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Oceanside in the FL Keys Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

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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.
Smart TV
Exterior
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

This vacation home places you within a 10-minute stroll of Venture Out Keys and Venture Key. The vacation home includes a kitchen, a balcony, and a refrigerator.
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
  • 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) - 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
  • ‪The Bent Prop - ‬6 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.

Oceanside in the FL Keys 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 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.
The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a balcony, and there's space to spread out with 2 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a coffee maker, and an ironing board.

Similar properties

Exterior
SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
  • Ocean view
  • Pool
  • Kitchen
  • Washer
9.8 out of 10, Exceptional, 93 reviews
$470 nightly
The price is $522
Aug 20 - Aug 21
Total with taxes and fees
SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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
  • Check-in: 3:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 24

We should mention

Details about charges, deposits, or other important information:

  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

Additional information about polices, regulations, and more:

  • There are no elevators.

Property is also known as

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

Frequently asked questions

What can I see close to this vacation home?

This vacation home in Summerland Key is within a 10-minute walk of Venture Out Keys, Venture Key, and Out Key. You'll also find Florida Keys Beaches and Upper Sugarloaf Key within a short drive.

Will I be able to park at Oceanside in the FL Keys Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball?

Yes, though there is a max of 1 space. You'll find a max of limited parking spaces.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, this vacation home doesn't have an indoor pool; however, there is a hot tub.

What do couples enjoy most about Oceanside in the FL Keys Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball?

Couples staying at this vacation home will appreciate amenities like a kitchen and a smart TV as well as a hot tub.

Does Oceanside in the FL Keys Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball have a hot tub?

No, but guests can enjoy a heated pool at this vacation home.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay free of charge?

No, pets aren't allowed at this vacation home.

Does Oceanside in the FL Keys Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball have connecting rooms available?

No, there aren't connecting guestrooms at this vacation home.

Where is the closest airport to this vacation home?

The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 21.3 mi away (31 minutes by car). Another top airport is Marathon, FL (MTH-Florida Keys Marathon), which is located 29.2 mi away (42-minute drive).

Can I book a room with a balcony at Oceanside in the FL Keys Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball?

Yes, every house at Oceanside in the FL Keys Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball comes with a balcony.

Oceanside in the FL Keys Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 229 out of 256 reviews
Rating 8 - Good. 21 out of 256 reviews
Rating 6 - Okay. 5 out of 256 reviews
Rating 4 - Poor. 0 out of 256 reviews
Rating 2 - Terrible. 1 out of 256 reviews

9.8/10

Cleanliness

9.4/10

Amenities

10/10

Property conditions & facilities

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

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

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

Lawrence W.

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

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

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

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

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

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

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

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

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

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

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

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

Kristi Z.

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

Cute place

Good accomodations
Stayed 3 nights in Dec 2024
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

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
Verified

8/10 Good

Elaine B.

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

Cudjoe Key Retreat

Great location and very nice community.
Stayed 7 nights in Feb 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

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