Title: Fleming Key Vacation Home Rentals from CA $587: Search Top Private Vacation Homes for Rent | Expedia.ca [Fleming Key Travel Guide](https://expedia.ca/Fleming-Key.dx180162)[Hotels in Fleming Key](https://expedia.ca/Fleming-Key-Hotels.d180162.Travel-Guide-Hotels)[Vacation Rentals in Fleming Key](https://expedia.ca/Fleming-Key-Vacation-Rentals.d180162.Travel-Guide-VacationRentals)[Flights to Fleming Key](https://expedia.ca/Cheap-Flights-To-Fleming-Key.d180162.Travel-Guide-Flights)[Fleming Key Car Rentals](https://expedia.ca/Car-Rentals-In-Fleming-Key.d180162.Car-Rental-Guide)[Fleming Key Vacation Packages](https://expedia.ca/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__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 Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=180162&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=180162&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=180162&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=180162&startDate=2026-03-13&endDate=2026-03-15&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 vacation homes ![Interior](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/b85cd3d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/a00c4a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/ee43d350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/5e338074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key [](https://www.expedia.ca/Key-West-Hotels-Waterfront-Luxury-Home-Tidelands-House.h115993610.Hotel-Information) CA $2,591 CA $4,340 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Key-West-Hotels-Waterfront-Luxury-Home-Tidelands-House.h115993610.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/d62d627a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/bf68a65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/f739e31d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/a03560e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Upper Sugarloaf Key [](https://www.expedia.ca/Summerland-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Palm.h94616487.Hotel-Information) 10/10 Exceptional (14 reviews) "Beautiful! Pool was amazing!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer B. [](https://www.expedia.ca/Summerland-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Palm.h94616487.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/cb4405b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/3ea1a6b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/cf536593.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/75000000/74140000/74132700/74132624/1f2966ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key [](https://www.expedia.ca/Key-West-Hotels-The-Seagate-Estate-At-Lunara-Bay.h74132624.Hotel-Information) 10/10 Exceptional (19 reviews) "The perfect House , everything was good " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CARLOS G. CA $971 CA $2,198 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Key-West-Hotels-The-Seagate-Estate-At-Lunara-Bay.h74132624.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/53dba367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/w2998h1999x1y1-68fba4ee.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) ![Outdoor pool](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/6ae9af34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Key West [](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-411.h76584886.Hotel-Information) 9.8/10 Exceptional (54 reviews) "Great little condo - perfect for our family to visit Key West! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie A. CA $460 CA $715 total includes taxes & fees Jan 24 - Jan 25 [](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-411.h76584886.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/61fc156d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/e32b0a4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/092ca3f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, stereo, offices](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/cf94feca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key [](https://www.expedia.ca/Key-West-Hotels-Parking.h115994655.Hotel-Information) 10/10 Exceptional (2 reviews) "Beautiful home with great outdoor space and we loved the pool and private dock" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon L. CA $2,215 CA $4,147 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Key-West-Hotels-Parking.h115994655.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) ![Marina](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/ea75861d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/w4000h2998x0y2-41f21691.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) ### Vacation Home in Key West [](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-412.h76568286.Hotel-Information) 9.2/10 Wonderful (28 reviews) "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 $359 CA $587 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-412.h76568286.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/d64c4dda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/a985c265.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/w2992h2242x4y4-6048533a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/ab752c80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key [](https://www.expedia.ca/Key-West-Hotels-Springtide-House-At-Lunara-Bay.h74132637.Hotel-Information) 9.6/10 Exceptional (44 reviews) "It was great. House was amazing" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ernest H. CA $971 CA $2,198 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Key-West-Hotels-Springtide-House-At-Lunara-Bay.h74132637.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/f4cb0461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/d6f3b413.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/e3fefed1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/c3afe913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key [](https://www.expedia.ca/Key-West-Hotels-Larkshine-House-At-Lunara-Bay.h108195321.Hotel-Information) 10/10 Exceptional (8 reviews) "well maintained, clean, easy to access" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raj P. CA $2,076 CA $3,897 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Key-West-Hotels-Larkshine-House-At-Lunara-Bay.h108195321.Hotel-Information) ![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) ![6 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96960000/96960000/96959915/1b939394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/97000000/96960000/96960000/96959915/3b0cbc2f.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) ### Vacation Home in Raccoon Key [](https://www.expedia.ca/Key-West-Hotels-New-The-Crestwood-House-Heated-Pool-Parking.h96959915.Hotel-Information) 10/10 Exceptional (1 review) "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 $1,248 CA $2,859 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Key-West-Hotels-New-The-Crestwood-House-Heated-Pool-Parking.h96959915.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994681/87ba1394.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994681/ba72c601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key [](https://www.expedia.ca/Key-West-Hotels-Waterfront.h115994681.Hotel-Information) 10/10 Exceptional (1 review) "The house was beautiful! The management team handling the house were extraordinary, they were so kind, responsive and friendly which made everything just perfect. I highly recommend this place and commend all of the staff from managers, to service people, pool, trash etc. Thank you all!!’" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eileen Z. CA $2,076 CA $4,038 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Key-West-Hotels-Waterfront.h115994681.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109120000/109115500/109115482/a2623807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](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/110000000/109120000/109115500/109115482/9c641387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109120000/109115500/109115482/w3000h2208x0y0-ddab4161.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key [](https://www.expedia.ca/Key-West-Hotels-Palmgale-House-In-Key-West.h109115482.Hotel-Information) CA $1,558 CA $3,089 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Key-West-Hotels-Palmgale-House-In-Key-West.h109115482.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) ![TV, offices](https://images.trvl-media.com/lodging/118000000/118000000/117997000/117996915/9c855c0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/118000000/117997000/117996915/268b6c12.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) ### Vacation Home in Raccoon Key [](https://www.expedia.ca/Key-West-Hotels-New-Waterfront-Home-Dreamside-House.h117996915.Hotel-Information) 10/10 Exceptional (2 reviews) "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 $2,076 CA $4,000 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Key-West-Hotels-New-Waterfront-Home-Dreamside-House.h117996915.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/237d62a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/bd64b13f.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/34000000/33500000/33496300/33496206/a8959ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/55f445db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Old Town Key West [](https://www.expedia.ca/Key-West-Hotels-Year-Rd-W7-Night-Stay-Get-10-OffFull-Kitchen-Outside-Area12-Mile-Beach.h33496206.Hotel-Information) 9.0/10 Wonderful (182 reviews) "We had such a delightful time staying here! While the space is small, it was absolutely perfect for two people. Everything was clean, comfortable, and conveniently located. We really enjoyed our time in Key West and would definitely stay here again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ALISHA CA $356 CA $663 total includes taxes & fees Jan 24 - Jan 25 [](https://www.expedia.ca/Key-West-Hotels-Year-Rd-W7-Night-Stay-Get-10-OffFull-Kitchen-Outside-Area12-Mile-Beach.h33496206.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/07101baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/5cc75497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/53e705db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key [](https://www.expedia.ca/Key-West-Hotels-Altair-House-At-Lunara-Bay.h97538167.Hotel-Information) 9.8/10 Exceptional (12 reviews) "Great house. Large space, everything you need is there. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CRIMSON A. CA $1,248 CA $2,902 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Key-West-Hotels-Altair-House-At-Lunara-Bay.h97538167.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994668/b1e7a3be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994668/3bc6e3c2.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/116000000/116000000/115994700/115994668/25273be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994668/0cd9d6c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key [](https://www.expedia.ca/Key-West-Hotels-New-Waterfront-Home-Sunray-Estate.h115994668.Hotel-Information) 10/10 Exceptional (2 reviews) "Amazing" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Byron D. CA $2,076 CA $4,038 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Key-West-Hotels-New-Waterfront-Home-Sunray-Estate.h115994668.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115050000/115046900/115046813/717fd5be.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/116000000/115050000/115046900/115046813/904d364d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/116000000/115050000/115046900/115046813/bd0fb9cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115050000/115046900/115046813/55f98a44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key [](https://www.expedia.ca/Key-West-Hotels-Parking.h115046813.Hotel-Information) 10/10 Exceptional (1 review) "This was a great house for a holiday getaway. The kitchen was well equipped with plenty of dishes as well as extra accessories that we don't always see like the crock pot, the beverage cooler and the extra kerig upstairs. Lots of pool towels and the ice machines upstairs and down made a huge difference. Although we came as a family, the extra room and the fact that each bedroom had its own bathroom makes this house fantastic for any group. The only thing we could think of to make it better would... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darlene M. CA $2,215 CA $4,215 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Key-West-Hotels-Parking.h115046813.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/97000000/96900000/96894500/96894451/997a222a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/97000000/96900000/96894500/96894451/bd7a3cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96900000/96894500/96894451/38c326a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/97000000/96900000/96894500/96894451/69634392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Sugarloaf Key [](https://www.expedia.ca/Summerland-Key-Hotels-Bungalows-At-Sugarloaf-Beach-Mi-Azucar.h96894451.Hotel-Information) 10/10 Exceptional (10 reviews) "The location of the home is great, beautiful and peaceful.Enjoyed the pool." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel N. CA $2,062 CA $3,541 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Summerland-Key-Hotels-Bungalows-At-Sugarloaf-Beach-Mi-Azucar.h96894451.Hotel-Information) ![TV, stereo, offices](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290613/222d03ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290613/6e8a6f83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290613/b4df8eab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290613/65c00493.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key [](https://www.expedia.ca/Key-West-Hotels-Floralee-House-At-Lunara-Bay.h109290613.Hotel-Information) 9.8/10 Exceptional (8 reviews) "Amazing house! Spacious, great pool, & good location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paige G. CA $1,248 CA $2,902 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Key-West-Hotels-Floralee-House-At-Lunara-Bay.h109290613.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290608/b52b5b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290608/bbfd43bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, stereo, offices](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290608/cc36095d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109300000/109290700/109290608/519603c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Raccoon Key [](https://www.expedia.ca/Key-West-Hotels-Palmgale-Estate-At-Lunara-Bay.h109290608.Hotel-Information) 10/10 Exceptional (8 reviews) "Place was beautiful and had everything we wanted in it. The pool was clean and a great temperature. Everyone did was close by. We stay at houses every year and this was the best one so far." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael F. CA $1,248 CA $2,857 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Key-West-Hotels-Palmgale-Estate-At-Lunara-Bay.h109290608.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/w800h599x0y1-b3246da6.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) ![Exterior](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/156e79e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/d36ebeba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Stock Island [](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.Hotel-Information) 9.8/10 Exceptional (117 reviews) "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 $437 CA $907 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.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=2026-01-29&endDate=2026-01-30®ionId=180162&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America®ionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America®ionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=APARTMENT) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America®ionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=CABIN) Condos [](https://www.expedia.ca/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America®ionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=CONDO) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America®ionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=COTTAGE) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America®ionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=VACATION_HOME) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Fleming+Key%2C+Florida%2C+United+States+of+America®ionId=180162&latLong=24.580237%2C-81.796422&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=HOUSE_BOAT) ![](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%2FFleming-Key-Private-Vacation-Homes.d180162-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FFleming-Key-Private-Vacation-Homes.d180162-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Fleming Key Hotel Reviews ![DoubleTree Resort by Hilton Grand Key - Key West](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cefb5fc2_y.jpg) ### DoubleTree Resort by Hilton Grand Key - Key West 10/10 Excellent "Beautiful room" [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "Perfect location " [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![NYAH Key West - Adults Only](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/77f11bb4_y.jpg) ### NYAH Key West - Adults Only 10/10 Excellent "Staff was exceptional. " [](https://expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ![Havana Cabana at Key West ](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/becea015_y.jpg) ### Havana Cabana at Key West 10/10 Excellent "Wonderful Christmas Week with our family! Can’t wait to come back and enjoy the pool, bar, and Cuban food." [](https://expedia.ca/Key-West-Hotels-Havana-Cabana-At-Key-West.h21241090.Hotel-Information) ![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 "Friendly staff and a great stay!" [](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![The Perry Hotel & Marina Key West](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg) ### The Perry Hotel & Marina Key West 10/10 Excellent "Room was spotless. Large shower with grab bars. Bathrobes provided. Quiet. great location. Used the shuttle every day and it was so convenient." [](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![Fairfield Inn and Suites by Marriott Key West](https://images.trvl-media.com/lodging/1000000/10000/9000/8946/7b2c8a2c_y.jpg) ### Fairfield Inn and Suites by Marriott Key West 10/10 Excellent "A safe in the room would be nice. Clean room, friendly staff, convenient to nearby places. I would definitely stay there again because of the convenience and location with restaurants and shopping nearby." [](https://expedia.ca/Key-West-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Key-West.h8946.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 "The staff was absolutely fantastic! Highly recommend." [](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.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 "Wonderful stay, clean room, attentive staff" [](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ## Find out more about Fleming Key ## Fleming Key Vacation Homes information | Number of reviews | 400 | | ----------------- | ------------------ | | Accommodation | 741 Vacation Homes | | Lowest Price | CA $587 | | Highest Price | CA $4,340 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Other - More ways to book - [Hotels near Duval Street ](https://www.expedia.ca/Duval-Street-Hotels.0-l6068616-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Flamingo ](https://www.expedia.ca/Flamingo-Apart-Hotels.d553248635074842070-aaApartHotels.Travel-Guide-Accommodation) - 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