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Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

Summerland Key vacation home with kitchen

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Photo gallery for Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

A coastal resort with a swimming pool, beach area, and a view of the ocean.
An aerial view of a sports complex with multiple tennis courts, a basketball court, and a large white dome structure.
A two-story building with a covered porch and a balcony.
A living room with a ceiling fan, a television, and a large fish decoration on the wall.
A beachside pool area with thatched umbrellas, lounge chairs, and a clear view of the ocean.

Reviews

9.8 out of 10
Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 6862 sq ft

Popular amenities

  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Explore the area

View in a map
Cudjoe, 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

Close to the beach.Within a 10-minute walk of the vacation home, you'll find Venture Out Keys and Venture Key. Also, Out Key is within half a mile (1 km) and Florida Keys Beaches is within 6 miles (10 km).
View more Vacation Homes 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
  • Boondocks Grille & Draft House - 10 min drive - 7.3 miles
  • Lower Sugarloaf Sound - 11 min drive - 7.6 miles

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
  • ‪Looe Key Tiki Bar & Restaurant - ‬9 min drive
  • ‪Square Grouper Bar and Grill - ‬20 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

This property has 2 bedrooms 2 baths and sleeps 6 with all updated appliances furniture.& wifi There are 4 single kayaks and 1 dual Kayak with carts for the kayaks 6 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. Each bed room has a 32" TV . 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. Bring your boat Venture out has a free boat ramp.A small nightly storage fee is collected by venture out for Boat/ trailer extra Vehicles storage on-site, Overflow parking lot.

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Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Pool/Spa

  • Heated pool
  • Hot tub

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Limited onsite parking (max 1 space)

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • No elevator
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near an outlet shopping mall
  • Near the marina

Things to do

  • Bicycles
  • Billiards/pool table
  • Heated pool
  • Kayak
  • Pickleball
  • Tennis
  • Basketball nearby
  • Cycling nearby
  • Fishing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Deadbolt lock
  • Fire extinguisher
  • First aid kit

General

  • Bicycles
  • Unit size: 862 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in available
Minimum check-in age: 24

Check-out

Check-out before 10:00 AM
Contactless check-out available

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 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
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. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Property is also known as

Vrbo Property
Paradise in the Florida Keys
Oceanside Paradise in the Florida Keys

Frequently asked questions

How close is Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball to the airport?

This vacation home is 21.3 mi (31-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball to the beach?

This vacation home is 4.1 mi (8-min drive) from Florida Keys Beaches and 11 mi (22-min drive) from Sugarloaf Beach. Don't forget your sunscreen!

Does Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball?

No, there is no casino at this vacation home.

What time is check-in at Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball?

Check-in begins at 3:00 PM.

Is there free parking at Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball?

Free parking is not available at this vacation home.

Does Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball have a pool?

Yes, there's a heated pool.

Does Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball have a spa?

There are no spa services available at this vacation home.

How close is Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball to downtown Summerland Key?

This vacation home is 2 mi away from Summerland Key.

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 232 out of 259 reviews
Rating 8 - Good. 21 out of 259 reviews
Rating 6 - Okay. 5 out of 259 reviews
Rating 4 - Poor. 0 out of 259 reviews
Rating 2 - Terrible. 1 out of 259 reviews

9.8/10

Cleanliness

9.4/10

Amenities

10/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay. The whole family loved it.
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was a nice property and we enjoyed our stay
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a great time at Oceanside Paradise, had everthing we needed and the fishing was fantastic.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved the home and the entire Venture out facility. Biking was so much fun.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property is very clean! Plenty of space for all five of us. Area for cooking was perfect.Great location!The owners are very helpful in providing information and answering questions!
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was our third year stay at this location. We have always thoroughly enjoyed our stay. Thanks for such a nice place.
Stayed 8 nights in Apr 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a Great Stay!
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Wonderful Stay

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

8/10 Good

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

6/10 Okay

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 review

10/10 Excellent

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

Great place

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The unit was immaculately clean, absolutely adorable and they even left a welcome Keylime pie in the refrigerator for us. I had one minor issue that required the property manager to attend to- I no sooner reached out to the owners & the property manager was there & fixed issue immediately. Pool and property is great. Unit is not far from pool or the water but not right on the water. Definitely recommend property.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

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

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