My Happy Place - Monthly Rental

2 Bedrooms

2 Bathrooms

4 Guests

5.0

If you are looking for a Key West vibe with modern amenities, look no further. This 2-bedroom, 2-bath shotgun style home doesn’t disappoint. With it's beautiful interior and refreshing dip pool, you won't want to leave!


Save 10% On May Monthly Rentals!

For a Limited Time Save 10% Select Monthly Rentals in May . Use Code: SAVE10MAY

Save 10% On June Monthly Rentals!

For a Limited Time Save 10% Select Monthly Rentals in June . Use Code: SAVE10JUNE


About the property

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!

THE PROPERTY: From its delightful mosaic-tiled, covered front porch to its back yard dip pool, this Key West home will surprise you! Petite yet grand, this home is walkable to many attractions.

As you enter the home via the living room, you will be surrounded by comfortable furnishings, hardwood floors, a vaulted ceiling and plenty of natural light. Proceed down the Dade County Pine hall to the guest bedroom and hall bath. Further down the hall is the primary bedroom and en-suite bath. Continue through the French doors towards the back of the home, to the well-appointed kitchen with vaulted ceiling. White cabinets and countertops, stainless-steel appliances, and a small island make this kitchen a dream to cook in. If hor d’ oeuvres and cocktails are more your style, you will love preparing them in the kitchen while enjoying a pool view.

Stroll beyond the kitchen’s double glass doors onto the covered deck and patio. Here you will find your private dip pool, lounge chairs, table with umbrella and additional seating as well as a grill. The backyard area is secluded and beautifully landscaped. Your own washer and dryer are housed in a spacious outdoor room near the pool. After a day strolling about Key West, this beautiful and classic home offers you a unique opportunity to relax and unwind, like you have been yearning for.

BED CONFIGURATION: The primary bedroom boasts a king size bed, ensuite bath and closet. The second includes a queen size bed and hall bath. Both bedrooms have TVs, ceiling fans, and ample closets.

OUTDOOR AMENITIES: With your own dip-pool and fenced-in yard, this home provides Key West privacy and tranquility. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. Enjoy morning coffee and people-watching from the covered front porch.

PARKING: No designated parking space. There is free on-street neighborhood parking.

LOCATION: Being in the heart of Old Town makes this a fabulous choice for access to all that Key West has to offer. Just 3 blocks to Duval Street and conveniently located near restaurants, groceries, shops and galleries, this home is walkable to attractions including Mallory Square and The Wharf.

PETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that are pet-friendly).

SMOKING: This is a non-smoking home and property.

***Guests must be 25 years of age or older unless accompanied by an adult.

***Please note that the cleaning fee includes a full "mid-stay" clean***

***Managed by Historic Key West Vacation Rentals***


Features & amenities

  • Type: House
  • pets not allowed
  • Outdoor Dining
  • Historic Old Town
  • Monthly
  • Nightly & Weekly: No
  • Air Conditioning
  • Internet Access
  • Kitchen
  • Washer / Dryer
  • Walk in Shower

Get Quote

Use the calendar to select your dates.

Have a question?

5.0 (6 reviews)

5.0

our happy place too!

This beautiful home is exactly what the pictures show on the HKWVR site. It is beautifully decorated and extremely clean. It is in a residential area but conveniently located for walking to the harbor,all things on and off Duval,Mallory Square and the Southernmost Point. We rented bikes for the month and they were easily stored out of the way in the fenced yard. The pool was absolute necessity since we were there the whole month of August. The pool service was weekly. Someone slips in and out cleaning up palm tree debris and taking the big trash cans to and from the curb on trash day. The management company was immediately responsive to the few issues we had sending Steve and others to fix those problems within an hour or two of us notifying them. We had 2 different couples stay a week each while there and they only had to pay for one night of parking because there are non resident spots available in the neighborhood. We would
definitely recommend this property to others.I would recommend HKWVR for any future Key West trips due to their fabulous service.

Submitted by St Louis MO on Sep 29, 2022

5.0

my happy place for a month!

We were there for a month and had a great stay. The property is so welcoming and accommodating. The property is well maintained. We were there when “Elsa” came through and didn’t have any problems then nor anytime during our stay. The location is great. It is an easy walk to the Wharf, Front Street, Duval, Southernmost Point, Fort Zachary, basically any location in that area of Key West. We used the grill and the pool daily. We loved sitting on the porch early mornings with our coffee and late evenings with a cocktail watching the passerby’s. The pool and landscaping have a maintenance crew that comes weekly so the property stays kept up during the entire stay. The office staff are very very helpful, pleasant and easy to communicate with
. We could not have asked for anything better. It was a great stay.

Submitted by Fort Worth TX on Aug 02, 2021

5.0

the most amazing stay!

After 2 failed attempts to book a 1 bedroom condo, Historic Key West Vacation Rentals went above and beyond to make our trip amazing! The property was flawless! Beautiful, amazing location, fantastic customer service! She even helped up book bikes and snorkeling! “My Happy Place” will always hold so many memories for us!

Submitted by Currie NC on Jun 12, 2021

5.0

wonderful rental; great management team

We moved to “My Happy Place” late March 2020 just as the COVID pandemic started to affect Key West. Although it was a difficult time, the house was perfect! Very clean with beautiful art and furniture. The kitchen was extremely well-outfitted with good pots and pans and ample cooking gear. This was fortunate as we cooked all our meals at home since restaurants were closed except for takeout. The house is in Old Town and we were within walking distance of Fausto's Market and the fantastic Eaton Seafood. We really couldn’t have asked for a better location.
The house has a nice back patio with a small dipping pool. The landscaping is wonderful and well-tended. Lounge seating and a dining table with chairs and a large umbrella were much appreciated. It would have been nice to have an outdoor shower but that’s a small matter.
Inside was all good, the AC functioned perfectly, and the bathrooms were well stocked and very clean. We could have used more storage but we adjusted. There were three working televisions. We couldn’t have asked for a better long-term rental and we were especially happy with all the help we got from The Historic Key West Vacation Rental Team. Our stay was extended because of the Covid crisis and thankfully we got all the help we needed!

Submitted by New York NY on Jun 17, 2020

5.0

a great vacation place.

The property has a great location, just three blocks from Duval Street. The house was very clean and well appointed. I would recommend this property to other travelers.

Submitted by Huntington WV on Jan 06, 2018

5.0

a month in key west

We had a great time. Great restaurants. Weather was terrific this year so we spent at least a few hours every day at a beach. We took in some local theater a couple of times which was very good. The great thing about Key West is that there is always something going on somewhere. From this location all you have to do is walk there or ride your bike. It was our second time renting for a month in Key West. It was our first time at Smugglers Cove. The best thing about this property was it's proximity to downtown as well as the Harbor/Marina. It is fairly roomy. We had weekend guests a couple times. It worked out very well. It is fairly well appointed. However, after a month there were a few minor details which would have made our stay more pleasurable. We spent most mornings and early evenings on the front porch. Some landscaping and flowers in the front of the house similar to what is pictured would be nice. Although the kitchen is appointed with new appliances, the washer and dryer in the outdoor storage could be replaced. The gates in front of the property could use some maintenance. These aren't deal breakers, just some suggestions. I can't say enough about how responsive HKWVR was to all of our needs and requests. They were great to work with.

Submitted by Elkhart IN on Mar 15, 2017

Location

May 14-14, 2025
Reserve
  • Key West Chamber of Commerce Logo
  • Key West Business Guild Logo
  • The Vacation Rental Travel Guide - Most Outstanding Award for 2017
  • Florida VRMA Logo
  • VRMA Logo
  • AirBnB Super Host Badge
  • Vrbo Premier Host Badge