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Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Cottage near Florida Keys Beaches in Summerland Key

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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 swimming pool area with palm trees and a view of the ocean.
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 single-story building with a flat roof, a small porch area, and a fenced yard.

Reviews

9.8 out of 10
Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 6

Popular amenities

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

Explore the area

View in a 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

Room options

About the neighborhood

Summerland Key

On waterfront.You'll find Venture Out Keys and Venture Key within a 15-minute walk of this Summerland Key cottage. Florida Keys Beaches and Out Key are also within 3 miles (5 km).
View more Cottages in Summerland KeyOpens in a new window

What's nearby

  • Upper Sugarloaf Key - 7 min drive - 4.5 miles
  • Florida Keys Beaches - 8 min drive - 4.6 miles
  • Upper Sugarloaf Sound - 8 min drive - 5.3 miles
  • Lower Sugarloaf Sound - 11 min drive - 7.6 miles
  • Big Pine Key Flea Market - 15 min drive - 11.4 miles

Getting around

  • Key West Intl. Airport (EYW) - 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
  • ‪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.

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.

Similar properties

Exterior
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
  • Ocean view
  • Pool
  • Kitchen
  • Washer
4.9 out of 5, Exceptional, 96 reviews
$354 nightly
The price is $395
Sep 27 - Sep 28
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Property amenities

Pool/Spa

  • Communal pool
  • Heated pool
  • Hot tub
  • Outdoor pool

Internet

  • Available in the cottage: WiFi

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Free toiletries
  • Shower
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Books
  • Games
  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Outdoor furniture

Laundry

  • Laundromat nearby

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a hospital
  • Near the marina
  • On the waterfront

Things to do

  • Bicycles
  • Billiards/pool table
  • Heated pool
  • Table tennis
  • Tennis
  • Basketball nearby
  • Fishing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing 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

  • Bicycles

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 20

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

Pets

  • No pets allowed

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 private host, not a professional engaged in trade or business. 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.

Frequently asked questions

How close is Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! to the airport?

This cottage is 21.1 mi (30-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! have an airport shuttle?

Airport shuttle services are not available at this cottage.

How close is Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! to the beach?

This cottage is 4.4 mi (9-min drive) from Florida Keys Beaches and 10.8 mi (21-min drive) from Sugarloaf Beach. Don't forget your sunscreen!

Does Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! offer free breakfast?

This cottage does not offer free breakfast.

Is there a casino at Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!?

No, there is no casino at this cottage.

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

Check-in begins at 3:00 PM.

Is there free parking at Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!?

Free parking is not available at this cottage.

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

This cottage features an outdoor pool.

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

There are no spa services available at this cottage.

How close is Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! to downtown Summerland Key?

This cottage is 1.9 mi away from Summerland Key.

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 16 out of 18 reviews
Rating 8 - Good. 1 out of 18 reviews
Rating 6 - Okay. 1 out of 18 reviews
Rating 4 - Poor. 0 out of 18 reviews
Rating 2 - Terrible. 0 out of 18 reviews

9.6/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Joseph R.

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

Verified traveler

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

Bryan M.

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

10/10 Excellent

Lisa F.

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

Kenneth C.

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

Andrew Y.

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

Bradi M.

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

Stephen L T.

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

Michelle L.

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

Deana C.

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

grace f.

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

Stephen C.

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

john h.

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

Beth R.

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

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