Title: Riley's Retreat - Venture Out 107 Reviews, Deals & Photos 2025 - 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 ![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99910000/99905900/99905884/3507a8a1.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Dining](https://images.trvl-media.com/lodging/100000000/99910000/99905900/99905884/ec77b728.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99910000/99905900/99905884/d234561a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99910000/99905900/99905884/31d34c88.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99910000/99905900/99905884/b1769cbe.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location 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. 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 ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/2fcc35d4.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Cudjoe Cottages, swimming pool, just 20 miles from Key West Cudjoe Key - Pool - Kitchen - Washer - Dryer 8.8 Excellent 146 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=34007879&PinnedHotelID=34007879&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33490000/33483800/33483790/w1917h1268x0y0-ddb8f2af.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West Cudjoe Key - Pool - Kitchen - Washer - Dryer 8.8 Excellent 153 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=33483790&PinnedHotelID=33483790&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/116000000/115560000/115555400/115555400/78a29cd6.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Diving Dolphin #268 - Ocean Views, Kayaks! 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Oceanfront, dockage, swimming pool Cutthroat Harbor Estates - Pool - Kitchen - Washer - Dryer 8.4 Very good 117 reviews £409 includes taxes & fees 6 Oct - 7 Oct [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-06&endDate=2025-10-07&selected=33547859&PinnedHotelID=33547859&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 36 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=94007975&PinnedHotelID=94007975&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/4480719e.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Reel Island Retreat #273 at Venture Out in the Florida Keys Cudjoe Key - Sea view - Pool - Hot tub - Kitchen 9.6 Exceptional 7 reviews £517 includes taxes & fees 6 Oct - 7 Oct [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-06&endDate=2025-10-07&selected=109794896&PinnedHotelID=109794896&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=2025-10-19&endDate=2025-10-20&selected=83440767&PinnedHotelID=83440767&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 ### 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 - 5.0 miles - Florida Keys Beaches - 10 min drive - 5.3 miles - Sugarloaf Beach - 23 min drive - 11.9 miles - Bahia Honda State Park - 31 min drive - 20.8 miles - Boca Chica Nude Beach - 41 min drive - 20.2 miles #### Getting around - Key West, FL (EYW-Key West Intl.) - 33 min drive #### Restaurants - ‪Kiki's Sandbar - ‬12 min drive - ‪Boondock's Grille & Drafthouse - ‬9 min drive - ‪Morning Joint - ‬3 min drive - ‪5 Brothers Two - ‬9 min drive - ‪Broil - ‬5 min drive ## Frequently asked questions ### Does Riley's Retreat - Venture Out 107 have a pool? > Yes, this property has a pool. ### Is Riley's Retreat - Venture Out 107 pet-friendly? > Yes, pets are allowed at this property. ### What time is check-in at Riley's Retreat - Venture Out 107? > Check-in begins at 3:00 PM. ### What time is check-out at Riley's Retreat - Venture Out 107? > Checkout is at 10:00 AM. ### Where is Riley's Retreat - Venture Out 107 located? > Situated on the waterfront, this cottage is steps away from Venture Key, Venture Out Keys and Out Key. Upper Sugarloaf Key and Crab Key are also within 6 miles (10 km). ## 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 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 ### 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 #### 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 #### 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 #### 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 ### 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 ### 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 ### 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. 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