Title: Cudjoe Key Vacation Home Rentals : Search Top Private Vacation Homes for Rent | Expedia.ca [Cudjoe Key Travel Guide](https://expedia.ca/Cudjoe-Key.dx3000430966)[Hotels in Cudjoe Key](https://expedia.ca/Cudjoe-Key-Hotels.d3000430966.Travel-Guide-Hotels)[Vacation Rentals in Cudjoe Key](https://expedia.ca/Cudjoe-Key-Vacation-Rentals.d3000430966.Travel-Guide-VacationRentals)[Flights to Cudjoe Key](https://expedia.ca/Cheap-Flights-To-Cudjoe-Key.d3000430966.Travel-Guide-Flights)[Things to do in Cudjoe Key](https://expedia.ca/Things-To-Do-In-Cudjoe-Key.d3000430966.Travel-Guide-Activities)[Cudjoe Key Car Rentals](https://expedia.ca/Car-Rentals-In-Cudjoe-Key.d3000430966.Car-Rental-Guide)[Cudjoe Key Vacation Packages](https://expedia.ca/Cudjoe-Key.d3000430966.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/1d07342ba59eb2e04b3a99e373967cc5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cudjoe 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 [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000430966&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=3000430966&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=3000430966&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=3000430966&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Cudjoe Key Vacation Homes ![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) ![Miscellaneous](https://images.trvl-media.com/lodging/123000000/122330000/122326100/122326088/1241c3ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/123000000/122330000/122326100/122326088/0918c287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 105 - Newly renovated house Oceanside and Pool Cudjoe Key CA $494 CA $1,082 total includes taxes & fees Nov 18 - Nov 19 [](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/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) ![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) ![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) ### NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS! Cudjoe Key 9.6/10 Exceptional (98) "This is a great place to stay, neighborhood is nice, very convenient with the marina and boat ramp on site. I would definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward H. CA $210 CA $611 total includes taxes & fees Nov 17 - Nov 18 [](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/e1bc9e10.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) "A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Javier CA $267 CA $881 total includes taxes & fees Nov 14 - Nov 15 [](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) ![Property grounds](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/5f412538.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) ![Marina](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/7f597dff.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) "Great property, owners were very helpful and we really enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lee J. CA $309 CA $740 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks.h44556643.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/109000000/108500000/108496400/108496393/357cfc90.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) ![Marina](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/bea2cf35.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 $296 CA $909 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Summerland-Key-Hotels-Island-Time-110-Ocean-Views-Cudjoe-Key.h108496393.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) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/w2500h1666x0y1-ef4cfe80.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) ### Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West Cudjoe Key CA $259 CA $874 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Summerland-Key-Hotels-Updated-2BR2BA-Venture-Out-Home-W-Pool-Access.h120816897.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) "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 $317 CA $760 total includes taxes & fees Nov 18 - Nov 19 [](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/119000000/118660000/118656100/118656049/c01d0a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118660000/118656100/118656049/w2499h1666x1y1-6b986066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/119000000/118660000/118656100/118656049/c518e45b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118660000/118656100/118656049/w2500h1666x0y1-475cf754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Galleon Getaway #533- Oceanfront Community Cudjoe Key CA $207 CA $809 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Summerland-Key-Hotels-Galleon-Getaway-533-Oceanfront-Community.h118656049.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) ![Beach](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/c2c1b6c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/37c753b4.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 $296 CA $909 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Summerland-Key-Hotels-Waterfront-2BR2BA-With-35-Dock.h121310574.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) ![Miscellaneous](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/5a7e1cda.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) ### 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 $346 CA $671 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/114000000/113460000/113458500/113458491/2a96627a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113460000/113458500/113458491/w2500h1666x0y1-fe00fd9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113460000/113458500/113458491/w2499h1562x1y1-92d1fa50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113460000/113458500/113458491/dd398ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mahi House #440 - 35' seawall Cudjoe Key 10/10 Exceptional (1) "The house was just right. Nice community. Quiet and peaceful. Just what we needed. The host was kind and responsive. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily P. CA $296 CA $909 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Summerland-Key-Hotels-Mahi-House-440-35-Seawall.h113458491.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/ccda6a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/af234045.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/3a5c1145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/d1b5e430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access Cudjoe Key CA $244 CA $855 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/112000000/111070000/111069900/111069858/8eed4109.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111070000/111069900/111069858/w2499h1666x1y1-59b013e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/112000000/111070000/111069900/111069858/a66e8c8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111070000/111069900/111069858/w2499h1665x1y1-b6427dee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sailfish Haven #390 - Ocean Views, 35' seawall Cudjoe Key 8.8/10 Excellent (6) "It was a perfect home to stay in cudokey" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia H. CA $296 CA $921 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Summerland-Key-Hotels-Sailfish-Haven-390-Ocean-Views.h111069858.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) ![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) ![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) ### Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key Cudjoe Key 9.0/10 Wonderful (7) "Great place! Perfect location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Troy B. CA $370 CA $1,015 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Summerland-Key-Hotels-Salty-Breeze-161-Canal-Front-Venture-Out-Home-On-Cudjoe-Key.h106911727.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) ![Dining](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/04d12b41.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) ### Reel Island Retreat #273 at Venture Out in the Florida Keys Cudjoe Key 9.6/10 Exceptional (7) "Very clean place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael T. CA $296 CA $909 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Summerland-Key-Hotels-Reel-Island-Retreat-273-At-Venture-Out-In-The-Florida-Keys.h109794896.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/115000000/114920000/114911900/114911827/b3dc4256.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114920000/114911900/114911827/w2499h1403x1y1-6be162c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/115000000/114920000/114911900/114911827/4679a595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114920000/114911900/114911827/w2500h1566x0y1-3795e49f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key Cudjoe Key CA $274 CA $892 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Summerland-Key-Hotels-Little-Piece-Of-Paradise-233-35-Seawall-Cudjoe-Key.h114911827.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310572/2af28832.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310572/ef9badd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310572/dd4c9be4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310572/30237e95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort Cudjoe Key CA $296 CA $914 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Summerland-Key-Hotels-Florida-Keys-Canal-Front-2BR2BA-W-35-Seawall.h121310572.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/4c3dc49f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/6f5e4f11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/8eb4c1e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/a935335c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key Cudjoe Key CA $370 CA $1,002 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Summerland-Key-Hotels-Waterfront-2BR2BA-35-Seawall-For-32-Boat-Beautiful-Sunrises-On-Cudjoe-Key.h120862073.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) ![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) ![Beach](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/3903b768.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) "Lovely property by the water in Cudjoe Key. Very comfortable and well equipped. Host was very communicative and location was great for getting to Key West and other local attractions. Would definitely stay again! " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Tom K. CA $407 CA $1,046 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Summerland-Key-Hotels-Relax-At-Keys-Time-2BR-Waterfront-Rental-W-Kayaks.h89084949.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) ![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116810000/116800200/116800175/w2500h1666x0y1-83fec5c6.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) ![Beach](https://images.trvl-media.com/lodging/117000000/116810000/116800200/116800175/62524a45.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) "Super spot and views of the Straits. Very clean with new modern appliances and amenities. Comfortable and relaxing. Roku TVs make it a challenge to watch major sporting events, but that’s not why we were there. Pool spa out of service due to “health concerns,” but the pool itself seemed ok. Overall, a peaceful and calm stay all about the soothing views with only the splashing sounds of the occasional fish chasing bait. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $703 CA $1,432 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) 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=2025-11-20&endDate=2025-11-21®ionId=3000430966&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%2FCudjoe-Key-Private-Vacation-Homes.d3000430966-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCudjoe-Key-Private-Vacation-Homes.d3000430966-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Cudjoe Key Hotel Reviews ## Find out more about Cudjoe Key ## Cudjoe 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 - 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