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Property Managers in Winter Haven, FL

10 investor-friendly Property Managers found in Winter Haven, FL as of November 10, 2025

  • business profile image

    Rental and Realty Group

    Long-term rental: 12+ mos.

    4.6 stars
    224 Reviews

    Long-term rental: 12+ mos.

    With more than 15 years of dedicated service in Central Florida and a portfolio encompassing over 200 meticulously managed homes, Rental & Realty Group epitomizes excellence in property management. We approach each property with the care and attention we would give our own, ensuring that your investment is in the best hands possible. Our competitive rates, bolstered by a committed support team and a plethora of rave reviews, offer you the assurance that selecting Rental & Realty Group is the ... view more
  • business profile image

    Allegiant Management Group

    Long-term rental: 12+ mos.

    4.6 stars
    185 Reviews
    47 forum posts

    Long-term rental: 12+ mos.

    Our tailored property management services help Central Florida real estate investors maximize their investment returns. Our comprehensive solutions go far beyond simple rent collection. We handle every aspect of property management, including tenant screening, property maintenance, financial reporting, and ensuring full legal compliance. We specialize in managing single-family homes, townhomes, condos, duplexes, vacant properties, and small multi-family units. We provide the professio... view more
  • business profile image

    Pro X Property Management the Swain Group

    Long-term rental: 12+ mos.

    Mid-term rental: 1-12 mos.

    HUD/Section 8

    Commercial

    Long-term rental: 12+ mos.

    Mid-term rental: 1-12 mos.

    HUD/Section 8

    Commercial

    When you work with us, there is absolutely no aspect of your rental property that will be overlooked. Owning a rental property can be a lot of work, but we will handle it all! Our team has a unique ability to access the highest quality maintenance for a great price. Our sister company is a residential and commercial construction company, which allows us to provide your property with excellent repairs without breaking the bank. No other property management company can compete with our expe... view more
  • business profile image

    Cosmic Vacations

    Mid-term rental: 1-12 mos.

    Short-term rental: <30 days

    4.9 stars
    65 Reviews
    923 forum posts

    Mid-term rental: 1-12 mos.

    Short-term rental: <30 days

    Unlock the full potential of your rental property with Cosmic Vacations' expert management services, where we transform your investment into a thriving haven for travelers. Experience stress-free ownership as we handle everything from marketing to maintenance, ensuring your property shines brighter than the stars. view more
  • business profile image

    PMI Arrico Realty and PM Lakeland

    Long-term rental: 12+ mos.

    HUD/Section 8

    4.5 stars
    270 Reviews
    2 forum posts

    Long-term rental: 12+ mos.

    HUD/Section 8

    Locally owned and operated in Polk County. Exceptional Service Complete tenant screening Full compliance with state and local landlord/tenant laws Prompt rent collection and any necessary follow-up Monthly itemized statements of income and disbursements Lease negotiations Lease Only and Full Management Available Attorney-prepared lease at a reasonable cost Regular maintenance and upkeep supervision Tenant and Owner Portals Online Payment Collection for Prompt Rent Collections ... view more
  • business profile image

    PMI Platinum FL

    Mid-term rental: 1-12 mos.

    Short-term rental: <30 days

    5.0 stars
    5 Reviews

    Mid-term rental: 1-12 mos.

    Short-term rental: <30 days

    PMI Platinum FL is a locally owned & operated short term property management company backed by a nationwide brand with over 400+ locations. So what does that mean? We have the systems & processes of a large brand with the quality & service of a family owned business. We strive to provide impeccable experiences for our homeowners and guests alike. What truly sets us apart is our dedication to treating every client like family. Whether you're planning a family vacation or looking for a reli... view more
  • business profile image

    Falconwood Stays

    Short-term rental: <30 days

    Short-term rental: <30 days

    Like you, we are STR owner-operators. We have the highest grossing properties in their respective resorts and submarkets. We have a 4.96 review score over 500+ reviews. We have an 85% occupancy rate over the past 2 years. We dynamically optimize ADRs to maximize revenue. We understand our guests, what makes them book, and how to get them to leave glowing 5-star reviews, keeping you elevated in search rankings. When you go with us, your property isn't one of hundreds - your property is treated... view more
  • business profile image

    Nearby Property Management

    Long-term rental: 12+ mos.

    Mid-term rental: 1-12 mos.

    Short-term rental: <30 days

    Commercial

    5.0 stars
    7 Reviews
    1 forum post

    Long-term rental: 12+ mos.

    Mid-term rental: 1-12 mos.

    Short-term rental: <30 days

    Commercial

    Our comprehensive rental management services cover both short-term and long-term properties. We take care of everything—from tenant screening and property maintenance to marketing and booking. Whether you're managing vacation rentals or long-term leases, our team ensures your investment is maximized while providing a hassle-free experience for both you and your tenants.. view more
  • business profile image

    Dwell

    Short-term rental: <30 days

    4.7 stars
    41 Reviews
    21 forum posts

    Short-term rental: <30 days

    Without any commitments, we'll provide you with a vacation rental assessment upfront that might save you money. So that you know we have skin in the game, we provide a two month guarantee. If after two months you're unsatisfied, we'll refund our commission. As Vacation Rental Consultants, we create custom built agreements for each individual owner depending on their needs. Often we support existing owners who: - Are frustrated with not earning enough money from their property -... view more
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    Resting Pearl Properties

    Short-term rental: <30 days

    5.0 stars
    5 Reviews
    10 forum posts

    Short-term rental: <30 days

    Resting Pearl Properties delivers full-service luxury property management for short term rental (STR) investors. As STR investors ourselves, we understand what it takes to operate a profitable STR and have tailored our services for homeowners and real estate professionals seeking maximum returns on high-end short-term rentals without the daily oversight. We manage everything, from premium guest experiences to meticulous home care, so clients enjoy a hands-off, revenue-generating investment. view more
Showing 1 - 10 of 10 Winter Haven Property Managers