Entire home

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

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A coastal building with a balcony, surrounded by palm trees and a boat.

A beach with palm trees, a clear sky, and a calm sea.

A beachside area with picnic tables and palm trees.

A beachside area with a wooden gazebo, a bench, and a rope barrier.

A row of bicycles parked outside a building.

Overview
Amenities
Location
Policies

Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 6864 sq ft

Popular amenities

Ocean view
Hot tub
Kitchen
Washer
Dryer

Explore the area

Cudjoe Key, FL

Place, Upper Sugarloaf Key
‪6 min drive‬
Place, Florida Keys Beaches
‪6 min drive‬
Place, Upper Sugarloaf Sound
‪7 min drive‬
Airport, Key West, FL (EYW-Key West Intl.)
‪37 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 - 6 min drive - 4.1 miles
Florida Keys Beaches - 6 min drive - 4.2 miles
Upper Sugarloaf Sound - 7 min drive - 4.9 miles
Boondocks Grille & Draft House - 9 min drive - 6.9 miles
Lower Sugarloaf Sound - 10 min drive - 7.1 miles

Getting around

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

Restaurants

‪Boondock's Grille & Drafthouse - ‬10 min drive
‪Morning Joint - ‬3 min drive
‪Kiki's Sandbar - ‬12 min drive
‪Looe Key Tiki Bar & Restaurant - ‬10 min drive
‪Square Grouper Bar and Grill - ‬4 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 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

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 washing machine, a sofa bed, and a coffee maker.

Similar properties

A clear blue pool with a smooth surface, surrounded by a concrete deck and palm trees in the background.

Ocean view
Pool
Hot tub
Kitchen

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
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
Washing machine

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

2 outdoor pickleball courts
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

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

Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:

Load and start the dishwasher

Strip any used beds, gather used towels, and store extra beds

Remove personal items, remove leftover food and drinks, and take out the trash

Turn off the lights

Failure to complete these may result in a negative review from the host.

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 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

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

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 meal delivery service and a kitchen in each house, and some feature ocean view.

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

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.

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

No, this vacation home doesn't feature connecting guestrooms.

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 house at Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security comes with a balcony and some offer ocean views.

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

9.8

Exceptional

9.8/10

Cleanliness

9.6/10

Amenities

9.6/10

Property conditions & facilities

Verified review

8/10 Good

Rebecca H.

Jun 7, 2026

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

We had an amazing time kayaking and biking around the area. Even saw a dead shark hunk up in the Venture key. It was clean and beautiful.

Stayed 6 nights in May 2026

Verified review

10/10 Excellent

Jennifer F.

May 30, 2026

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

We had a great Vacation stay. The house was well stocked with what we needed. The house was clean. We loved the location on the keys. Cudjoe was perfect. The pool was nice in the afternoon. Thanks for a great stay!

Stayed 7 nights in May 2026

Verified review

10/10 Excellent

Michael C.

Apr 14, 2026

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 review

10/10 Excellent

William V.

May 20, 2026

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

This property was clean and comfortable and had everything we needed. The best part was access to the Kayaks, multiple bikes, beach umbrellas, chairs, towels and fishing gear. The appliances were new and everything worked great. There are (2) bedrooms and the beds are a bit small but they were comfortable.

Stayed 3 nights in May 2026

Verified review

10/10 Excellent

Mohammad H.

May 26, 2026

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

The property and Venture Out community were as described and very well maintained. The check in process was smooth and the whole experience is turn key. The house itself was very clean with several extras supplied, including linens, towels, and daily use kitchen items, in addition to Kayaks and bicycles. Highly recommend this home and the community as a base camp if you’re looking for a peaceful setting with an easy commute to Key West or the middle keys

Stayed 7 nights in May 2026

Verified review

10/10 Excellent

Brittany

Dec 28, 2025

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 review

10/10 Excellent

Constance L.

Apr 15, 2026

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 review

10/10 Excellent

Dan R.

Oct 1, 2025

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

Great place to stay in Venture Out

Stayed 8 nights in Sep 2025

Verified review

10/10 Excellent

Matthew W.

Oct 14, 2025

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

Clean and awesome location

Stayed 5 nights in Sep 2025

Verified review

10/10 Excellent

Shelley

Dec 25, 2025

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 review

10/10 Excellent

Elizabeth T.

Dec 9, 2025

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

Great House and amenities

Stayed 3 nights in Dec 2025

Verified review

10/10 Excellent

Chad B.

Sep 21, 2025

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

We had a great vacation. House was wonderful.

Stayed 7 nights in Sep 2025

Verified review

10/10 Excellent

Deborah F.

Apr 9, 2025

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 review

10/10 Excellent

Kylene B.

Jul 30, 2025

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 review

10/10 Excellent

Amy B.

Aug 7, 2025

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 review

10/10 Excellent

Dawn K.

Aug 30, 2025

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 review

10/10 Excellent

Cindy G.

Oct 21, 2025

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 review

10/10 Excellent

Edward M.

Apr 25, 2025

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 review

10/10 Excellent

JOHN S.

Mar 28, 2025

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 review

10/10 Excellent

Crystal B.

Sep 16, 2025

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 review

10/10 Excellent

Jamie G.

Apr 19, 2025

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 review

10/10 Excellent

James M.

Jan 2, 2026

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 review