Title: Riley's Retreat - Venture Out 107 Reviews, Deals & Photos 2026 - Expedia.co.uk [See all properties](http://www.expedia.co.uk/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Riley's Retreat - Venture Out 107 Waterfront cottage in Summerland Key with a hot tub ## Photo gallery for Riley's Retreat - Venture Out 107 ![Outdoor dining - Riley's Retreat - Venture Out 107 (Cudjoe Key)](https://images.trvl-media.com/lodging/100000000/99910000/99905900/99905884/3507a8a1.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Fridge, microwave, oven, stovetop - Riley's Retreat - Venture Out 107 (Cudjoe Key)](https://images.trvl-media.com/lodging/100000000/99910000/99905900/99905884/31d34c88.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Dining - Riley's Retreat - Venture Out 107 (Cudjoe Key)](https://images.trvl-media.com/lodging/100000000/99910000/99905900/99905884/ec77b728.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop - Riley's Retreat - Venture Out 107 (Cudjoe Key)](https://images.trvl-media.com/lodging/100000000/99910000/99905900/99905884/b1769cbe.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds - Riley's Retreat - Venture Out 107 (Cudjoe Key)](https://images.trvl-media.com/lodging/100000000/99910000/99905900/99905884/d234561a.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Located on a 60' wide canal, Riley's Retreat offers open water views from the dock and porch. With laminate wood flooring, central air conditioning, and Tommy Bahama furnishings throughout this beautifully decorated home is perfect for boating enthusiasts who want to unwind in style. ## Reviews 9.0 Wonderful ### Entire home 2 bedrooms2 bathroomsSleeps 6800 sq ft ## Popular amenities - Parking available - Dryer - Hot tub - Pet-friendly - Washer - Pool ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire cottage to yourself and will only share it with other guests in your party. ### Riley's Retreat - Venture Out 107 Riley's Retreat 2Bd/2Ba 35' Dockage Open Water Views, Free WiFi This sparkling clean 2Bd/2Ba vacation rental is located on a 60' wide canal overlooking look down views of the wide L-shaped canal with open water views from the dock and porch and dining room. Perfect boating property, features 35' concrete seawall, dock posts, fish cleaning table, cleats and swim ladder. Interior features laminate wood flooring, central air conditioning, stack washer and dryer, microwave, dishwasher with kitchen and dining open to the living room. The master bedroom features a queen size bed with full bathroom. The guest bedroom features a queen size bed with access to the hallway full bathroom. For additional sleeping, there is a pull out sofa sleeper in the living room. This home is beautifully decorated with Tommy Bahama furnishings and is open and bright with high ceilings throughout. Additional amenities include FREE WIFI, ceiling fans, gas grill, 2 bicycles and outdoor patio furniture. Pet friendly, please refer to Venture Out pet rules. OVERFLOW PARKING IS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME. VO REGISTRATION FEE $125.00- DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE ## Property amenities ### Pool/Spa - Communal pool - Hot tub ### Internet - Available in the cottage: Free WiFi ### Parking and transport - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Hob - Ice maker - Microwave - Oven - Refrigerator ### Bedrooms - 2 bedrooms - Bedsheets provided - Sofa bed ### Bathroom - 2 bathrooms - Shower - Towels provided ### Living spaces - Living room ### Entertainment - TV with cable/satellite channels ### Outdoor areas - Gas grill - Outdoor furniture - Porch/lanai ### Laundry - Washing machine ### Comfort - Air conditioning ### Pets - Pet friendly ### Suitability/Accessibility - Hardwood flooring in public areas - Smoke-free property ### Location highlights - Near the sea - On the waterfront ### Things to do - Basketball nearby - Fishing nearby - Jet skiing nearby - Kayaking nearby - Scuba diving nearby - Snorkelling nearby - Swimming nearby ### Safety features - Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector) - Smoke detector not reported (host has not indicated whether there is a smoke detector on the property) ### General - Unit size: 800 square feet ## Similar properties ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104210000/104205400/104205389/bacca2df.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Paradise Escape - VO466 35' Dockage Cudjoe Key - Pool - Hot tub - Kitchen - Washer 9.0 Wonderful 4 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-12-18&endDate=2025-12-19&selected=104205389&PinnedHotelID=104205389&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/114000000/113460000/113458500/113458491/2a96627a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Mahi House #440 - 35' seawall Cudjoe Key - Sea view - Pool - Hot tub - Kitchen 10 Exceptional 2 reviews £548 includes taxes & fees 11 Dec - 12 Dec [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-12-11&endDate=2025-12-12&selected=113458491&PinnedHotelID=113458491&HadPinnedHotel=true®ionId=-1&adults=2) ![2 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/92962431.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Old Wooden Bridge Resort and Marina Punta Brisa - Pool - Pet-friendly - Parking included - Free WiFi 8.6 Excellent 274 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-12-18&endDate=2025-12-19&selected=17102343&PinnedHotelID=17102343&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/88788395.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Island Oasis \~ YOUR Paradise awaits in Venture Out Resort! Cudjoe Key - Sea view - Pool - Hot tub - Kitchen 9.6 Exceptional 12 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-12-18&endDate=2025-12-19&selected=83440767&PinnedHotelID=83440767&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94010000/94008000/94007975/962e758d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Shangri-la in the Keys! Enjoy the water views and a 45' dock space! Cudjoe Key - Pool - Hot tub - Kitchen - Washer 9.4 Exceptional 37 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-12-18&endDate=2025-12-19&selected=94007975&PinnedHotelID=94007975&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/504ad77a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Relax by Florida Keys Beaches, just a 7-min drive away Cudjoe Key - Sea view - Pool - Hot tub - Kitchen 9.8 Exceptional 197 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-12-18&endDate=2025-12-19&selected=34323967&PinnedHotelID=34323967&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115560000/115555400/115555400/w2500h1666x0y1-32f7610a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Diving Dolphin #268 - Ocean Views, Kayaks! Cudjoe Key - Sea view - Pool - Hot tub - Kitchen 9.4 Exceptional 3 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-12-18&endDate=2025-12-19&selected=115555400&PinnedHotelID=115555400&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/73acf8f1.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Island Time #110 Ocean Views - Cudjoe Key Cudjoe Key - Sea view - Pool - Hot tub - Kitchen 9.6 Exceptional 11 reviews £498 includes taxes & fees 5 Dec - 6 Dec [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-12-05&endDate=2025-12-06&selected=108496393&PinnedHotelID=108496393&HadPinnedHotel=true®ionId=-1&adults=2) ![Marina](https://images.trvl-media.com/lodging/94000000/93680000/93679500/93679498/cc79d145.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Endless Water Views - Venture Out 526 Cudjoe Key - Hot tub - Kitchen - Washer - Dryer 8.8 Excellent 17 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-12-18&endDate=2025-12-19&selected=93679498&PinnedHotelID=93679498&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/9e50721e.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock Cudjoe Key - Sea view - Pool - Hot tub - Kitchen 9.4 Exceptional 27 reviews £543 includes taxes & fees 17 Dec - 18 Dec [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-12-17&endDate=2025-12-18&selected=89084949&PinnedHotelID=89084949&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 3:00 PM Contactless check-in and check-out are available Minimum check-in age - 27 ### Check-out Check-out before 10:00 AM ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions Information provided by the property may be translated using automated translation tools ### Rules Venture Out charges a $125 registration fee upon arrival paid via cash or cc only. https://ventureoutcondo.com/wp-content/uploads/2025/02/Renter-Rules-Packet-2.24.25.pdf Only 1 vehicle is allowed at/under the unit at any time. Other vehicles MUST park on the street during the day and pay for overflow at night. ### Pets Pets are allowed Service animals are welcome, and are exempt from fees ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## Important information ### You need to know This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed On-site parties or group events are strictly prohibited Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip Host has not indicated whether there is a smoke detector on the property This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal. ### Property is also known as 277418 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C24.64986%2C-81.47439&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=SFXXmNMolIWPvmSuVMm-fk4HS_I=) Cudjoe Key, FL #### What's nearby - Upper Sugarloaf Key \- 9 min drive \- 4.5 miles - Upper Sugarloaf Sound \- 11 min drive \- 5.3 miles - Florida Keys Beaches \- 11 min drive \- 4.4 miles - Lower Sugarloaf Sound \- 14 min drive \- 7.8 miles - Sugarloaf Beach \- 21 min drive \- 11.4 miles #### Getting around - Key West, FL (EYW-Key West Intl.) - 33 min drive #### Restaurants - ‪Boondock's Grille & Drafthouse - ‬9 min drive - ‪Kiki's Sandbar - ‬12 min drive - ‪5 Brothers Two - ‬9 min drive - ‪Morning Joint - ‬3 min drive - ‪Broil - ‬5 min drive ## Frequently asked questions ### Does Riley's Retreat - Venture Out 107 have a pool? ### Is Riley's Retreat - Venture Out 107 pet-friendly? ### How much is parking at Riley's Retreat - Venture Out 107? ### What time is check-in at Riley's Retreat - Venture Out 107? ### What time is check-out at Riley's Retreat - Venture Out 107? ### Where is Riley's Retreat - Venture Out 107 located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Riley's Retreat - Venture Out 107 Reviews ## Reviews 9.0 ### Wonderful All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.co.uk/lp/b/content-guidelines) 10 - Excellent 6 8 - Good 4 6 - Okay 1 4 - Poor 0 2 - Terrible 0 ### 8.6/10 Cleanliness ## Reviews ### 10/10 Excellent #### Brandon K. 7 Jul 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great house Great place to stay had a great time at Riley’s retreat had the boat in the back overall great place to stay with family and friends and catch fish ##### Brandon K. Stayed 6 nights in Jun 2025 ### 8/10 Good #### Carl B. 24 Mar 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Relaxing Stay Lovely place to stay and great resort. ##### Carl B. Stayed 3 nights in Mar 2024 ### 10/10 Excellent #### Verified traveller 18 Nov 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great stay Quiet neighborhood close enough yet far enough from Key West madness ##### Verified traveller Stayed 5 nights in Nov 2024 ### 8/10 Good #### Mario G. 5 Sept 2025 Liked: Check-in, communication, location, listing accuracy Disliked: Cleanliness Ants and doorlock was broken. We had a baby and that was inconvenient. Had to be very careful and block the door. We couldn’t lock it. ##### Mario G. Stayed 3 nights in Aug 2025 ### 10/10 Excellent #### Melissa M. 7 Mar 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Love Venture Out! The property was as expected. It was very clean to be older double wide. Overall I made some suggestions about just some more comfy chairs in living space but we very much enjoyed our stay! We would stay again! The people that help manage the property are very nice and attentive to your needs! ##### Melissa M. Stayed 6 nights in Mar 2025 ### 10/10 Excellent #### Dorin O. 30 Apr 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great Place As advertised. Very clean and well furnished with everything you need! ##### Dorin O. Stayed 4 nights in Apr 2024 ### 10/10 Excellent #### Sandy B. 22 Jan 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Fun time This property was clean and loved the decor. It was great to have the boat at the dock. Friendly neighbors! ##### Sandy B. Stayed 13 nights in Jan 2024 ### 8/10 Good #### Tks T. 17 Jan 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Allows pets and clean! We would stay here again. Very clean. Kitchen well supplied. The beds could be more comfortable, but that could be a preference of bed type. The blinds in the bedrooms did not close completly so if you sleep late the light could be an issue. Itwasnt for us. ##### Tks T. Stayed 4 nights in Jan 2025 ### 8/10 Good #### Amanda H. 24 Jun 2024 Liked: Cleanliness, location, listing accuracy Disliked: Check-in, communication #### Overall nice place to stay Overall nice place to stay. Community well kept with 24 hour security. The unit was accommodating to our needs. Only a few issues we noticed: Air conditioning subpar and felt like unit could not keep up at 77 degrees, living room furniture uncomfortable and pull out sofa bed was unusable. ##### Amanda H. Stayed 5 nights in Jun 2024 ### 6/10 Okay #### Ann Marie Q. 6 Jan 2025 Liked: Location, listing accuracy #### Not exactly great but not awful The unit could have been cleaner, white door frame covered in black mold, shower had mildew as well. No AC the first night and noone monitors emails overnight so no response or action taken till next mid morning. Supposed to be 2 bikes but only 1.Railing on deck came loose as someone was leaning on it, just a thank you for letting us know. Location was nice, checking in could be smoother and quicker, stood in line at guard gate for about 30 minutes.Common areas in unit was roomy but bedrooms are tiny. Sofa pull out mattress needs replacing. For the price point really expected more, overall just okay, probably not somewhere I would stay again. ##### Ann Marie Q. Stayed 6 nights in Dec 2024 ### 10/10 Excellent #### Yudeisy B. 25 Jun 2025 ##### Yudeisy B. Stayed 8 nights in May 2025 ## Expedia's Latest Trends ### Hotels > [The Sands - Sea Front Apartments](https://www.expedia.co.uk/Scarborough-Hotels-The-Sands-Sea-Front-Apartments.h17452330.Hotel-Information) > > [Stella Beach Resort & Spa - Makadi Bay](https://www.expedia.co.uk/Hurghada-Hotels-Stella-Di-Mare-Beach-Resort-Spa-Makadi-Bay.h11577543.Hotel-Information) > > [Omni Orlando Resort at ChampionsGate](https://www.expedia.co.uk/Orlando-Hotels-Omni-Orlando-Resort-At-ChampionsGate.h1029950.Hotel-Information) > > [Winery Hotels in Reims](https://www.expedia.co.uk/Reims-Hotels-Winery-Hotels.0-0-d2987-tWineryHotels.Travel-Guide-Filter-Hotels) > > [Oceans Edge Key West Resort, Hotel & Marina](https://www.expedia.co.uk/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) > > [NH Collection Milano Touring](https://www.expedia.co.uk/Milan-Hotels-NH-Milano-Touring.h19557.Hotel-Information) > > [Gay-Friendly Hotels in Tunis](https://www.expedia.co.uk/Tunis-Hotels-Gay-Friendly-Hotel.0-0-d6025910-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) > > [Champions Gate Resort](https://www.expedia.co.uk/Orlando-Hotels-Champions-Gate-Resort.h14593168.Hotel-Information) > > [Hotels in Castelldefels](https://www.expedia.co.uk/Castelldefels-Hotels.d5770.Travel-Guide-Hotels) > > [Knockinaam Lodge ](https://www.expedia.co.uk/Stranraer-Hotels-Knockinaam-Lodge.h921566.Hotel-Information) > > [Hotels in St Sampsons](https://www.expedia.co.uk/St-Sampsons-Hotels.d3000403529.Travel-Guide-Hotels) > > [Olde Marco Island Inn and Suites](https://www.expedia.co.uk/Naples-Hotels-Olde-Marco-Island-Inn-And-Suites.h486461.Hotel-Information) > > [Hanover House](https://www.expedia.co.uk/London-Hotels-Hanover-House.h39218236.Hotel-Information) > > [Hotel Gran Duca Di York](https://www.expedia.co.uk/Milan-Hotels-Hotel-Gran-Duca-Di-York.h1074523.Hotel-Information) > > [The Shore at Katathani](https://www.expedia.co.uk/Phuket-Hotels-The-Shore-At-Katathani.h3555818.Hotel-Information) > > [Paradise Cove Beach Villas](https://www.expedia.co.uk/Paphos-Hotels-Paradise-Cove-Luxurious-Beach-Villas.h3952867.Hotel-Information) > > [Schwabinger Wahrheit by Geisel](https://www.expedia.co.uk/Munich-Hotels-Schwabinger-Wahrheit-By-Geisel.h22877763.Hotel-Information) > > [Hotels near Poniente Beach](https://www.expedia.co.uk/Poniente-Beach-Hotels.0-l6157906-0.Travel-Guide-Filter-Hotels) > > [Lido Beach Resort](https://www.expedia.co.uk/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information) > > [Hotels near Hardwick Hall](https://www.expedia.co.uk/Hardwick-Hall-Hotels.0-l6087745-0.Travel-Guide-Filter-Hotels) > > [King Hotel Ksamil](https://www.expedia.co.uk/Ksamil-Hotels-King-Hotel-Ksamil.h54215532.Hotel-Information) ### Flights > [Flights from Seawell (BGI) to Miami (MIA)](https://www.expedia.co.uk/lp/flights/bgi/mia/bridgetown-to-miami) ### General