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Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Photo gallery for Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Exterior
Outdoor dining
Property grounds
Terrace/patio
Living area

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area
2 bedrooms2 bathroomsSleeps 6862 sq ft

Popular amenities

  • Heated Pool
  • Hot tub on site
  • Onsite parking available
  • Kitchen
  • Washer
  • Air conditioning

Explore the area

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

Rooms & beds

2 bedrooms (sleeps 6)

Living Room 1

1 Double Sofa Bed

Master

1 Queen Bed

Second

3 Twin Beds

2 bathrooms

Hall

Toilet · Shower only

Master

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Dining area

About this property

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

This oceanside property has 2 beds 2 baths and sleeps 6 with all updated appliances and furniture. There are kayaks and carts for the kayaks Bikes, BBQ Grill, ice machine on the property for your use . The home is on stilts with covered porch and sitting area with Table for relaxing and taking in the view. On Venture Out property, there is a large pool, hot tub, tennis court, ocean access with a ramp at the marina with fuel, and tackle for your fishing needs. There is also a convience store for food and drink.
THIS IS A GATED COMMUNITY AND THE GATE WILL CHARGE $125.00 DOLLARS FOR THE GROUP NO MATTER HOW MANY DAYS! THIS REGISTRATION FEE IS DUE AT CHECK-IN. IT is charged and collected solely by VENTURE OUT RESORT. That is a separate fee from the home and will be collected at the gate when you arrive. A parking permit will be given to you at the gate while you are renting the house only one car is permitted under the home. A nightly storage fee is collected by venture out for Boat/ trailer extra Vehicles storage on-site, Overflow parking lot.
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 3:00 PM
Minimum age to rent: 24
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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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 indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock

About the neighborhood

Summerland Key

Located in Summerland Key, this vacation home is near the beach. Florida Keys Beaches and Coupon Bight Aquatic Preserve reflect the area's natural beauty and area attractions include Blue Hole and Wilhelmina Harvey Park. Big Munson Island and Looe Key National Marine Sanctuary are also worth visiting. Kayaking, scuba diving, and snorkeling offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
View more Vacation Homes in Summerland KeyOpens in a new window
Map
Cudjoe, FL

What's nearby

  • Florida Keys Beaches - 7 min drive - 7.1 km
  • Upper Sugarloaf Key - 7 min drive - 7.3 km
  • Upper Sugarloaf Sound - 8 min drive - 8.6 km
  • Lower Sugarloaf Sound - 12 min drive - 12.1 km
  • National Key Deer Refuge Visitor Center - 16 min drive - 17.9 km

Getting around

  • Key West Intl. Airport (EYW) - 31 min drive

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Morning Joint - ‬16 min walk
  • ‪Kiki's Sandbar - ‬11 min drive
  • ‪Mangrove Mama's - ‬7 min drive
  • ‪Square Grouper Bar and Grill - ‬20 min walk

Frequently asked questions

Does Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill have a pool?

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

How much does it cost to stay at Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill?

As of May 2, 2026, prices found for a 1-night stay for 2 adults at Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill on May 4, 2026 start from $457, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill?

Check-in begins at 3:00 PM.

What time is check-out at Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill?

Check-out is at 10:00 AM.

Where is Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill located?

Situated near the beach, this vacation home is within a 10-minute walk of Venture Out Keys, Venture Key, and Out Key. Florida Keys Beaches and Upper Sugarloaf Key are also within 6 mi (10 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 220 out of 247 reviews
Rating 8 - Good. 21 out of 247 reviews
Rating 6 - Okay. 5 out of 247 reviews
Rating 4 - Poor. 0 out of 247 reviews
Rating 2 - Terrible. 1 out of 247 reviews

9.8/10

Cleanliness

9.4/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

9.8/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Andrea B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The accommodation was very clean and equipped with everything one could possibly need for a comfortable stay. We enjoyed it very much.
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Amy A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a beautiful updated propery in a geat resort setting. The entire house is fully equipped.we had a lovely stay and look forward to going back!
Stayed 16 nights in Mar 2026
Verified

10/10 Excellent

Lori R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Was fully stock. Everything was very nice!
Stayed 5 nights in Apr 2026
Verified

10/10 Excellent

Gayle S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Do not hesitate to rent this house. Well stocked, comfy beds, bikes and kayaks are an added bonus! Great gated safe community. Everything perfect!
Stayed 6 nights in Mar 2026
Verified

10/10 Excellent

Colleen V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our amenities were above what was expected compared to other properties. Our place was a home away from home.
Stayed 16 nights in Feb 2026
Verified

10/10 Excellent

Thomas W.

Liked: Cleanliness, check-in, communication, listing accuracy
Host was very responsive and amenities were great. It was clean and comfortable.
Stayed 14 nights in Jan 2026
Verified

10/10 Excellent

Nikki M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was communicative and quick to respond. Amenities were beautiful and enjoyable.
Stayed 4 nights in Feb 2026
Verified

6/10 Okay

Kristina J.

Liked: Cleanliness, check-in, communication, listing accuracy
Disliked: Location
The unit and facility were well equipped. The listing did not explain that the unit was within a trailer park which was disappointing.
Stayed 5 nights in Mar 2026
Verified

10/10 Excellent

Nancy A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay, and especially enjoyed having easy access to kayaks and bicycles that were in good condition.
Stayed 3 nights in Nov 2025
Verified

8/10 Good

Liz H.

Liked: Cleanliness, communication
Disliked: Listing accuracy
Host, amenities
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Mark S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We really enjoyed the bikes. Would have liked to use the kayaks but the weather was too cold.
Stayed 4 nights in Dec 2025
Verified

10/10 Excellent

Kathleen C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice place. Perfect size for family with 2 college age kids. Biked around the complex. Used the hot tub. Easy drive to Key West. Kitchen well stocked. Beds comfortable.
Stayed 4 nights in Dec 2025
Verified

10/10 Excellent

Maureen F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved the unit— it was immaculately clean, tastefully decorated, and well maintained. The Key Lime pie was a nice surprise, but the cherry on the top was the bicycles and kayaks. It was great fun riding around the park, and kayaking in and out of the canals! Thank you so much!!
Stayed 2 nights in Dec 2025
Verified

10/10 Excellent

Aleshia F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an amazing time. The house was great and loved the neighborhood.
Stayed 5 nights in Aug 2025
Verified

10/10 Excellent

Sheila L.

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

Wonderful Stay

We really enjoyed staying here.
Stayed 5 nights in May 2022
Verified

10/10 Excellent

Emma T.

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

Two day stay!

My mom and I were absolutely amazed by the property, we loved everything and hope to come back again!
Stayed 2 nights in Apr 2025
Verified

8/10 Good

kyle t.

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

Family vacation

House was clean and neighborhood nice. Plenty of room for entire family. Nice deck and good amenities.
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Keida G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is by far the best property we have rented in Venture Out. Everything was amazing, everything was well thought out, super clean, and the extra little thoughtful touches went a long way! We really enjoyed the complimentary pie and the book was very well put together and helpful!
Stayed 4 nights in Aug 2025
Verified

10/10 Excellent

Chanh H.

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

Great Stay!

Great stay! Great amenities and clean
Stayed 2 nights in Feb 2022
Verified

10/10 Excellent

Michael B.

Liked: Cleanliness, communication, location, listing accuracy
The kitchen was fully equipped except for a toaster....very well organized.The porch had a great view. was very clean outside. we liked the bikes, towels and coolers. it could use beach chairs. our property manager was great! She popped her head in our house when we arrived at 3:00 when our email said. our only complaint is we arrived early at the guard shack before 3:00 and the lady was rude to us by saying we need to wait until 4:00. No greeting of welcome to Venture Out or let me check on your house status if its ready.
Stayed 6 nights in Jan 2026
Verified

10/10 Excellent

Brett W.

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

Great place

Great place. Would stay here again
Stayed 4 nights in May 2023
Verified

10/10 Excellent

David A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location. Very affordable and very well cared for. Short drive to Key West or any other things you may want to do in the Keys. Nice community swimming pool and sure. Great access to the water for boating or fishing.
Stayed 4 nights in Jun 2025
Verified

10/10 Excellent

Betty Z.

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

Wonderful Spring Vacation

A very nice place for a vacation with friends
Stayed 5 nights in Mar 2024
Verified

10/10 Excellent

Amber

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

Paradise awaits

The property and all of the amenities were absolutely amazing! Hosts Rick and Laura were very kind and made sure we enjoyed our stay. This was my first trip to the keys and I will definitely book again with them!
Stayed 3 nights in Apr 2025
Verified

10/10 Excellent

Susan F.

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

Great family vacation placr

We loved our stay here! This place had everything that we needed. The resort was safe for my kids to roam around for pickleball, swimming, and fishing. Thank you!
Stayed 6 nights in Mar 2025

About the host

Hosted by Rick & Laura Penn

Host profile image
Hi! As a child we always vacationed in the Florida Keys and love being on the water fishing and enjoying the atmosphere in the keys. It's been our dream to own a vacation home in the keys, we would like to share our Paradise with you!

Languages:

English

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