536 Fleming St #2, Key West, FL 33040
Property image
Property image
FOR RENT
APPLY INSTANTLY
PET FRIENDLY
FURNISHED

$17,500/mo

Original price: $17,000
  • 3 Beds
  • 2 Baths
  • 1,800 sqft

536 Fleming St #2, Key West, FL 33040

Old Town
Cost and fees breakdown
Price may not include required fees and charges.
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Home Highlights

Apartment
Dogs allowed
Dishwasher
Washer, Dryer
Central Air

Local Information

  • Map ViewExplore the area around 536 Fleming St #2.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

About this House

Woven throughout this 2,000+ square foot luxury penthouse is a story that can only be revealed by experience.

The Maloney encompasses the entire second story of the historic red brick building on the corner of Fleming and Simonton. Originally built in 1908 as the first pharmacy in Key West, the building now houses two penthouse units and a first-floor clothing and arts boutique.

Idyllic Key West mornings are sure to take place at the Maloney, where the soft light of sunrise meanders through the 19th century brick framed windows, offering the perfect pairing for a velvety cup of cafe con leche and a slow drip of energy to start your day. Enjoy vibrant Key West evenings where the curated collection of local paintings and carvings compete with the glow of the 100 year-old Dade county pine floors make the perfect setting to host a quiet dinner or serve cocktails to friends.

General Policies: Renters will not receive any refund or reimbursement within 60 days of arrival. Outside of 60 days renters can receive a full refund. Renters must provide a written request.

OTHER INFO:
- House is fully furnished.
- All utilities are included.
- Full payment for the entire term is required in order to rent this property, however, some rental periods may be subject to a payment plan upon request.
- We do not accept checks or cash, payments must be made with a credit card or debit card.
- There are required additional fees.

Details for 536 Fleming St #2

Days on Market

Days on Market: 33 days on Trulia

Property Information

Property Type / Style
Property Type: Apartment

Rental Terms, Policies & Fees

Lease Term: 1 monthSmall dogs allowed

Interior Features

Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Heating & Cooling
Air Conditioning
Levels, Entrance, & Accessibility
Floors: Hardwood
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Costs and Fees

Required monthly rent & fees
  • Base rent
    $17,500/mo
Optional monthly rent & fees
  • Pet rent
    $450/mo
Required one-time fees
  • Security deposit
    $0
  • Application fee
    Contact for details
  • Administrative fee
    Contact for details
Pricing is subject to change. All calculations are estimates and provided for informational purposes only. Actual amounts may include additional mandatory or optional fees. Please consult the community manager for a complete breakdown of all rental costs.
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Rental Market Trends in Old Town

Last updated Sep 2026
Trulia Rent Estimate$6,036/mo
Average rent
$4.5K
$500MoM
Available listings
30
View rental market trends in Key West, FL

Around this home

Neighborhood Overview

Old Town
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Old Town

At least 1 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 100 % Say people would walk alone at night

  • 100 % Say there are sidewalks

  • 100 % Say streets are well-lit

  • 100 % Say neighbors are friendly

  • 100 % Say it's quiet

  • 100 % Say it's walkable to grocery stores

  • 100 % Say it's walkable to restaurants

  • 100 % Say parking is easy

  • 100 % Say car is needed

  • 67 % Say there's holiday spirit

  • 60 % Say they plan to stay for at least 5 years

  • 50 % Say there are community events

  • 50 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.
  • David Atkinson
    "I so look forward to getting to Key West. I volunteer at the Tropic and love it. It feels like home."
    0
    Flag
  • Trulia User
    "Dogs are welcomed at 90% of the restaurants. Everyone will remember your dogs name but not yours! I love living here with my dog Jack."
    0
    Flag
  • Trulia User
    "Key West is a huge dog community. They even are allowed in some restaurants . When I walk my dog on the main tourist street (Duval St) I get stopped many times from people wanting to pet my dog. A group of dog owners meet up at the park in the morning every day."
    0
    Flag
  • Sgarvin3281
    " Bikes are all you need small island. Safe and secure. No commute I do t work here it is a vacation community."
    0
    Flag
  • Trulia User
    "Everywhere dogs are welcome here in key west, Florida. Come joining us here in key west. Most food and service places, boats, and entertainment venues are good with dogs."
    0
    Flag
  • Trulia User
    "Feels very safe, super clean, super walkable in old town, and Catholic school looks very vibrant. "
    0
    Flag
  • Trulia User
    "Great people, great neighborhood, great police, family friendly events. Lots of things to do within a decent drive. Very family friendly generally "
    0
    Flag
  • Key W. B. F.
    "Gatherings on the local Mangia Mangia bench at 900 Southard street, safe & friendly town. Feel connected & welcomed in Key West. Enjoy the peaceful neighborhood & the tropical weather! You can walk or bike to everything you need & want!"
    0
    Flag
  • Kfowler
    "I am not currently aware of any neighborhood events that would bring the neighbors closer. However, both my husband and I would be open to any such event that would do so and would improve the neighborhood. The area is beautiful and well maintained, with a few exceptions. "
    2
    Flag
  • Hannah B.
    "Vintage Cottage houses, small island feel, Duval Street in a few minutes with hundreds of worldly trendy restaurants "
    6
    Flag
  • Drlynmar
    "Neighborhood newsletter. Proximity to OldTown events, festivals and parades. Walk to everything. Parks, beaches, dog park. Grocery and restaurant delivery. "
    2
    Flag
  • Venomousink1970
    "the neighborhood is great I myself do not like living in Key West anymore and looking to relocate and Asheville North Carolina or the surrounding areas people are very friendly here except for the homeless vagrants that beg for money and yell at you when you don't give them any"
    0
    Flag
  • Lorettamdt
    "Old Town is historic. Our neighbors are friendly. We walk everywhere. No need for a car. Restaurants are within walking distance. Beaches are a bicycle ride away. "
    0
    Flag
  • mangiamangia
    "Lived in this neighborhood for 25 years. Walk and anywhere. Far enough of Duval to escape the noise and drunks."
    0
    Flag
  • Sajsk
    "vacationed in that area -- charming and great location and amenities, yet quiet."
    0
    Flag
  • Rjones
    "This is a great street and great neighborhood. Qiet, yet close enough to Duval and White streets to enjoy all Key West has to offer. "
    0
    Flag

Local Legal Protections

LGBTQ • Source of Income

Price and Tax history

DateEventPrice
Aug 24, 2026
Source: Zillow Rentals
PriceChange
$17,500
Price increased by 3%
Aug 19, 2026
Source: Zillow Rentals
Listed For Rent
$17,000
Aug 3, 2026
Source: Zillow Rentals
ListingRemoved
$17,000
Jun 8, 2026
Source: Zillow Rentals
PriceChange
$17,000
Price decreased by 3%
Apr 27, 2026
Source: Zillow Rentals
Listed For Rent
$17,500
Brightwild

Frequently asked questions about 536 Fleming St #2

  • What income do you need to rent 536 Fleming St #2?
    Most landlords look for monthly gross income of about 3× rent, or roughly $630K per year to rent 536 Fleming St #2 in Key West, FL at $17,500/mo.
  • What is the pet policy at 536 Fleming St #2?
    536 Fleming St #2 in Key West, FL allows small dogs.
  • What's the average rent in Old Town?
    The average rent in Old Town is $4,633 per month.
  • How does the rent for 536 Fleming St #2 compare to similar 3-bedroom apartments in Old Town?
    536 Fleming St #2 in Key West, FL rents about 98% above the area average for 3-bedroom apartments in Old Town ($8,834/mo).
  • Does 536 Fleming St #2 have laundry facilities?
    Yes, 536 Fleming St #2 in Key West, FL has in-unit laundry.

Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
$630,000 PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.

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536 Fleming St #2, Key West, FL is a 3 bedroom, 2 bathroom, 1,800 sqft apartment. 536 Fleming St #2 is located in Old Town, Key West. 536 Fleming St #2 was listed for rent for $17,500/month on Aug 19, 2026. This property is pet friendly.