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
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Air conditioning
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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. Sails To Rails Museum at Flagler Station and Mel Fisher Maritime Museum are also worth visiting. Discover the area's water adventures with jet skiing, scuba diving and snorkelling nearby, or enjoy the great outdoors with ecotours.
Key West, FL
What's nearby
Duval Street - 3 min walk - 0.3 km
Florida Keys Beaches - 6 min walk - 0.5 km
Key West Aquarium - 7 min walk - 0.7 km
Harry S. Truman Little White House - 8 min walk - 0.7 km
Mallory Square - 9 min walk - 0.8 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
Schooner Wharf Bar - 3 min walk
Kermit's Key West Key Lime Shoppe - 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 23 April 2026, prices found for a 1-night stay for 2 adults at Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location! on 28 June 2026 start from NZ$691, 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.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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.
2 December 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.
John R.
About the host
Hosted by The Team at Preferred Properties
Languages:
English
Premier Host
They consistently provide great experiences for their guests