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Riley's Retreat - Venture Out 107

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Outdoor dining
Fridge, microwave, oven, stovetop
Property grounds
Dining
Fridge, microwave, oven, stovetop

Reviews

9.0 out of 10
Wonderful

Entire home

2 bedrooms2 bathroomsSleeps 6800 sq ft

Popular amenities

  • Parking available
  • Hot Tub
  • Dryer
  • Washer
  • Pool
  • Pet friendly

Explore the area

View in a map
Cudjoe Key, FL
  • Venture Out Keys
  • Upper Sugarloaf Key
    ‪9 min drive‬
  • Florida Keys Beaches
    ‪10 min drive‬
  • Key West, FL (EYW-Key West Intl.)
    ‪40 min drive‬

Room options

About the neighborhood

Summerland Key

Seaside stay .Within a 5-minute walk of the cottage, you'll find Venture Key and Venture Out Keys. Also, Out Key is within half a mile (1 km) and Florida Keys Beaches is within 3 miles (5 km).
View more Cottages in Summerland KeyOpens in a new window

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 Intl. Airport (EYW) - 33 min drive

Restaurants

  • ‪Kiki's Sandbar - ‬12 min drive
  • ‪5 Brothers Two - ‬9 min drive
  • ‪Morning Joint - ‬3 min drive
  • ‪Broil - ‬5 min drive
  • ‪Square Grouper Bar and Grill - ‬4 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

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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

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 welcome
  • Service animals 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

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    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. Onsite parties or group events are strictly prohibited.

Property is also known as

277418

Frequently asked questions

How close is Riley's Retreat - Venture Out 107 to the airport?

This cottage is 21.6 mi (33-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Riley's Retreat - Venture Out 107 have an airport shuttle?

Airport shuttle services are not available at this cottage.

How close is Riley's Retreat - Venture Out 107 to the beach?

This cottage is 4.3 mi (9-min drive) from Florida Keys Beaches and 11.4 mi (20-min drive) from Sugarloaf Beach. Don't forget your sunscreen!

Does Riley's Retreat - Venture Out 107 offer free breakfast?

This cottage does not offer free breakfast.

Is there a casino at Riley's Retreat - Venture Out 107?

No, there is no casino at this cottage.

What time is check-in at Riley's Retreat - Venture Out 107?

Check-in begins at 3:00 PM.

Is there free parking at Riley's Retreat - Venture Out 107?

Free parking is not available at this cottage.

Does Riley's Retreat - Venture Out 107 have a pool?

Yes, there's a pool.

Does Riley's Retreat - Venture Out 107 have a spa?

There are no spa services available at this cottage.

How close is Riley's Retreat - Venture Out 107 to downtown Summerland Key?

This cottage is 2 mi away from Summerland Key.

Riley's Retreat - Venture Out 107 Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 6 out of 10 reviews
Rating 8 - Good. 3 out of 10 reviews
Rating 6 - Okay. 1 out of 10 reviews
Rating 4 - Poor. 0 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 reviews

9.2/10

Cleanliness

Reviews

10/10 Excellent

Brandon K.

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
Stayed 6 nights in Jun 2025

10/10 Excellent

Yudeisy B.

Stayed 8 nights in May 2025

10/10 Excellent

Melissa M.

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!
Stayed 6 nights in Mar 2025

8/10 Good

Tks T.

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.
Stayed 4 nights in Jan 2025

6/10 Okay

Ann Marie Q.

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.
Stayed 6 nights in Dec 2024

10/10 Excellent

Verified traveler

Liked: Cleanliness

Great stay

Quiet neighborhood close enough yet far enough from Key West madness
Stayed 5 nights in Nov 2024

8/10 Good

Amanda H.

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.
Stayed 5 nights in Jun 2024

10/10 Excellent

Dorin O.

Liked: Cleanliness

Great Place

As advertised. Very clean and well furnished with everything you need!
Stayed 4 nights in Apr 2024

8/10 Good

Carl B.

Liked: Cleanliness

Relaxing Stay

Lovely place to stay and great resort.
Stayed 3 nights in Mar 2024

10/10 Excellent

Sandy B.

Liked: Cleanliness

Fun time

This property was clean and loved the decor. It was great to have the boat at the dock. Friendly neighbors!
Stayed 13 nights in Jan 2024