Entire home

Riley's Retreat - Venture Out 107

Waterfront cottage in Summerland Key with a hot tub

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.

Wonderful

Entire home

2 bedrooms2 bathroomsSleeps 674 sq m

Popular amenities

Parking available
Dryer
Pet-friendly
Washer
Hot tub
Pool

Add dates for prices

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

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

Ocean view
Pool
Hot tub
Kitchen

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

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

Property is also known as

277418

About the area

Cudjoe Key, FL

What's nearby

Upper Sugarloaf Key - 9 min drive - 8.0 km
Florida Keys Beaches - 10 min drive - 8.5 km
Sugarloaf Beach - 23 min drive - 19.1 km
Bahia Honda State Park - 31 min drive - 33.5 km
Boca Chica Nude Beach - 41 min drive - 32.6 km

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
‪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?

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. Florida Keys Beaches is 2.4 mi (3.9 km) away.

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Riley's Retreat - Venture Out 107 Reviews

9.0

Wonderful

8.6/10

Cleanliness

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

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.

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

Stayed 5 nights in Nov 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!

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!

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!

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.

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.

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.

Stayed 6 nights in Dec 2024

10/10 Excellent

Yudeisy B.

25 Jun 2025

Stayed 8 nights in May 2025

Riley's Retreat - Venture Out 107

Photo gallery for Riley's Retreat - Venture Out 107

Reviews

Entire home

Popular amenities

Add dates for prices

About this property

Entire place

Riley's Retreat - Venture Out 107

Property amenities

Pool/Spa

Internet

Parking and transport

Kitchen

Bedrooms

Bathroom

Living spaces

Entertainment

Outdoor areas

Laundry

Comfort

Pets

Suitability/Accessibility

Location highlights

Things to do

Safety features

General

Similar properties

The Diving Dolphin #268 - Ocean Views, Kayaks!

The Diving Dolphin #268 - Ocean Views, Kayaks!

Policies

Check-in

Check-out

Special check-in instructions

Rules

Pets

Children and extra beds

Events

Smoking

Important information

You need to know

Property is also known as

About the area

What's nearby

Getting around

Restaurants

Frequently asked questions

Have a question?

Riley's Retreat - Venture Out 107 Reviews

Reviews

Wonderful

8.6/10

Reviews

10/10 Excellent

Brandon K.

Great house

Brandon K.

8/10 Good

Carl B.

Relaxing Stay

Carl B.

10/10 Excellent

Verified traveller

Great stay

Verified traveller

10/10 Excellent

Melissa M.

Love Venture Out!

Melissa M.

10/10 Excellent

Dorin O.

Great Place

Dorin O.

10/10 Excellent

Sandy B.

Fun time

Sandy B.

8/10 Good

Tks T.

Allows pets and clean!