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Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

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A balcony with two wooden chairs and a small table, overlooking a marina with boats and palm trees. - Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! (Cudjoe Key)
A swimming pool area with palm trees and a view of the ocean. - Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! (Cudjoe Key)
A single-story building with a flat roof, a small porch area, and a fenced yard. - Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! (Cudjoe Key)
A compact kitchen with white cabinets, a microwave, a stove, and a refrigerator. - Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! (Cudjoe Key)
A bedroom with a bed, two bedside lamps, a nightstand, a framed picture, and star-shaped wall decorations. - Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! (Cudjoe Key)
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! provides a hot tub and more. Adventurous travelers may like the bicycling at this cottage. Stay connected with in-room WiFi.

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Ocean view
  • Pool
  • Hot tub
  • Kitchen
  • Air conditioning
  • Barbecue grill

Add dates for prices

About this property

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

  • Enjoy our little peace of paradise! Come and make memories at this laid back and family-friendly waterfront home. Located in a gated community, just 20 miles from Key West, this cottage is the perfect place if you want to relax and re-energize after a day of adventures and activities during your time in the Florida Keys!

    VO 453 - Island Oasis
    Open Water Views 17' Seawall
    Enjoy expansive open water views from this beautiful midrise, a 2bd/1.5Ba vacation home in a highly desired 24 hour gated community. This home features a 17' seawall overlooking a 60' wide canal and Atlantic Ocean, great for launching your kayaks, paddleboards or small boat. Enjoy stunning sunrises and peaceful evenings right from your porch!

    Both bedrooms feature a queen sized bed and flat screen tv. The smaller bedroom is attached to a half bath. The main bathroom has a standup shower and plenty of counter space. The kitchen is fully equipped, including a coffee maker, filters, sugar and tea.

    Additional amenities include: Central air conditioning, ceiling fans, WIFI, streaming cable, family games, iron, dishwasher, queen size blowup mattress for the surprise extra guest/s, BBQ Grill and BBQ utensils.

    We are located in a spotlessly clean gated community with 24 hour security, marina, ship store, boat ramps, picnic garden, heated pool, hot tub, basketball, playground, pickle ball, bocce ball and tennis, pavilion and club house for activities, over 4 miles of paved streets.
    SECURITY DEPOSIT REQUIRED, NO SMOKING,
    7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL,
    OVERFLOW PARKING ADDITIONAL FEE 14 DAYS MAX
    *** IMPORTANT *** WHEN ENTERING, THERE IS A ONE TIME AMENITIES FEE OF $125.00 - DUE UPON ARRIVAL. THIS FEE IS PAID DIRECTLY TO VENTURE OUT AND GOES TOWARDS ALL OF THE GREAT AMENITIES THIS RESORT HAS TO OFFER.

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About the neighborhood

Located in Summerland Key, this cottage is on the waterfront. Florida Keys Beaches and Coupon Bight Aquatic Preserve reflect the area's natural beauty and area attractions include Blue Hole and Big Munson Island. With jet skiing, kayaking, and scuba diving nearby, you'll find plenty of adventures in the water. Visit our Summerland Key travel guide
View more Cottages in Summerland Key
Map
FL, Cudjoe Key

What's nearby

  • A wooden signpost with city names and distances, a beach with umbrellas, and lounge chairs.
    Florida Keys Beaches
    8 min drive - 7.4 km
  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    44 min drive - 45.3 km
  • A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.
    Southernmost Point
    45 min drive - 45.7 km
  • A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.
    Mallory Square
    45 min drive - 45.9 km
  • A beach with clear turquoise water, white sand, and palm trees.
    Sombrero Beach
    49 min drive - 60.9 km

Getting around

  • Key West Intl. Airport (EYW)
    30 min drive

Restaurants

  • Morning Joint
    3 min drive
  • Kiki's Sandbar
    12 min drive
  • Boondock's Grille & Drafthouse
    10 min drive
  • Tonio's Seafood Shack & Tiki Bar
    7 min drive
  • Square Grouper Bar and Grill
    4 min drive

Frequently asked questions

Does Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!?

Check-in begins at 3:00 PM.

What time is check-out at Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!?

Check-out is at 10:00 AM.

Where is Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! located?

Situated on the waterfront, this cottage is 0.6 mi (1 km) from Venture Out Keys and 2.4 mi (3.9 km) from Florida Keys Beaches. Venture Key and Out Key are also within 15 minutes.

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Reviews

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! Reviews

9.8

Exceptional

9.6

Cleanliness

10

Location
Rating 10 - Excellent. 17 out of 19 reviews
Rating 8 - Good. 1 out of 19 reviews
Rating 6 - Okay. 1 out of 19 reviews
Rating 4 - Poor. 0 out of 19 reviews
Rating 2 - Terrible. 0 out of 19 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

Cozy place with a great view. Everyone was so friendly!
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was great!!! Unit very clean well stocked with beautiful view.
Stayed 10 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect get away.

Clean. Comfortable. Great location. We will be staying again.
Stayed 3 nights in Aug 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Last minute trip to the Keys

The property was in a great location, just 30 mins from Key West. The owners allowed us early access to the property and were quick to respond to our questions. Property and contents are just as described online. We truly enjoyed our stay and we WILL be returning to this property, as soon as we can.
Stayed 2 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Wonderful communication and warm welcome feeling to the place we really enjoyed our visit and the kayaking was wonderful to have outside the house
Stayed 6 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Ocean view
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Overall an amazing place

Even if it was a short stay, we enjoyed it and will be staying here again in the future.
Stayed 3 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Spot

The owners were fantastic to deal with and the house was great.
Stayed 4 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
All was excellent
Stayed 14 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice place!

Clean, cute place! As described ! Owner very nice and easy to get ahold of!
Stayed 2 nights in Oct 2022
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent vacation stay

The house was extremely clean and very cute. Having the bicycles available for use was a huge plus since we were visiting family near by. The AC in the bedroom was a little warm and the lock on the front door was a bit tricky. Overall a great stay!
Stayed 3 nights in Feb 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spiritual retreat

My husband and 2 of our friends came to Big Pine for a spiritual retreat. We've stayed at venture out previously in other rentals. This was by far the best! Comfortable and clean. We will be staying again for sure!
Stayed 3 nights in Apr 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place on the canal.

Nice little 2 bedroom place at the end of the canal. Owners made it simple to check-in and check-out. There was no onsite trailer parking available at Venture Out but there were several places nearby that had available storage. Place was clean and comfortable.
Stayed 2 nights in Aug 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Host

We had no problems with the property and the only questions we had were answered very promptly. We will book this property again. If you are going to dock a boat behind the house, communicate with host first as the wet slip can not accommodate a very large boat.
Stayed 3 nights in Jul 2025
Verified review

6/10 Okay

Liked: Cleanliness, location
Disliked: Check-in, communication, listing accuracy

expensive

It was close to Key West, but the resort fee was unexpected
Stayed 1 night in Apr 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house in a great location. Venture Out is a wonderful spot for people of all ages, including activities for all my kids (4-11) and one of the nicer pools I’ve enjoyed. House had everything we needed for a successful Keys adventure staging area. Only negative is the master bed was a little soft for our tastes.
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Check-in, communication, location, listing accuracy
Host was very responsive and cordial. Would definitely book again.
Stayed 5 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 5 nights in Apr 2025