Entire home

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

Family-friendly vacation home with an outdoor pool and a hot tub

Choose dates to view prices

Where to?

Dates

October 2025

November 2025

Overview
Amenities
Policies
Location

Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 6864 sq ft

Popular amenities

Parking available
Kitchen
Dryer

Explore the area

Cudjoe Key, FL

Place, Venture Out Keys
Place, Upper Sugarloaf Key
‪7 min drive‬
Place, Florida Keys Beaches
‪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 leisurely stroll of Venture Out Keys and Venture Key. The vacation home includes a kitchen, a balcony, and a sofa bed.

View more Vacation Homes in Summerland Key

What's nearby

Upper Sugarloaf Key - 7 min drive - 4.3 miles
Florida Keys Beaches - 8 min drive - 4.6 miles
National Key Deer Refuge Visitor Center - 16 min drive - 10.7 miles
Sugarloaf Beach - 21 min drive - 11.2 miles
Bahia Honda State Park - 29 min drive - 20.2 miles

Getting around

Key West Intl. Airport (EYW) - 30 min drive

Restaurants

‪Kiki's Sandbar - ‬12 min drive
‪Boondock's Grille & Drafthouse - ‬10 min drive
‪5 Brothers Two - ‬9 min drive
‪Morning Joint - ‬3 min drive
‪Broil - ‬5 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 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 hammock, 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 new 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, 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, 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 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 4 beach chairs 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 is an additional daily charge by the park.) It is also a great spot for Kayaks. You can swim or fish from our open water areas. There is a big TIKI HUT 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, SCUB 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

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 expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a washer/dryer, a sofa bed, and a coffee maker.

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Pool
Pet friendly
Parking included
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$220 nightly

Oct 26 - Oct 27

Total with taxes and fees

Property amenities

Beach

Beach loungers
Beach towels

Pool/Spa

Communal pool
Fenced private pool
Heated pool
Hot tub
Outdoor pool

Internet

Available in the house: Free WiFi

Parking and transportation

Car recommended
RV/bus/truck parking (surcharge) on site

Kitchen

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

Dining

Dining table

Bedrooms

2 bedrooms
Bedsheets provided
Sofa bed

Bathroom

2 bathrooms
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided

Living spaces

Dining table
Living room

Entertainment

Books
CD player
DVD player
Games
Music library
Smart TV with cable/satellite channels
Stereo
Video library

Outdoor areas

Balcony
Gas grill
Outdoor furniture
Picnic area

Laundry

Laundry facilities
Washer/dryer

Work spaces

Printer

Comfort

Air conditioning
Ceiling fan
Heating

Pets

No pets allowed

Suitability/Accessibility

If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
Upper floors accessible by stairs only
Wheelchair accessibility
Wheelchair-accessible path of travel
Designated smoking areas
Note from host: ONLY outside the unit with proper disposal.

Services and conveniences

Iron/ironing board
Meal delivery service
Phone

Location highlights

Near the bay
Near the marina
Near the ocean
On the waterfront

Things to do

Arcade/game room
Bicycles
Billiards/pool table
Fish cleaning table
Heated pool
Kayak
Table tennis
Tennis
Water sports equipment
Basketball nearby
Birdwatching nearby
Cycling nearby
Ecotours nearby
Fishing nearby
Golfing nearby
Jet skiing nearby
Kayaking nearby
Motor boating nearby
Parasailing nearby
Sailing nearby
Scuba diving nearby
Snorkeling nearby
Swimming nearby
Water skiing nearby
Water tubing nearby
Wildlife walks nearby
Windsurfing nearby

Safety features

No carbon monoxide detector or gas appliances (host has indicated there are no carbon monoxide detectors or gas appliances on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
First aid kit
Fire extinguisher

General

Bicycles
Gated community
Property located in a resort
Unit size: 864 square feet

Policies

Check-in

Check-in time starts at 3:00 PM

Minimum check-in age: 25

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

Rules

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.

Pets

This property doesn't allow pets

Children and extra beds

Note from host: Some children's games, movies, and 2 bikes

Events

Events allowed

Smoking

Smoking allowed: in designated areas

ONLY outside the unit with proper disposal.

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 there are no carbon monoxide detectors or gas appliances on the property

Host has indicated there is a smoke detector on the property

Safety features at this property include a fire extinguisher and a first aid kit

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: 25

Driving? For a fee, this property offers RV, bus, and truck parking.

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.
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.
Parties and events are allowed on site. Maximum attendees: 6.
Onsite safety features include a fire extinguisher, a smoke detector, and a first aid kit.

Additional information about polices, regulations, and more:

There are no elevators.

Frequently asked questions

What's there to see around this vacation home?

This vacation home is located in Summerland Key, a short 12-minute walk from Venture Out Keys and also 12 minutes on foot from Venture Key. You'll also find Florida Keys Beaches and Upper Sugarloaf Key within a short drive.

Is there parking available at this vacation home?

Yes, there is RV/bus/truck parking available.

Is this vacation home associated with 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 are an outdoor pool and a hot tub.

Is Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security good for couples?

Amenities that appeal to couples at this historic vacation home include a kitchen and a meal delivery service in each accommodation with some featuring ocean views.

Are there hot tubs at Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security?

Yes, guests can enjoy a spa tub 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.

Are there connecting rooms at this vacation home?

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

What 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 mi away (30 minutes by car). Another top airport is Marathon, FL (MTH-Florida Keys Marathon), which is located 28.9 mi away (41-minute drive).

Are there rooms with balconies at Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security?

Yes, every accommodation at Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security comes with a balcony with some featuring ocean views.

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

9.8

Exceptional

9.8/10

Cleanliness

9.4/10

Amenities

9.4/10

Stayed 5 nights in Aug 2025

10/10 Excellent

Dawn K.

Aug 30, 2025

Liked: Cleanliness

The property was spacious, clean and as listed. We had a very nice day.

Stayed 4 nights in Aug 2025

10/10 Excellent

Amy B.

Aug 7, 2025

Liked: Cleanliness

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

10/10 Excellent

Kylene B.

Jul 30, 2025

Liked: Cleanliness

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

10/10 Excellent

Doug D., Newport News, VA

Jul 11, 2025

Liked: Cleanliness

Best Family Vacation!

Our trip was so good we were already talking about booking it for next year!Mike and Carol were great to work with. I’ve never had someone so quick to respond, take care of any issues, and provide recommendations during a stay.Their home was a perfect place for us and convenient to so much throughout the keys. It was clean, spacious, and had everything you could want or need during your stay. The kitchen was fully stocked with everything you could think of. The appliances were great with a dishwasher, washer, and dryer on hand. Underneath is a grill, bikes, helmets, kayaks, life jackets, fishing equipment, chairs, a cooler, etc. They have everything you need!The resort has a community store, that my kids would bike to sometimes multiple times per day. There’s a pool, boat ramp, and tiki huts to hang out under!We spent much of our time at Bahia Honda state park at one of the most beautiful beaches I’ve ever been to, snorkeling, soaking up the sun, and taking in the breathtaking views. My oldest son and I did a party fishing charter (Gulfstream IV - highly recommended) and my wife and youngest son went to the Turtle Hospital in Marathon (highly recommended). We made a couple trips to Key West, which is a short drive away, to shop, see the sights, and had some of the best food I’ve ever had (great recommendations from Mike). It truly was a memorable vacation and we owe a lot of it to Mike and Carol for allowing us to use their wonderful home! Thank you!

Stayed 7 nights in Jun 2025

10/10 Excellent

sandra c., New Orleans

Jun 30, 2025

Liked: Cleanliness

Great spot to enjoy paradise

This is our second stay in this unit and the perfect spot to use as base to enjoy the Lower Keys. Unit has excellent appliances, comfortable furniture, and all of the household items needed for a good vacation. The Venture Out resort itself has a range of nice amenities and I like the 24 hour security and restricted access. Property rules are reasonable and easy to abide by. The bonus equipment like bikes, hammock, grill, and kayaks are very much appreciated. Watching the sun rise from the deck is one of my favorite views.

Stayed 11 nights in Jun 2025

10/10 Excellent

Amy W.

Jun 18, 2025

Liked: Cleanliness

The house was amazing! Very pleased.

Stayed 4 nights in Jun 2025

10/10 Excellent

Lillian B., Saint Augustine, Fl

Jun 2, 2025

Liked: Cleanliness

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.

Stayed 4 nights in May 2025

8/10 Good

Kiane C.

May 30, 2025

Liked: Cleanliness

1st time in Cudjoe Key

Stayed 5 nights in May 2025

10/10 Excellent

Jessica R.

May 25, 2025

Liked: Cleanliness

Great Getaway!!

My sister and I booked this property for our week long trip to explore the Keys. We wanted a location that where we could relax on days we were not traveling and Venture Out delivered! The home was very clean and provided the basic necessities that gave it a home-like feel. Although we did not use them, we felt that the outdoor activity amenities were very convenient and thoughtful. We both agreed that we would stay here again.

Stayed 5 nights in May 2025