Title: Lower Sugarloaf Key Vacation Home Rentals : Search Top Private Vacation Homes for Rent | Expedia.ca [Lower Sugarloaf Key Travel Guide](https://expedia.ca/Lower-Sugarloaf-Key.dx553248635976195908)[Hotels in Lower Sugarloaf Key](https://expedia.ca/Lower-Sugarloaf-Key-Hotels.d553248635976195908.Travel-Guide-Hotels)[Vacation Rentals in Lower Sugarloaf Key](https://expedia.ca/Lower-Sugarloaf-Key-Vacation-Rentals.d553248635976195908.Travel-Guide-VacationRentals)[Flights to Lower Sugarloaf Key](https://expedia.ca/Cheap-Flights-To-Lower-Sugarloaf-Key.d553248635976195908.Travel-Guide-Flights)[Lower Sugarloaf Key Car Rentals](https://expedia.ca/Car-Rentals-In-Lower-Sugarloaf-Key.d553248635976195908.Car-Rental-Guide)[Lower Sugarloaf Key Vacation Packages](https://expedia.ca/Lower-Sugarloaf-Key.d553248635976195908.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498234-sugarloaf-key.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Lower Sugarloaf 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 [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976195908&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976195908&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976195908&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 four months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976195908&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) ## Browse Select Lower Sugarloaf Key Vacation Homes ![Smart TV, books](https://images.trvl-media.com/lodging/117000000/116670000/116666900/116666823/a0c4a639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/117000000/116670000/116666900/116666823/a5b1dd6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116670000/116666900/116666823/9f86efca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116670000/116666900/116666823/0999e99e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom house in Big Pine Key near Beach and Key West Sands CA $264 CA $794 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Big-Pine-Key-Hotels-Charming-3-Bedroom-House-In-Big-Pine-Key-Near-Beach-And-Key-West.h116666823.Hotel-Information) ![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) ![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) ### NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS! Cudjoe Key 9.6/10 Exceptional (99) "The house was very clean. Friendly and quiet location. The hosts were extremely helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy F. CA $180 CA $573 total includes taxes & fees Nov 24 - Nov 25 [](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) ![Beach](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/5498fbd6.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) ![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) ### 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 Nov 21 - Nov 22 [](https://www.expedia.ca/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.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) ![Outdoor dining](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/611ec5f5.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) ### Kelly's Kabin - Adorable Private Summerland Key Cottage Summerland Key 9.8/10 Exceptional (120) "We enjoyed our stay! Great little house and location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa K. CA $315 CA $756 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Summerland-Key-Hotels-Kellys-Kabin-Adorable-Private-Summerland-Key-Cottage.h84046253.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 9.6/10 Exceptional (11) "Our family had an amazing vacation! We love the house and hope to come back!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tammy G. CA $294 CA $866 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Summerland-Key-Hotels-Island-Time-110-Ocean-Views-Cudjoe-Key.h108496393.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) ![Property grounds](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/5f412538.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) ### NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS! Cudjoe Key 9.8/10 Exceptional (82) "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 $348 CA $782 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks.h44556643.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) ![Pool](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/82d61a90.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) ### Old Florida Style, wrap around porch, boat basin for dockage, open water Little Torch Key 9.6/10 Exceptional (85) "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 $524 CA $1,108 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Little-Torch-Key-Hotels-Old-Florida-Style.h73238458.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/50d75af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/bb5499e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/5a7e1cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/b22a7d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key Cudjoe Key 10/10 Exceptional (2) "Absolutely love it here… Randy is great to work with and always available. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeannine R. CA $308 CA $621 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Summerland-Key-Hotels-Charming-2-Bedroom-House-With-WiFi.h117678152.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) ![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/7c5d926a.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) ### Just 20 miles from Key West! Oceanfront, dockage, swimming pool Cutthroat Harbor Estates 8.4/10 Very good (117) "Great experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peyton S. CA $315 CA $754 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/ccc6991c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/4b59c6b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/c3e9677e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/w1719h1144x6y0-9b572dbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### One of the very few beach houses with a daily, rental license in the Keys. Summerland Key 8.8/10 Excellent (64) "My family and I had an incredible stay. We utilized every available component of the home including the dock. Property manager provided us with 2 available free ramps to drop off our jet-skis. We settled on the ramp located on Blimp Road, which was a 10 minute drive and 15-20 minute ride on the skis. We were able to tie off our skis our whole stay with no issues. Home was exactly as disclosed and worked great for our family. Communication was great, with quick respond time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yissel W. CA $754 CA $1,840 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Summerland-Key-Hotels-Acreage-Beach-House-W-Pool-Billiards.h38413504.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/e0161319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/c295ed72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/9443bf1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/f6a09985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spanish Queen @Venture Out, Cudjoe Key Cudjoe Key 9.4/10 Exceptional (19) "This is our third time staying here. It is a great property and works perfectly for a three-person family." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly G. CA $489 CA $941 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Spanish-Queen-Venture-Out.h90010009.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) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/b38fa56b.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) ![Dining](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/04d12b41.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 $866 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Summerland-Key-Hotels-Reel-Island-Retreat-273-At-Venture-Out-In-The-Florida-Keys.h109794896.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/49000000/48330000/48322700/48322610/330a7ec6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/49000000/48330000/48322700/48322610/419ca4ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/49000000/48330000/48322700/48322610/d6ee0078.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/49000000/48330000/48322700/48322610/acc24a3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fishermen\`s Paradise | Waterfront home with huge pool, 220-foot dock & gorgeous interior Big Pine Key 9.8/10 Exceptional (21) "The location was very nice and secluded. The house was perfect for a family of five. The pool was great spent a lot of time in it. Lots to do in the area. The only complaint we had is the master bedroom bed mattress needs to be replaced. It seemed like it was very old possibly even broken communication with Karen was perfect. Everything about the trip was good :) " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle S. CA $860 CA $1,972 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Big-Pine-Key-Hotels-Fishermens-Paradise-3-Bed.h48322610.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/9e50721e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/3903b768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/25598d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/w2500h1666x0y1-6df08e77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock Cudjoe Key 9.4/10 Exceptional (27) "Close to Key West and lots of great boating" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Simon S. CA $330 CA $912 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Summerland-Key-Hotels-Relax-At-Keys-Time-2BR-Waterfront-Rental-W-Kayaks.h89084949.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) ![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/c54b4cae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/50ec79ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/ee961b10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palm - Beach Houses Key West Upper Sugarloaf Key 10/10 Exceptional (14) "Excellent place to stay if you are seeking a getaway off the beaten path. Well landscaped to give privacy to each bungalow. 2 amazing piers to fish/jet ski from. The pool and grill area is a PERFECT place to cool off and escape the heat with the swim up bar. The staff even gave us coconuts to enjoy fresh from their trees. Each day we saw amazing wildlife and even had key deer visit us. We are considering booking the whole place for a family reunion. Would also make for a great corporate... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert K. CA $1,082 CA $2,219 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Summerland-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Palm.h94616487.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/117000000/116810000/116800200/116800175/w2499h1666x1y1-11741275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/117000000/116810000/116800200/116800175/62524a45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/117000000/116810000/116800200/116800175/68b2ea34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116810000/116800200/116800175/w1666h2499x1y1-3446235e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly Cudjoe Key 10/10 Exceptional (2) "Beautiful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa P. CA $698 CA $1,304 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Summerland-Key-Hotels-Oceanfront-2BR-In-Venture-Out-35-Dock.h116800175.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) ![Marina](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/w3000h1999x0y1-09a4d9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books, video library](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/w3000h1999x0y1-215da3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/46a74ee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Poolside Cottage #411 Key West 9.8/10 Exceptional (53) "Clean and as advertised " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John H. CA $259 CA $459 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-411.h76584886.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/ee43d350.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) ### Waterfront Luxury Home - Tidelands House Raccoon Key CA $2,000 CA $3,609 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Key-West-Hotels-Waterfront-Luxury-Home-Tidelands-House.h115993610.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/123000000/122330000/122326100/122326088/1ec12bbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122330000/122326100/122326088/w1393h948x0y12-d52a0b1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122330000/122326100/122326088/862d13b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/123000000/122330000/122326100/122326088/5acb3203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 105 - Newly renovated house Oceanside and Pool Cudjoe Key CA $489 CA $1,085 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Summerland-Key-Hotels-105-Newly-Renovated-House-Oceanside-And-Pool.h122326088.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/111000000/110190000/110181100/110181084/b6ab72d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/111000000/110190000/110181100/110181084/ae7ff7b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/111000000/110190000/110181100/110181084/w2500h1666x0y1-50402af6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/111000000/110190000/110181100/110181084/w2500h1666x0y1-2e2bd1a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community Cudjoe Key 9.8/10 Exceptional (10) "Beautiful place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sara C. CA $551 CA $1,211 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Summerland-Key-Hotels-Caribbean-Blue-517-Oceanfront-Property.h110181084.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-03&endDate=2025-12-04®ionId=553248635976195908&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=Lower+Sugarloaf+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976195908&latLong=24.644738%2C-81.564406&adults=2&startDate=2026-02-17&d1=2026-02-17&endDate=2026-02-20&d2=2026-02-20&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Lower+Sugarloaf+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976195908&latLong=24.644738%2C-81.564406&adults=2&startDate=2026-02-17&d1=2026-02-17&endDate=2026-02-20&d2=2026-02-20&lodging=APARTMENT) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Lower+Sugarloaf+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976195908&latLong=24.644738%2C-81.564406&adults=2&startDate=2026-02-17&d1=2026-02-17&endDate=2026-02-20&d2=2026-02-20&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Lower+Sugarloaf+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976195908&latLong=24.644738%2C-81.564406&adults=2&startDate=2026-02-17&d1=2026-02-17&endDate=2026-02-20&d2=2026-02-20&lodging=COTTAGE) Condos [](https://www.expedia.ca/Hotel-Search?destination=Lower+Sugarloaf+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976195908&latLong=24.644738%2C-81.564406&adults=2&startDate=2026-02-17&d1=2026-02-17&endDate=2026-02-20&d2=2026-02-20&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Lower+Sugarloaf+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976195908&latLong=24.644738%2C-81.564406&adults=2&startDate=2026-02-17&d1=2026-02-17&endDate=2026-02-20&d2=2026-02-20&lodging=VILLA) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Lower+Sugarloaf+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976195908&latLong=24.644738%2C-81.564406&adults=2&startDate=2026-02-17&d1=2026-02-17&endDate=2026-02-20&d2=2026-02-20&lodging=VACATION_HOME) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Lower+Sugarloaf+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976195908&latLong=24.644738%2C-81.564406&adults=2&startDate=2026-02-17&d1=2026-02-17&endDate=2026-02-20&d2=2026-02-20&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%2FLower-Sugarloaf-Key-Private-Vacation-Homes.d553248635976195908-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FLower-Sugarloaf-Key-Private-Vacation-Homes.d553248635976195908-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Lower Sugarloaf Key Hotel Reviews ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "enjoyed my stay. very nice room." [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg) ### Hyatt Vacation Club at Windward Pointe, Key West 10/10 Excellent "The staff was wonderful and the room was very nice. " [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ![Casa Marina Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450_y.jpg) ### Casa Marina Key West, Curio Collection by Hilton 10/10 Excellent "Amenities" [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![Margaritaville Beach House Key West](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/32e70782_y.jpg) ### Margaritaville Beach House Key West 10/10 Excellent "Beach is directly across the road. A very short walk. Pool was heated. Nice options for food. We enjoyed our stay." [](https://expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.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 "Staffs are really nice" [](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.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 "Everything was awesome except breakfast. No meat or very many options. But very well maintained Thank you to juan, nathalia, and albert." [](https://expedia.ca/Key-West-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Key-West.h8946.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 nice & clean. Enjoyed the balcony overlooking the marina." [](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg) ### Oceans Edge Key West Resort, Hotel & Marina 10/10 Excellent "Staff was wonderful, helpful, happy to help!" [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.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 great location. Plenty of parking. Our stay was wonderful! Close to everything, amazing breakfast! We would 100%stay here again! " [](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ## Find out more about Lower Sugarloaf Key ## Lower Sugarloaf 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 - Other - More ways to book - [Aparthotels in Bay Point](https://www.expedia.ca/Bay-Point-Apart-Hotels.d553248635976383913-aaApartHotels.Travel-Guide-Accommodation) - [Guest Houses in Bay Point](https://www.expedia.ca/Bay-Point-Guest-Houses.d553248635976383913-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Bay Point](https://www.expedia.ca/Bay-Point-Hotels-Cheap-Hotels.0-0-d553248635976383913-tCheapHotels.Travel-Guide-Filter-Hotels) - [Bay Point Hotels](https://www.expedia.ca/Bay-Point-Hotels.d553248635976383913.Travel-Guide-Hotels) - [Inns in Bay Point](https://www.expedia.ca/Bay-Point-Inns.d553248635976383913-aaInns.Travel-Guide-Accommodation) - 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[Sugarloaf Key Hotels](https://www.expedia.ca/Sugarloaf-Key-Hotels.d183126.Travel-Guide-Hotels) - [Inns in Sugarloaf Key](https://www.expedia.ca/Sugarloaf-Key-Inns.d183126-aaInns.Travel-Guide-Accommodation) - [Motels in Sugarloaf Key](https://www.expedia.ca/Sugarloaf-Key-Motels.d183126-aaMotels.Travel-Guide-Accommodation) - [Resorts in Sugarloaf Key](https://www.expedia.ca/Sugarloaf-Key-Resort-Hotels.d183126-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Sugarloaf Key](https://www.expedia.ca/Sugarloaf-Key-Townhomes.d183126-aaTownhomes.Travel-Guide-Accommodation) - [Villas in Sugarloaf Key](https://www.expedia.ca/Sugarloaf-Key-Villas.d183126-aaVillas.Travel-Guide-Accommodation) - [Adults Only Resorts & in Sugarloaf Shores](https://www.expedia.ca/Sugarloaf-Shores-Summerland-Key-Hotels-Adults-Only-Resorts.0-n6270983-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Remington Hotels in Sugarloaf Shores](https://www.expedia.ca/Sugarloaf-Shores-Summerland-Key-Hotels-Remington.0-n6270983-0--bRemington.Travel-Guide-Filter-Hotels) - [Sugarloaf Shores Hotels](https://www.expedia.ca/Sugarloaf-Shores-Summerland-Key-Hotels.0-n6270983-0.Travel-Guide-Filter-Hotels) - [Flights to Lower Florida Keys](https://www.expedia.ca/Cheap-Flights-To-Lower-Florida-Keys.d553248635975748710.Travel-Guide-Flights) - [Flights to Sugarloaf Key](https://www.expedia.ca/Cheap-Flights-To-Sugarloaf-Key.d183126.Travel-Guide-Flights) - [Flights from Baltimore to Sugarloaf Key](https://www.expedia.ca/lp/flights/178235/183126/baltimore-to-sugarloaf-key) - [Flights from Boston to Sugarloaf Key](https://www.expedia.ca/lp/flights/178239/183126/boston-to-sugarloaf-key) - [Flights from Detroit to Sugarloaf Key](https://www.expedia.ca/lp/flights/178255/183126/detroit-to-sugarloaf-key) - [Flights from Québec City to Sugarloaf Key](https://www.expedia.ca/lp/flights/180017/183126/quebec-city-to-sugarloaf-key) - [Flights from Sugarloaf Key](https://www.expedia.ca/lp/flights/183126/flights-from-sugarloaf-key) - [Flights from Bay Point](https://www.expedia.ca/lp/flights/553248635976383913/flights-from-bay-point) - 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