Title: Summerland Key Holiday Homes from £341: Search Holiday Homes in Summerland Key | Expedia.co.uk [Summerland Key Travel Guide](https://expedia.co.uk/Summerland-Key.dx6177802)[Hotels in Summerland Key](https://expedia.co.uk/Summerland-Key-Hotels.d6177802.Travel-Guide-Hotels)[Holiday Rentals in Summerland Key](https://expedia.co.uk/Summerland-Key-Holiday-Rentals.d6177802.Travel-Guide-HolidayRentals)[Flights to Summerland Key](https://expedia.co.uk/Cheap-Flights-To-Summerland-Key.d6177802.Travel-Guide-Flights)[Summerland Key Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Summerland-Key.d6177802.Car-Hire-Guide)[Summerland Key Holidays](https://expedia.co.uk/Summerland-Key.d6177802.Holidays-City-Breaks) ![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__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6177802&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [3 Apr - 5 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=6177802&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [1 May - 3 May](https://www.expedia.co.uk/Hotel-Search?regionId=6177802&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [29 May - 31 May](https://www.expedia.co.uk/Hotel-Search?regionId=6177802&startDate=2026-05-29&endDate=2026-05-31&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 holiday homes ![Exterior](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/d56a9a80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LED TV, DVD player, ping pong, books](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/787fb31a.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/33000000/32670000/32660400/32660303/9e0e4056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS [](https://www.expedia.co.uk/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.Hotel-Information) Cudjoe Key 9.4/10 Exceptional (103 reviews) "Great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Davian k. £341 includes taxes & fees 8 Feb - 9 Feb [](https://www.expedia.co.uk/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/a01f4162.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, ping pong, books](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/99097ad0.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 [](https://www.expedia.co.uk/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.Hotel-Information) Cudjoe Key 9.2/10 Wonderful (7 reviews) "Close to Key West. Would stay there again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) elisa b. £434 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.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) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/6db1494c.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) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/a9f31955.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 [](https://www.expedia.co.uk/Summerland-Key-Hotels-Updated-2BR2BA-Venture-Out-Home-W-Pool-Access.h120816897.Hotel-Information) Cudjoe Key £502 includes taxes & fees 3 Mar - 4 Mar [](https://www.expedia.co.uk/Summerland-Key-Hotels-Updated-2BR2BA-Venture-Out-Home-W-Pool-Access.h120816897.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) ![Smart TV, ping pong, books](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/627e8283.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) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/d1732c67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access [](https://www.expedia.co.uk/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.Hotel-Information) Cudjoe Key £450 includes taxes & fees 4 Mar - 5 Mar [](https://www.expedia.co.uk/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/7fa52371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/60a3d49e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach towels](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/f6d4e696.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/35000000/34330000/34324000/34323967/463cda70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax by Florida Keys Beaches, just a 7-min drive away [](https://www.expedia.co.uk/Cudjoe-Key-Hotels-Waterfront-Fresh-Cozy-2-Bedroom-35-Sea-Wall-New-UV-Light-Air-Purification-Safe.h34323967.Hotel-Information) Cudjoe Key 9.8/10 Exceptional (201 reviews) "Will definitely stay here again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeannine R. £490 includes taxes & fees 27 Feb - 28 Feb [](https://www.expedia.co.uk/Cudjoe-Key-Hotels-Waterfront-Fresh-Cozy-2-Bedroom-35-Sea-Wall-New-UV-Light-Air-Purification-Safe.h34323967.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) ![Exterior](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/20d90f2f.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/c8d44015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key [](https://www.expedia.co.uk/Summerland-Key-Hotels-Waterfront-2BR2BA-35-Seawall-For-32-Boat-Beautiful-Sunrises-On-Cudjoe-Key.h120862073.Hotel-Information) Cudjoe Key 10/10 Exceptional (1 review) "Very clean! Good location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) January M. £575 includes taxes & fees 25 Feb - 26 Feb [](https://www.expedia.co.uk/Summerland-Key-Hotels-Waterfront-2BR2BA-35-Seawall-For-32-Boat-Beautiful-Sunrises-On-Cudjoe-Key.h120862073.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/2f0f66a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/b5a934e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/29ebdd14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/d9484c64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hemingway - Beach Houses Key West [](https://www.expedia.co.uk/Sugarloaf-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Hemingway.h77064022.Hotel-Information) Upper Sugarloaf Key 9.6/10 Exceptional (8 reviews) "Perfect location way off the path if you like seclusion." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan L. £1,129 includes taxes & fees 17 Feb - 18 Feb [](https://www.expedia.co.uk/Sugarloaf-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Hemingway.h77064022.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) ![Dining](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/dc4f2745.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) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/6fdc38c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cudjoe Cottages, swimming pool, just 20 miles from Key West [](https://www.expedia.co.uk/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.Hotel-Information) Cudjoe Key 8.8/10 Excellent (150 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. £542 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.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) ![Beach towels](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/86d1247e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/w1282h819x1y0-b2147544.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) ### Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds! [](https://www.expedia.co.uk/Cudjoe-Key-Hotels-Oceanview-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h70541336.Hotel-Information) Cudjoe Key 7.6/10 Good (13 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. £373 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/Cudjoe-Key-Hotels-Oceanview-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h70541336.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) ![Smart TV, ping pong, books](https://images.trvl-media.com/lodging/124000000/123230000/123228800/123228788/84ed301b.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) ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123230000/123228800/123228788/ac295bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors [](https://www.expedia.co.uk/Summerland-Key-Hotels-Waterfront-Getaway-With-23-Seawall.h123228788.Hotel-Information) Cudjoe Key £507 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/Summerland-Key-Hotels-Waterfront-Getaway-With-23-Seawall.h123228788.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408131/12b8b185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408131/1bd7d565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408131/367a13e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408131/00933dda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southern Exposure in Cudjoe Key #49 [](https://www.expedia.co.uk/Summerland-Key-Hotels-Southern-Exposure-In-Cudjoe-Key-49.h106408131.Hotel-Information) Cudjoe Key 7.6/10 Good (4 reviews) "The house is nice and sitting on the balcony feels like you're floating. It was a nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Colleen G. £504 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Summerland-Key-Hotels-Southern-Exposure-In-Cudjoe-Key-49.h106408131.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/78d41425.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/03f59755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 [](https://www.expedia.co.uk/Summerland-Key-Hotels-Kellys-Kabin-Adorable-Private-Summerland-Key-Cottage.h84046253.Hotel-Information) Summerland Key 9.8/10 Exceptional (123 reviews) "We enjoyed our stay! Great little house and location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa K. £420 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Summerland-Key-Hotels-Kellys-Kabin-Adorable-Private-Summerland-Key-Cottage.h84046253.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/89000000/88300000/88296100/88296003/bf1a4e0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/89000000/88300000/88296100/88296003/f9948293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/89000000/88300000/88296100/88296003/ccf18e96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/89000000/88300000/88296100/88296003/5e9a36aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private and Exclusive Beach Getaway [](https://www.expedia.co.uk/Sugarloaf-Key-Hotels-Hammock-House-At-Sugarloaf-Beach.h88296003.Hotel-Information) Sugarloaf Key 8.0/10 Very good (2 reviews) "If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samat S. £2,004 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Sugarloaf-Key-Hotels-Hammock-House-At-Sugarloaf-Beach.h88296003.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) ![Smart TV, ping pong, books](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/23ac2d25.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) ### Reel Island Retreat #273 at Venture Out in the Florida Keys [](https://www.expedia.co.uk/Summerland-Key-Hotels-Reel-Island-Retreat-273-At-Venture-Out-In-The-Florida-Keys.h109794896.Hotel-Information) Cudjoe Key 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. £558 includes taxes & fees 10 Feb - 11 Feb [](https://www.expedia.co.uk/Summerland-Key-Hotels-Reel-Island-Retreat-273-At-Venture-Out-In-The-Florida-Keys.h109794896.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122330000/122326100/122326088/5cf2b74d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/123000000/122330000/122326100/122326088/2661692e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122330000/122326100/122326088/4a8c25f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/123000000/122330000/122326100/122326088/1ec12bbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 105 - Newly renovated house Oceanside and Pool [](https://www.expedia.co.uk/Summerland-Key-Hotels-105-Newly-Renovated-House-Oceanside-And-Pool.h122326088.Hotel-Information) Cudjoe Key £611 includes taxes & fees 10 Feb - 11 Feb [](https://www.expedia.co.uk/Summerland-Key-Hotels-105-Newly-Renovated-House-Oceanside-And-Pool.h122326088.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) ![Sports court](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/25a85f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/00d34243.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) ### Spanish Queen @Venture Out, Cudjoe Key [](https://www.expedia.co.uk/Cudjoe-Key-Hotels-Spanish-Queen-Venture-Out.h90010009.Hotel-Information) Cudjoe Key 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. £505 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Cudjoe-Key-Hotels-Spanish-Queen-Venture-Out.h90010009.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) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/27011986.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, ping pong, books](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/222af626.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 [](https://www.expedia.co.uk/Summerland-Key-Hotels-Relax-At-Keys-Time-2BR-Waterfront-Rental-W-Kayaks.h89084949.Hotel-Information) Cudjoe Key 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. £580 includes taxes & fees 6 Mar - 7 Mar [](https://www.expedia.co.uk/Summerland-Key-Hotels-Relax-At-Keys-Time-2BR-Waterfront-Rental-W-Kayaks.h89084949.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) ![Outdoor pool](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/84aef88f.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) ![Exterior](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/fd63c9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West [](https://www.expedia.co.uk/Summerland-Key-Hotels-Oceanfront-Home-Shared-Swimming-Pool.h57259241.Hotel-Information) Cudjoe Key 8.6/10 Excellent (90 reviews) "We had a great time and will be back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle K. £566 includes taxes & fees 10 Feb - 11 Feb [](https://www.expedia.co.uk/Summerland-Key-Hotels-Oceanfront-Home-Shared-Swimming-Pool.h57259241.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) ![Marina](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/7f597dff.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) ### SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS! [](https://www.expedia.co.uk/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks-King-Queen-Beds.h44556643.Hotel-Information) Cudjoe Key 9.8/10 Exceptional (82 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. £536 includes taxes & fees 5 Mar - 6 Mar [](https://www.expedia.co.uk/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks-King-Queen-Beds.h44556643.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/7303809e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/2b45d993.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) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/22d297cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Time #110 Ocean Views - Cudjoe Key [](https://www.expedia.co.uk/Summerland-Key-Hotels-Island-Time-110-Ocean-Views-Cudjoe-Key.h108496393.Hotel-Information) Cudjoe Key 9.4/10 Exceptional (12 reviews) "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. £574 includes taxes & fees 21 Feb - 22 Feb [](https://www.expedia.co.uk/Summerland-Key-Hotels-Island-Time-110-Ocean-Views-Cudjoe-Key.h108496393.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.co.uk/Hotel-Search?startDate=2026-02-20&endDate=2026-02-21®ionId=6177802&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America®ionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America®ionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APART_HOTEL) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America®ionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APARTMENT) Houseboats [](https://www.expedia.co.uk/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America®ionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=HOUSE_BOAT) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America®ionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VILLA) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America®ionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CONDO) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America®ionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=COTTAGE) ![](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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSummerland-Key-Private-Holiday-Homes.d6177802-aaPrivateHolidayHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSummerland-Key-Private-Holiday-Homes.d6177802-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ## Top Summerland Key Hotel Reviews ![Parmer's Resort](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/6492712a_y.jpg) ### Parmer's Resort 10/10 Excellent "The rooms were very clean! Views were beautiful. Pool was heated the cool days we were there. The breakfast was good and fresh. Loved the afternoon tea, hot chocolate, and coffee selections. Staff were very welcoming!" [](https://expedia.co.uk/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.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 "What a pleasant surprise. Over a holiday weekend, our other booking had overbooked us. We scrambled, and found this suite. It’s really, an apartment.. Oh my gosh, we were so happy. It was much better than the original lodging. There were two adults, two 21 year old sons. There was plenty of room for all of us. Clean, comfortable. 25 minutes outside of Key West. The 21-year-olds are coming back and staying here for spring break with their friends. To the owners of the KOA, they better behave." [](https://expedia.co.uk/Sugarloaf-Key-Hotels-Sugarloaf-Key-Hotel.h101135765.Hotel-Information) ![Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill](https://images.trvl-media.com/lodging/42000000/41050000/41049600/41049569/1a914b14_y.jpg) ### Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill 10/10 Excellent "Host was very responsive and amenities were great. It was clean and comfortable." [](https://expedia.co.uk/Cudjoe-Key-Hotels-Paradise-In-The-Florida-Keys.h41049569.Hotel-Information) ![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 very clean and comfortable. Small room but had a very comfortable small sofa and had an abundance of thick towels as well as beach towels. I was impressed with the room and check in/check out. " [](https://expedia.co.uk/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.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, convenient location. " [](https://expedia.co.uk/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Charming cottages, dockage, pool, just minutes to Key West](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/fadc9b44_y.jpg) ### Charming cottages, dockage, pool, just minutes to Key West 10/10 Excellent "Everything was really nice. Bed was a little firm for my liking but thats just me. Place was great. " [](https://expedia.co.uk/Summerland-Key-Hotels-Charming-Cottages.h33548243.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 "Great location!" [](https://expedia.co.uk/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.Hotel-Information) ![Old Florida Style, wrap around porch, boat basin for dockage, open water](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/60b95cd9_y.jpg) ### Old Florida Style, wrap around porch, boat basin for dockage, open water 10/10 Excellent "Amazing little spot. We had an octopus show up two nights of the three we were there. I can not wait to stay again. This was PERFECT on every way. I celebrated my 40th" [](https://expedia.co.uk/Little-Torch-Key-Hotels-Old-Florida-Style.h73238458.Hotel-Information) ![Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/13a191dd_y.jpg) ### Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West 10/10 Excellent "Everything was great! " [](https://expedia.co.uk/Summerland-Key-Hotels-Old-Florida-Style.h74236945.Hotel-Information) ## Find out more about Summerland Key ## Summerland Key Holiday Homes information | Number of reviews | 846 | | ----------------- | ----------------- | | Accommodation | 411 Holiday Homes | | Lowest Price | £341 | | Highest Price | £2,004 | ## Explore a world of travel with Expedia - More ways to book - [Book Holiday Homes in Summerland Key on Expedia.com ](https://www.expedia.com/Summerland-Key-Private-Vacation-Homes.d6177802-aaPrivateVacationHomes.Travel-Guide-Accommodation)