8/10 Good
Mario G.
Sep 5, 2025
Disliked: Cleanliness
Mario G.
Stayed 3 nights in Aug 2025
Entire home
Riley's Retreat - Venture Out 107
Waterfront cottage in Summerland Key with a hot tub
Choose dates to view prices
Photo gallery for Riley's Retreat - Venture Out 107
Reviews
9.09.0 out of 10
Wonderful
Entire home
2 bedrooms2 bathroomsSleeps 6800 sq ft
Popular amenities
- Parking available
- Hot Tub
- Dryer
- Pool
- Pet friendly
- Washer
Explore the area
Cudjoe Key, FL
- Upper Sugarloaf KeyPlace, Upper Sugarloaf Key9 min drive
- Upper Sugarloaf SoundPlace, Upper Sugarloaf Sound11 min drive
- Florida Keys BeachesPlace, Florida Keys Beaches11 min drive
- Key West, FL (EYW-Key West Intl.)Airport, Key West, FL (EYW-Key West Intl.)46 min drive
Room options
About the neighborhood
Summerland Key
This cottage places you next to Venture Key and Venture Out Keys. The cottage includes a kitchen, a sofa bed, and a refrigerator.
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 Intl. Airport (EYW) - 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
About this property
Entire place
You'll have the entire home 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
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
The cottage is air-conditioned and features a kitchen and 2 bathrooms, and there's space to spread out with 2 bedrooms. Guests can enjoy a TV and stay connected with free WiFi. Other standard amenities include a washing machine, a sofa bed, and a coffee maker.
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Property amenities
Pool/Spa
- Communal pool
- Hot tub
Internet
- Available in the cottage: Free WiFi
Parking and transportation
- Parking on site
Kitchen
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dishwasher
- Ice maker
- Microwave
- Oven
- Refrigerator
- Stovetop
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
- Smoking not allowed
Location highlights
- Near the sea
- On the waterfront
Things to do
- Basketball nearby
- Fishing nearby
- Jet skiing nearby
- Kayaking nearby
- Scuba diving nearby
- Snorkeling 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
Policies
Check-in
Check-in time starts at 3:00 PM
Contactless check-in 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
- This property welcomes pets
- Service animals exempt from fees
Children and extra beds
Children allowed: ages 0-17
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
Onsite 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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
- Check-in: 3:00 PM
- Check-out: 10:00 AM
- Minimum check-in age: 27
We should mention
Details about charges, deposits, or other important information:
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
- This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
- Charges for extra guests may apply and vary depending on the property's policy.
- A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
- Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
- Onsite parties or group events are strictly prohibited.
Property is also known as
277418
Frequently asked questions
What's there to do near this cottage?
Located steps from Venture Out Keys, this cottage is in Summerland Key, and within a 10-minute walk of Venture Key and Out Key. You'll also find Florida Keys Beaches and Upper Sugarloaf Key within a short drive.
Is parking available on site at this cottage?
No, there isn't parking available at the cottage.
Is this cottage adjacent to a casino?
No, this cottage is not connected to a casino.
Will I find an indoor pool at this cottage?
No, this cottage doesn't have an indoor pool; however, there is a hot tub.
What will couples enjoy most about a stay at Riley's Retreat - Venture Out 107?
With a stay at this waterfront cottage, couples will appreciate amenities like a kitchen in each accommodation plus kitchens and water views in some.
Are there hot tubs at Riley's Retreat - Venture Out 107?
Yes, this cottage has a spa tub.
Does this cottage include breakfast service?
No, this cottage doesn't offer breakfast.
Will this cottage allow pets to stay for free?
Although pets can't stay for free, they are welcome at this cottage.
Are there connecting rooms at this cottage?
No, this cottage doesn't feature connecting guestrooms.
How close is the airport from this cottage?
The closest major airport to this cottage is Key West Intl. Airport (EYW), which is 21.6 mi away (33 minutes by car). Another top airport is Marathon, FL (MTH-Florida Keys Marathon), which is located 29.5 mi away (40-minute drive).
Are there rooms with balconies that I can book at Riley's Retreat - Venture Out 107?
Yes, every accommodation at Riley's Retreat - Venture Out 107 comes with a porch with some featuring water views.
Reviews
Riley's Retreat - Venture Out 107 Reviews
9.0
Wonderful
All reviews shown are from real guest experiences. Only travelers 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.
8.6/10
Cleanliness
Rating 10 - Excellent. 6 out of 11 reviews
10 - Excellent
6
Rating 8 - Good. 4 out of 11 reviews
8 - Good
4
Rating 6 - Okay. 1 out of 11 reviews
6 - Okay
1
Rating 4 - Poor. 0 out of 11 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 11 reviews
2 - Terrible
0
Reviews
10/10 Excellent
Brandon K.
Jul 7, 2025
Liked: Cleanliness
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
10/10 Excellent
Yudeisy B.
Jun 25, 2025
Yudeisy B.
Stayed 8 nights in May 2025
10/10 Excellent
Melissa M.
Mar 7, 2025
Liked: Cleanliness
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
8/10 Good
Tks T.
Jan 17, 2025
Liked: Cleanliness
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
6/10 Okay
Ann Marie Q.
Jan 6, 2025
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
Verified traveler
Nov 18, 2024
Liked: Cleanliness
Great stay
Quiet neighborhood close enough yet far enough from Key West madness
Verified traveler
Stayed 5 nights in Nov 2024
8/10 Good
Amanda H.
Jun 24, 2024
Liked: Cleanliness
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
10/10 Excellent
Dorin O.
Apr 30, 2024
Liked: Cleanliness
Great Place
As advertised. Very clean and well furnished with everything you need!
Dorin O.
Stayed 4 nights in Apr 2024
8/10 Good
Carl B.
Mar 24, 2024
Liked: Cleanliness
Relaxing Stay
Lovely place to stay and great resort.
Carl B.
Stayed 3 nights in Mar 2024
10/10 Excellent
Sandy B.
Jan 22, 2024
Liked: Cleanliness
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