Title: Rockland Key Vacation Home Rentals : Search Top Private Vacation Homes for Rent | 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)[Vacation Rentals in Rockland Key](https://expedia.ca/Rockland-Key-Vacation-Rentals.d553248635976197596.Travel-Guide-VacationRentals)[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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Rockland Key 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 [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Rockland Key Vacation Homes ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/9c267ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/f2ffe64a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/w1024h630x0y0-e267420a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/d57de0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS Cudjoe Key 9.6/10 Exceptional (98) "Clean place with room for 2 couples. Everything you need." CA $194 CA $586 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/3c8eff21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/w2500h1666x0y1-8de3e595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/c7065ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/5498fbd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Lobster Lodge - Venture Out #543 - Cudjoe Key Cudjoe Key 9.2/10 Wonderful (7) "Close to Key West. Would stay there again!!" CA $264 CA $820 total includes taxes & fees Oct 10 - Oct 11 [](https://www.expedia.ca/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/28679789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/8e7ed1a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/6bfc69e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/5f412538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS! Cudjoe Key 9.8/10 Exceptional (81) "Great location near Key West. Awesome property, will book again." CA $222 CA $620 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks.h44556643.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/78d41425.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/85000000/84050000/84046300/84046253/2fb13370.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/359e6f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/03f59755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kelly's Kabin - Adorable Private Summerland Key Cottage Summerland Key 9.8/10 Exceptional (119) "We enjoyed our stay! Great little house and location. " CA $314 CA $756 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Summerland-Key-Hotels-Kellys-Kabin-Adorable-Private-Summerland-Key-Cottage.h84046253.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/49000000/48230000/48220200/48220112/82f72492.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/49000000/48230000/48220200/48220112/2761e1ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48230000/48220200/48220112/0d75fd5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48230000/48220200/48220112/def4d659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach Getaway in the Florida Keys SUGARLOAF KEY 8.4/10 Very good (7) "Amazing property and views. Tom was great and very helpful with places to go and things to do. Will definitely recommend!!" CA $1,688 CA $3,320 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Sugarloaf-Key-Hotels-Beach-House-At-Sugarloaf-Key-W430ft-Dock-5ft-Drft.h48220112.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/73acf8f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/bea2cf35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/357cfc90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/22584e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Time #110 Ocean Views - Cudjoe Key Cudjoe Key 9.8/10 Exceptional (9) "Greta property, really enjoyed the water view and the bbq grill " CA $256 CA $812 total includes taxes & fees Oct 10 - Oct 11 [](https://www.expedia.ca/Summerland-Key-Hotels-Island-Time-110-Ocean-Views-Cudjoe-Key.h108496393.Hotel-Information) ![House](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/b85cd3d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/a7ddb2fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/5e338074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/a00c4a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Luxury Home - Tidelands House Raccoon Key CA $1,874 CA $3,465 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Key-West-Hotels-Waterfront-Luxury-Home-Tidelands-House.h115993610.Hotel-Information) ![On the beach, beach towels](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/f3afeb85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/5796fc96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/94858c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/356d9302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes Cudjoe Key 9.8/10 Exceptional (237) "Lovely property. Well equipped, nicely decorated, perfect for our stay." CA $488 CA $1,141 total includes taxes & fees Oct 10 - Oct 11 [](https://www.expedia.ca/Summerland-Key-Hotels-Gated-Community-On-Open-Water-With-Dock.h19709378.Hotel-Information) ![House](https://images.trvl-media.com/lodging/121000000/120240000/120237500/120237469/00cf6ad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120240000/120237500/120237469/b96c2686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120240000/120237500/120237469/95657be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120240000/120237500/120237469/cf3c6484.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brand New The Greenmoor House With Pool Raccoon Key CA $1,334 CA $2,857 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Key-West-Hotels-Brand-New-The-Greenmoor-House-With-Pool.h120237469.Hotel-Information) ![House](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239522/dbf348bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239522/f79f25b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239522/1814e3bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239522/8d24d53c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Joyrise House at Solaire Lunara Bay Raccoon Key CA $1,381 CA $2,910 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Key-West-Hotels-The-Joyrise-House-At-Solaire-Lunara-Bay.h120239522.Hotel-Information) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003214/51c58de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003214/e2cc27c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003214/4fccee84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003214/cd2b5497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brand New Build Larkshine House - Pool Raccoon Key CA $1,896 CA $3,405 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Key-West-Hotels-Brand-New-Build-Larkshine-House-Pool.h109003214.Hotel-Information) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003217/0844b7f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003217/e43a464c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003217/w3000h1920x0y0-aa2bc90a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003217/001e0905.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brand New Catchlight House With Private Pool Raccoon Key CA $1,349 CA $2,789 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Key-West-Hotels-Brand-New-Catchlight-House-With-Private-Pool.h109003217.Hotel-Information) ![House, Smoking](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003089/e5be84b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Smoking](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003089/3da1070d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Smoking](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003089/b6ba9c9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Smoking](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003089/dbee1111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Springtide House by Brightwild Waterfront Pool Raccoon Key CA $1,468 CA $2,584 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Key-West-Hotels-Springtide-House-By-Brightwild-Waterfront-Pool.h109003089.Hotel-Information) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003168/8118908a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003168/f372f6f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003168/2d8d89c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003168/d2d6ae84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Crestwood House by Brightwild Huge Pool Raccoon Key CA $1,381 CA $2,825 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Key-West-Hotels-New-Crestwood-House-By-Brightwild-Huge-Pool.h109003168.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/110000000/109120000/109115500/109115482/9c641387.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) ![House](https://images.trvl-media.com/lodging/110000000/109120000/109115500/109115482/75e7846c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palmgale House in Key West Raccoon Key CA $1,349 CA $2,789 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Palmgale-House-In-Key-West.h109115482.Hotel-Information) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003165/ab72996c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003165/44733879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003165/fc3c0b0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003165/c65c6ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Altair House by Brightwild Pool Pets Raccoon Key CA $1,381 CA $2,825 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Key-West-Hotels-New-Altair-House-By-Brightwild-Pool-Pets.h109003165.Hotel-Information) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003077/w2997h2000x0y0-fea84ea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003077/6ec081bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003077/105adf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003077/493aac8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Capmar House by Brightwild Huge Home Pool Raccoon Key 10/10 Exceptional (1) "Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay" CA $1,136 CA $2,211 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Key-West-Hotels-Capmar-House-By-Brightwild-Huge-Home-Pool.h109003077.Hotel-Information) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003083/786a3bcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003083/6e0e4244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003083/0c037394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003083/bdcb3e13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mirador House by Brightwild Pool Dock Raccoon Key CA $1,568 CA $2,925 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Key-West-Hotels-Mirador-House-By-Brightwild-Pool-Dock.h109003083.Hotel-Information) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003076/5f1f3478.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003076/7a5a0c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003076/f5961fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003076/1617d5c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aquaria House by Brightwild Pool Boat Dock Raccoon Key CA $1,468 CA $2,584 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Key-West-Hotels-Aquaria-House-By-Brightwild-Pool-Boat-Dock.h109003076.Hotel-Information) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003085/a171a6f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003085/a6c433b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003085/a94154d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/110000000/109010000/109003100/109003085/88e459b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterlane House by Brightwild Pool Boat Dock Raccoon Key CA $1,468 CA $2,584 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Key-West-Hotels-Waterlane-House-By-Brightwild-Pool-Boat-Dock.h109003085.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=2025-10-23&endDate=2025-10-24®ionId=553248635976197596&adults=2&lodging=VACATION_HOME&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-Private-Vacation-Homes.d553248635976197596-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FRockland-Key-Private-Vacation-Homes.d553248635976197596-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Rockland Key Hotel Reviews ![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 "Great views from our room excellent staff service. Would definitely stay again" [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ![Parrot Key Hotel & Villas](//images.trvl-media.com/lodging/1000000/30000/24700/24615/b83a5985_y.jpg) ### Parrot Key Hotel & Villas 10/10 Excellent "Impeccable service" [](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) ![Pier House Resort & Spa](//images.trvl-media.com/lodging/1000000/20000/19400/19307/ed076ab9_y.jpg) ### Pier House Resort & Spa 10/10 Excellent "Nice rooms" [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![Hilton Garden Inn Key West / The Keys Collection](//images.trvl-media.com/lodging/1000000/10000/1400/1376/5c83029c_y.jpg) ### Hilton Garden Inn Key West / The Keys Collection 10/10 Excellent "Clean grounds, clean room, loved the shuttle service to town and back to hotel, access to all 3 properties and pools which were wonderful and staff professional and courteous." [](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ![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 "Very beautiful, clean, pet friendly resort definitely going back as soon as possible " [](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![La Concha Key West, Autograph Collection](//images.trvl-media.com/lodging/1000000/10000/3900/3853/a3b28d11_y.jpg) ### La Concha Key West, Autograph Collection 10/10 Excellent "Perfect place to stay in key west " [](https://expedia.ca/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information) ![Casa Marina Key West, Curio Collection by Hilton](//images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450_y.jpg) ### Casa Marina Key West, Curio Collection by Hilton 10/10 Excellent "The property was very pretty. Loved that it is on the beach. There was an elevator that was down so we had to use another one that I think was the staff elevator. It wouldn’t open the one time we used it for several minutes. The inside was very hot as it was not air conditioned. It was kind of scary, thankfully it opened after several minutes. " [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.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 "Wonderful stay. Bar staff could be more friendly but overall very decent for the price. " [](https://expedia.ca/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.Hotel-Information) ![Hyatt Centric Key West Resort and Spa](//images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249_y.jpg) ### Hyatt Centric Key West Resort and Spa 10/10 Excellent "Beautiful hotel rooms are awesome " [](https://expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ## Find out more about Rockland Key ## Rockland Key Vacation Homes information | Number of reviews | | | --- | --- | | Accommodation | Vacation Homes | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in Stock Island](https://www.expedia.ca/5Star-Stock-Island-Hotels.s50-0-d180166.Travel-Guide-Filter-Hotels) - [B&B in Big Coppitt Key](https://www.expedia.ca/Big-Coppitt-Key-Bed-And-Breakfast.d553248635975850102-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hostels in Big Coppitt Key](https://www.expedia.ca/Big-Coppitt-Key-Hostels.d553248635975850102-aaHostels.Travel-Guide-Accommodation) - 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