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 Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [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 one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2025-12-19&endDate=2025-12-21&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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/f111b153.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) ### OCT. & NOV. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS! Cudjoe Key 9.6/10 Exceptional (98) "Clean place with room for 2 couples. Everything you need." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason W. CA $194 CA $591 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.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) ![Exterior](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/6bfc69e0.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) ![Marina](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/7f597dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### OCT. & NOV. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS! Cudjoe Key 9.8/10 Exceptional (81) "The place is clean and convenient for anyone wanting to spend time on the water in the keys" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ubaldo G. CA $222 CA $626 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks.h44556643.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/w905h683x60y0-701bb32b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/w907h683x59y0-59367592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/w509h683x258y0-3618efad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/6b75217d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paradise found Stock Island 9.8/10 Exceptional (30) "Very nice! Had everything we needed and then some! Bonus there a a few great places for breakfast and lunch across the street! Thanks for a great vacation!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mandi C. CA $349 CA $766 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Key-West-Hotels-Paradise-Found.h79683240.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48230000/48220200/48220112/0d75fd5b.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!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robyn M. CA $1,224 CA $2,714 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/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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/e1bc9e10.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!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) elisa b. CA $264 CA $826 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.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) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/f620b37f.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 9.4/10 Exceptional (10) "Greta property, really enjoyed the water view and the bbq grill " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William B. CA $294 CA $868 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Summerland-Key-Hotels-Island-Time-110-Ocean-Views-Cudjoe-Key.h108496393.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) ![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) ![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) ![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) ### Kelly's Kabin - Adorable Private Summerland Key Cottage Summerland Key 9.8/10 Exceptional (119) "We enjoyed our stay! Great little house and location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa K. CA $283 CA $722 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Summerland-Key-Hotels-Kellys-Kabin-Adorable-Private-Summerland-Key-Cottage.h84046253.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/a00c4a77.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) ### Waterfront Luxury Home - Tidelands House Raccoon Key CA $1,826 CA $3,415 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Waterfront-Luxury-Home-Tidelands-House.h115993610.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) ![Outdoor pool](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/46a74ee5.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) ![Marina](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/w3000h1999x0y1-09a4d9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Poolside Cottage #411 Key West 9.8/10 Exceptional (53) "Nice area, quiet and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary S. CA $233 CA $414 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-411.h76584886.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/37a1453e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/c54b4cae.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/95000000/94620000/94616500/94616487/7c92d095.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) ### Palm - Beach Houses Key West Upper Sugarloaf Key 10/10 Exceptional (14) "We had a great time at this out-of-the-way spot. It was quiet, beautiful, and comfortable. Lots to do around the property. The pool area is especially beautiful. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Crystal G. CA $885 CA $1,912 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Summerland-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Palm.h94616487.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) ![Outdoor pool](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/cd6c698d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Poolside Cottage #412 Key West 9.2/10 Wonderful (26) "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 $233 CA $414 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-412.h76568286.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/8ea08bd9.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 (84) "The secluded dock is a nice feature. The driveway is tricky to exit. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) drywall c. CA $490 CA $1,053 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Little-Torch-Key-Hotels-Old-Florida-Style.h73238458.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/0c89d58b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/b25eb073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/e93bd5d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/3835dc3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Just 20 miles from Key West! Oceanfront, dockage, swimming pool Cutthroat Harbor Estates 8.4/10 Very good (117) "Deer in the front yard, perfect location, clean and friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sara H. CA $315 CA $754 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/a0a288d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, table tennis, books](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/54d787f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/62b4ca8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/96aae30a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key Cudjoe Key 9.0/10 Wonderful (7) "Place was perfect for our trip. Staff was super nice and helpful as well. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca G. CA $330 CA $909 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Summerland-Key-Hotels-Salty-Breeze-161-Canal-Front-Venture-Out-Home-On-Cudjoe-Key.h106911727.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/673fe9bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes Cudjoe Key 9.8/10 Exceptional (238) "Lovely property. Well equipped, nicely decorated, perfect for our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen M. CA $490 CA $1,144 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Summerland-Key-Hotels-Gated-Community-On-Open-Water-With-Dock.h19709378.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/51bad23a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/7f2df60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/c2c1b6c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/80c5c4f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape Cudjoe Key CA $294 CA $863 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Summerland-Key-Hotels-Waterfront-2BR2BA-With-35-Dock.h121310574.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/2f1a1fda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Pool](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/1e7f74ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/d979d3d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Larkshine House at Lunara Bay Raccoon Key 10/10 Exceptional (6) "well maintained, clean, easy to access" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raj P. CA $1,679 CA $3,425 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Brand-New-Build-Larkshine-House-Pool.h108195321.Hotel-Information) ![House](https://images.trvl-media.com/lodging/118000000/118000000/117995500/117995431/f42e4485.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/118000000/118000000/117995500/117995431/2a6c0772.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/118000000/118000000/117995500/117995431/208a6937.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/118000000/118000000/117995500/117995431/bfa871fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Waterfront Home - Dreamside House Raccoon Key CA $1,784 CA $3,368 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-New-Waterfront-Home-Dreamside-House.h117995431.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/9d72c172.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/30527523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/130b2801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/40a49494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West Cudjoe Key CA $257 CA $818 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Summerland-Key-Hotels-Updated-2BR2BA-Venture-Out-Home-W-Pool-Access.h120816897.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/4480719e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/94e8538a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/04d12b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/b5098a17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Reel Island Retreat #273 at Venture Out in the Florida Keys Cudjoe Key 9.6/10 Exceptional (7) "We really enjoyed our stay here. We really loved sitting on the back porch by the water and the closeness to the community pool and courts. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lindsay C. CA $294 CA $863 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Summerland-Key-Hotels-Reel-Island-Retreat-273-At-Venture-Out-In-The-Florida-Keys.h109794896.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=2025-11-08&endDate=2025-11-09®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 ![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 "Staff was very helpful reported to front desk that ac unit was not working properly. When we return to hotel they informed us they were going to switch our room and give us a balcony room too" [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.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 "Was great!" [](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 "." [](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.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 "Our stay at the Hilton Garden Inn Key West was fantastic. The rooms were well appointed, well stocked, and clean. The pool area is beautiful and includes an outdoor bar with great drinks and exceptional staff. The front desk team were all an absolute pleasure to deal with. And the free shuttle to downtown was a great way to explore the entertainment district in Key West. I can absolutely recommend a stay at this hotel. " [](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ![Oceans Edge Key West Resort, Hotel & Marina](//images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/3a4457a0_y.jpg) ### Oceans Edge Key West Resort, Hotel & Marina 10/10 Excellent "Beautiful setting - great water views. Room was clean and comfortable - pools were great. " [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.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 "All great! " [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.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 "Yes" [](https://expedia.ca/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.Hotel-Information) ![Beachside Resort & Residences](//images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "Wonderful room, Brilliant friendly staff that go the extra mile. Great shuttle service and amazing restaurant. All in all a very memerable stay to celebrate my husbands 60th Birthday. Thank you xx" [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ![Margaritaville Beach House Key West](//images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/32e70782_y.jpg) ### Margaritaville Beach House Key West 10/10 Excellent "Room was clean. Felt safe. Staff was great, very friendly." [](https://expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.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) - [Beach Hotel Hotels in Big Coppitt Key](https://www.expedia.ca/Big-Coppitt-Key-Hotels-Beach-Hotel.0-0-d553248635975850102-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Big Coppitt Key](https://www.expedia.ca/Big-Coppitt-Key-Hotels-Cheap-Hotels.0-0-d553248635975850102-tCheapHotels.Travel-Guide-Filter-Hotels) - 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