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Waterfront Cottage with Stunning Views & Resort Amenities Near Key West!

Photo gallery for Waterfront Cottage with Stunning Views & Resort Amenities Near Key West!

Dock side of the cottage on a windy day
Outside bar seating on the deck and a small dining table inside
Dock and deck with kayaks stored away
Airy great room with ceiling fans, large TV, and plenty of seating.
Pool is located right on the ocean. Watch boats come and go through the channel

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area
2 bedroomsSleeps 4

Popular amenities

  • Heated pool
  • Hot tub on site
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

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

Rooms & beds

2 bedrooms (sleeps 4)

Great Room

1 Double Futon

Master Bedroom

1 Queen Bed

Twin Beds

2 Single Beds

Main Bath

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Outdoor play area
Garden

About this property

Waterfront Cottage with Stunning Views & Resort Amenities Near Key West!

Located on a private and quiet open water lot, this charming cottage offers a wonderful view even to those people who do not want to go outside. While sitting inside or lazing out on a lounger, the tranquility and beauty of the tropics are yours.

Fabulous open water from 35 foot seawall with dock posts, cleats and fish cleaning table, and swim ladder. Cook your catch on the outdoor grill or eat inside still enjoying the relaxing ocean view from the bright great room facing the canal. Kitchen has beautiful wood cabinets and breakfast bar.

The Master bedroom has large mirrored closet, built-in drawers. The comfy guest bedroom has a full closet, bureau and twin beds. Both rooms are equipped with cable TV.

40” flat-screen TV placed for convenient viewing from living and dining area. New tile flooring throughout this home, Washer/ Dryer, Central Air provided for comfort and relaxation.

Venture Out Resort is a quiet little secret located just 20 miles from Key West, and is a water-lover’s dream! This 64-acre condominium resort was created to put the ocean right at your backdoor. We are located on Kemp Channel, which is one of the most accessible boating channels to both the beautiful back country, as well as a quick, ten-minute ride to the open Atlantic and it’s coral reefs, including the world-famous Looe Key National Marine Sanctuary

Venture Out is a gated community. There are an abundance of amenities, including an 80' olympic-sized, heated pool, which is located ocean-side, with a separate kiddie pool; saltwater swimming/snorkeling area adjacent to the pool; and a newly remodeled bath house.

The marina has two boat ramps, a fuel dock, and a convenience store, which is open seven days a week. The store has everything from beer and wine, to bait, ice, fishing licenses, milk, bread, cheese, snacks, and more! There are two tennis courts, which are lighted at night, a Bocce ball court, basketball court, and shuffleboard area. The Recreation Hall has dart boards, a ping pong table, and a billiard table, as well as a self-checkout library.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Please do not store bait in the refrigerator or freezer
Please return kayaks to their original place under the deck
BOAT TRAILER AND EXTRA CAR PARKING IS NOT GUARANTEED ON VENTURE OUT PROPERTY. PLEASE USE AN OFFSITE LIST OF POSSIBLE PARKING ALTERNATIVES.

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
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

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 Wilhelmina Harvey Park. Travelling with kids? Consider Big Munson Island and Looe Key National Marine Sanctuary. Discover the area's water adventures with kayaking and scuba diving nearby, or enjoy the great outdoors with hiking and cycling.
View more Holiday homes in Summerland KeyOpens in a new window
Map
Cudjoe Key, FL

What's nearby

  • Florida Keys Beaches - 7 min drive - 7.1 km
  • Upper Sugarloaf Key - 7 min drive - 7.3 km
  • Upper Sugarloaf Sound - 8 min drive - 8.6 km
  • Lower Sugarloaf Sound - 12 min drive - 12.1 km
  • National Key Deer Refuge Visitor Center - 16 min drive - 17.9 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 31 min drive

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Morning Joint - ‬16 min walk
  • ‪Kiki's Sandbar - ‬11 min drive
  • ‪Mangrove Mama's - ‬7 min drive
  • ‪Square Grouper Bar and Grill - ‬20 min walk

Frequently asked questions

Does Waterfront Cottage with Stunning Views & Resort Amenities Near Key West! have a pool?

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

How much does it cost to stay at Waterfront Cottage with Stunning Views & Resort Amenities Near Key West!?

As of 4 May, 2026, prices found for a 1-night stay for 2 adults at Waterfront Cottage with Stunning Views & Resort Amenities Near Key West! on 25 Jun, 2026 start from S$374, 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 Waterfront Cottage with Stunning Views & Resort Amenities Near Key West! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Waterfront Cottage with Stunning Views & Resort Amenities Near Key West!?

On-site parking is available at the property.

What time is check-in at Waterfront Cottage with Stunning Views & Resort Amenities Near Key West!?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront Cottage with Stunning Views & Resort Amenities Near Key West!?

Checkout is at 10:00 AM.

Where is Waterfront Cottage with Stunning Views & Resort Amenities Near Key West! located?

This family-friendly Summerland Key holiday home is located on the waterfront, 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 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. 114 out of 131 reviews
Rating 8 - Good. 12 out of 131 reviews
Rating 6 - Okay. 4 out of 131 reviews
Rating 4 - Poor. 0 out of 131 reviews
Rating 2 - Terrible. 1 out of 131 reviews

9.6/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Amy W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay!
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Lorilie L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay, enjoyed our time greatly. Everything was well kept and , kitchen had everything you might need. We would definitely stay again.
Stayed 7 nights in Mar 2026
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay at miles away. Everything was perfect. Beautiful spot right on the ocean. The pool did not disappoint. The kitchen was fully stocked. The kayaks were tons of fun as well. If we had to say anything we did not realize there was 125 fee for the Venture Out association when we checked in.
Stayed 7 nights in Apr 2026
Verified

10/10 Excellent

Michael K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Second time staying at Venture Out and we will definitely be back to Robin’s house in the future. Very good communicator and the house was as described. Loved it.
Stayed 6 nights in Mar 2026
Verified

10/10 Excellent

jeffery B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay. The facilities are very nice.
Stayed 6 nights in Jan 2026
Verified

10/10 Excellent

Debra M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was very clean and well stocked. The view was amazing. We enjoyed coffee on the back deck every morning. The resort community was very friendly. We loved the community pool. The place has a book with recommendations that covers everything you might want to know from who delivers pizza to best place to rent a boat which we found very helpful. The host was quick to respond to questions as well. We would definitely stay here again.
The back deck
View from back deck
Lots of bird, boat and kayak watching
Stayed 7 nights in Jan 2026
Verified

10/10 Excellent

Devin S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The House was in great shape and perfect for the 2 of us. We enjoyed our waterfront view/access and the use of the kayaks provided. Thanks.
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Mohamed A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice house and host ,,enjoyed our stay ,recommended for everyone
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Shawna G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay! The home is exactly as pictured. It was clean, well equipped, and met all of our needs. The beds were comfy! Our host was responsive and easy to talk to. We enjoyed fishing from the deck and kayaking from the canal into the ocean bay. For VentureOut - We ate a pancake breakfast at the resort pavilion and played board games in the library. Neighbors are close but everyone (including resort park staff) was friendly. The amenity fee charged by the park is reasonable given everything they make available. The area is quiet and felt safe/secure. My only downside was the outdoor swim lagoon - the water was not clean enough to swim. But the pool and hot tub were well maintained and clean. This was our first trip to the keys and it was magical! We loved having this home as a comfy base to relax after exploring the islands.
Stayed 5 nights in Mar 2026
Verified

10/10 Excellent

Bill S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and friendly neighborhood. Would stay again next year
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Robert B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was great except for the weather didn't co-operate. it got cold and the heat wouldn't come on, thankfully you had a small area heater that helped. Hope you got the heat element fixed. Definitely enjoyed our stay! Thanks again! Bob & Penny Barnes
Stayed 4 nights in Jan 2026
Verified

10/10 Excellent

Jennifer L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great communication, lovely little home on the water canal, finishing kayaks and bikes available. Gated community had nice people and quiet.
Stayed 5 nights in Nov 2025
Verified

10/10 Excellent

Matthew D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay. We caught a ton of fish, loved snorkeling and using the kayaks. The welcome book was super helpful. Highly recommend.
Stayed 5 nights in Sep 2025
Verified

10/10 Excellent

M B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved this place! Homey, clean, right-sized for us, with all the amenities we could've have wanted. Kayaks, fishing equipment, beach towels, and umbrellas, brand new cooking pan set, a cozy little balcony overlooking the canal and key across the way. If only we had a boat to dock at our private dock!
Stayed 5 nights in Nov 2025
Verified

10/10 Excellent

Michelle P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We stay at Venture Out Resort every year, this was our BEST STAY!! Very clean! Definitely will stay again!
Stayed 8 nights in Aug 2025
Verified

10/10 Excellent

Howard K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Is the perfect spot for a quiet getaway. My wife and I love fishing and being by the water. This was the perfect spot for both and so much more.
Stayed 9 nights in Sep 2025
Verified

10/10 Excellent

Bryan I.

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

Nice quiet place on the water with a central location

Overall the place is a fantastic little home in a quiet area on the water. We had just enough room and simple features that were great for our four person family. The pool area was fantastic and the location was great for travel to many different areas of the FL Keys for adventures.
Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

Casey G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved it. Nice place. Worked for the boat we had. Nice host. Hoping we can be back next year.
Stayed 5 nights in Aug 2025
Verified

10/10 Excellent

Diego C.

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

Love the view

We had a wonderful stay at the cottage in the Keys. The view was absolutely beautiful, and the property had everything we needed for a comfortable and relaxing visit. Robin was always very responsive and helpful throughout our stay. We also enjoyed using the community pool, which was clean and well-maintained. Having a security guard at the entrance made the property feel very safe. Overall, it was a great experience and we would definitely come back!
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Natalie T.

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

A slice of Paradise in the Keys!

This quaint home is very comfortable, stocked with everything you could need, and in a great location to visit all the best sites from Bahia Hondo State Park to Key West. Book your stay here for a great getaway!
Stayed 5 nights in Jun 2024
Verified

10/10 Excellent

Eric L.

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

Venture Out Stay

A nice stay, description of property is accurate. It was clean and had everything we needed. I would stay here again.
Stayed 4 nights in May 2024
Verified

10/10 Excellent

Steven G.

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

Quick end of summer trip

Clean, cute, comfy, one of favorite places to stay in the keys now.
Stayed 4 nights in Aug 2023
Verified

10/10 Excellent

Charles B.

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

Location

Great location. Close to a lot of interesting spots in the Keys!
Stayed 5 nights in Jan 2024
Verified

10/10 Excellent

Verified traveller

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

Spring Key’s vacation

Love the area. Have stayed in Venture out many times.
Stayed 5 nights in Apr 2024
Verified

10/10 Excellent

Christopher R.

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

Beautiful place to stay

This was in a word, perfect. It fit the budget and the view was great.
Stayed 4 nights in Feb 2023

About the host

Hosted by Robin Miles

Host profile image
I bought this cottage after my divorce and rented it until my kids graduated High School in Connecticut. Now it is my permanent residence and I mostly rent it in the winter months when I stay in St. Augustine or travel in my RV.
I used to camp in the Keys with my parents when I was a kid. I remember a lot of these canals being cut and actually drove over the old 7 mile bridge. Now my sisters and I have places here in Venture Out and it is our go-to destination to be with family and relax.

Why they chose this property

I like that Venture Out is a gated community that offers so many amenities. Being at MM23 also makes it an easy ride to get to Key West and all the action, but the property is so relaxing it's hard to pull yourself away.

What makes this property unique

Everyone has their favorite spots in Venture Out, but what I like about 162 is being at the end of a canal and having an open water view. I can watch all the boats coming in and out. It is an active wide canal and fun watching boaters heading in or out for the day.
If your bringing a boat it is an easy turnaround to dock on the wide canal and you don't have to deal with seaweed that can be traped at the end of the canal.
This cottage being my actual home brings me here often to check on things and keep the property well maintained and stocked with items I would actually be looking for.

Languages:

English

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