Title: Summerland Key Vacation Home Rentals from CA $681: Search Top Private Vacation Homes for Rent | Expedia.ca [Summerland Key Travel Guide](https://expedia.ca/Summerland-Key.dx6177802)[Hotels in Summerland Key](https://expedia.ca/Summerland-Key-Hotels.d6177802.Travel-Guide-Hotels)[Vacation Rentals in Summerland Key](https://expedia.ca/Summerland-Key-Vacation-Rentals.d6177802.Travel-Guide-VacationRentals)[Flights to Summerland Key](https://expedia.ca/Cheap-Flights-To-Summerland-Key.d6177802.Travel-Guide-Flights)[Things to do in Summerland Key](https://expedia.ca/Things-To-Do-In-Summerland-Key.d6177802.Travel-Guide-Activities)[Summerland Key Car Rentals](https://expedia.ca/Car-Rentals-In-Summerland-Key.d6177802.Car-Rental-Guide)[Summerland Key Vacation Packages](https://expedia.ca/Summerland-Key.d6177802.Destination-Travel-Guides) ![Aerial view of road to Key West with turquoise water and small island, Summerland Key, Florida, United States.](https://images.trvl-media.com/place/6177802/f131c6a4-614b-4692-9e06-db0aca0a1329.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6177802/f131c6a4-614b-4692-9e06-db0aca0a1329.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6177802&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) In two months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Summerland Key vacation homes ![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/c7aff2d5.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) ![Outdoor dining](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/611ec5f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Summerland Key [](https://www.expedia.ca/Summerland-Key-Hotels-Kellys-Kabin-Adorable-Private-Summerland-Key-Cottage.h84046253.Hotel-Information) 9.8/10 Exceptional (123 reviews) "Great location and Host was very helpful and responsive." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dennis G. CA $339 CA $781 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Summerland-Key-Hotels-Kellys-Kabin-Adorable-Private-Summerland-Key-Cottage.h84046253.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) ![TV](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/a03560e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/2ea056a2.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) ### Vacation Home in Upper Sugarloaf Key [](https://www.expedia.ca/Summerland-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Palm.h94616487.Hotel-Information) 10/10 Exceptional (14 reviews) "Beautiful! Pool was amazing!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer B. CA $746 CA $1,585 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Summerland-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Palm.h94616487.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/d56a9a80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/33000000/32670000/32660400/32660303/9e0e4056.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) ### Vacation Home in Cudjoe Key [](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.Hotel-Information) 9.4/10 Exceptional (104 reviews) "Janet was great; quick to respond and very kind. Also the kayaks were fun and the beds were super comfy. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lauren D. CA $273 CA $681 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.Hotel-Information) ![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) ![Property grounds](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/080e8cfe.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) ### Vacation Home in Cudjoe Key [](https://www.expedia.ca/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks.h44556643.Hotel-Information) 9.8/10 Exceptional (85 reviews) "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 $341 CA $771 total includes taxes & fees Mar 5 - Mar 6 [](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/117000000/116670000/116667100/116667062/8bf693c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/d1732c67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/35103395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/627e8283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cudjoe Key [](https://www.expedia.ca/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.Hotel-Information) 10/10 Exceptional (1 review) "Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl V. CA $287 CA $847 total includes taxes & fees Feb 27 - Feb 28 [](https://www.expedia.ca/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/37ba1c6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/25a85f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/4a876812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/a6150bdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cudjoe Key [](https://www.expedia.ca/Cudjoe-Key-Hotels-Spanish-Queen-Venture-Out.h90010009.Hotel-Information) 9.4/10 Exceptional (19 reviews) "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 $479 CA $936 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Spanish-Queen-Venture-Out.h90010009.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/08f26cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/a9f31955.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/75d37db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/5fa1ecc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cudjoe Key [](https://www.expedia.ca/Summerland-Key-Hotels-Updated-2BR2BA-Venture-Out-Home-W-Pool-Access.h120816897.Hotel-Information) CA $343 CA $920 total includes taxes & fees Mar 3 - Mar 4 [](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/121000000/120870000/120862100/120862073/4c3dc49f.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) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/393a2acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/20d90f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cudjoe Key [](https://www.expedia.ca/Summerland-Key-Hotels-Waterfront-2BR2BA-35-Seawall-For-32-Boat-Beautiful-Sunrises-On-Cudjoe-Key.h120862073.Hotel-Information) 10/10 Exceptional (1 review) "Very clean! Good location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) January M. CA $467 CA $1,078 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Summerland-Key-Hotels-Waterfront-2BR2BA-35-Seawall-For-32-Boat-Beautiful-Sunrises-On-Cudjoe-Key.h120862073.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/6e3c9448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/w1284h2247x0y0-fe8bc1e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach towels](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/86d1247e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/w1282h837x1y0-05f17a6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cudjoe Key [](https://www.expedia.ca/Cudjoe-Key-Hotels-Oceanview-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h70541336.Hotel-Information) 7.8/10 Good (14 reviews) "Good experience. The property is well place and the Venture is really nice and quiet." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Primeau J. CA $339 CA $707 total includes taxes & fees Mar 7 - Mar 8 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Oceanview-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h70541336.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/c3050189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/b6f371a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/6fdc38c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/30086228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cudjoe Key [](https://www.expedia.ca/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.Hotel-Information) 8.8/10 Excellent (151 reviews) "Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) bryan c. CA $513 CA $997 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/a01f4162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/67b94030.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/e29d300c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/99097ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cudjoe Key [](https://www.expedia.ca/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.Hotel-Information) 9.4/10 Exceptional (8 reviews) "Close to Key West. Would stay there again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) elisa b. CA $272 CA $829 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408135/9627a6b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408135/4384cc83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408135/f4fe44d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408135/eff8416f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cudjoe Key [](https://www.expedia.ca/Summerland-Key-Hotels-Fun-In-The-Sun-In-Cudjoe-Key-51.h106408135.Hotel-Information) 8.6/10 Excellent (9 reviews) "This was a beautiful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debbie A. CA $315 CA $946 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Summerland-Key-Hotels-Fun-In-The-Sun-In-Cudjoe-Key-51.h106408135.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/beabdb4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/222af626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/27011986.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/55a25975.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cudjoe Key [](https://www.expedia.ca/Summerland-Key-Hotels-Relax-At-Keys-Time-2BR-Waterfront-Rental-W-Kayaks.h89084949.Hotel-Information) 9.2/10 Wonderful (29 reviews) "Close to Key West and lots of great boating" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Simon S. CA $467 CA $1,078 total includes taxes & fees Mar 6 - Mar 7 [](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/124000000/123230000/123228800/123228788/64bb49ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123230000/123228800/123228788/ac295bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123230000/123228800/123228788/29c04407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123230000/123228800/123228788/2fb28220.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cudjoe Key [](https://www.expedia.ca/Summerland-Key-Hotels-Waterfront-Getaway-With-23-Seawall.h123228788.Hotel-Information) CA $359 CA $942 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Summerland-Key-Hotels-Waterfront-Getaway-With-23-Seawall.h123228788.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/90000000/89820000/89810800/89810800/e8302fa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/90000000/89820000/89810800/89810800/9fe4ba70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/90000000/89820000/89810800/89810800/f1fd924c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89820000/89810800/89810800/ae1e02d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Upper Sugarloaf Key [](https://www.expedia.ca/Sugarloaf-Key-Hotels-BUNGALOWS-AT-SUGARLOAF-BEACH-THE-LIGHTHOUSE.h89810800.Hotel-Information) 9.6/10 Exceptional (11 reviews) "Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter Q. CA $1,655 CA $2,815 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/Sugarloaf-Key-Hotels-BUNGALOWS-AT-SUGARLOAF-BEACH-THE-LIGHTHOUSE.h89810800.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/27d3efc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/5018018b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/ca8e91e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/e65d43dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Summerland Key [](https://www.expedia.ca/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-With-Stunning-Views.h111873736.Hotel-Information) CA $547 CA $1,170 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-With-Stunning-Views.h111873736.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/3f698bba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/fd63c9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/da1c9823.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/b30e05a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cudjoe Key [](https://www.expedia.ca/Summerland-Key-Hotels-Oceanfront-Home-Shared-Swimming-Pool.h57259241.Hotel-Information) 8.6/10 Excellent (92 reviews) "We had a great time and will be back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle K. CA $493 CA $1,058 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Summerland-Key-Hotels-Oceanfront-Home-Shared-Swimming-Pool.h57259241.Hotel-Information) ![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/3d9bbd48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/1f10acb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/w3000h1968x0y0-d4c36356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Private kitchen](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/f9199920.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Summerland Key [](https://www.expedia.ca/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-W-Stunning-Views.h111872953.Hotel-Information) CA $684 CA $1,247 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-W-Stunning-Views.h111872953.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) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/2903bcd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/5c8f33a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/586730d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Summerland Key [](https://www.expedia.ca/Summerland-Key-Hotels-Acreage-Beach-House-W-Pool-Billiards.h38413504.Hotel-Information) 8.8/10 Excellent (66 reviews) "If you are looking to see spectacular sunrises in the Keys, this location is great. Kitchen is well stocked with everything you need. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paula D. CA $956 CA $2,120 total includes taxes & fees Mar 26 - Mar 27 [](https://www.expedia.ca/Summerland-Key-Hotels-Acreage-Beach-House-W-Pool-Billiards.h38413504.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/3e905f47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/1e949ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/6ea5f149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/23ac2d25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cudjoe Key [](https://www.expedia.ca/Summerland-Key-Hotels-Reel-Island-Retreat-273-At-Venture-Out-In-The-Florida-Keys.h109794896.Hotel-Information) 9.4/10 Exceptional (8 reviews) "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 $431 CA $1,032 total includes taxes & fees Mar 8 - Mar 9 [](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=2026-03-10&endDate=2026-03-11®ionId=6177802&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_6177802) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America®ionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=VACATION_HOME) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America®ionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=HOUSE_BOAT) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America®ionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=APART_HOTEL) Condos [](https://www.expedia.ca/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America®ionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=CONDO) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America®ionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=APARTMENT) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America®ionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=COTTAGE) Villas [](https://www.expedia.ca/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America®ionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=VILLA) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America®ionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=CABIN) ![](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%2FSummerland-Key-Private-Vacation-Homes.d6177802-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSummerland-Key-Private-Vacation-Homes.d6177802-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Summerland Key Hotel Reviews ![Looe Key Reef Resort](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/63d12f01_y.jpg) ### Looe Key Reef Resort 10/10 Excellent "Room was clean and included amenities, Mike at registration was very friendly and helpful." [](https://expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information) ![Relax by Florida Keys Beaches, just a 7-min drive away](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/504ad77a_y.jpg) ### Relax by Florida Keys Beaches, just a 7-min drive away 10/10 Excellent "We had a lovely stay at this property in Kudjo Key. The unit was nice and as described. The host was also very attentive and also answered any messages right away. We would love to return in the future! " [](https://expedia.ca/Cudjoe-Key-Hotels-Waterfront-Fresh-Cozy-2-Bedroom-35seawall.h34323967.Hotel-Information) ![Parmer's Resort](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/6492712a_y.jpg) ### Parmer's Resort 10/10 Excellent "Ver nice , quiet stay highly recommend" [](https://expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information) ![Sugar Loaf Lodge](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e_y.jpg) ### Sugar Loaf Lodge 10/10 Excellent "Clean room and great staff" [](https://expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!](https://images.trvl-media.com/lodging/97000000/96270000/96267500/96267436/w902h683x61y0-db678eab_y.jpg) ### SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here! 10/10 Excellent "Room was very clean the website list stovetop that didn’t exist and 5 minutes walk to area beaches that is not true there is no beach access on Summerland Keys that I found everything else was great nice relaxing stay " [](https://expedia.ca/Summerland-Key-Hotels-SEA-SHELL-COTTAGE-UNIT-2.h96267436.Hotel-Information) ![Sugarloaf Key Hotel at KOA Resort](https://images.trvl-media.com/lodging/102000000/101140000/101135800/101135765/3a7e709a_y.jpg) ### Sugarloaf Key Hotel at KOA Resort 10/10 Excellent "Excellent " [](https://expedia.ca/Sugarloaf-Key-Hotels-Sugarloaf-Key-Hotel.h101135765.Hotel-Information) ![Cottage with swimming pool and dockage, just minutes to Key West!](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/49b733bd_y.jpg) ### Cottage with swimming pool and dockage, just minutes to Key West! 10/10 Excellent "Location was perfect. Oceanfront dock had beautiful sunsets. Oceanfront pool lovely and warm with incredible view. Very friendly vibe and relaxed atmosphere. " [](https://expedia.ca/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.Hotel-Information) ![Just 20 miles from Key West! Oceanfront, dockage, swimming pool](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/0c89d58b_y.jpg) ### Just 20 miles from Key West! Oceanfront, dockage, swimming pool 10/10 Excellent "Everything was great!" [](https://expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) ![Cottage with Pool and Boat Dockage just minutes to Key West!](https://images.trvl-media.com/lodging/34000000/33920000/33912100/33912031/2c7b5ad1_y.jpg) ### Cottage with Pool and Boat Dockage just minutes to Key West! 10/10 Excellent "Wonderful location pleasant vibe. We were there during a cold windy time ( locals said it was unusual weather), so didn't get to enjoy the outside facilities much. Cottage was small but had everything we needed, " [](https://expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Boat-Dockage-Just-Minutes-To-Key-West.h33912031.Hotel-Information) ## Find out more about Summerland Key ## Summerland Key Vacation Homes information | Number of reviews | 584 | | ----------------- | ------------------ | | Accommodation | 411 Vacation Homes | | Lowest Price | CA $681 | | Highest Price | CA $2,815 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [B&B in Big Pine Key ](https://www.expedia.ca/Big-Pine-Key-Bed-And-Breakfast.d7195-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Capsule Hotels in Big Pine Key ](https://www.expedia.ca/Big-Pine-Key-Capsule-Hotels.d7195-aaCapsuleHotels.Travel-Guide-Accommodation) - [Holiday Park Resorts in Big Pine Key ](https://www.expedia.ca/Big-Pine-Key-Holiday-Parks.d7195-aaHolidayParks.Travel-Guide-Accommodation) - [Lodges in Big Pine Key ](https://www.expedia.ca/Big-Pine-Key-Lodges.d7195-aaLodges.Travel-Guide-Accommodation) - 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