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

Waterfront holiday home with outdoor pool and Hot tub

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

9.6 out of 10
Exceptional
2 bedroomsSleeps 40.1 sq m

Popular amenities

  • Dryer
  • Washer
  • Air conditioning
  • Hot tub

Explore the area

View map
  • Place, Venture Out Keys
  • Place, Upper Sugarloaf Key
  • Place, Florida Keys Beaches
  • Airport, Key West, FL (EYW-Key West Intl.)

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.

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi

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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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
View more Holiday homes in Summerland KeyOpens in a new window
Map
Cudjoe Key, FL

What's nearby

  • Upper Sugarloaf Key - 9 min drive - 6.9 km
  • Florida Keys Beaches - 11 min drive - 7.8 km
  • Sugarloaf Beach - 21 min drive - 18.0 km
  • National Key Deer Refuge Visitor Center - 24 min drive - 17.5 km
  • Bahia Honda State Park - 38 min drive - 32.4 km

Getting around

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

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Kiki's Sandbar - ‬11 min drive
  • ‪5 Brothers Two - ‬8 min drive
  • ‪Morning Joint - ‬16 min walk
  • ‪Broil - ‬4 min drive

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.

Is Waterfront Cottage with Stunning Views & Resort Amenities Near Key West! pet-friendly?

No, pets are not allowed at this 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

9.6

Exceptional

9.6/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.8/10

Location

9.6/10

Listing accuracy
Rating 10 - Excellent. 102 out of 119 reviews
Rating 8 - Good. 12 out of 119 reviews
Rating 6 - Okay. 4 out of 119 reviews
Rating 4 - Poor. 0 out of 119 reviews
Rating 2 - Terrible. 1 out of 119 reviews

Reviews

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

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

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

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

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

10/10 Excellent

Barbara P., Ravena

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

Perfect location

Although we did not take advantage of the resort amenities, this home was a good central location for all of your Florida Keys explorations.
Stayed 3 nights in Mar 2023

10/10 Excellent

Amy S.

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

Vacation

Nice area, place was nice. Fishing right off dock was nice. Place had a huge pool.
Stayed 7 nights in May 2024

10/10 Excellent

Sandra W.

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

Comfortable, easy stay!

We thoroughly enjoyed our stay at Miles Away! The atmosphere was clean, comfortable, and relaxed. The location was good and security gives peace of mind. Kayaks were perfect for 360 views. Overall, very happy with our stay.
Stayed 4 nights in Apr 2023

10/10 Excellent

John H.

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

Stay

Great very relaxing
Stayed 4 nights in Jun 2023

10/10 Excellent

Phyllis V.

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

Lovely place

Very enjoyable. Decorations are very cute. Spent a lot of time sitting on the deck looking at the water. Convenient location for a day trip to Key West. Enjoyed a couple of local restaurants.
Stayed 3 nights in Feb 2024

10/10 Excellent

Richard M.

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

Perfect Location

The house was great with direct water access. We used the kayaks every day to explore the little islands and surrounding waterways. The house had all the essentials needed for cooking meals at home. We loved it!!
Stayed 8 nights in Jun 2024

10/10 Excellent

Mary G.

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

Cudjoe Quick Trip

What a lovely, clean, and well appointed rental property. The hostess is very responsive. The property is also easy to find and a super location to restaurants and outdoor activities.
Stayed 2 nights in Feb 2024

10/10 Excellent

Jim S., O'Fallon, MO

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

Great place with a spectacular view

We had a great time at this place. Great location and lots of things to do. Easy drive to Key West. Rented a boat and fished and explored the water. Owners are responsive however didn’t have any problems. Had everything we needed for cooking and frying up fresh fish. Highly recommend this place!!
Stayed 7 nights in Jan 2023

10/10 Excellent

Cynthia Z., Englewood, CO

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

Cute house

Property was as shown. It was clean, well stocked and had a lot of information about the area in a book in the house. We enjoyed the view but sadly the weather didn't always cooperate 😕 Would recommend.
Stayed 2 nights in Dec 2023

10/10 Excellent

Hard Enduro A., Cincinnati

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

Best spot in the Keys

We've been traveling to the keys for years. This is the best. Laid back, amazing boating, and all the fishing! Awesome islands and sandbars to relax on, reefs to snorkel on, laid back restaurants. Quick shot down to key west. The neighborhood is very quiet, house has everything you need. We loved it, thanks for letting us stay here ! Tim and Chelsea
Stayed 4 nights in Sep 2023

10/10 Excellent

Linda B.

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

Miles Away is “Paradise Found”

We were very happy with our stay at Miles Away. Walking in the door to a view of beautiful blue water was exactly what we were hoping for, and this home did not disappoint! Everything was just as pictured, clean, comfortable and cozy. Anything we might need was provided and we felt right at home. Prior to our arrival we had a few requests, Robin was always available and accommodating. We appreciated the notes in the Welcome booklet, and actually went to No Name Pub twice based on your recommendation. The pizza was excellent, and it is definitely a place to see once for sure! Thank you for sharing your home with us, Robin!
Stayed 9 nights in Feb 2020

8/10 Good

Julieta S., Shady Side, Maryland

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

cute bungalow with great views

Overall it was a fun, relaxing last-minute getaway weekend on the porch of this cute bungalow. Home amenities were good (having use of kayaks was great). The Park is very well kept and organized and staff is very friendly and helpful. Unfortunately (because we still had to work), the wifi didn't work all weekend despite various communications with the manager. There are lots AND LOTS of rules both for the house and for the Park. The nearest restaurant, the Square Grouper, was fantastic. Hoped to go again but it's closed on Sundays.
Stayed 3 nights in Jan 2021

10/10 Excellent

Mike P.

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

Perfect spot with beautiful views!

We were a family of 4 who stayed at this beautiful little gem. 2 adults and 2 teens. Check in was a breeze and security were very welcoming and helpful. Getting to Robin’s place was a short drive. Once inside we had everything we needed to make our stay comfortable. It was very clean and everything was in working order. We had zero issues. The resort itself was well organized and also very clean. We made use of all of the amenities. The people in the resort were also very friendly. Including Robins next door neighbour who had a nice chat with my oldest daughter. We had a great time and would absolutely recommend this place to anyone. Thanks Robin for the great stay!
Stayed 6 nights in Feb 2024

8/10 Good

Kyle R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was a nice stay.
Stayed 3 nights in Oct 2025

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

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

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

10/10 Excellent

Summer R.

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

Absolutely Incredible!!

We had an amazing stay at this beautiful rental in Cudjoe Key! The house was incredibly cozy, clean, and fully stocked with everything we needed — from kitchen essentials to beach gear. It truly felt like a home away from home.What really made our trip unforgettable was the stunning view. Waking up to those peaceful water views every morning was a dream. The community was just as impressive — so many great amenities that kept the whole family entertained, from the pool and marina to the clubhouse and more.We honestly couldn’t have asked for a better experience and are already looking forward to our next stay. Highly recommend to anyone looking for a relaxing, family-friendly escape in the Keys!
Stayed 4 nights in Jul 2025

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

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

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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