Entire home

Heart of Downtown Key West Cottage With Off-Street Parking

Cottage near Duval Street in Key West

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Southwinds Motel

Old Town Key West
  • Pool
  • Breakfast included
  • Restaurant
  • Air conditioning
4.3 out of 5, Excellent, 1,321 reviews
$233 nightly
The price is $262
May 10 - May 11
Total with taxes and fees
Southwinds Motel

About the neighborhood

Key West

Heart of Key West.Within a 10-minute walk of this Key West Historic District cottage, you'll find Duval Street and Mallory Square. Also, Florida Keys Beaches is within half a mile (1 km) and Southernmost Point is within 2 miles (3 km).
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What's nearby

  • Duval Street - 2 min walk - 0.1 miles
  • Harry S. Truman Little White House - 3 min walk - 0.2 miles
  • Key West Aquarium - 5 min walk - 0.3 miles
  • Mallory Square - 6 min walk - 0.4 miles
  • Ernest Hemingway Home and Museum - 11 min walk - 0.6 miles

Getting around

  • Key West Intl. Airport (EYW) - 13 min drive

Restaurants

  • ‪Sloppy Joe's Bar - ‬7 min walk
  • ‪Irish Kevin's - ‬7 min walk
  • ‪Stinkin Crawfish Key West - ‬7 min walk
  • ‪Key Lime Pie Factory - ‬7 min walk
  • ‪Captain Tony's Saloon - ‬7 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Heart of Downtown Key West Cottage With Off-Street Parking

A Historic Cigar-Makers Conch Home, privately owned by a native hospitable family in the heart of Downtown, a few minutes walk from Duval St. Accommodates 1-2 couples. Your car will be safe in this parking spot, nowhere near the street. The Cottage is set back from the sidewalk so you are not subjected to traffic noises.


Note two things:
1. The price listed is for 2 guests only. There is an additional charge of $75/night for an additional guest.

2. The cottage is set back from the street but nearby at Hank's there is live music...luckily
as of around 10.18.23 - their music is now set further back from us! The music ends at midnight.


Kitchen with Dishwasher (not fully equipped)
Full Size Refrigerator and Stove
1 King Bed, 1 Queen Bed
Central Air Conditioning
TVs with Premiere Cable
Full Size private Washer & Dryer on premises. For use by tenant and this tenant only.
Free Internet
Parking: Off-Street, 1 parking space, only to be used for those staying at the cottage.
Adults only. No Pets. No Smoking. No raw fish in the refrigerator or freezer.

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Property amenities

Internet

  • Available in the cottage: Free internet

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Full-sized refrigerator/freezer
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Stovetop

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Living room

Entertainment

  • TV

Outdoor areas

  • Patio

Laundry

  • Laundromat nearby
  • Washer/dryer

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near a health/beauty spa
  • Near a hospital

Things to do

  • Fishing nearby
  • Jet skiing nearby
  • Parasailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Property does not allow children

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 30

Check-out

Check-out before 10:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

No kids allowed and no college students.
No raw fish in frig or freezer. If booking longer than 2 weeks, please send a message first before booking.
3 guests max. Also parking is only for the guests who are staying there. No smoking of any kind inside cottage.

Pets

  • No pets allowed

Children and extra beds

  • This property does not allow children.
  • Note from host: No kids allowed, sorry.

Events

No events allowed

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
Onsite 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher and a smoke detector in each accommodation.

Property is also known as

Vrbo Property
Heart of Downtown Key West Cottage With Off Street Parking

Frequently asked questions

How close is Heart of Downtown Key West Cottage With Off-Street Parking to the airport?

This cottage is 4 mi (13-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Heart of Downtown Key West Cottage With Off-Street Parking have an airport shuttle?

Airport shuttle services are not available at this cottage.

How close is Heart of Downtown Key West Cottage With Off-Street Parking to the beach?

This cottage is a short 12-minute walk from Florida Keys Beaches and 1 mi (8-min drive) from South Beach. Don't forget your sunscreen!

Does Heart of Downtown Key West Cottage With Off-Street Parking offer free breakfast?

This cottage does not offer free breakfast.

Is there a casino at Heart of Downtown Key West Cottage With Off-Street Parking?

No, there is no casino at this cottage.

What time is check-in at Heart of Downtown Key West Cottage With Off-Street Parking?

Check-in begins at 4:00 PM.

Is there free parking at Heart of Downtown Key West Cottage With Off-Street Parking?

Free parking is not available at this cottage.

Does Heart of Downtown Key West Cottage With Off-Street Parking have a pool?

This cottage does not have a pool.

Does Heart of Downtown Key West Cottage With Off-Street Parking have a spa?

There are no spa services available at this cottage.

How close is Heart of Downtown Key West Cottage With Off-Street Parking to downtown Key West?

This cottage is 0.2 mi away from Key West.

Heart of Downtown Key West Cottage With Off-Street Parking Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 147 out of 157 reviews
Rating 8 - Good. 8 out of 157 reviews
Rating 6 - Okay. 2 out of 157 reviews
Rating 4 - Poor. 0 out of 157 reviews
Rating 2 - Terrible. 0 out of 157 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Sarah T.

Liked: Cleanliness
The parking was great off street, the cottage was well within walking distance to all the attractions. The bed was very comfortable. Plenty of supplies. I would definitely stay there again. And a bonus was the washer and dryer. Loved sitting on the back porch in the evenings to unwind from the day. We did not have any problems.
Stayed 4 nights in Apr 2026

10/10 Excellent

Ken C.

Liked: Cleanliness
Love staying here to put me in Key West mode. Cottage is always clean and the location is great. Hosts are very communicative and accommodating.
Stayed 7 nights in Mar 2026

10/10 Excellent

Carol Ann S.

Liked: Cleanliness
We have stayed several times and will continue. Excellent communication and best location to everything.
Stayed 7 nights in Apr 2026

10/10 Excellent

Terry M.

Liked: Cleanliness
Great location. Perfect for up to 4 adults.
Stayed 7 nights in Mar 2026

10/10 Excellent

chris g.

Liked: Cleanliness
Great location. Close to everything, but still a quiet house set far off from the street.
Stayed 6 nights in Feb 2026

8/10 Good

Lynn K.

Liked: Cleanliness
Host was very responsive. Proximity of cottage was great. Easily walked to all destinations and points of interest.
Stayed 4 nights in Feb 2026

10/10 Excellent

Susie M.

Liked: Cleanliness
We have stayed at this cozy very clean house for several years now. The host is just wonderful -communicates well-and always offers a warm welcome. The house is conveniently located within walking distance of many restaurants and downtown Key West as well as the Pier. This house is part of the overall “Simple Living” lifestyle of Key West.
Stayed 7 nights in Feb 2026

10/10 Excellent

Laura P., East Falmouth, MA USA

Liked: Cleanliness
The host, the home and the location - win, win, win!!!
Stayed 4 nights in Feb 2026

10/10 Excellent

Marlene C.

Liked: Cleanliness
The location was great! So close to everything. The host was very responsive and easy to deal with. The bedding was very nice and comfortable. Would definitely stay here again!
Stayed 4 nights in Jan 2026

10/10 Excellent

Terry B.

Liked: Cleanliness
Great place to stay! Loved the location and the host was excellent. Door was unlocked and easy to get into. Lots of room and great TV.
Stayed 10 nights in Jan 2026

10/10 Excellent

Kristin C.

Liked: Cleanliness
Lovely place and great location. Would definitely recommend.
Stayed 4 nights in Jan 2026

10/10 Excellent

George P.

Liked: Cleanliness
A place was very clean. Check in process was seamless. Location is perfect.
Stayed 8 nights in Jan 2026

10/10 Excellent

Allison L., Poughquag, NY

Liked: Cleanliness
Perfect location…very happy with everything
Stayed 5 nights in Dec 2025

10/10 Excellent

Wendy C.

Liked: Cleanliness
Marcela was a very friendly, communicative, and accommodating host before, during and after our stay. The location of the property was perfect right in the heart of the Duval and Old Town areas. We were able to easily walk everywhere. The house was just as pictured online. If you are looking to prepare meals, there is the bare minimum of essentials, but we were able to make it work. I would definitely stay here again.
Stayed 6 nights in Dec 2025

10/10 Excellent

Marianne G.

Liked: Cleanliness
Marcela and her family are the best!!Always keeping in touch to make sure everything is ok. Perfect location. Been coming here for over 5 years. Love it.
Stayed 7 nights in Dec 2025

10/10 Excellent

Jami O.

Liked: Cleanliness
Cottage was everything and more! Great location, clean, beds were comfortable. Will definitely be booking again!
Stayed 7 nights in Nov 2025

10/10 Excellent

Michael W.

Liked: Cleanliness
Exactly as advertised. Very clean and great location!
Stayed 4 nights in Nov 2025

10/10 Excellent

Kerri S., Greensboro, North Carolina

Liked: Cleanliness
Perfect location very walkable to Duval Street and marina. Loved that the house was off the Main Street had parking and full kitchen. Front bedroom was quiet and had king bed.
Stayed 4 nights in Oct 2025

10/10 Excellent

Nancy M., Davenport Iowa

Liked: Cleanliness
Excellent location to everything! This charming cottage has everything you need including parking! Our host were wonderful to work with. We enjoyed our visit very much.
Stayed 8 nights in Oct 2025

8/10 Good

sandy k.

Liked: Cleanliness
Stayed 5 nights in Sep 2025

10/10 Excellent

Joe A.

Liked: Cleanliness
Safe, secure, and private. Exactly as described. We felt a warm, genuine, feeling with the Hosts, and Owners. Priceless!
Stayed 4 nights in Sep 2025

10/10 Excellent

Tom H.

Liked: Cleanliness
As always, the host and house provided a great experience in KW. We have stayed there multiple times and will continue coming back!
Stayed 4 nights in Sep 2025

10/10 Excellent

Dave S., Naugatuck, CT

Liked: Cleanliness
Great location and fantastic property. This felt like a home away from home! This cottage is central to most sites, restaurants, bars, shopping, and seaside. No car required! The owners were very easy to reach and communicate with. It was a great experience.
Stayed 4 nights in Sep 2025

10/10 Excellent

Sapphire D., Palm Desert

Liked: Cleanliness

Perfect Getaway

The king bed was so comfortable (didn't sleep in the queen bed). The AC was wonderful and necessary. Perfect location for walking to see all the sights. Comfortable couch. Shower could use more water pressure. Convenient parking spot. Nice little kitchen. Good size tv.
Stayed 7 nights in Aug 2025

10/10 Excellent

Andrew J.

Liked: Cleanliness

Great place to stay in heart of Old Town

The place is nice, but it's really all about location. We were able to use this as a base of operation to explore all of Old Town easily. It's really about .5 mile or less from most stuff you might want to do. The Hemingway house is just a short walk down the street away. Get tired or want to drop off something? Just pop back in, no trouble. The owners were also very nice and easy to communicate with. Would definitely stay here again the next time I am in Key West!
Stayed 4 nights in Jul 2025