Entire home

Key West Dreamin' - Private Pool Steps Off Duval

Photo gallery for Key West Dreamin' - Private Pool Steps Off Duval

living room
street view
gate entrance
pool
living room

Reviews

9.6 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 699 sq m

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Kitchen
  • Barbecue grill

Explore the area

Map
Key West, FL
  • Duval Street
    ‪1 min walk‬
  • South Beach
    ‪5 min walk‬
  • Southernmost Point
    ‪6 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪9 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

Common spaces

1 Double Sofa Bed

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Deck or patio
Kitchen
Garden
Dining area

About this property

Key West Dreamin' - Private Pool Steps Off Duval

Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one that links us to our Cuban heritage back to the late 1800's. A stroll through this charming Upper Duval neighborhood is to rendezvous with an important part of our island's rich cigar and rum history.

A Little Bit of History: It is noteworthy that in 1876, one of our most prominent Cuban immigrants, Eduardo H. Gato, built a stunning marble Cigar Factory on the corner of Simonton and Catherine Streets to create the city's largest producing hand-rolled cigar factory. As the cigar industry boomed, so did the immediate need for neighborhood housing. Houses for merchants and workers alike sprang up side-by-side, right to the street, to form the Old Town Key West "Gato" neighborhood which includes Louisa, Catherine, Amelia, Virginia and Simonton Streets; indeed at one point this end of the island was once called "Gatoville."

Located just off Duval on Catherine Street, Key West Dreamin', is an important representation of how the history of our architectural culture is tied to the boom of the cigar industry in the late 1800's. Today the neighborhood is part of Key West's historic preservation district. So the front facade of the houses look very similar to how they originally looked, giving the wonderful effect of maintaining the charm of the neighborhood.

You don't have to smoke Cohibas (flagship brand of Cuban Cigars) or drink Cubra Libras (1.25 oz Rum, and fill with coke and always lime wedge), to enjoy the dynamic impact the early cigar and rum industries had on our architectural culture. Choosing to stay in this historic neighborhood will help take you back to a simpler time in history. Come and enjoy this authentic Key West house in this important part of our island. And why not have rum... And maybe even a cigar.

Interior Layout: The interior of this one-of-a-kind property has been luxuriously renovated and reconfigured to bring the joy of indoor-outdoor pool-garden living to focus. In the fall of 2014, the kitchen and bathrooms received a major renovation for the specific purpose of redesigning it as a luxury vacation rental home.

As you step into the front door, the ‘shot gun’ style hallway leads from the front all the way to the back of the house to the great-room. Eyes are immediately drawn to the back of the house since the back wall is light-filled and gorgeous. A broad bank of French doors and large transom windows span the entire width of the room and the whole effect is made even more dynamic with a soaring cathedral ceiling. The French doors adjoin the great-room to the lushly landscaped back yard and generous size swimming pool.

A beautiful renovation has created the feeling of a grand great-room with soaring open-beamed ceilings and custom transom windows that meet the ceiling. Set to one side of the room, the upscale kitchen offers bright white cabinets, state-of-the-art stainless steel appliances, cream colored granite counter tops, and glistening subway tile back splashes, creating an artistic and functional space. I love the over-sized dining island which is set in the center of everything so you can enjoy the cooking, the large screen TV and turn your gaze to the tropical back deck and swimming pool.

Since the great-room is connected to the outdoors with French doors that extend the entire width of the house, the stage for the indoor - outdoor island lifestyle is set. Whether you choose to cozy inside or lounge around the pool you're always sure to enjoy the quintessential outdoor tropical scene. Just outside the kitchen door, the back yard offers a lovely lounge room complete with an open beam ceiling and shuttered walls making this a unique open-air sitting area that is delightful to enjoy all year around.

The two large bedrooms with en-suite bathrooms are just off the hallway that joins the front to the back of the house. Both bedrooms are made to feel more spacious with open beam cathedral ceilings. Facing the front of the house the master bedroom is to the right. This bedroom offers a king size bed, and in addition to a private bath the master bedroom has a set of French doors that connect it with the back yard and swimming pool.

The second bedroom is a similar design to the master bedroom in that it also has cathedral ceilings and a private en-suite bath. This bedroom situated off the hall to the left as you face the house, offers two twin beds that can be joined to make a king size bed. Bathrooms for each bedroom suite are luxurious and similar in design, donning fabulous Key lime colored granite vanity tops, brilliant white subway tiles, and floor-to-ceiling frameless clear glass walls that create double size shower rooms. A fashion stripe of shining colored glass tiles and designer bath fixtures complete the look.

Grounds: The curb appeal is endearing with a white garden wall and wrought iron fence toppers. The symmetrical entrance is appointed with garden-basket wall statues and is gated with a charming wrought iron gate. Once inside the gate the spacious front porch invites you to pause and "sit a spell" on the porch swing. The front side and back yards are nicely landscaped and artful flagstone has been used to cover the entire grounds.

The original back yard is fully fenced with a white picket fence. A pretty garden trellis holds a showy tropical vine which flowers during different times of the year, and a wide variety of beautiful palm trees and colorful tropical foliage create privacy and a romantic tropical setting. The back yard garden was redesigned to accommodate a nice size swimming pool and flagstone pavers are set throughout the back to create a beautiful garden and sun deck.

Bedding Summary:

Master bedroom - King size bed
Second bedroom - 2 twin beds (can be made up as a king bed)
Living Room - Queen sleeper sofa
Amenities: Swimming pool, large flagstone deck, tropical gardens, front porch with porch swing, privacy fences. Fully equipped kitchen, central a/c, telephone, large flat-screen TV, stereo, washer / dryer, grill. Linens and towels are provided.

Parking: Off - Street Parking for one standard or compact size car. "Big Rigs" won't fit.

Activities: Uptown Key West - Close to the Southern Most Point of the United States and Key West South Beach and the delightful Key West Butterfly Conservatory. This Uptown neighborhood features art galleries and boutiques, wonderful eateries and internationally famous fine restaurants (Martin's is just down the street), coffee and tea house, fine gift and clothing stores, Grand Vin wine tasting, Flamingo Crossing home made tropical ice cream. Start at the top of Duval St. near the Atlantic Ocean and can take the 20 min stroll to the Gulf of Mexico (remember it takes 3 to 4 Key West streets to equal the distance of a typical city block). Sailing, boating, diving, museums, nightlife. South Beach and the Southernmost Point are just a 6-minute stroll away from Key West Dreamin'.

Restrictions: Smoke free house. Smoking permitted outside only. No pets. (Please don't ask!). We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.

PAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.

Property manager

VHKW - Vacation Homes of Key West
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted

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
This property accepts cash
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

We should mention

A car is not required for transport to and from this property

About the area

Key West

Located by the sea, this holiday home is in Old Town Key West, a neighbourhood in Key West. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and South Beach. Key West Butterfly and Nature Conservatory and MLK Community Pool & Community Center are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Key West, FL

What's nearby

  • Duval Street - 1 min walk - 0.1 km
  • South Beach - 5 min walk - 0.4 km
  • Southernmost Point - 6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum - 7 min walk - 0.6 km
  • Mallory Square - 4 min drive - 1.8 km

Getting around

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

Restaurants

  • ‪Old Town Tavern Key West - ‬5 min walk
  • ‪Southernmost Beach Café - ‬5 min walk
  • ‪Southernmost Point Bar In the USA - ‬5 min walk
  • ‪Rum Bar at the Speakeasy Inn - ‬2 min walk
  • ‪Banana Cafe - ‬2 min walk

Frequently asked questions

Does Key West Dreamin' - Private Pool Steps Off Duval have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Key West Dreamin' - Private Pool Steps Off Duval pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Key West Dreamin' - Private Pool Steps Off Duval?

Check-in begins at 4:00 PM.

What time is check-out at Key West Dreamin' - Private Pool Steps Off Duval?

Checkout is at 10:00 AM.

Where is Key West Dreamin' - Private Pool Steps Off Duval located?

Located in Old Town Key West, this holiday home is steps away from City Zoo Gallery and Duval Street. South Beach and Florida Keys Beaches are also within 5 minutes.

Reviews

9.6

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. 36 out of 45 reviews
Rating 8 - Good. 8 out of 45 reviews
Rating 6 - Okay. 1 out of 45 reviews
Rating 4 - Poor. 0 out of 45 reviews
Rating 2 - Terrible. 0 out of 45 reviews

9.6/10

Cleanliness

9.8/10

Check-in

9.6/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

Reviews

10/10 Excellent

Laura F.

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

Great location

My friends and I loved our stay at this property and took full advantage of the living space and pool while catching up on our lives. The location couldn’t have been more convenient to shops, bars, and restaurants.Our car did not fit in the one parking space, but we were prepared for that possibility since the listing clearly explains that the space would only fit a compact car (we had a Subaru Outback). Luckily, we were able to grab one of the very few street parking spots near the property upon arrival.
Stayed 4 nights in Mar 2025

10/10 Excellent

Tracy C.

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

Incredible Location

We loved our time at this property. The house was clean and charming. The location was excellent! We walked everywhere. It was a convenient spot - close to areas of interest, yet a quiet spot to relax and unwind!
Stayed 5 nights in Mar 2025

8/10 Good

Kevin R.

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

Key west first timers

The property was very nice. The location was very close to everything. It’s Not a place to drive to and from venues. However you can uber from the home to further away events. The town is cruise port so on days you may have wait times as thousands of extra people are in town. It’s a beautiful island. The home is very nice for two couples or family’s up to 6 as the couch turns into a bed as well. The pool is nice if you want to get sun on the trip. I recommend going to a beach. The back yard is well shaded. So getting sun doesn’t fit this set up just a few hrs a day. The home was very clean and tidy. Parking is limited to a 15x9 space so if you have a compact or jeep it will fit. Otherwise you will need to find a pay lot to park. On our stay the pool area needed cleaning Powerwashing as it was pretty weathered. Iguanas come and go frequently in the pool area. So be prepared to be startled often. The back fence was falling over and needs repair. the hammock was pretty dirty and we didn’t feel comfortable using it. Yes we would stay here again. It’s a great place and location.
Stayed 4 nights in Mar 2025

10/10 Excellent

Rebecca B.

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

Paradise

Beautiful property, great pool, great location! Well appointed. Weather cooperated which was a plus. Definitely recommend and will stay here again!
Stayed 7 nights in Mar 2025

10/10 Excellent

Ashley E.

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

Cute home

It was a great location, very clean and the rental company was amazing.
Stayed 5 nights in Jul 2024

10/10 Excellent

Mark H.

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

vacation stay

We had a great time and really enjoyed our stay here. Everything was super clean and the location is perfect.
Stayed 4 nights in May 2024

10/10 Excellent

Carolyn L.

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

House with pool

Great house for our family. Clean and loved that towels and laundry facilities were available. Pool was a great size
Stayed 4 nights in Jan 2024

10/10 Excellent

Elizabeth M.

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

Fabulous getaway spot

Cute, cozy and wonderful location!
Stayed 4 nights in Jan 2024

8/10 Good

Monica G.

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

10 Day Vacay

Wonderful property overall. Been coming to KW every December for 15 years. This would be in my top 5. Great location-close to points of interest, great parking. Bedrooms are very large and beds are incredibly comfortable. Bathrooms are nice. Pool and pool area are relaxing - surface is pretty uneven but still a great perk. Kitchen is well appointed-a few more mugs/glasses would be a good idea. The only reason for 4 stars is because the couch is incredibly uncomfortable. I feel strongly that it is time for it to be replaced. With such a cozy space, the seating in the common are should be comfortable. In addition, the TV should be updated to a smart tv. We had a stretch of weather that forced us inside and the cable tv options weren’t very good. It would have been nice to stream Netflix or Amazon. I ended up ordering an apple adapter with flash and hdmi connections so I could connect my iPad to the TV and stream that way. It cost me $50 - but was worth it. If we had better weather, it’s possible that the couch and TV wouldn’t have made it into my review since we would have much preferred to spend our time outside. The trees at the front of the house where the parking spot is should probably be manicured/maintained. Even in moderately breezy weather they bang against the house very loudly - making it difficult to sleep. Overall - very nice stay - just a few minor suggestions that I think could really improve the guest experience.
Stayed 11 nights in Dec 2023

8/10 Good

Ivey I.

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

Great house

Overall the stay was great. The house is in a great location and walking to everything is super easy. I would suggest getting a scooter to get around the rest of the island but if you’re just wanting to checkout Duval or surrounding historical sites, walking is good. Communication with the owner/property management was perfect. They were super responsive and VERY helpful throughout our stay. There are iguanas and chickens around so had to clean the back patio multiple times due to poop but that’s normal. The pots and pans could use updating. I had to use the grill instead because the pans were old and everything stuck to them. That’s my only area around room for improvement.
Stayed 7 nights in Nov 2023

10/10 Excellent

Leigh D.

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

Great location and home

We had a great time staying at this rental unit. The management company was very responsive to our questions and promptly sent a maintenance person over to solve the small pool issue we had. Otherwise great experience!!
Stayed 7 nights in Oct 2023

6/10 Okay

Jane H.

Liked: Cleanliness, check-in, communication, location

Key west vacation

House was fine but the air conditioning in the master bedroom was minimal at best. Backyard was not maintained and the pool was very dirty when we arrived. Overall the backyard was very uninviting. Even though it was in the mid 90’s our entire trip we only used the pool twice for a few minutes each time.
Stayed 4 nights in Oct 2023

10/10 Excellent

Laura E.

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

Great time in Key West!

We really enjoyed our stay- property was as described, conveniently located, clean and well stocked! My family had a great time - especially enjoyed the pool!
Stayed 5 nights in Aug 2023

8/10 Good

Bekki W.

Liked: Cleanliness, location, listing accuracy

Great vacation rental

Great location, had everything we needed for our stay in Key West. Would stay in this property again.
Stayed 4 nights in May 2023

10/10 Excellent

Tina C.

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

Great grounds, good location, clean and PM was great!

Wonderful place to stay with kids!
Stayed 7 nights in Nov 2022

10/10 Excellent

avner v.

Liked: Cleanliness, check-in, communication, location

A hotel with calmness

As a family we really enjoyed our stay at the hotel
Stayed 6 nights in Oct 2022

10/10 Excellent

James T.

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

Great house & location

We really enjoyed our stay. The house was the perfect size for our family of four & the location was perfect. Close to Duval Street, shopping & restaurants.
Stayed 8 nights in Oct 2022

8/10 Good

Brett B.

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

Great location

The house was great but the a/c broke one night making it 86 degrees inside.
Stayed 4 nights in Sep 2022

8/10 Good

Kathryn M.

Liked: Cleanliness, check-in, communication, location

The property interior has been nicely remodeled & the floors are gorgeous! Bedrooms are huge!

It was a really nice home & area was very convenient to everything we like to do. My only criticism would be the backyard needs attention: the flagstone needs repair in many places causing lose stones & sharp edges. All furniture needs replacing/repair.
Stayed 10 nights in Nov 2021

10/10 Excellent

Karen P.

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

Great vacation home.

The house was perfect for 2 couples. Close to walk to all the restaurants and shops . The pool was great for relaxing after being out in the heat!! We loved the area because it was on a quiet street and half a block to Duval street . The Butterfly Conservatory and Southern Most Point were couple blocks away. Definitely hope to come back in the future.
Stayed 4 nights in Sep 2021

8/10 Good

John B., Peachtree City

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

Fun time in key West

We enjoyed the property and appreciated the pool and towels, the fully stocked kitchen, nice grill, lovely backyard, and large bedrooms. The cleanliness is 4, not 5. I would also suggest better lighting in the bathrooms. Other than that, we would most likely stay again.
Stayed 4 nights in Aug 2021

10/10 Excellent

Rajnita S.

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

Great place to stay

Had a great stay, perfect for my family. The parking for a rental is small but you can park on the side of the street. Kitchen is nice and they provide dishes and basic cable. Pool is amazing. I would definitely stay here again. We really enjoyed our stay. Everything was easy and smooth. Walking distance to food and shopping
Stayed 8 nights in Jun 2021

10/10 Excellent

Denise S.

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

Key West Escape

A nice, cozy rental with a private pool. Easy access to all the Key West sites.
Stayed 4 nights in Jun 2021

10/10 Excellent

Kathy B.

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

Great location.

Property managers were very responsive. Great location and house was perfect for our group of four. Would definitely stay here again.
Stayed 6 nights in May 2021

10/10 Excellent

Verified traveller

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

Beautiful house with pool

We really enjoyed our stay at Key West Dreamin. The house was clean, cozy and so cute. The pool is nice sized and there was ample seating to enjoy outdoors. We had a great time!
Stayed 7 nights in Feb 2021

About the host

Hosted by VHKW - Vacation Homes of Key West

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests