Condo

Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location!

Photo gallery for Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location!

A covered porch with wicker furniture, a staircase, and a view of the street.
A two-story house with a white picket fence, palm trees, and a black gate.
A modern kitchen with a central island, a dining area with a sofa, and a spiral staircase leading to an upper level.
A spacious kitchen with a central island, a dining area with a sofa and coffee table, and a staircase leading to an upper level.
A swimming pool with a stone wall, surrounded by lush greenery and a small white building.

Reviews

10 out of 10
Exceptional
With space for 4 guests, this condo features 2 bedrooms and 2 bathrooms. It offers access to nearby golf, along with scuba diving at the marina. Explore local attractions like Duval Street and Curry Mansion Museum while enjoying adventure activities such as birdwatching and sailing.

Highlights

  • Discover nearby landmarks
    Near Duval Street
2 bedrooms2 bathroomsSleeps 4

Popular amenities

  • Heated pool
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Balcony
  • Internet access

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪3 min walk‬
  • Place, Mallory Square
    ‪7 min walk‬
  • Place, Harry S. Truman Little White House
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪12 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Spaces

Kitchen
Balcony

About this property

Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location!

This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting experience. The location is highlighted as a key factor, emphasizing the significance of its surroundings.

As you enter "Caroline on My Mind," you'll notice a stairway adorned with wainscoting, leading you to the entry. The home boasts an open and comfortable living area, allowing ample natural light to fill the space. The living room features high-vaulted ceilings and cathedral windows, creating an instant vacation-like ambiance.

There is a flat-top electric stove, two-door refrigerator, and dishwasher available to facilitate your cooking needs. The countertop seating for three also provides a convenient space for dining or socializing while in the kitchen. Overall, the kitchen offers functionality and amenities that will allow you to enjoy preparing meals during your stay.

The guest room is located on the same floor, accompanied by a full shower bathroom and a washer/dryer for added convenience.

One of the standout features of this home is the large balcony that overlooks Caroline Street below. Equipped with fans, the balcony serves as a perfect spot for savoring morning coffee or enjoying cocktails. A four-person table allows for al fresco dining, while you can also engage in people-watching and relish the refreshing evening breezes of Key West.

To access the floor above, a spiral staircase takes you to the treetops, providing a unique vantage point. The primary bedroom on this floor features a queen-sized bed that can be converted into two twins upon request. Additionally, for those who need to work while in paradise, there is a functional desk with great views, enabling mental breaks amidst the scenic surroundings.

Lastly, there's a skylight in the primary bedroom, offering the opportunity for star gazing while lying in bed at night, adding to the enchanting atmosphere of this Key West home.

Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know.

Guests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check.

Monthly Rental Only

Shared Pool/6 units

Pets Not Allowed
Virtual Tour Url: https://my.matterport.com/show/?m=TXf1ngy4X89

Add dates for prices

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, service animals permitted
default

Smoking

Smoking is not permitted

Important information

You need to know

Property # 9723480
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
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 not indicated whether there is a smoke detector on the property

About the area

Key West

Located near the beach, this condo is in Key West Historic District, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Discover the area's water adventures with jet skiing, scuba diving and snorkelling nearby, or enjoy the great outdoors with ecotours.
Map
Key West, FL

What's nearby

  • Duval Street - 3 min walk - 0.3 km
  • Oldest House Museum and Garden - 5 min walk - 0.4 km
  • Florida Keys Beaches - 6 min walk - 0.5 km
  • Mallory Square - 7 min walk - 0.7 km
  • Harry S. Truman Little White House - 8 min walk - 0.7 km

Getting around

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

Restaurants

  • ‪Sloppy Joe's Bar - ‬5 min walk
  • ‪Conch Republic Seafood Company - ‬7 min walk
  • ‪Kermit's Key West Key Lime Shoppe - ‬3 min walk
  • ‪Schooner Wharf Bar - ‬3 min walk
  • ‪Irish Kevin's - ‬4 min walk

Frequently asked questions

Does Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location! have a pool?

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

How much does it cost to stay at Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location!?

As of 12 Sept 2026, prices found for a 1-night stay for 2 adults at Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location! on 14 Sept 2026 start from AU$12,401, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location! pet-friendly?

No, only service animals are welcome at the property.

What time is check-in at Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location!?

Check-in begins at 4:00 PM.

What time is check-out at Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location!?

Checkout is at 10:00 AM.

Where is Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location! located?

Located in Key West Historic District, this condo building is within a 5-minute walk of Curry Mansion Museum and Duval Street. Florida Keys Beaches and Mallory Square are also within 10 minutes.

About the host

Hosted by The Team at Preferred Properties

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback