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Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

Photo gallery for Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

Front / Side View of home
Front View
Well stocked Kitchen with new Stainless Appliances
Dining Room with seating for 6
Covered upper deck with tables and chairs for dining or entertaining

Reviews

9.8 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 680.3 sq m

Popular amenities

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer

Explore the area

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

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Convertible bed(s)

1 Queen Sofa Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Dining area

About this property

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

Description:

Beautiful newer 2 bedroom / 2 bath elevated tropical home near a waterfront common area in Venture Out, an Oceanside residential community (Unit #618). Relax on a large elevated covered deck for outdoor dining and entertaining and a downstairs covered area with high top table, lounge chairs and covered parking. A stainless steel gas grill enhances the outdoor dining. The home can sleep up to 6 adults in comfort.

The open Living area includes a cathedral ceiling, a full kitchen with stainless steel appliances with all dishes, silverware and cooking equipment, a dining room with a table for 6 and a living room.

The living room has a queen size sleeper sofa, chairs and love seat, a 50' Flat Screen Roku TV w/ enhanced cable and DVD game inputs, AM/FM CD player. Also included is a wheeled beverage cart that can be used indoors or on the deck.

The Master Bedroom has a queen bed with a 32' flat screen HD Smart Roku TV w/DVD, a double walk in mirrored closet and a full-size master bathroom with shower, vanity sink, toilet, and towels.

The Guest room has a queen bed, a 40” flat screen Smart Roku HDTV, DVD player, a walk in closet and a 2nd full-sized bathroom with shower, vanity sink, toilet, and towels just a few steps down the hall. Off of this bathroom is a stacked washer and dryer combo for your use.

Additional unit amenities include: Free Use of 4 kayaks, adult and children's bikes, Central Air Conditioning, Free WIFI, Washer/Dryer, Dishwasher, Ceiling fans, Microwave, Regular and K Cup Coffee maker, AM/FM CD player, Ice-maker, Ironing board, iron, hair dryers and beach towels for the pool or beach.

The community amenities include: 24 hour security, Lighted tennis and pickle ball courts, Olympic-sized heated pool, kiddie pool, spa Jacuzzi, ping pong, bocce ball courts, pickle ball, lighted basketball court, children's playground, pool table, darts, Marina complete with 2 ramps, gas, store, ATM and fish cleaning station, boat trailer parking onsite, open water picnic areas, ocean front tiki hut, lending library, post office - and MORE - ALL IN A GATED COMMUNITY with a mixture of RV sites and manufactured homes where you can feel safe and secure.

Six bikes (4 adult - 2 child) are provided for your riding pleasure at no extra charge. We also have sports equipment, fishing poles with basic tackle, a cooler and 6 beach chairs and umbrellas for trips to the beach, pool or off site.

Bring your boat! There is no charge for launching in at the Venture Out Marina (There is a small charge for overnight parking). The Florida Keys have some of the best fishing in the world! (Boat and trailer parking, as available is an additional daily charge by the park.) It is also a great spot for launching Kayaks. You can swim or fish from our open water areas. There are several Tiki Huts on the open water where picnicking is perfect!

KEY WEST is a twenty five minute drive down US Route 1. Experience the fabulous SUNSET CELEBRATION every night at Mallory Square. Take a day trip to the Dry Tortugas. DANCE the night away at Hog's Breath Saloon, Sloppy Joe's or one of the many bars of Key West. VISIT the Southernmost point, Hemmingway’s house, Key West Light and Fort Zachary Taylor. Take a sightseeing tour on the Key West Trolley or Conch Train. ENJOY a beautiful sunset cruise, snorkeling, SCUBA diving, fishing, parasailing and so much more.

Or you can simply enjoy a good book or the company of your family or spouse on the grounds of the resort.

Within several minutes we have some great restaurants. They include The Square Grouper, Boondocks and Loo Key Restaurant to name a few. Most offer good food, open air dining, reasonable prices and a relaxed atmosphere.

The Marina Store within walking distance in the park stocks many necessities, such as soft drinks, BEER and WINE. The Store also has a 24 hour ATM

SORRY, THIS IS A NO SMOKING / NO PET HOUSE. Smoking is allowed in the lower area (ground level) of the home.

This is a very clean rental unit with numerous amenities offered at a very reasonable rate. You will not be disappointed! We know you will have a marvelous time here in the gorgeous FLORIDA KEYS!

Please note that there is a $125.00 one time per party entry fee for our gated community that you will have to pay at the front gate.

Driving Distance: 3 Hours from Miami, and 3 1/2 Hours from FT. Lauderdale. 25 Minutes from Key West and Big Pine Key, home of the famous Key Deer.


Keywords: House
*Free WiFi
*A/C
*Outdoor Grill

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
Some children's games, movies, and 2 bikes
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Events

Events allowed
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Pets

No pets allowed
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Smoking

Smoking allowed: in designated areas
ONLY outside the unit with proper disposal.
1-vehicle parking only at the unit. Additional vehicles will need to go into overflow for $5-$10 per night depending on size if space available
A 1-time per reservation Venture Out registration fee of $125.00 is due upon arrival paid cash or credit card.

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
Parties and events are allowed on site. Maximum attendees: 6
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

About the area

Summerland Key

Located in Summerland Key, this holiday home 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. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with ecotours and cycling.
Map
Cudjoe Key, FL

What's nearby

  • Florida Keys Beaches - 6 min drive - 6.4 km
  • Upper Sugarloaf Key - 6 min drive - 6.6 km
  • Upper Sugarloaf Sound - 7 min drive - 7.9 km
  • Lower Sugarloaf Sound - 11 min drive - 11.5 km
  • National Key Deer Refuge Visitor Center - 15 min drive - 17.2 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
  • ‪Mangrove Mama's - ‬8 min drive
  • ‪Square Grouper Bar and Grill - ‬4 min drive

Frequently asked questions

Does Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security have a pool?

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

How much does it cost to stay at Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security?

As of 1 May 2026, prices found for a 1-night stay for 2 adults at Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security on 5 July 2026 start from NZ$296, 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: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security pet-friendly?

No, pets are not allowed at this property.

How much is parking at Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security?

On-site parking is available at the property.

What time is check-in at Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security?

Check-in begins at 3:00 PM.

What time is check-out at Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security?

Checkout is at 10:00 AM.

Where is Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security located?

This family-friendly Summerland Key holiday home is located on the waterfront, within a 15-minute walk of Venture Out Keys, Venture Key and Out Key. Florida Keys Beaches and Upper Sugarloaf Key are also within 6 miles (10 km).

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. 229 out of 264 reviews
Rating 8 - Good. 31 out of 264 reviews
Rating 6 - Okay. 2 out of 264 reviews
Rating 4 - Poor. 1 out of 264 reviews
Rating 2 - Terrible. 1 out of 264 reviews

9.8/10

Cleanliness

9.6/10

Amenities

9.6/10

Property conditions & facilities

9.8/10

Check-in

9.6/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Michael C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay at Venture out, the facilities were great. Location to everything was nice. We would definitely stay again.
Stayed 7 nights in Apr 2026
Verified

10/10 Excellent

Constance L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Spent most of my time out on the Deck, both day and night. Weather fantastic!! Loved having kayaks & bicycles at anytime. Host takes extreme pride in their property and it shows!!! Neighbors very friendly and helpful! Loved having paper instructions to activate TV and learn about activities within the complex. Definitely a 20 out of 10 property and I’d love to stay again!!! Thank you!!
Stayed 30 nights in Mar 2026
Verified

10/10 Excellent

Brittany

Liked: Cleanliness, amenities, property conditions & facilities, communication
This place was perfect for Our Christmas Vacation. It really was paradise. When i come back this place is where ill be staying
Stayed 4 nights in Dec 2025
Verified

10/10 Excellent

Shelley

Liked: Cleanliness, property conditions & facilities, communication
Absolutely love love love Venture Out! This unit is phenomenal! We had an amazing family vacay!
Stayed 6 nights in Dec 2025
Verified

10/10 Excellent

Elizabeth T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great House and amenities
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Dan R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay in Venture Out
Stayed 8 nights in Sep 2025
Verified

10/10 Excellent

Matthew W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean and awesome location
Stayed 5 nights in Sep 2025
Verified

10/10 Excellent

Chad B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great vacation. House was wonderful.
Stayed 7 nights in Sep 2025
Verified

10/10 Excellent

James M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay here with our 2 kids. The pool is awesome and heated to a very comfortable temperature. There are lots of chairs around the pool and places to sit. We liked the variety of common areas around the property and really enjoyed the bicycles. It was too rough for kayaking due to wind but it looks like a great area to kayak. The house is clean and comfortable with every amenity you could need. Some reviews mention aggressive security personnel but we found them to be polite and friendly. I appreciate the extra level of security that keeps the area nice and very family friendly.
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Kylene B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was great from check in to the venture out community and facilities to the actual home we loved it all.
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Cindy G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was very clean when we arrived. There was every cooking item available for cooking. The distance to Key West was very nice.
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Amy B.

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

Clean, affordable vacay rental

The home was clean, well decorated and has everything we needed plus some for our vacation. Highly recommended for families.
Stayed 6 nights in Jul 2025
Verified

10/10 Excellent

Dawn K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was spacious, clean and as listed. We had a very nice day.
Stayed 4 nights in Aug 2025
Verified

10/10 Excellent

Deborah F.

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

Great place to stay!

Home was clean and great location! Would definitely stay here again!
Stayed 3 nights in Mar 2025
Verified

10/10 Excellent

Crystal B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home was very nice and exactly like photos. Just a little distance from the pool so rented a golf cart which was nice. Owner was very responsive when we had an issue with the grill and had it fixed promptly.
Stayed 13 nights in Aug 2025
Verified

10/10 Excellent

Edward M.

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

Great homebase in Keys

Wonderful place to stay in the Keys for our family. All the items you need and great location. Would return again!
Stayed 3 nights in Apr 2025
Verified

10/10 Excellent

JOHN S.

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

Spring break getaway

Had a great time at the property many amenities to enjoy. Perfect location to bounce from key to key would definitely come back again.
Stayed 5 nights in Mar 2025
Verified

10/10 Excellent

Amy W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was amazing! Very pleased.
Stayed 4 nights in Jun 2025
Verified

10/10 Excellent

Jamie G.

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

Girls trip

Had a great time. And the pool was excellent.
Stayed 7 nights in Apr 2025
Verified

10/10 Excellent

ryan q.

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

Fantastic Property

Very well maintained and well stocked property. Development is well maintained and managed, along with good amenities. Location is convienent for this area of the Keys.
Stayed 7 nights in Apr 2025
Verified

10/10 Excellent

Lillian B.

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

Clean, Inviting, Relaxing

Overall, we had a great time. The rental was clean, well equipped, if you chose to cook. My sister and I loved it being close to Key West, plus several good restaurants in immediate area. Neighbors were quiet. Love having car under house, it was always cool.
Sunrise
Sunset
Stayed 4 nights in May 2025
Verified

10/10 Excellent

Jenn S.

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

Christmas Getaway

Clean, easy access, friendly complex/neighborhood.
Stayed 7 nights in Dec 2024
Verified

10/10 Excellent

Verified traveller

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

Denise

Beautiful place! Great location!
Stayed 5 nights in Nov 2024
Verified

10/10 Excellent

Smith's Island R.

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

Family Keys 2025

We loved our stay. Our friends took us out to the Gulf and Atlantic almost every day. It was a lovely stay. Our kids loved the bikes and pool. We enjoyed the hot tub. We hope to be back soon!
Stayed 7 nights in Mar 2025
Verified

8/10 Good

Cathy

Liked: Cleanliness, amenities, property conditions & facilities, communication
It was located where we wanted to stay
Stayed 3 nights in Aug 2022

About the host

Hosted by Waterfront Keys Realty

Host profile image
We are a retired couple with a vacation home in a great location. We enjoy traveling and sight seeing. We especially love the Florida Keys and try to spend several weeks there each year.

Why they chose this property

We fell in love with the Florida Keys on our first visit. The tropical weather, attractions and relaxed atmosphere were exactly what we were looking for. To us, this is a tropical paradise with out leaving the US! It is a bonus that we don't have to fly to get here.

What makes this property unique

The resort amenities, The relaxed atmosphere, the tropical weather, the scenery, the open air dining, the fishing and the fun of Key West and .many islands.

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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