VRBO is part of the HomeAway family, the world leader in vacation rentals with over 1 million listings. We offer the largest selection of properties for any travel occasion and every budget. We’re committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together. Learn More
This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
Recent Private Homes, Old Town reviews
Absolutely perfect location, would return and highly recommend
"The location of this little sleepy bungalow is a block from Sloppy Joe's and two blocks from the sunset cruise catamarans. A block in the other direction is Caroline Street, which has an even better bar than the ones on Duval, Pepe's. It is quiet and yet in the middle of everything. There is a smallish pool, yet big for Key West, which helps a lot when you work up a sheen of sweat walking around, which is inevitable.
I can't say enough about this little place. The photos do it justice; it is beautiful. It's a bit small, but the secluded patio really make it feel isolated. We chose this place for our honeymoon and are extremely pleased.
We definitely plan on returning - to this location specifically. One thing to keep in mind is there is no parking - at all. As you plan your trip, make sure to keep that in mind."
Guest: Bill E.Date of Stay: October 2014Review Submitted: October 13, 2014
"Our stay at Tropical Dreaming was the perfect way for our family of four to enjoy the Christmas Holiday week. The property provided great comfort for us in a great location on the island. We walked everywhere.....to Duval to shop.....to the port to watch the sunset.....to the beaches for relaxation in the sun.
The outside area was just right. We could sit on the deck to eat every meal.....jump in the pool to cool down after a morning run.......sit in the sun to enjoy the December warmth. The only unfortunate part was that the sun was not as high in the sky during the winter trip that only part of the back was constantly in the sun.
We would definitely stay again at Tropical Dreaming on a future trip the Keys."
Guest: FourmartinsDate of Stay: December 2014Review Submitted: January 19, 2015
"This is a great place in a perfect location. Being so close to Duval makes everything great. The studio is the perfect size and having a full kitchen and BBQ area allowed us to eat some meals in. The pool is great for relaxing in during the afternoon. The owner was very accommodating and also helpful with bike rentals, which we think is a must for cruising the island. We would definitely recommend and would stay here again."
Guest: MichaelDate of Stay: April 2015Review Submitted: April 21, 2015
"My financee and I and 2 other couples stayed here and it was fantastic. First the place was immaculate and clean and had that Hemingway style. It was close to everything including Duval Street. It had every amenity possible. The private swimming pool was delightful as we sipped wine deciding where to go and what to. The oldest owner Ron was very helpful with ideas and very easy to work with. My finanncee and I aree thinking about changing our date, having the wedding down here and staying here. What a place!"
Guest: RobbieDate of Stay: March 2015Review Submitted: April 24, 2015