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USA Florida Key West Old Town Key West Listing #10778

Helen's Hideaway - Key West, FL

48 reviews
Max occupancy: 6 2 King Bed, 1 Sofa Bed 2 bedrooms 2 bathrooms 4 dog max  (30 lb weight limit) 
720 Simonton Lane #RR, Key West, FL 33040

Worry-free booking

Enjoy peace of mind with flexible options to change or cancel your trip.

If your check-in date is at least 30 days away, you can reschedule your trip, cancel and receive 100% of the cost as a Future Stay Credit, or cancel for a refund (minus the booking fee).

Expert cleaning

Professional housekeepers clean and stock each home, using an EPA-approved disinfectant.

Local support

Each trip is backed by 24/7 customer support and local teams everywhere we operate.


Many Vacasa homes use smart locks or lockboxes for a smooth, contactless check-in.

A Key West gem w/ a private pool - close to shops & restaurants, dog-friendly

Escape to Key West with the family at this charming Floridian home on a quiet street with a furnished patio, private, heated swimming pool, and space for up to six guests and a dog for a small nightly fee. This home also offers off-street, private parking for one vehicle. Two dogs (up to 30 pounds each) are welcome to join you.

Located alongside several historic homes and other structures, this rental is just a short walk from Duval Street, the most popular street in Key West and home to restaurants, cafes, and unique local shops. Duval Street also hosts a number of special events and festivals held throughout the year as well as the area's hottest bars and live music venues. History buffs will want to visit the Ernest Hemingway Home and Museum, just a quarter-mile away, as well as the Truman Little White House, less than a mile west.

Take a dip in your private pool, or just chill poolside with a refreshing drink and a good book. This rental offers free WiFi and there are also two cable TVs in case you want to relax at home and catch up on your favorite shows after an exciting day out.

If you're looking for an ideal home away from home in Key West, choose this rental today.

*Please note that last-minute bookings cannot be made online. Call Vacasa for details.*A damage waiver, covering up to $2,000 of accidental damage to the property or its contents, is included in the cost of your reservation.

You must be 25 years or older to rent this property.

Property tax ID: 83964: Monroe County BTR
Property permit ID: 584 / 5881: Key West BTR




Washer/dryer : Private

Heating & cooling

Central AC

Kitchen & dining





Internet : Comcast


Cable : Comcast

On-site activities

Pool : Private

Heated pool


Gas grill : Private

Beach towels




48 reviews

Jaclyn K. Jun 2020
Helen's hideaway was perfect for a private getaway. It is just steps away from Duval and the private pool was perfect to enjoy the Key West weather but avoid the crowds.
Trent T. Jun 2020
Perfect location and great pool. All in all would definitely book this place again.
Mark W. Jun 2020
It was like having our own place for a week. Perfectly located and all the necessities for a family to cook, swim, relax, and sleep,
Dan H. Feb 2020
Perfect location for walking and bicycling the island! Very short walk to all the fun of the Duval St. restaurants, bars, galleries, and shops. This is the perfect home for two couples traveling together, offering private bedroom suites, but a roomy living/dining area. Everything in the home was clean, comfortable, and in good working order, including the pool! I have no reservations recommending this property, and would stay again.
Heather G. Feb 2020
Helen’s Hideaway was a great little spot to stay close to all the fun stuff on Duval and a short walk to Higgs beach. The place was clean and very suitable for 2 couples. We loved the outdoor sitting area. The area around the home was quiet and it was easy to get into upon check in. The parking spot was a plus although we did not need it. Great little spot to relax after a day of sightseeing and wandering the streets of Key West.
Stuart L. Feb 2020
The property representative was wonderful from our initial contact until we left at the end of our stay.
John B. Oct 2019
We loved the separate master bedroom/bathroom. The main part of the house was great as well. The PRIVATE pool was great after we turned down the heat (was set at 95!) This place is very secluded and quiet but yet right in the middle of everything. It was perfect for 2 couples, you could have a 3rd couple but they would have to sleep on the pull out in the living room and share a bathroom in the main quarters which wouldn’t be very private.
Roberto P. Aug 2019
Clean, Great location.
Laurie K. Aug 2019
This is a cute rental steps away from Duval. Tucked off of a main street, it's a little hard to find at first. There is very little in the kitchen in terms of pantry items (not even coffee filters - although we left ours for the next renter), so don't expect salt, pepper, any of that. No dishwasher either. Solve that problem by not cooking!

Having a pool was a bonus. The water is very warm in Aug though, so be aware it may not be super refreshing. Main bathroom is really nice with a huge shower and double sinks. We appreciated shampoo, conditioner and soap. Our towels were changed out on our next to last day too, which was unexpected. Overall, good property and we would look at it again if we get back to Key West.
Jennifer C. Jul 2019
Just got back and words can not express how much we enjoyed staying at Helen’s Hideaway.
The house is in a great location, close to Duval. Tons of room and the private pool was awesome. Only problem we had was the WiFi. Would definitely stay there again. ❤️☀️🐔
Manager response:
Hello Jennifer, Thank you for your feedback! We are so glad that you enjoyed your stay. Please know that our team is available for any issues a guest may experience during their stay and help troubleshoot any WiFi issues. We look forward to hosting you again soon!
Sandra A. Jul 2019
Property is in need of some serious TLC. Even little things such as a drawer hanging by one hinge, no toilet paper holder in bathroom, wifi never worked entire stay, pool covered in algae with filtering system leaking - was requested not to run filtering, Fixtures and furniture pretty old. Could be a nice little place with some updates and maintenance.
Manager response:
We appreciate your feedback as we are continually trying to improve this rental. The sofa has been replaced and the pool pump and wifi are now working properly. We hope to have the chance to impress you in the future.
Lisa R. Jul 2019
We had such an amazing weekend staying at Helen’s Hideaway! Perfect location close to all the action, yet far enough away you can relax without all the noise. This house had all the amenities you need. All you have you do is show up ready to relax and enjoy! The pool was the perfect ending to each day! And the icing on the cake was the sleep we got in the bed! The most comfortable bed I have ever slept in hands down! Helen’s is a hidden gem! If it’s available to book for your trip, I highly recommend staying here. We will definitely be back soon!
Tiffany N. May 2019
Helen’s Hideaway is the quintessential Key West home! The highlight was definitely the spacious private pool. The interior was very comfortable with cute tropical accents. The privacy of the separate bungalow with the second bedroom was very nice and gave us a lot of room to spread out. Being walking distance from Duval Street was super convenient and there’s a ton to do in the area. If you’re going to be in Key West, Helen’s Hideaway is definitely a great place to call home for your stay!
Todd V. May 2019
Helen's Hideaway was perfect for us as we were traveling with two couples. It was like having 2 separate houses, each with privacy. The kitchen was adequate for our needs, but did lack a dishwasher. We at meals out, so that wasn't much of an issue. Other than that, everything there we needed (microwave, blender, coffee maker, toaster, etc.) I did accidentally discover that running the coffee maker, toaster and microwave was too much for the circuit, but that was a quick fix. The pool area was perfect...great afternoon sun on all 4 chairs, with plenty of shade around the table under the overhang. Plenty of towels for the bathrooms and pool area. Both bathrooms had soap and shampoo, as well as a hair dryer (although it appeared one hair dryer wasn't working at the time.) Beds were comfortable and the A/C worked great. We loved the location, and with the back gate by the pool equipment, we could slide out of there and be less than 1/2 block from Duval. Neighbors were quiet, and we rarely heard any noise. This was my first rental and I was a little curious renting someplace sight unseen, but it worked out wonderfully. I'd recommend Helen's Hideaway in a heartbeat.
Ichele W. May 2019
Loved the location of the house, the swimming pool and the tropical yard. House could use some updated furniture. Lots of fans throughout the house. Nice amenities. Would stay here again.
Jane R. May 2019
Small but perfect. Non smoking on entire property was new. Right around the corner from Duval.
Robert W. Apr 2019
Great location!! Pool area is very private and nice. Beds were very comfortable. Lighting in house was lacking and difficult to figure out. No dishwasher . Still a Great little getaway!!
Kelly R. Mar 2019
Ok, this place is a great little place. It’s nothing extravagant or fancy, a bit campy. Only in Key West would i find such a place to be perfect and charming. Although it’s surrounded by other places, it’s totally a private little enclave. It’s down a little alley and surrounded by a privacy fence. The pool is small and sweet. The 2nd bedroom is completely separate and private which made it perfect for my 17 year old and her friends. The beds are comfortable and it has almost everything you need- A blender and a cookie sheet for the oven would be nice (the cookie sheet there does not fit in the small oven). The location is perfect in my opinion. The ‘better than sex dessert bar’, a short walk up the road, is a must try!
I would stay here again and I would recommend it to anyone looking for the real Key West experience.
Sandy S. Mar 2019
The lay out of the home is awesome. The house needs updating though
Lynn K. Feb 2019
My family and I enjoyed the house. It does need outside lighting around the grill and the parking is a bit rough. Dirt type alley with others parking close to you. Overall did enjoy the stay.
Manager response:
It was a pleasure hosting your family, Lynn! We’ll certainly pass your feedback onto our management team, so that we can check that the lighting is adequate outside. Please visit with us again in the near future!
Darla E. Sep 2018
This home offers plenty. Private pool, full kitchen, cabana style 2nd bedroom w/bathroom (perfect for 2 couples), secret gate leading out to Duval Street and plenty of privacy.
Reid W. Jul 2018
Perfect place for 2 couples. The location and amenities cannot be beat! Will be back.
Nobutaka T. Jul 2018
This was our second time stay and it has been about 3 years in between but we sure enjoyed as much as first time. Very clean, perfect location from all attractions yet very quiet. Lots of space. Looking forward to have another visit soon.
Jacob M. Jun 2018
We had a great time on our trip. Very private place and close enough to Duval for anyone.
Laurell A. Jun 2018
A great and quiet spot close to Duval. The pool is a great place to relax!
Chantal S. May 2018
Beautiful home with lots of traditional Key West charm. Very comfortable accommodations and clean. Kitchen, although small, is equipped with everything you may need and bathrooms have amenities such as hair dryer, shampoo, conditioner, soap and body lotion. They also provided extra towels the 2nd day of our stay. Wonderful, hotel like amenities and service. Great outdoor space complete with beach towels and pool noodles to hang out by the pool. The second bedroom has it's own bathroom, so this is perfect for 2 couples that want their own space. The best part of this home is the location. EVERYTHING is walking distance. You are not more than 5-10 mins on foot to Duval Street and all the great restaurants, bars and shops this area has to offer. I will DEFINITELY stay at this home again when I visit Key West.
Mary L C. Apr 2018
Conveniently located and yet magically private. Clean with great water pressure.
Josh P. Feb 2018
A great place to stay for two couples. We enjoyed the pool it was great to knock the Key West morning edge off.
Sven H. Jan 2018
This property was ideal for us. The private bedrooms with en-suites were perfect for the 4 adults and the toddler could not stay out of the pool. The location is within walking distance from the main strip and many good restaurants and bars. The off-street parking is an added bonus. We absolutely loved our stay here and would definitely recommend it.
Frank P. Jan 2018
Nice spot, one block off Duval. Great for two couples to share and still have some privacy.
Walter B. Dec 2017
We have taken many trips to Key West but first around XMas and it is really a great time to go. Helen's Hideaway worked out very well. We had 5 people are grown up children and guest. The cottage was great and the sleep sofa was great for 1 person. The house is very quaint and pretty well taken care and we liked the house a lot. Especially nice is to hang out at the pool without having to make plans like at a hotel and traverse a hotel to hang out. WiFi was a little sketch in pool area. The kitchen is small but we did some small cooking which fit nicely with going out to eat and worked well for us. Would definitely stay at house again.
Terry M. Dec 2017
You won't be disappointed.
Wayne W. Nov 2017
Stayed there last year this year and will be back again next year!!