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24 Vacation Property Managers in Winter Park, FL, USA

Discover the top short-term vacation rental property managers in Winter Park, FL, USA. Use the list below to find and compare the top property managers for your Airbnb property.

Market Overview

Market Leaders

Winter Park

Owner Ratings

4

& Above

3

& Above

2

& Above

Airbnb logo

4

& Above

3

& Above

2

& Above

VRBO logo

4

& Above

3

& Above

2

& Above

Google logo

4

& Above

3

& Above

2

& Above

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Founded In 2017

AvantStay

Headquarters Los Angeles, California

Employees 275

Owner Rating 4.9 (5)
Airbnb Rating 4.8 (65202)
VRBO Rating 4.8 (23328)
Google Rating 4.6 (1141)
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Owner Rating 4.9 (5)
Airbnb Rating 4.8 (65202)
VRBO Rating 4.8 (23328)
Google Rating 4.6 (1141)
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AvantStay is the best way to travel for groups, offering a diverse portfolio of 1,800+ premier vacation rental properties across 140 destinations. As the next generation hospitality platform redefining the way in which people travel an... View full profile

Checkmate Rentals

Headquarters Pennsylvania

Airbnb Rating 4.9 (362)
Google Rating 4.9 (73)
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Airbnb Rating 4.9 (362)
Google Rating 4.9 (73)
Checkmate Rentals changes the way you get to enjoy your vacation homes. With our professional, local caretaking teams in every market we manage, central support staff, and 24/7 customer service, we’ll be there every step of the way.W... View full profile

Orlando Holiday Management

Headquarters Davenport, Florida

Airbnb Rating 4.5 (3106)
Google Rating 5.0 (1)
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Airbnb Rating 4.5 (3106)
Google Rating 5.0 (1)
At Orlando Holiday Management LLC our mission is to provide exceptional short-term property management services in the vibrant state of Orlando. We are committed to optimizing the experience for property owners and guests alike, ensuri... View full profile
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Founded In 1985

Southern Select Villas

Headquarters Celebration, Florida

Employees 2

Airbnb Rating 4.2 (280)
Google Rating 3.3 (3)
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Airbnb Rating 4.2 (280)
Google Rating 3.3 (3)
Choosing the company that will represent and safeguard your vacation home is a monumental decision. We believe owning a vacation home should be a fun and rewarding experience. Your vacation home can become the place and the means to re... View full profile

Yirental Vacation Rental Management

Headquarters Seattle, Washington

Google Rating 5.0 (10)
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Google Rating 5.0 (10)
Yirental was founded in 2017 out of Seattle. Since then, we’ve helped over 200,000 users find rental accommodations across several countries!Since its beginning, Yirental has been dedicated to optimizing the rental experience for any... View full profile

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Founded In 2023

Wandermore Vacation Rental Hosting

Headquarters Orlando, Florida

Employees 2

Google Rating 5.0 (4)
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Google Rating 5.0 (4)
We Aim to Empower Property Owners with a Hassle-Free Vacation Rental Management Experience.Join us at WanderMore Hosting, where your property’s potential is our priority. Discover the ease of vacation rental investing with our expert... View full profile
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Founded In 2024

XENORENTALS LLC

Headquarters Orlando, Florida

Employees 4

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We are XENO GmbH, and we take great pride in our partnership with Delta Estates to manage over 60 exceptional properties in key locations. Our team is passionate about providing top-notch hospitality and creating memorable experiences... View full profile
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Founded In 2014

Casiola vacation homes

Headquarters Orlando, Florida

Employees 80

Owner Rating 4.8 (15)
Airbnb Rating 4.6 (17211)
VRBO Rating 4.3 (5621)
Google Rating 4.4 (906)

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Owner Rating 4.8 (15)
Airbnb Rating 4.6 (17211)
VRBO Rating 4.3 (5621)
Google Rating 4.4 (906)
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We create everlasting memories through EXTRA ordinary hospitality! Casiola is an award winning vacation rental management company where your vacation rental is in safe hands while you earn effortless income . We handle everything from... View full profile
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Founded In 2015

B&D Florida Property Management LLC

Headquarters Polk city, Florida

Employees 13

Owner Rating 5.0 (2)
Airbnb Rating 4.9 (82)
Google Rating 5.0 (13)

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Owner Rating 5.0 (2)
Airbnb Rating 4.9 (82)
Google Rating 5.0 (13)
We are a family-owned operating business founded in 2015 in Florida by "Dwight husband and Bertha wife". We are passionate about what we do, we strive to not only provide top-notch services, but also treat our customers as members of o... View full profile
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Founded In 2015

Wonder Vacation Homes

Headquarters Kissimmee, Florida

Employees 35

Airbnb Rating 4.3 (6941)
VRBO Rating 4.1 (1298)
Google Rating 3.9 (793)

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Airbnb Rating 4.3 (6941)
VRBO Rating 4.1 (1298)
Google Rating 3.9 (793)
Discover the Ultimate Vacation Experience with Wonder Vacation Homes: providing exceptional short and long-term vacation rentals in the vibrant Orlando, Florida area. Our commitment to 24/7 on-call guest support, expert trip planning a... View full profile

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The Best Vacation Homes

Headquarters Orlando, Florida

Airbnb Rating 4.5 (888)
VRBO Rating 4.3 (628)
Google Rating 4.1 (55)

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Airbnb Rating 4.5 (888)
VRBO Rating 4.3 (628)
Google Rating 4.1 (55)

Shine Villas

Headquarters Davenport, Florida

Airbnb Rating 4.7 (2676)
VRBO Rating 3.5 (4)
Google Rating 4.7 (612)

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Airbnb Rating 4.7 (2676)
VRBO Rating 3.5 (4)
Google Rating 4.7 (612)
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Founded In 2019

Orlando Luxury Stays dba

Headquarters Kissimmee, Florida

Airbnb Rating 4.8 (1255)
VRBO Rating 4.6 (0)
Google Rating 5.0 (10)

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Airbnb Rating 4.8 (1255)
VRBO Rating 4.6 (0)
Google Rating 5.0 (10)
Our Purpose Adasa Properties and Orlando Luxury Stays consistently provides top rated experiences and stays, responsive customer services, and premium locations and benefits in our short term rentals properties and markets. We are a Tr... View full profile
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Founded In 2004

Midfloridavacationhomes

Headquarters Lakeland, Florida

Airbnb Rating 4.6 (1855)
Google Rating 4.5 (4)

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Airbnb Rating 4.6 (1855)
Google Rating 4.5 (4)

Sunnyside Homes FKA PMI Sunny Side

Headquarters orlando, Florida

Airbnb Rating 5.0 (153)

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Airbnb Rating 5.0 (153)
Here’s a little about us. We are Alex and Irina, a husband and wife team. Alex is the technical maestro, ensuring all the cogs in our operation turn smoothly. Irina, a seasoned realtor and an expert in residential property management... View full profile

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Founded In 2009

iTrip Orlando

Headquarters Florida

Google Rating 4.3 (12)

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Google Rating 4.3 (12)
Local Ownership & Management True Dynamic Pricing VRBO Elite Software Partner (One of only a Handful in the World) Unlimited Owner Use No Flat Monthly Management Fees Listing on over 80 websites Free Light Maintenance Does this sound l... View full profile
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Founded In 2014

Upstay

Headquarters Florida

Employees 180

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Upstay consistently delivers above-market returns for vacation rental homeowners. We manage the entire vacation rental process from interior design to cleaning and repairs. Upstay properties are analyzed and tracked as unique investmen... View full profile
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Founded In 2023

SkyRun Orlando

Headquarters Lake Mary, Florida

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SkyRun is a full-service short term property management company, serving Orlando and Kissimmee.  We handle all bookings, cleanings, maintenance, and inspections.  We make vacation rental dreams possible for homeowners, guests, and e... View full profile