Property Management in Windsor Island Resort

We are a small family-owned property management company that cares about the success of your vacation rentals. FunStay Florida Vacation Homes was founded on the idea that if we take excellent care of our Owners and their homes and guests, the rest will fall into place and we all will succeed. Contact us to learn more about our promises. 


We Love What We Do!
Don't believe us?  Read our reviews!

Are you currently one of the lucky owners of a new home in one of the newest and nicest resorts in all of Orlando - Windsor Island Resort?  

Managing short term vacation homes is a full-time job that we are extremely passionate about. We understand how challenging it is to provide the best service because we also took that giant leap of faith once upon a time. After successfully managing our own five properties, we made it a priority to help owners achieve their financial goals too by providing the most stellar experience for all their guests.

In this industry, there are no secrets or shortcuts. Every single day will require a lot of hard work to get the most bookings. Your property is special and deserves the most revenue it can get. A lot of other management companies may not own vacation homes, as these are completely different from other types of properties. When customers book a vacation home, they only have a short amount of time to enjoy it. That is why they expect nothing less than the best. Guests will reserve your property as an escape from their busy lives and deserve to treat themselves to the best experience possible.

That is why it is essential to ensure that your home is clean, attractive, and a great deal of fun. This will make them come back for every holiday! Especially if your booking rates are also strategically competitive. We have a wealth of experience to maximize your profits by readying your home to provide the dream vacation for your guests. That way, your home will easily achieve the highest rankings on popular booking platforms such as Airbnb and HomeAway. Instead of being property managers, we look at achieving your goals from a vacation owner’s perspective because that is who we are. This is why we always have your best interests at heart.

Our support starts from day one, where we can help you purchase your first vacation home. Then we can provide continued support through all renovations and furnishings for your property, as your full-time property management team. We will also take care of lowering your expenses to generate more profit from bookings. You can always rely on us to take great care of your property, as though it was our own home.

There is no guarantee of how much revenue a holiday home can make. However, the most effective way to manage short term vacation rentals is by looking after your guests from start to finish. Answer all their inquiries promptly and provide as much information as possible. Make them feel welcome before they have even checked-in, until their departure date. Even then you should follow up with them to ask about their experience. After all, that is the secret to success in the service and hospitality industry, where the customer is king. If your guests are always satisfied, their reviews will do most of the marketing for you to bring more traffic to your property listings. If you are still unsure if we are the right people to manage your homes, check out some of our reviews, and then give us a call so that we can help! Let us and your vacation homework hard for you, not the other way around!



Windsor Island Resort is now building new vacation homes for rent. The perfect choice for your next Disney vacation! With a location that can't be beaten near Orlando's world-class attractions, ample shopping, dining and entertainment, and resort-style amenities, this community is bound to have everything you are looking for.



A-  Zero Entry Main Pool
B - Pool Deck
C - Lazy River
D - Children's Water Park
E - Double Water Slide
F - Spa
G - Covered Bar
H - Outdoor Seating Area
I - Pool/Bar Restrooms
J - Children's Free Play Area
K - Family Cabanas
L - Rental Cabanas
M - Tropical Walk
N - 9-Hole Mini Golf Course
O - Fire Pit with View to Fireworks
P - Basketball Court
Q - Sand Volleyball Court
R - Dual Cornhole Court
S - Hammock Garden
T - Event Lawn
U - Parking Area
V - Windsor Island Clubhouse 


V1- Restrooms
V2 - Fitness Room
V3 - Multi-Purpose Room
V4- Great Rom
V5-Game Room
V6-Cafe and Ice Cream ShopV-7 - Office


Location, location, location. It’s finally here - Windsor Island Resort located in Orlando Florida! This new, 600+ vacation home community, is located just a short drive from Windsor at Westside Resort and about 8-10 minutes from Walt Disney World. 


  • 617 Unit Master Planned Community
  • Resort Amenities On Site
  • International Brand Recognition
  • 24 Hour Manned Gated Community
  • Minutes from World Class Attractions
  • Floor Plans to maximize Rentals/Returns
  • Key Home Features
    – Shingle Roof
    – Private Heated Pool
    -5, 6, 7 Bedrooms with 12′ x 24′ Pool
    – 8, 9 & 10 Bedrooms with 12′ 28 Pool
    – Townhomes with 7.5′ x 18′ Pool
    – Brick Paver Driveways and Pool Decks
    – Stainless Steel Appliances
    – Owners Storage Closet
    – Granite and Tile Throughout Kitchens
    and All Bathrooms
    – Blinds Included
    – Covered Lanai with Child Safety Fence
    – Washer & Dryer


  • Most Visited City in the US with 80 Million Annual Visitors
    – Year Round Rental Season with Large Variety of Online Vacation Rental
    & Management Booking Sites
  • Named One of the Fastest Growing Cities in the US by Forbes Magazine
    – Major Industries: Aerospace & Defense, Tourism, Technology
    – Second Largest Convention Center in US
  • Expansive International Airport
    – Premier Global Gateway with over 135 Domestic and
    International Destinations
    – #1 Ranked Airport in FL, 10th Busiest Airport in US
  • Home to Internationally known Walt Disney World Resort and
    Theme Parks, Universal Orlando®, SeaWorld Orlando®,
    LEGOLAND Florida Resort and Much More!
  • World Class Shopping and Entertainment
  • Favorable Climate Year Round
  • Close Proximity to East and West Coast Beaches