=2026-03-11&d2=2026-03-11&lodging=HOUSE_BOAT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Key+West%2C+Florida%2C+United+States+of+America®ionId=1187&latLong=24.554807%2C-81.802079&adults=2&startDate=2026-03-08&d1=2026-03-08&endDate=2026-03-11&d2=2026-03-11&lodging=CONDO) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Key+West%2C+Florida%2C+United+States+of+America®ionId=1187&latLong=24.554807%2C-81.802079&adults=2&startDate=2026-03-08&d1=2026-03-08&endDate=2026-03-11&d2=2026-03-11&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Key+West%2C+Florida%2C+United+States+of+America®ionId=1187&latLong=24.554807%2C-81.802079&adults=2&startDate=2026-03-08&d1=2026-03-08&endDate=2026-03-11&d2=2026-03-11&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Key+West%2C+Florida%2C+United+States+of+America®ionId=1187&latLong=24.554807%2C-81.802079&adults=2&startDate=2026-03-08&d1=2026-03-08&endDate=2026-03-11&d2=2026-03-11&lodging=APARTMENT) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Key+West%2C+Florida%2C+United+States+of+America®ionId=1187&latLong=24.554807%2C-81.802079&adults=2&startDate=2026-03-08&d1=2026-03-08&endDate=2026-03-11&d2=2026-03-11&lodging=COTTAGE) Villas [](https://www.expedia.ca/Hotel-Search?destination=Key+West%2C+Florida%2C+United+States+of+America®ionId=1187&latLong=24.554807%2C-81.802079&adults=2&startDate=2026-03-08&d1=2026-03-08&endDate=2026-03-11&d2=2026-03-11&lodging=VILLA) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Key+West%2C+Florida%2C+United+States+of+America®ionId=1187&latLong=24.554807%2C-81.802079&adults=2&startDate=2026-03-08&d1=2026-03-08&endDate=2026-03-11&d2=2026-03-11&lodging=CABIN) ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FKey-West-Private-Vacation-Homes.d1187-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FKey-West-Private-Vacation-Homes.d1187-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Key West Hotel Reviews ![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263_y.jpg) ### Winslow's Bungalows - Key West Historic Inns 10/10 Excellent "Room was very private everything was within walking distance. Only down side was the breakfast it was very basic. " [](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "Great view and unit was large and very clean. " [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ![Parrot Key Hotel & Villas](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/67735d0c_y.jpg) ### Parrot Key Hotel & Villas 10/10 Excellent "Ambiance of the grounds, front and back door, back porch, " [](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) ![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg) ### Hyatt Vacation Club at Windward Pointe, Key West 10/10 Excellent "The Hyatt at Windward Pointe is a beautiful property with outstanding views of the water. The pool area and grounds are clean & well taken care of. Our room was very spacious, clean and had everything we needed. We also like the close proximity to airport and Smathers Beach. " [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ![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 "Wonderfull 100 yr old hotel" [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg) ### Oceans Edge Key West Resort, Hotel & Marina 10/10 Excellent "Very nice clean and big room. Great view over the pools and harbor." [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![Hilton Garden Inn Key West / The Keys Collection](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/449c6937_y.jpg) ### Hilton Garden Inn Key West / The Keys Collection 10/10 Excellent "Hotel is great and a shuttle to Old Town. Did not use the pool and Key West always has some construction going on. " [](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ![Hampton Inn Key West FL](https://images.trvl-media.com/lodging/1000000/20000/15800/15720/4075e8ff_y.jpg) ### Hampton Inn Key West FL 10/10 Excellent "Yes" [](https://expedia.ca/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.Hotel-Information) ![Margaritaville Beach House Key West](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/32e70782_y.jpg) ### Margaritaville Beach House Key West 10/10 Excellent "Great swimming pool area" [](https://expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information) ## Find out more about Key West ## Key West Vacation Homes information | Number of reviews | 286 | | ----------------- | ------------------- | | Accommodation | 1043 Vacation Homes | | Lowest Price | CA $411 | | Highest Price | CA $3,769 | ## Explore a world of travel with Expedia - Lodging - Packages - More ways to book - [Cabin Rentals in Boca Chica Key ](https://www.expedia.ca/Boca-Chica-Key-Cabins.d553248635083916609-aaCabins.Travel-Guide-Accommodation) - 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