Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Photo gallery for Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

A balcony with two wooden chairs and a small table, overlooking a marina with boats and palm trees.
A compact kitchen with white cabinets, a microwave, a stove, and a refrigerator.
A bedroom with a bed, two bedside lamps, a nightstand, a framed picture, and star-shaped wall decorations.
A swimming pool area with palm trees and a view of the ocean.
A single-story building with a flat roof, a small porch area, and a fenced yard.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.

Popular amenities

  • Balcony
  • Spa pool on site
  • Outdoor pool
  • Barbecue
  • Air-conditioning
  • Refrigerator

Explore the area

View map
Cudjoe Key, FL
  • Place, Upper Sugarloaf Key
    ‪7 min drive‬
  • Place, Florida Keys Beaches
    ‪8 min drive‬
  • Place, Upper Sugarloaf Sound
    ‪8 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪38 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet

Spaces

Porch or lanai
Kitchen
Balcony

Add dates for prices

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  • Pool
  • Kitchen
  • Washing machine
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About the area

Summerland Key

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.
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Map
Cudjoe Key, FL

What's nearby

  • Upper Sugarloaf Key - 7 min drive - 7.3 km
  • Florida Keys Beaches - 8 min drive - 7.4 km
  • Upper Sugarloaf Sound - 8 min drive - 8.5 km
  • Boondocks Grille & Draft House - 10 min drive - 11.7 km
  • Lower Sugarloaf Sound - 11 min drive - 12.1 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 30 min drive

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬10 min drive
  • ‪Morning Joint - ‬3 min drive
  • ‪Kiki's Sandbar - ‬12 min drive
  • ‪Looe Key Tiki Bar & Restaurant - ‬10 min drive
  • ‪Tonio's Seafood Shack & Tiki Bar - ‬7 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!?

Checkout 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.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
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

9.6/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

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, 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
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

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

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

Nice place!

Clean, cute place! As described ! Owner very nice and easy to get ahold of!
Stayed 2 nights in Oct 2022
Response from VrboOwner on 20 Oct 2022
Thank you so much for choosing Island Oasis Oasis for your getaway! We loved hosting your group and look forward to seeing you again someday!
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

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, 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

Stayed 4 nights in May 2026
Verified review

10/10 Excellent

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