Key West Historic District stay.Within a 10-minute walk of this Key West Historic District condo, you'll find Duval Street and Florida Keys Beaches. Also, Mallory Square is within half a mile (1 km) and Southernmost Point is within 2 miles (3 km).
Harry S. Truman Little White House - 8 min walk - 0.4 miles
Mallory Square - 9 min walk - 0.5 miles
Ernest Hemingway Home and Museum - 15 min walk - 0.8 miles
Getting around
Key West Intl. Airport (EYW) - 13 min drive
Restaurants
‪Sloppy Joe's Bar - ‬5 min walk
‪Schooner Wharf Bar - ‬3 min walk
‪Conch Republic Seafood Company - ‬7 min walk
‪Kermit's Key West Key Lime Shoppe - ‬3 min walk
‪Irish Kevin's - ‬4 min walk
About this property
Entire place
You'll have the entire condo to yourself and will only share it with other guests in your party.
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
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 not reported (host has not indicated whether there is a smoke detector on the property)
General
Housekeeping (on request)
Unit size: 980 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age: 25
Check-out
Check-out before 10:00 AM
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
Pets
No pets allowed, but service animals are welcome
Children and extra beds
Children are welcome.
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 not indicated whether there is a smoke detector on the property
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.
Property is also known as
2302-240326
Frequently asked questions
How close is Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location! to the airport?
This condo is 3.8 mi (13-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.
Does Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location! have an airport shuttle?
Airport shuttle services are not available at this condo.
How close is Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location! to the beach?
This condo is a short 6-minute walk from Florida Keys Beaches and 1 mi (8-min drive) from South Beach. Don't forget your sunscreen!
Does Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location! offer free breakfast?
This condo does not offer free breakfast.
Is there a casino at Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location!?
No, there is no casino at this condo.
What time is check-in at Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location!?
Check-in begins at 4:00 PM.
Is there free parking at Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location!?
Free parking is not available at this condo.
Does Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location! have a pool?
Yes, there's a heated pool.
Does Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location! have a spa?
There are no spa services available at this condo.
How close is Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location! to downtown Key West?
This condo is 0.3 mi away from Key West.
Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location! Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
This place has everything you need. We stayed here for a month and had a wonderful time. The hosts were always responsive and ready to address any issue. We hadn't realized we had a very large patio all to ourselves.
Jax R.
Stayed 29 nights in Feb 2024
From a partner site
10/10 Excellent
John R.
Dec 2, 2025
Perfect for two
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Beautiful colonial Key West house in historic Key West. Compact, two-story with two bedrooms, two baths, with counter-table eating, but no dining area.