Title: Rockland Key Vacation Rentals from CA $281: Short-Term Rentals for 2025 | Expedia.ca [Rockland Key Travel Guide](https://expedia.ca/Rockland-Key.dx553248635976197596)[Hotels in Rockland Key](https://expedia.ca/Rockland-Key-Hotels.d553248635976197596.Travel-Guide-Hotels)[Flights to Rockland Key](https://expedia.ca/Cheap-Flights-To-Rockland-Key.d553248635976197596.Travel-Guide-Flights)[Rockland Key Car Rentals](https://expedia.ca/Car-Rentals-In-Rockland-Key.d553248635976197596.Car-Rental-Guide)[Rockland Key Vacation Packages](https://expedia.ca/Rockland-Key.d553248635976197596.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) # Rockland Key Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 Tonight [Sep 24 - Sep 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2025-09-24&endDate=2025-09-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2025-09-25&endDate=2025-09-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Rockland Key ## Our top choices for Rockland Key vacation rentals ![Restaurant](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/d6422035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/bc5aedd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Bungalow | Private kitchen](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/920119e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/3a268cdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aqua Lodges at Hurricane Hole Marina Stock Island 9.0/10 Wonderful (162) "The stay was beautiful " CA $99 CA $345 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Key-West-Hotels-Aqua-Lodges-At-Hurricane-Hole-Marina.h89832384.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/eca90904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/489ad80a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![20-inch TV with satellite channels, DVD player](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/45293052.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/376faaf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Vacation Club at Sunset Harbor, Key West Old Town Key West 8.4/10 Very good (314) "Great hotel with excellent location " [](https://www.expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Sunset-Harbor.h857964.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27690000/27682400/27682303/79d0a981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach towels](https://images.trvl-media.com/lodging/28000000/27690000/27682400/27682303/3a198a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/28000000/27690000/27682400/27682303/5ae34cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27690000/27682400/27682303/0fa3fcec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Steps from Duval, Pool on Site & Bikes Included! Old Town Key West 9.6/10 Exceptional (402) "this was exactly as advertised and close to all the action" CA $124 CA $312 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Key-West-Hotels-Steps-From-Duval.h27682303.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21700000/21690900/21690843/81510f43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21700000/21690900/21690843/ee58575e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free internet, bed sheets](https://images.trvl-media.com/lodging/22000000/21700000/21690900/21690843/13c903c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21700000/21690900/21690843/8dc353de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC Old Town Key West 8.8/10 Excellent (231) "Property was cute and in a great location! " CA $82 CA $281 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Key-West-Hotels-Downtown-Dog-Friendly-Cottage-Like-Studio-With-Patio.h21690843.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/130000/120600/120544/fde9bad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/130000/120600/120544/9652c070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dock](https://images.trvl-media.com/lodging/1000000/130000/120600/120544/fdc5083f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/120600/120544/b80557b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coconut Mallory Resort And Marina By Kees Vacations Key West 8.2/10 Very good (819) "Great place really nice rooms" [](https://www.expedia.ca/Key-West-Hotels-Coconut-Mallory-Resort-And-Marina-By-Kees-Vacations.h120544.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33070000/33065700/33065693/d362e5da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33070000/33065700/33065693/9b558ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, DVD player, stereo](https://images.trvl-media.com/lodging/34000000/33070000/33065700/33065693/5885fdb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33070000/33065700/33065693/60e1258d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval! Old Town Key West 9.2/10 Wonderful (182) "Great location; excellent property management " [](https://www.expedia.ca/Key-West-Hotels-TIDES-ON-SIMONTON-Perfectly-Located-Just-Off-Duval-And-All-The-Fun.h33065693.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/681d666f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/682ba7e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/6d55c844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/5017edad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!! Stock Island 7.8/10 Good (22) "Loved everything about the stay, " CA $346 CA $699 total includes taxes & fees Sep 26 - Sep 27 [](https://www.expedia.ca/Key-West-Hotels-Viking-Yacht-Getaway-In-The-Keys-NEW-LOCATION-Tons-Of-Amenities.h92965988.Hotel-Information) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161435/77611362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161435/3b340556.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161435/90ef6ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161435/97f1383f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval! Old Town Key West 10/10 Exceptional (22) "We had a wonderful stay here with our kids. Can’t beat the location." CA $119 CA $439 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Key-West-Hotels-Pelican-Suite-Cozy-Cottage.h110161435.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/60b95cd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/8ea08bd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/ade06e4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/21ae09eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Florida Style, wrap around porch, boat basin for dockage, open water Little Torch Key 9.6/10 Exceptional (80) "The secluded dock is a nice feature. The driveway is tricky to exit. " [](https://www.expedia.ca/Little-Torch-Key-Hotels-Old-Florida-Style.h73238458.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/34000000/33070000/33065800/33065733/bf3b8fb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33070000/33065800/33065733/3df0d93d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33070000/33065800/33065733/5ef6628c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33070000/33065800/33065733/18130751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action! Old Town Key West 9.6/10 Exceptional (188) "Bucket list trip. Great location. Property was just what was expected. Perfect for 2!" [](https://www.expedia.ca/Key-West-Hotels-RIPTIDES-Stylish-Studio-Located-In-A-Central-Location-Near-All-The-Action.h33065733.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737094/762ed9e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737094/a154a94d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737094/89626030.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737094/39c00051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion! Old Town Key West 9.6/10 Exceptional (141) "This property was great, it had everything needed, extremely clean and walking distance to Davual st.The pool area is wonderful and it was the perfect temperature!Would highly recommend." CA $126 CA $335 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Key-West-Hotels-COHIBA-Adults-Only.h57737094.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/112000000/111020000/111019600/111019535/d6d1bef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/112000000/111020000/111019600/111019535/e35982fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/112000000/111020000/111019600/111019535/42465d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111020000/111019600/111019535/54e33093.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West Stock Island 6.6/10 (12) "Unfortunately this stay was very disappointing. The marina was awesome. Tessa was awesome. The boat itself was disgusting. The pictures are very deceiving. What you see is not what you get. " CA $229 CA $485 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Key-West-Hotels-Charming-4-Bedroom-Yacht-With-AC.h111019535.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/64000000/63730000/63723300/63723258/db6f8e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63730000/63723300/63723258/4bc41e4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63730000/63723300/63723258/ab55eadb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/64000000/63730000/63723300/63723258/738506c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heart of Downtown Key West Cottage With Off-Street Parking Key West Historic District 10/10 Exceptional (136) "Great Location, Free Parking, comfortable beds" [](https://www.expedia.ca/Key-West-Hotels-Heart-Of-Downtown-Key-West-Cottage-With-Off-Street-Parking.h63723258.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/36000000/35060000/35053400/35053355/3bbf9cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/36000000/35060000/35053400/35053355/6940d922.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35060000/35053400/35053355/b7fc350c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/36000000/35060000/35053400/35053355/0807cfe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect Location, Private Heated Pool, Pristine Luxury Home! Old Town Key West 10/10 Exceptional (189) "Outstanding place to stay, centrally located!" CA $1,063 CA $2,308 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Key-West-Hotels-Steps-From-Duval-St-Historical-Charm-Meets-Modern-Design-In-Old-Town-Key-West.h35053355.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/100000000/99890000/99882200/99882182/017ce471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/100000000/99890000/99882200/99882182/480812c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99890000/99882200/99882182/317159c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99890000/99882200/99882182/74a49171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Living the Dream Key West Style Stock Island 9.8/10 Exceptional (23) "Great hosts and great accommodations!" CA $372 CA $469 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Key-West-Hotels-Living-The-Dream-Key-West-Style.h99882182.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/117000000/116690000/116686500/116686462/86b3bc46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116690000/116686500/116686462/eae757f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116690000/116686500/116686462/d103709c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/117000000/116690000/116686500/116686462/04d40c42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town! Old Town Key West 10/10 Exceptional (4) "Beautiful property, perfectly located, and one of the best VRBO experiences we have ever had." [](https://www.expedia.ca/Key-West-Hotels-THE-DELANEY-HOUSE-4-BR.h116686462.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/120000000/119500000/119492800/119492759/184a49f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119500000/119492800/119492759/6c0cd1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oven, stovetop](https://images.trvl-media.com/lodging/120000000/119500000/119492800/119492759/2420637e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119500000/119492800/119492759/a08d8288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools Stock Island CA $346 CA $470 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Key-West-Hotels-1-Bedroom-Boat-At-The-Perry-With-AC.h119492759.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109600000/109591700/109591659/48dd2a5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109600000/109591700/109591659/900ddbd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/110000000/109600000/109591700/109591659/4179464b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109600000/109591700/109591659/a653b225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Duval Delight | Recently Remodeled Condo on Duval! Old Town Key West 10/10 Exceptional (32) "This place has everything you need and is in an excellent location. We would definitely stay here again. " CA $168 CA $566 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Key-West-Hotels-Duval-Delight-Recently-Remodeled-Condo-On-Duval.h109591659.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/111000000/110840000/110834300/110834272/076ea7f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110840000/110834300/110834272/79fb9a1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110840000/110834300/110834272/27f9243f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110840000/110834300/110834272/3362add5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Shared Heated Pool! Old Town Key West 9.6/10 Exceptional (17) "Short walk to Duval street, quiet and very clean and comfortable." CA $120 CA $326 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Key-West-Hotels-THE-GATO-ROOM-2nd-Floor-King-Suite-Inn-On-Fleming-W-Shared-Pool.h110834272.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737038/7fd3cc8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737038/787ce1b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737038/dc2ee4a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737038/8b5ac86d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool! Old Town Key West 9.6/10 Exceptional (146) "Rating Details: The property manager was very helpful. The vacation rental was spotless. 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: This darling Conch house in the heart of the island was very comfortable and clean. Will definitely book again." CA $120 CA $323 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Key-West-Hotels-HAVANA-VIEJA-Adults-Only.h57737038.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=2025-10-09&endDate=2025-10-10®ionId=553248635976197596&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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%2FRockland-Key-Vacation-Rentals.d553248635976197596.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FRockland-Key-Vacation-Rentals.d553248635976197596.Travel-Guide-VacationRentals) ## Top Rockland Key Hotel Reviews ![The Perry Hotel & Marina Key West](//images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg) ### The Perry Hotel & Marina Key West 10/10 Excellent "Highly recommend. My only regret is we only stayed for one night. LOVED the shuttle into town. Aaron at the front desk was very accommodating. We had a great experience. " [](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![Hyatt Vacation Club at Windward Pointe, Key West](//images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg) ### Hyatt Vacation Club at Windward Pointe, Key West 10/10 Excellent "Awesome!!" [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ![Fairfield Inn and Suites by Marriott Key West](//images.trvl-media.com/lodging/1000000/10000/9000/8946/7b2c8a2c_y.jpg) ### Fairfield Inn and Suites by Marriott Key West 10/10 Excellent "Everyone that worked there was very friendly and helpful. The room was clean and the bed was comfy. Great place to stay" [](https://expedia.ca/Key-West-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Key-West.h8946.Hotel-Information) ![The Reach Key West, Curio Collection by Hilton](//images.trvl-media.com/lodging/1000000/460000/457900/457821/888fac6b_y.jpg) ### The Reach Key West, Curio Collection by Hilton 10/10 Excellent "Everything was good, good location, private beach good food at marlins good service with the waiter filip " [](https://expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) ![Beachside Resort & Residences](//images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "Out of 100 stars I would give this place a 99! The only thing that would keep me from giving it that last star is the cost of the drinks poolside. Ordered 2 drinks we would normally pay around $7-$10 each and was blown away when we were told the bill was $46 for two drinks….in plastic cups no less. Other than that we loved the resort. Stop in the Tavern restaurant on site and see Ramon behind the bar. He will hook you up and keep you laughing!" [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ![Hampton Inn Key West FL](//images.trvl-media.com/lodging/1000000/20000/15800/15720/4075e8ff_y.jpg) ### Hampton Inn Key West FL 10/10 Excellent "Across the street from the ocean. Beautiful view. Nice breakfast!" [](https://expedia.ca/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.Hotel-Information) ![DoubleTree Resort by Hilton Grand Key - Key West](//images.trvl-media.com/lodging/1000000/480000/470900/470834/be4147fb_y.jpg) ### DoubleTree Resort by Hilton Grand Key - Key West 10/10 Excellent "Great stay. Helpful and attentive staff, transportation provided to the old town and to the beach. " [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Blue Flamingo Resort Key West](//images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/cb0a4c1e_y.jpg) ### Blue Flamingo Resort Key West 10/10 Excellent "Pet friendly, safe, quiet, helpful staff, good location, shuttle to the old town, nice amenities " [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Southernmost Beach Resort and Guesthouses](//images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "I love that everything is at arms reach. The pool, beach, restaurants, stores. Everything is a hop skip & a jump. " [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ## Find out more about Rockland Key **Everything you need to know about** **Rockland Key** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Rockland Key vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rockland Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Rockland Key vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Rockland Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rockland Key vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rockland Key vacation rentals we have selected for you start as low as CA $281 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Rockland Key rentals** At Expedia, we put the best Rockland Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Rockland Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rockland Key vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rockland Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Rockland Key ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)