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 ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/9c267ac9.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) ![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 $181 CA $576 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) ![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/117000000/116670000/116666900/116666823/134724c2.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) ![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 $266 CA $798 total includes taxes & fees Nov 23 - Nov 24 [](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 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) ![Property grounds](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/5f412538.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) ![Exterior](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/6bfc69e0.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 $350 CA $786 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) ![Exterior](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/8ea08bd9.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) ![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 $527 CA $1,113 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Little-Torch-Key-Hotels-Old-Florida-Style.h73238458.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) ![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) ![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/c7065ca6.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 $266 CA $830 total includes taxes & fees Nov 20 - Nov 21 [](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) ![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) ![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 (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 $316 CA $760 total includes taxes & fees Nov 20 - Nov 21 [](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) ![Beach](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/22584e28.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) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/f620b37f.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 $295 CA $866 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Summerland-Key-Hotels-Island-Time-110-Ocean-Views-Cudjoe-Key.h108496393.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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/3835dc3a.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) ![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/7c5d926a.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 $316 CA $758 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.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) ![Interior](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/9443bf1a.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) ![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 2 - Dec 3 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Spanish-Queen-Venture-Out.h90010009.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) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/996d51b7.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) ### 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 $758 CA $1,849 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Summerland-Key-Hotels-Acreage-Beach-House-W-Pool-Billiards.h38413504.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) ![TV](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/a4dfc6ce.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) ![Miscellaneous](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/5a7e1cda.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 $281 CA $588 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Summerland-Key-Hotels-Charming-2-Bedroom-House-With-WiFi.h117678152.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) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/39025159.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) ### 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 $332 CA $913 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Summerland-Key-Hotels-Relax-At-Keys-Time-2BR-Waterfront-Rental-W-Kayaks.h89084949.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) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/b38fa56b.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 $295 CA $866 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Summerland-Key-Hotels-Reel-Island-Retreat-273-At-Venture-Out-In-The-Florida-Keys.h109794896.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) ![Beach nearby](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/50ec79ae.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/f739e31d.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) ![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/ee43d350.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 $2,565 CA $4,252 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Key-West-Hotels-Waterfront-Luxury-Home-Tidelands-House.h115993610.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 $664 CA $1,268 total includes taxes & fees Nov 30 - Dec 1 [](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/80000000/79690000/79683300/79683240/w905h683x60y0-701bb32b.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) ![Pool](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/c6ea30d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paradise found Stock Island 9.8/10 Exceptional (31) "Nice stay and budget friendly. Hard to find a place to house 5 guys but this an accomplished that easily. Conveniently located to the airport and the restaurants in the area were great. If your trip in Key West involves the marina, the marina is just behind the hogfish grill. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike Q. CA $558 CA $1,001 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Key-West-Hotels-Paradise-Found.h79683240.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) ![Miscellaneous](https://images.trvl-media.com/lodging/123000000/122330000/122326100/122326088/eb5db2d7.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) ![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 $1,075 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Summerland-Key-Hotels-105-Newly-Renovated-House-Oceanside-And-Pool.h122326088.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-e258b195.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) ![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) "Clean and as advertised " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John H. CA $260 CA $462 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-411.h76584886.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/111000000/110190000/110181100/110181084/35b861e0.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) ### 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=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&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=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&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=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&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=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&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=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&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=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&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=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&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=2026-02-16&d1=2026-02-16&endDate=2026-02-19&d2=2026-02-19&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 ### 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) ### 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 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 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 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 10/10 Excellent "Staff was wonderful, helpful, happy to help!" [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ### Hyatt Vacation Club at Beach House, Key West 10/10 Excellent "Pool and hot tub were great" [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Beach-House.h857962.Hotel-Information) ### Hilton Garden Inn Key West / The Keys Collection 10/10 Excellent "staff was extremely courteous and made a pont of going out of there way" [](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ### Blue Flamingo Resort Key West 10/10 Excellent "What a fun little resort. The amenities are fabulous! They have live music. We heard Ike Kanakanaui. He was REALLY good!" [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.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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