Tropical Dream - Monthly Rental

4 Bedrooms

4.5 Bathrooms

8 Guests

5.0

A mere 5 blocks from Duval Street or the Marina and close to several restaurants, this spacious two-story home on Millionaire’s Row awaits you. The private pool, porches, parking, and indoor-outdoor living are easy to get used to.


Save 10% On May Monthly Rentals!

For a Limited Time Save 10% Select Monthly Rentals in May . Use Code: SAVE10MAY

Save 10% On June Monthly Rentals!

For a Limited Time Save 10% Select Monthly Rentals in June . Use Code: SAVE10JUNE


About the property

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!

THE PROPERTY: As you enter the carport and begin to unwind, you will be greeted by beautiful porches and tropical greenery. Drop your luggage at the door and go for a swim. Around back, a private pool with waterfall feature awaits you. Later, you can cozy up to a bedroom of your choice.

The first-floor queen ensuite bedroom includes a desk, dresser, ceiling fan and access to the pool. The second floor is home to three additional bedrooms. The first is a king suite with TV, wet bar, and walk-in/walk-through closet with access to the washer/dryer. Its ensuite bath has a large soaking tub with a laminar flow filler that fills from the ceiling, and a spacious walk-in shower with multiple heads. The room also provides access to a private balcony. The second is a queen suite with nightstands, ceiling fan, TV, dresser, and glass doors leading to the sun deck. The third bedroom on the second floor includes twin beds that may be converted to a king. This bedroom accesses a full bath from the hallway. It also has access to the second-floor balcony in front of the home that overlooks Fleming Street. This balcony wraps around the side of the house and connects to the sun deck. Its spiral stairs will lead you down to the pool area.

Back downstairs you will pass the half bath on your way to the open concept great room. Here you will find sunshine, happiness and the home’s living room and kitchen. Stainless steel appliances, a triple sink, and granite counters round out the gourmet kitchen. The adjoining living room has a queen sleeper sofa, plenty of seating for your family and friends, a large screen TV, ceiling fans, and storage. From this area you will also find table seating for six, a wet bar with wine fridge, and access to the pool area via the expansive wall of windows. This home embodies the Key West lifestyle and is yours to enjoy while here on the island.

BED CONFIGURATION: This home has 4 beautifully appointed bedrooms. A queen ensuite bedroom is located on the first floor for those who may not prefer stairs. Three additional bedrooms are located on the second floor. They include one king ensuite, one queen ensuite and one twin bedroom. The twin beds may be converted to a king size bed and have access to a full bath in the hall.

OUTDOOR AMENITIES: A small sitting pool spills into the larger pool with waterfall feature and will cool you down after a day exploring the island. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. There is a deck and outdoor dining area for al fresco meals.

PARKING: There is designated parking for 2 vehicles in the carport.

LOCATION: Old Town, North of Truman. Many tourist attractions are located here as well as restaurants, shops, and galleries. Just 5 blocks to Duval Street or the Marina and walkable for those who like to park their car and chill. The neighborhood boasts historic homes, shotgun, and conch style homes.

PETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats not allowed.

SMOKING: This is a non-smoking home.

***Guests must be 25 years of age or older unless accompanied by an adult.

***Please note that the cleaning fee includes a full "mid-stay" clean***

***Managed by Historic Key West Vacation Rentals***


Features & amenities

  • Type: House
  • Private Pool
  • pets considered
  • Outdoor Dining
  • Historic Old Town
  • Monthly
  • Nightly & Weekly: No
  • Air Conditioning
  • Internet Access
  • Kitchen
  • Washer / Dryer
  • Walk in Shower

Get Quote

Use the calendar to select your dates.

Have a question?

5.0 (14 reviews)

5.0

wonderful keys rental property

Very positive stay in all regards. Has all the necessary amenities. Very pleasant patio area. Great location. Quiet but easy walk up to Duval or harbor area.

Submitted by Rochester NY on Mar 02, 2025

5.0

tropical dream

We had a great time at the place.

Submitted by Shinnston WV on Jul 30, 2024

5.0

best rental property ever

I’ve been renting in key west for 7 years and this is by far the best rental property I’ve had!

Submitted by Southport NC on Apr 02, 2024

5.0

escape to paradise

Wonderful home in a great location. Easy walk to some great neighborhood restaurants. Plenty of room for all. The folks at Historic Key West Rentals were very responsive and accommodating. Have used them several times before with no issues or disappointments. Will reach out to them again for our next visit. Miss Key West already.

Submitted by San Antonio TX on Dec 05, 2023

5.0

wonderful stay

We had a great time at this wonderful house. Perfect location, great space, and all the amenities. Great to be able to easily park and close enough to everything that we never moved the car again after. Porches are great for people watching. The few issues we had were quickly dealt with by the great team at HKWVR. Can't wait to come back next time I can justify leaving home for a month :)

Submitted by Washington DC on Nov 28, 2023

5.0

winter rental

Key west has great weather, the house was nice. If you plan on cooking bring your own pans, very few and old and damaged. The sitting area in the living room only accommodates 5 adults but house sleeps eight. I would purchase a pit with more sitting. Location noisy at night a lot of street walking and talking late at night. pool was great.

Submitted by Lake Forrest IL on Mar 05, 2021

5.0

wonderful getaway!!!

We stayed for one marvelous month and wish we could have stayed longer. The home was perfectly situated in the heart of Old Town. It is FULLY equipped with everything you could possibly need and want. From kitchen supplies to bed linens and BBQ tools - everything was perfect!
As far as the rental company, I can’t say enough good things about these ladies! They are marvelous! Our BBQ was not working one day, so they gave us a gift card to the lovely restaurant down the street to enjoy while the repair was underway.
If you’re on the fence don’t be! You will not be disappointed.
For reference, this glowing review is coming from two very picky frequent travelers who only write reviews in response to terrible experiences. That's how much we enjoyed our time at Tropical Dream.
Perfect home and perfect service! 10 stars.

Submitted by Miami Beach FL on Oct 20, 2020

5.0

906 fleming

Great experience, nice home in a great location. Management company was outstanding .

Submitted by Belmont OH on Nov 18, 2019

5.0

tropical dream monthly rental

Our family rented Tropical Dream for July 2018. The home was very well located in Old Town. The location to Key West Bight Marina, off street parking and pool were critical amenities for our family. We easily walked everywhere despite having brought bikes. The home was clean and well appointed for our family of five plus three extra friends. We had an issue with the water not working in one bathroom and the management company immediately replaced the faucet. We would definitely recommend Tropical Dream as well as KW Historic Rentals as a management company.

Submitted by Tampa FL on Aug 26, 2019

5.0

wonderful summer in key west!!!

Could not possibly say enough good things about our 10 week stay in Key West this past summer but will try to point out a few of the more outstanding features! First, hats off to my new friend Thomas Lane at Historic Key West Vacation Rentals! Since my wife and I were pretty much moving to Key West for the summer there were a host of questions I had for the six months prior to our arrival and Thomas was always readily available to answer all of them! As a corollary thereto let me say that when we arrived, we received that same standard of service as whatever questions/issues we had were immediately addressed! Second, my hats are off to the owners of 906 Fleming as well! The AC units were getting a little long in the tooth and were struggling a bit with the heat and after diligent follow up by the guys at HKWV without further hesitation the Owner replaced both units and HKWV even gave us a gift certificate to a (very fine) local restaurant for our trouble. That's the way a first class operation works! Third, if you are not familiar with Key West as a couple that has spent a lot of time there (including the 10 weeks straight we just returned from) 906 Fleming could not possible be more perfectly located! Fleming is within about three blocks of the marina and easy walking distance to Duval and Starbucks (an every morning venture for me and my wife I might add) and there is even a super nice and surprisingly large grocery store (Faustos) right down the street in addition to the all organic boutique store directly across the street such that the wife and I probably did not get in the jeep to drive somewhere maybe 5-6 times the entirety of our stay. Also, Fleming is a one way street and though it is very close to pretty much anything that you might want to go visit (even over the course of 10 weeks) it has very little traffic which makes walking it everyday feel like a Sunday morning stroll down the streets of an old southern town like Charleston for example!!!

Submitted on Sep 08, 2018

5.0

tropical dream

Excellent house. Excellent location. Excellent support from management staff. In stay complete cleaning was an added bonus.

Submitted by Jeffersonville IN on Jan 29, 2018

5.0

tropical dream

Nice place, great location

Submitted by Ft Lauderdale FL on Nov 29, 2017

5.0

helping in a crisis

I rented a home in Key West Florida when Hurricane Irma struck...I was there with 90 year old parents and a large black lab. Historic Key West Vacations went out of their way to encourage us to evacuate before the mass evacuations and probably helped to save my parents lives....I cannot say enough about their concern and SMART advise...

Submitted by Chicago IL on Oct 02, 2017

5.0

great stay in a great location!

Thoroughly enjoyed our month long stay at Tropical Dream. The location is very convenient (a few blocks to Duval, the market and several great restaurants). All beds were comfy and we had everything we needed for a pleasant stay. The patio was small but the pool was cool, which was a big plus for a hot June/July stay. Would definitely stay here again.

Submitted by Willis TX on Aug 07, 2017

Location

May 14-14, 2025
Reserve
  • Key West Chamber of Commerce Logo
  • Key West Business Guild Logo
  • The Vacation Rental Travel Guide - Most Outstanding Award for 2017
  • Florida VRMA Logo
  • VRMA Logo
  • AirBnB Super Host Badge
  • Vrbo Premier Host Badge