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

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

A waterfront house with a porch, a flag, and a dock.
A waterfront property with a dock, a boat, and a row of houses with balconies and a pool area.
A dining area with a table set for two, overlooking a body of water.
A dining area with a table set for two, overlooking a body of water.
A house with a porch, a set of stairs, and two boats.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Spa pool on site
  • Patio
  • Outdoor pool
  • Toys
  • Barbecue
  • Air-conditioning

Explore the area

View 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 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

Add dates for prices

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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.
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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
  • Boondocks Grille & Draft House - 10 min drive - 11.7 km
  • Lower Sugarloaf Sound - 11 min drive - 12.1 km

Getting around

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

Restaurants

  • ‪Morning Joint - ‬16 min walk
  • ‪Kiki's Sandbar - ‬11 min drive
  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Looe Key Tiki Bar & Restaurant - ‬9 min drive
  • ‪Tonio's Seafood Shack & Tiki Bar - ‬6 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.

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. 123 out of 143 reviews
Rating 8 - Good. 14 out of 143 reviews
Rating 6 - Okay. 5 out of 143 reviews
Rating 4 - Poor. 0 out of 143 reviews
Rating 2 - Terrible. 1 out of 143 reviews

9.4/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful stay! Thank you!
Stayed 7 nights in Oct 2026
Response from Management on 2 November 2026
I'm glad your stay was great, come visit again!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay!
Stayed 4 nights in Jul 2026
Response from VrboOwner on 14 September 2026
Thanks! Glad you had a great stay! Visit again!!
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness
Robin was a great host. Unit was very clean. Wonderful view and great if you have a boat. We truly enjoyed our stay.
Stayed 6 nights in Sep 2026
Response from VrboOwner on 25 September 2026
Thanks Brenda, I'm so glad you enjoyed your stay!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The place is always great and clean and the host always responds quickly. This is our second year there and we already want to reserve for next year. Thanks for a great place to stay.
Stayed 5 nights in Aug 2026
Response from VrboOwner on 17 August 2026
Thanks for the great review. Look forward to hosting you again next year!
Verified review

10/10 Excellent

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

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
We liked the location of the house and the amenities the Venture Out community offered. We spent a lot of time at the pool. The inside of the house could use some updating but everything was functional. When I booked the house I didn't realize there was only 1 bathroom which was tough with our family of 4. The kayaks need some repair work and were pretty dirty from being outside.
Stayed 4 nights in Sep 2026
Response from VrboOwner on 18 September 2026
Thanks for leaving the note about the door, I had someone go over today to take a look. Im heading down at the end on the month to look at updating. The salt water pool is really magnificent, I'm glad you enjoyed it!
Verified review

6/10 Okay

Liked: Communication, listing accuracy
Nice little house with a great view.
Stayed 5 nights in May 2026
Response from VrboOwner on 17 May 2026
Hi Juan, I wish you had explained more about the terrible experience you had at check-in. It was just so unprofessional and I've contacted the supervisor and board members to look into it. You are such a lovely family and based on your photos it looks like you were able to enjoy yourselves. Thanks for sharing the pictures on your review and again my apologies for your negative check-in experience.
Verified review

10/10 Excellent

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 review

10/10 Excellent

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

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had such a wonderful experience staying at this house. The house was supplied with everything you could possibly think of, including a variety of fishing supplies and tackle, which we used every day fishing off the dock out back. The house is clean and the owner put such great details into the decor of it. The check in process was very easy and the gated community makes you feel very safe. We will definitely be recommending this place to friends and family and coming back to stay.
Stayed 5 nights in May 2026
Response from VrboOwner on 4 June 2026
Thank you for your thoughtful review. I'm so glad you enjoyed your stay and come visit again soon!
Verified review

8/10 Good

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

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Everything was wonderful. Couldn’t ask for more.
Stayed 7 nights in Mar 2026
Response from VrboOwner on 30 March 2026
So glad you enjoyed your stay! Come back and visit again!
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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
Response from VrboOwner on 8 April 2026
Thank you Michael! You have such a lovely family, and I'm glad you enjoyed your vacation so much. Thanks also for sharing recommendations to pass along to other guests. I look forward to hosting you again in the future.
Verified review

10/10 Excellent

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
Response from VrboOwner on 26 April 2026
Im so glad you enjoyed your stay. The salt water pool really is amazing! I wish there was a way i could collect that facility fee during booking, but the condo association wants to handle that separatly. I do list the fee on the booking acceptance letter, but its understandable people forget about it. Have a safe trip home and do come visit again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a pretty quiet key, which we enjoyed. Check-in was super easy, the house was small, but clean and comfortable. The AC can only be set down to 72, so we were thankful for the ceiling fans in each bedroom. The pool was great and we even got to see a manitee in the canal right next to the house! There was fishing equipment, a steel drum, and an umbrella with some mats for the beach, so there was plenty to do. The restaurants were great, but we also appreciated having a grocery store 10 min away so we could eat some meals at home. Overall a great stay - would recommend!
Stayed 6 nights in Apr 2026
Response from VrboOwner on 7 May 2026
I'm so glad your family enjoyed the vacation and that certainly was a treat to see a manatee in the canal! Do come visit again!
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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
Response from VrboOwner on 17 February 2026
Im so glad you enjoyed your stay.! Please do come visit again!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great 9-day stay at this wonderful cottage. We met the security team on our arrival around 11:00 pm with the boat in tow, but they had already been briefed by our gracious and very.helpful host regarding the (very) late arrival, and checked us in smoothly and allowed us to park the trailer overnight. The cottage is neat and tidy, with a large open floor plan in the kitchen and den area. Everything worked, and we had everything we needed during our stay: a well-stocked kitchen, laundry facilities, comfortable beds, and a safe docking area, with well-maintained pilings and cleats in all the right places. The location at the end of the canal was a perfect jumping-off point for our daily fishing trips, and the cottage was a comfortable and inviting destination at the end of each day on the water. We couldn’t have asked for anything more, well recommended!
Stayed 9 nights in May 2026
Response from VrboOwner on 18 May 2026
Thank you for such a detailed review. That is a nice wide canal to get in and out of. I'm so glad you were comfortable and found everything you needed. You had such a long trip, I'm glad your check in went smoothly. Do come visit again!!
Verified review

10/10 Excellent

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
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