Skip to main content
Entire home

Piece Of Eight - Venture Out 279

Photo gallery for Piece Of Eight - Venture Out 279

Exterior
Exterior
Exterior
Property grounds
Exterior

Reviews

9.4 out of 10
Exceptional

Highlights

  • Dive into relaxation
    Unwind in the top-rated pool, your perfect spot for relaxation.
  • Games
    A rare find - enjoy a variety of games available on-site.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
2 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Heated Pool
  • Hot tub on site
  • Onsite parking available
  • Kitchen
  • Washer
  • Air conditioning

Explore the area

View in a map
Cudjoe Key, 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

Rooms & beds

2 bedrooms (sleeps 6)

Common Space

1 Double Sofa Bed

Guest

1 Queen Bed

Master

1 Queen Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Spaces

Kitchen
Balcony
Dining area

About this property

Piece Of Eight - Venture Out 279

Piece Of Eight - Venture Out 279
Stilt 2Bd/2Ba 35' Dockage

Close to Everything!

Recently updated 2 BR/2 BA stilt home has 35' seawall on wide canal. Newly renovated dock features custom paver surface, heavy duty padded dock posts, cleats, 20a electric outlet, swim ladder, plumbed fish cleaning table, fishing rod racks, shower with hot and cold running water, and open water views. Close to all the amenities including sports courts, pool, marina and overflow parking. Very quick boat access to open water and the marina.

Interior features all hard flooring, washer/dryer, ceiling fans, and central air. Open living/dining with water views includes ample seating with a queen size sleeper sofa with memory foam mattress, leather reclining loveseat, recliner and armchair as well as storage ottomans. Well-appointed kitchen boasts plentiful counter space and includes new fridge with ice and water in the door.

Master suite includes a queen bed, lots of drawers, spacious closets and access to the private bath. Bath features a large walk-in shower with rain shower head and built-in bench, elongated toilet, comfort height vanity and two medicine cabinets.

Guest bedroom has a queen bed, dual lamps with USB and 120 volt charging outlets, and direct access to the front balcony.

Second bath also offers a walk-in shower with rain shower head, built-in bench, elongated toilet and two medicine cabinets.

Tech includes complementary high speed internet with WIFI, Smart TVs in the living area and master bedroom, DVD player in living room, wireless printer/scanner/copier, Nest thermostat and personal weather station.

Covered balconies front and rear provide the perfect setting to enjoy your morning coffee, al fresco dining, or an evening nightcap. Spacious downstairs covered area includes propane grill with side burner, comfortable lounge seating and a larger dining set for all your entertaining needs. Covered parking, with a 7' 2” clearance, is also provided for one truck or auto.

Downstairs storage room provides space to store fishing tackle or dive gear and provides access to another full size fridge and separate bait freezer.

Kayaks, 2 paddle boards, bicycles, pickleball equipment and numerous board/card games are also provided for your recreational enjoyment! Golf cart is available for exploring within the community only.

SECURITY DEPOSIT REQUIRED, NO SMOKING, NO PETS,
7 DAY MINIMUM LOBSTER SEASON,
FREE WIFI IN REC HALL, OVERFLOW PARKING IS NOT GUARANTEED.IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.
VO REGISTRATION FEE is $125** DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE.
Our prices include all fees. No hidden fees.

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Terrace/patio
The Diving Dolphin #268 - Ocean Views, Kayaks!
Cudjoe Key
  • Ocean view
  • Pool
  • Hot tub
  • Kitchen
9.4 out of 10, Exceptional, (3 reviews)
The Diving Dolphin #268 - Ocean Views, Kayaks!

House Rules

Check in after 3:00 PM
Minimum age to rent: 27
Check out before 10:00 AM
default

Children

Children allowed: ages 0-17
default

Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted
Venture Out charges a $125 registration fee upon arrival paid via cash or cc only.
https://ventureoutcondo.com/wp-content/uploads/2025/02/Renter-Rules-Packet-2.24.25.pdf
Only 1 vehicle is allowed at/under the unit at any time. Other vehicles MUST park on the street during the day and pay for overflow at night.

Important information

You need to know

Property # 3409268
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 are no carbon monoxide detectors or gas appliances on the property
Host has indicated there is a smoke detector on the property

About the neighborhood

Summerland Key

Located in Summerland Key, this vacation home is on the waterfront. Florida Keys Beaches and Bahia Honda State Park reflect the area's natural beauty and area attractions include Blue Hole and Big Munson Island. With jet skiing, kayaking, and scuba diving nearby, you'll find plenty of adventures in the water.
View more Vacation Homes in Summerland KeyOpens in a new window
Map
Cudjoe Key, FL

What's nearby

  • Upper Sugarloaf Key - 7 min drive - 7.3 km
  • Florida Keys Beaches - 8 min drive - 7.4 km
  • Upper Sugarloaf Sound - 8 min drive - 8.6 km
  • Lower Sugarloaf Sound - 11 min drive - 12.1 km
  • National Key Deer Refuge Visitor Center - 16 min drive - 18.9 km

Getting around

  • Key West Intl. Airport (EYW) - 32 min drive

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Morning Joint - ‬17 min walk
  • ‪Kiki's Sandbar - ‬11 min drive
  • ‪The Bent Prop - ‬7 min drive
  • ‪Square Grouper Bar and Grill - ‬3 min drive

Frequently asked questions

Does Piece Of Eight - Venture Out 279 have a pool?

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

How much does it cost to stay at Piece Of Eight - Venture Out 279?

As of Jun 19, 2026, prices found for a 1-night stay for 2 adults at Piece Of Eight - Venture Out 279 on Sep 8, 2026 start from $526, 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 Piece Of Eight - Venture Out 279 pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Piece Of Eight - Venture Out 279?

Check-in begins at 3:00 PM.

What time is check-out at Piece Of Eight - Venture Out 279?

Check-out is at 10:00 AM.

Where is Piece Of Eight - Venture Out 279 located?

Situated on the waterfront, this vacation home is within a 10-minute walk of Venture Out Keys, Venture Key, and Out Key. Florida Keys Beaches and Upper Sugarloaf Key are also within 6 mi (10 km).

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 16 out of 23 reviews
Rating 8 - Good. 6 out of 23 reviews
Rating 6 - Okay. 0 out of 23 reviews
Rating 4 - Poor. 1 out of 23 reviews
Rating 2 - Terrible. 0 out of 23 reviews

9.8/10

Cleanliness

9.6/10

Check-in

8.4/10

Communication

9.2/10

Location

9.6/10

Listing accuracy

Reviews

Verified

8/10 Good

Fred C.

Liked: Cleanliness, check-in, communication, listing accuracy
Nice place
Stayed 7 nights in Jan 2026
Response from VrboOwner on Feb 13, 2026
thanks fred...see you again soon..
Verified

8/10 Good

Mary P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Love the property. Great amenities, pool, paddle boards and kayaks and use of the golf cart were all enjoyable. Easy check in. Loved the security of the property. My only recommendation would be to get new mattresses for the beds. Everyone likes to sleep well on vacation. Otherwise a great place to stay. Has something for everyone and every age.
Stayed 4 nights in Apr 2026
Response from VrboOwner on Apr 13, 2026
Thank you Mary. It's great to hear your family had a fun stay with us. We appreciate your feedback and do hope you consider us for future bookings. WFR
Verified

10/10 Excellent

Nichole D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We absolutely loved this place and potentially will stay again next year. Amenities were nice, host was quick to get back to us with any questions or concerns. 10/10 recommend!
Stayed 7 nights in Feb 2026
Response from VrboOwner on Feb 13, 2026
Thanks for the great review Nichole...Look forward to hosting both your families in the future. Carmen @ WF
Verified

10/10 Excellent

Steven B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time at the house. It had everything we needed in our stay. The location was perfect for us to dock our boat and we enjoyed all the amenities the area had to offer. We would definitely stay again!
Stayed 7 nights in Nov 2025
Response from VrboOwner on Dec 1, 2025
Thank you for the great review Steven. We're happy you enjoyed your stay and hope to see you return. WFR
Verified

10/10 Excellent

teresa r.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay and truly enjoyed both the location and all of the amenities the home had to offer. The golf cart was a great added bonus and made getting around even more convenient. Our kids especially loved having pickleball and basketball right by the house, it kept them entertained the entire time!The pool area was fantastic, and we really appreciated the friendly, welcoming atmosphere from both guests and the community. It made the experience even more enjoyable.Another highlight was how easy it was to access the other Keys, which added to the overall convenience and adventure of the trip.Overall, it was a great stay, and we would definitely come back!
Stayed 6 nights in Mar 2026
Response from VrboOwner on Apr 5, 2026
teresa, So glad you enjoyed your stay. Loved your music station :) hope to host you again soon. WFR
Verified

8/10 Good

Cory S.

Liked: Cleanliness, check-in, listing accuracy
The house is located next to the basketball And pickle ball courts. The golf cart has dead batteries and the grill
Stayed 7 nights in Oct 2025
Verified

10/10 Excellent

Sandy B.

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

Keys trip

Very nice Love the decor. Well supplied. Lots of room!
Stayed 14 nights in Feb 2025
Verified

10/10 Excellent

Kelly W.

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

Fishing Cudjoe Key

Great location for our fishing guide, and the house was super clean!!
Stayed 5 nights in May 2024
Response from VrboOwner on May 24, 2024
Kelly, Thanks for your review. So happy you enjoyed your stay and we look forward to seeing you again soon. Waterfront keys realty
Verified

10/10 Excellent

marina a.

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

Getaway

This was a wonderful place to stay for our getaway! All amenities were perfect. I just wish I could have stayed longer. I will be back!!
Stayed 4 nights in Feb 2025
Response from VrboOwner on Feb 19, 2025
marina, Thanks so much for the great review. Glad you enjoyed your stay. See you again soon. WFR
Verified

8/10 Good

Kristi H.

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

Family fun

We had a great time, made good use of all the amenities of the community and theextras (golf cart, bikes, paddleboards, etc) provided by the property. The house has everything you need to enjoy a stay in the Keys. We will be back!
Stayed 6 nights in Apr 2025
Response from VrboOwner on May 8, 2025
Thank you Kristi for booking with us, we are happy to hear you enjoyed your vacation. We look forward to seeing you back down.
Verified

10/10 Excellent

Marcus B.

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

As advertised

Very convenient with kayaks, paddle boards, pickle ball, and a golf cart. Nice safe community with restaurants close by and 20 minute drive to Key West.
Stayed 3 nights in Mar 2025
Response from VrboOwner on Mar 24, 2025
marcus, Thanks for the great review. Glad you enjoyed your time with us and look forward to seeing you again soon. WFR
Verified

10/10 Excellent

Lorane M.

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

Our anniversary getaway.

The property was great. Everything was as advertised. The property is close to restaurants and local hang outs. The Square Grouper and the Morning Joint are a must. Our kayak ride was amazing , as well as the fishing. We would definitely stay again. Thank you for a wonderful visit.
Stayed 3 nights in Dec 2024
Response from VrboOwner on Dec 9, 2024
Lorane, So happy to hear you enjoyed your stay. We look forward to seeing you again soon. waterfront keys realty
Verified

10/10 Excellent

connie m.

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

A little piece of paradise.

Sitting right on a very wide canal looking out into the ocean with beatiful breezes. The house made it feel like paradise for us. It was very clean, offered every thing needed, also with paddle boards, bikes and a golf cart! Our stay was way too shortshort though.
Stayed 3 nights in Feb 2025
Response from VrboOwner on Feb 12, 2025
Thank you Connie, we are happy to know you enjoyed your stay here with us in the beautiful Florida Keys. We hope to see you back.
Verified

10/10 Excellent

Beverly B.

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

Venture Out

Nice clean place within walking distance of my daughter.
Stayed 4 nights in Mar 2024
Response from VrboOwner on Apr 6, 2024
Beverly, Thanks for the review. So happy you enjoyed your stay and we look forward to seeing you again soon. waterfront keys realty
Verified

10/10 Excellent

Karmen W.

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

Enjoyably

Loved the SUP and kayaks and bikes. Used them more than going into Key West.
Stayed 5 nights in May 2024
Response from VrboOwner on May 29, 2024
Karmen, So glad you enjoyed your stay at Casa Dolphin and we look forward to seeing you again soon. waterfront keys realty
Verified

10/10 Excellent

KAREN M.

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

January getaway

Loved our stay! Pickle/tennis ball courts right next door, my husband could play and I could watch from the balcony. Home was clean and included little extras, spices, coffee filters, laundry soap. Loved the use of the golf cart! The weather wasn’t great so we didn’t use the kayaks. The community was great with activities. Loved the pancake breakfast!
Stayed 5 nights in Jan 2025
Response from VrboOwner on Jan 27, 2025
Thank you Karen for sharing your positive feedback. We are happy you enjoyed your stay with us. Hopefully we'll see you back again.
Verified

10/10 Excellent

Zach M.

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

Quite, with plenty of access

Overall nothing to complain about. Few things to keep in mind, everything on and off site closes by 10 at the latest so plan accordingly.
Stayed 4 nights in Apr 2024
Response from VrboOwner on Apr 15, 2024
Zach, Thanks for the review. Look forward to seeing you again soon. waterfront keys realty
Verified

10/10 Excellent

Mike D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
the property had everything we needed,we liked the short canal ride, an umbrella for shade over the cleaning table would be a great addition, we were able to borrow the very nice and generous neighbors witch helped tremendously very grateful. thanks again, you know who you are. the downsrairs room with fridge and freezer were a big plus and also a deciding factor in renting this property, all in all a great time.we will probably look at this property in the future, maybe next year.
Stayed 4 nights in Jul 2025
Response from VrboOwner on Jul 21, 2025
Mike, So happy you enjoyed your stay. It was our pleasure to host you and will make sure the unit gets it own umbrella :) Look forward to seeing you again in the future. WFR
Verified

10/10 Excellent

Jake T.

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

Amazing time!

This home truly has it all. It’s been fully renovated and stocked. The golfcart was so easy to use and helpful for getting around the park. The canal frontage was amazing! We saw lobster, stone crab and blue crab in it every night. Even though the tennis and pickleball courts are right next to it you can’t hear them and the games don’t start until 8:30am. We will for sure be coming back every year!
Stayed 6 nights in Feb 2025
Verified

8/10 Good

Dean S.

Liked: Cleanliness, listing accuracy
Disliked: Communication, location

First time in the Keys

Very nice community of seasonal residents. Trying to communicate with the agent after hours was less than desirable. The “24 hour agent” was a loop of computer responses. The loop response should have indicated that someone at the entrance security gate would be available to answer any questions 24/7. Which they were very nice and friendly. All in all, enjoyed our stay and would recommend.
Stayed 4 nights in Mar 2024
Response from VrboOwner on Mar 27, 2024
Dean, Happy to hear you enjoyed your stay. The community does have 24hr security and we will review our documents to make sure it explains our after hours number and that security is also there. Hope to see you again soon. waterfront keys realty
Verified

8/10 Good

Maso O.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Nice House - great amenities!

The house is very clean and has the kid’s park right next door. The gulf cart, kayaks, and paddle boards are the cherry on top for the property compared to the other properties we’ve stayed at VO. The only minus is that the property is located at the end of the canal, so you get the accumulation of sargassum (floating sea weed) and that makes for a bad smell as well as its not best thing for the boat. Oh, forgot to mention, the checkout list - “clean the dishes and store them” is a bit over the top. Usually you can leave the dishwasher machine running and that enough. The property manager is non-existent.
Stayed 3 nights in May 2025
Response from VrboOwner on May 28, 2025
Maso, We are so happy you enjoyed your stay. Unfortunately the wind did blow out of the east for your entire stay. Air curtains help but weather is the boss. We ask you leave the unit in the same condition when you arrived. All the property management members live in the park so we can better assist our guests. Hope to see you again soon. WFR
Verified

4/10 Poor

Amanda P.

Liked: Cleanliness
Disliked: Communication

Incomplete listing and terrible management company

Our family had never been to Venture Out before, so I really did not know what to expect. This neighborhood is a mixture of mobile homes, small homes, and empty RV lots. Most of the people here are full timers, or people who rent and stay many months at a time. It’s not really conducive to people only coming for a few days or a week. There are also several important points missing from this listing (see Cons below). Here are my pros and cons of the home and the neighborhood. Pros: lot is right on the water (canal), community pool and hot tub, Pickleball and tennis, kitchen had everything needed to cook meals, owner allowed use of paddle boards, bikes and other sports equipment, generally friendly people Cons: HVAC did not work the whole time we were there and it got up to 81 degrees in the house, management had no interest in helping fix it, management company is awful, the house is right next to (a few feet away) the Pickleball courts and they start playing loudly at 7am, the house is at the end of the canal where all of the grass/debris builds up and you can’t really jump in to swim right there, no beach at the resort
Stayed 3 nights in Mar 2024
Response from VrboOwner on Mar 15, 2024
Amanda, Thank you for the review. The quiet hours in the park are 11a to 7a and there were other units in the same price range that were not next to the pickleball courts. The AC required a service call as the unit was set into the 60deg range and it froze the unit up even with a note stating please not to turn down that far. The owners had just left 2 days prior to arrival and had no issues for the whole 2 months with the ac. Also we do apologize but we can not control which way the wind blows the seagrass in from the ocean. Unfortunately the keys are a bunch of rocks in the middle of the ocean and there are only 3 beaches in the entire 125 miles that makes up the keys. We look forward to seeing you again in the future at Venture Out a condo association. Waterfront Keys Realty
Verified

10/10 Excellent

Missy Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 5 nights in Apr 2025
Response from VrboOwner on May 21, 2025
We are happy you enjoyed your stay at unit 279. Our guests satisfaction is our goal. We hope to see you return.

About the host

Hosted by Waterfront Keys Realty

Host profile image
Venture Out charges a $125 registration fee upon arrival paid via cash or cc only. There is no boat trailer parking and the overflow lot for a 2nd vehicle is not guaranteed and is first come first serve and may not be reserved in advance.

Languages:

English

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback