Looking for a place to stay?

Photo gallery for Looking for a place to stay?

An aerial view of a modern building with a flat roof, surrounded by palm trees and a swimming pool.
A canal with boats, palm trees, and buildings along the water's edge.
A swimming pool with a small water feature, surrounded by palm trees and shaded areas.
A marina with boats docked, surrounded by lush greenery and residential buildings.
A two-story house with a pool, outdoor seating, and a covered patio.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Balcony
  • Private pool
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Washing machine

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
    ‪9 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪38 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Garden
Dining area

Add dates for prices

Similar properties

Property grounds
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Cudjoe Key
  • Ocean view
  • Pool
  • Spa pool
  • Kitchen
9.6 out of 10, Exceptional, (145 reviews)
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon

About the area

Summerland Key

Located on the waterfront, this holiday home is in Cutthroat Harbor Estates, a neighbourhood in Summerland Key. Florida Keys Beaches and Coupon Bight Aquatic Preserve reflect the area's natural beauty and area attractions include Blue Hole and Wilhelmina Harvey Park. Big Munson Island and Looe Key National Marine Sanctuary are also worth visiting. Discover the area's water adventures with jet skiing, kayaking and scuba diving nearby, or enjoy the great outdoors with cycling.
View more Holiday homes in Summerland KeyOpens in a new window
Map
Cudjoe Key, FL

What's nearby

  • Upper Sugarloaf Key - 7 min drive - 7.6 km
  • Florida Keys Beaches - 8 min drive - 7.7 km
  • Upper Sugarloaf Sound - 9 min drive - 8.9 km
  • Boondocks Grille & Draft House - 11 min drive - 12.1 km
  • Lower Sugarloaf Sound - 12 min drive - 12.5 km

Getting around

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

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Morning Joint - ‬3 min drive
  • ‪Kiki's Sandbar - ‬12 min drive
  • ‪Looe Key Tiki Bar & Restaurant - ‬10 min drive
  • ‪Tonio's Seafood Shack & Tiki Bar - ‬7 min drive

Frequently asked questions

Does Looking for a place to stay? have a pool?

Yes, this property has an outdoor pool.

Is Looking for a place to stay? pet-friendly?

No, only service animals are welcome at the property.

How much is parking at Looking for a place to stay??

On-site parking is available at the property.

What time is check-in at Looking for a place to stay??

Check-in begins at 3:30 PM.

What time is check-out at Looking for a place to stay??

Checkout is at 10:00 AM.

Where is Looking for a place to stay? located?

Located in Cutthroat Harbor Estates, this holiday home is within a 15-minute walk of Venture Key, Venture Out Keys and Out Key. Florida Keys Beaches and Upper Sugarloaf Key are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 49 out of 51 reviews
Rating 8 - Good. 2 out of 51 reviews
Rating 6 - Okay. 0 out of 51 reviews
Rating 4 - Poor. 0 out of 51 reviews
Rating 2 - Terrible. 0 out of 51 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Another great stay at “A place to Stay”
Stayed 32 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Always an excellent experience.
Stayed 29 nights in Sep 2025
Verified review

10/10 Excellent

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

Nice comfy spot

We enjoyed our time here. Very clean and comfortable home. Good location.
Stayed 30 nights in Jan 2021
Response from VrboOwner on 2 Feb 2021
We are happy to hear that you and your beautiful family enjoyed your stay. Thank you for the review.
Verified review

10/10 Excellent

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

Another great experience

We have stayed at this property several times and enjoyed it tremendously. The check-in and check out is very efficient and the property owners are very responsive to any needs you may have. The pool is great as well as the porch in the evenings.
Stayed 31 nights in Jan 2024
Verified review

10/10 Excellent

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

Wonderful property so well appointed. Very touch seems intentional to pamper and spoil.

Very nicely done loved
Stayed 28 nights in Oct 2024
Verified review

10/10 Excellent

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

Lovely home and location

Located at the end of the road it was quiet and peaceful. Enjoyed the pool. It was great not being far from great restaurants, shopping and Key West. Hope to have the opportunity to visit the area in the future. Thank you, Waddys and Ralph for this opportunity.
Stayed 28 nights in Feb 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We stayed the month of Dec 2025… the home was very clean and spacious! The kitchen had everything we needed for our stay! I cook a lot and I was in need of nothing. Outside near the pool they have a great area set up for grilling. We grilled our 3xs (which isn’t common). We used the pool every day and in the evenings as well. The host was extremely friendly and very helpful! We plan on staying there next year!
Stayed 29 nights in Dec 2025
Response from VrboOwner on 31 Dec 2025
Thank you so much for your kind review! We're really glad you enjoyed your stay and hope to welcome you back soon. Waddys & Ralph
Verified review

10/10 Excellent

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

Just what we needed

Quiet and tranquil location with everything we needed for a relaxing month away from it all.We love to visit KW for all the activity but it's not where we want to be when its time to unwind.
Stayed 30 nights in Oct 2023
Verified review

10/10 Excellent

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

Always a joy and great place to stay

We have stayed with Ralph and Waddys for 3 years now. They house is clean and well kept with everything you will need for a Keys vacation. The pool is wonderful after a day in Key West and the boat access is great. They host are extremely responsive and I feel like they are friends now. Thank you Waddys and Ralph for another great year.
Stayed 32 nights in Dec 2024
Verified review

8/10 Good

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

Cudjoe

Property worked great for our Keys vacation. Good access to gulf and ocean. Installing a pool, so construction was ongoing during our visit, but the pool will be an asset to future guests
Stayed 29 nights in Jun 2019
Response from VrboOwner on 3 Apr 2020
Dear Guest, We appreciate your positive feedback. We are also pleased to hear that you enjoyed your stay. We were hoping the pool was completed and ready for your enjoyment. Unfortunately, we had very little control over the county proceedings for permits and inspections. We apologize for the inconvenience if any. Looking forward to seeing you in the near future. Attentively, Waddys & Ralph Cosme
Verified review

10/10 Excellent

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

Great experience in Cudjoe

Everyting worked as planned and the house was great for us. We were able to do some boating and fishing and also spend some time at Looe Key. Overall gret experience! Thanks to our great host.
Stayed 30 nights in Jan 2023
Response from VrboOwner on 19 Feb 2023
Thank you for the review. We are glad you and your family enjoyed the stay. Best, Waddys & Ralph
Verified review

10/10 Excellent

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

November on Cudjoe

Great place in a very chill, safe location. House has everything you need to relax and enjoy the sun and water. Waddys was easy to communicate with and very helpful with any questions. Close enough to Key West that we ate lunch and dinner there often, but far enough not to get the crowds and crazy. Would definitely stay again. Thanks!
Stayed 29 nights in Nov 2020
Response from VrboOwner on 30 Nov 2020
Thank you for the kind review. We are very happy that you and your family enjoyed your stay at the property as well as the local area. Best wishes, Waddys & Ralph
Verified review

10/10 Excellent

Magical, perfect place

Our first time to book a place through vrbo - and we absolutely fell in love with it! The home itself is beautiful and open and clean - easy maintenance. The beautifully landscaped grounds and the canal harbor all sorts of interesting critters and sea creatures. The covered deck was perfect, rain or shine. Location is fabulous with so many fantastic eateries nearby. Waddys and Ralph have been very nice and accommodating - a pleasure to work with.
Stayed 76 nights in Jan 2019
Response from VrboOwner on 3 Apr 2020
Thank you for the great review. I’m glad you enjoyed the winter in our property.
Verified review

10/10 Excellent

The property had a beachy feel with all the cute wall hangings and sayings.

We stayed at this rental in May 2018 and loved it. You are not renting a house - this is a home. You enjoy a welcome feeling the minute you open the door. It is tastefully decorated with whimsical, beachy items. A truly wonderful tropical vacation home. Also after spending the day in Key West, you are just a short drive back home. The owners, Waddys and Ralph were the nicest people to deal with. Thanks for letting us rent your home. We definitely enjoyed it.
Stayed 30 nights in May 2018
Response from VrboOwner on 3 Apr 2020
Dear Guest. Thank you for taking the time to review our property. I’m glad to hear that your stay was a memorable one! We look forward to welcoming you back soon. Waddys & Ralph Cosme
Verified review

10/10 Excellent

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

Charming Keys Cottage

We had a wonderful stay at this charming Keys style home owned by Ralph and Waddys! The place was very inviting, beautifully decorated, clean and had all of the supplies needed for a months stay of boating and fishing. We enjoyed our days with early morning fishing trips and afternoon swims in the pool and evening visits to the local restaraunts. On poor boating weather days we took short trips to Key West to visit the attractions down there. The communication between Ralph and Waddys was abundant from before our stay all the way through the end. I would hihghly recommend this place and all of it's charm!
Stayed 29 nights in Jun 2023
Verified review

10/10 Excellent

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

To Escape the Northeast Cold to a tropical oasis

So many thanks to Waddys and Ralph! Your home is a delightful escape. We enjoyed our month here so much that we started looking for our own property! Your house was the perfect set up for our family and visits with friends. The swimming pool and sandy area in the yard is a big plus. We loved kayaking in the mangroves and even had a visit from a Manatee in the canal. Lots of great restaurants close by. Great diving and snorkeling🐠 We leave here fully refreshed and yes, tanner than ever! We hope to visit again in the near future!
Stayed 28 nights in Apr 2023
Verified review

10/10 Excellent

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

Perfect in Every Way!

This is an outstanding home in every way! It was the cleanest, most inviting, well equipped home we've stayed in. The location is perfect, the neighborhood is wonderful, we felt like we were instantly part of a very special community. The second you walk in...you felt welcomed. I use the word 'home' instead of house because you can see and feel the love Waddys and Ralph have put into it. The communication was so reassuring as well...we knew we could count on them. We have been dreaming of this stay for years and it was everything we imagined and more.
Stayed 30 nights in Dec 2023
Verified review

10/10 Excellent

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

Best home in the lower Keys!

Let me start off by saying this place looks even better in person. Very spacious, very clean, comfortable beds, kitchen has absolutely everything you could need and more. The neighborhood is quiet. We also loved walking and riding our bikes everywhere. The pool I spent almost everyday relaxing in. We brought our pontoon boat for the monthly stay. It can be tricky at first getting in and out of there until you get use to it. But follow Waddy’s & Ralphs instructions and they also have a colored photo on where to go to avoid shallow areas to get to the canal. So many great restaurants very close by and some you could walk too. Key West is only 20 minutes away. Waddy’s and Ralph were such amazing host. Best house we have ever stayed at. This will be our go to place for now on.
Stayed 29 nights in Apr 2025
Verified review

10/10 Excellent

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

July adventure

Property was great. Neighbors that we met were nice. Canal was a little tight for our boat thankfully my son solved that issue and the neighbors across the way didn’t have their boat in the water. Waterways a little tricky but we managed it. Lots of storage. Yard could have used some cleanup but had nothing to do with our stay Shade over the pool area was a fabulous surprise The freezer in the refrigerator upstairs doesn’t work well but their was a second freezer downstairs Had a great time just wish it wasn’t blowing so much Over all a very nice home Hopefully it’s available again when we plan our next trip
Stayed 30 nights in Jul 2022
Verified review

10/10 Excellent

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

Cudjoe Key delightful vacation home

Everything worked out smoothly. The owner is very organized ,check in and checkout was a breeze. Any questions you may have, the owner responds immediately. A comfortable adorable home. Loved the deck which showcased some gorgeous sunsets.The sail canopy kept the pool at a nice temperature from the hot sun . We enjoyed the pool everyday.. Thanks for sharing your home!
Stayed 28 nights in May 2022
Verified review

10/10 Excellent

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

Great location, large property.

Great location, property owners are very easy to work with. We had a problem with the refrigerator that was corrected immediately. Canal is a bit tight but no problem with our 23’. Pool was added bonus. Two freezers available for bait and catch. Minor issues with tv remote controls not working.
Stayed 28 nights in Jan 2022
Verified review

10/10 Excellent

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

Amazing Experience!

My wife and I came down with our two kids and dog, and we had such a great time. Waddys was such a pleasure to work with and did an amazing job making the process easy and welcoming for us. She was in contact with us making sure everything was alright and gave us recommendations for the area. The house and yard area is perfect for a relaxing stay. There are so many places to play and hangout with the family. The pool was obviously a huge hit with our toddler, and it was so nice not having to pack up everything and head out just to get a little swimming in. We loved the neighborhood being tucked away, but also only about a 30 minute drive to Key West. It made us feel like we were living an authentic Florida Keys lifestyle. We definitely hope to make it back sometime!
Stayed 28 nights in Nov 2021
Response from VrboOwner on 26 Dec 2021
Thank you so much for your kind words, Matthew. We really appreciate you taking the time out to share your experience with us. Happy you and your family enjoyed the property. Happy Holidays!
Verified review

10/10 Excellent

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

Paradise Perfection!

Our family has been renting homes in the Florida Keys every year for numerous years. Our overall experience with this home and the owners Waddys and Ralph (especially Waddys) was absolutely the best experience ever. First and foremost Waddys is awesome to work with. Communication from beginning to end with her made our vacation flawless. She is such a kind and caring owner who wants to ensure her guests have a perfect experience which we absolutely did! When we arrived at the home after a difficult journey (trailer issues) we were so thrilled with the beautiful and immaculate home. This is by far the cleanest home we have ever stayed in and it was evident this is a well cared for home and not just a rental property. The home is tastefully decorated with a gorgeous coastal theme. The home is updated and stocked with everything you could possibly need including access to cleaning devices and cleaning products which helped maintain the cleanliness of the home. The kitchen is so well equipped with every possible item. Every bed is beyond comfortable with foam mattresses and beautiful decor. There is plenty of space with the open concept kitchen and living room for our family. The level of comfort in this home is unparalleled. The home is located only a few homes down from the ocean in a very quiet friendly neighborhood. which was awesome! The downstairs is also perfect with a large outdoor space that is extremely private with a privacy fence on a large corner lot. The vegetation between the next door neighbor also provides more privacy. There is a covered porch adjacent to the amazing pool which we enjoyed for many, many hours while there. The beach area that looks down the canal to the ocean is fantastic! We enjoyed sitting in this area in the evenings for a nice ocean breeze. The large porch upstairs was also well utilized for morning coffee and dinners and served as the perfect outdoor space. We also were thrilled with the large downstairs storage with two freezers for bait and fresh catches. We were able to easily unload in this area and bring items up as needed which made life so much easier. We brought our 13.5 year old fur baby with us which we are so appreciative to the owners for allowing us to have her in their home. Waddys made sure we had the perfect vacation and we are so thankful we were able to share their home for a month. We were We will definitely be returning next year and beyond and will look forward every day until we return!
Stayed 31 nights in May 2021
Response from VrboOwner on 22 June 2021
Thank you so much for your kind words, Alisa. We really appreciate you taking the time out to share your experience with us . We count ourselves lucky for customers like you. We look forward to working with you again in the future!
Verified review

10/10 Excellent

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

Wonderful Stay in Cudjoe

Waddys is a great communicator. We appreciated how organized the house and supplies were as well as the size of the kitchen and how well equipped it was. Especially during these crazy Covid times where we ate in more often. The location for boating was awesome too! We enjoyed soaking in the pool at the end of a long day on the water. Would definitely return.
Stayed 28 nights in Feb 2021
Verified review

10/10 Excellent

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

Another great stay!

Great house,great area. A no brainer,rent this house if you can get it.
Stayed 30 nights in Aug 2020
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