Looking for STR Community in Orlando – Pool Homes with Amenities

[Fab Ragh]

Hey everyone, I am looking for insight on STR-friendly communities with pool homes and strong amenities that make renting easier .

I’ve stayed at Windsor Hills before and liked it, but unsure if buying there is a good idea due to its age. I’ve also heard of Windsor Cay and am interested in newer communities with similar features.

Does anyone have experience with these communities or recommendations for others that perform well as short-term rentals? Looking for something with strong occupancy potential and resort-style amenities.

Looking to network as well with locals experts and agents specializing in STR in Kissimmee, Orlando area.

[Ryan Moyer]

Windsor Hill's age is not really a problem.  The proximity to Disney makes up for it.  And while their amenities are much smaller than the newer resorts, they did a good job with them such that they look great in listing photos, with the big bright water slides etc.  

Storey Lake's amenity area is much larger and more comprehensive than Windsor's, but Windsor's actually LOOKS better in photos to people scrolling quickly on Airbnb.

Additionally, Windsor's age means it has a reputation, so there are people that seek it out exclusively (IE they don't search for "Orlando" or "Disney", they search for "Windsor Hills").  Maintenance costs are also less becuase you have more international families compared to the other resorts that attract plenty of party locals.  

Lastly, the age their can be a boon at times if you do updates to make the home more modern.  When people search out Windsor you'll be competing against a bunch of people with old 2004 oak cabinets etc, so you can make your place stand out beyond just the theming.  Compared to Storey Lake, Windsor at Westside, etc where everyone is going to have the same modern kitchen, living room, etc.

That said, it's not necessarily my favorite if ROI is a primary concern.

Windsor Hills - Closest "real" resort to Disney.  Quieter, attracts more families, international travelers.  Modestly priced homes but max out at 6br,

Champions Gate - Far from Disney, but most travelers arent savvy enough to know the travel time is further than the map indicates.  Great amenities.  Best acquisition prices here relative to the home you're getting.  If you want to put most of your money into theming, at a lower acquisition price, this is the place.  Like Windsor, there are people that have been coming here for a long time and specifically search out CG.  Much more of a party vibe when you drive through the neighborhood though.

Storey Lake - In between.  Not as close as Windsor, but east of Disney instead of south so you avoid I-4 and actual travel time is much shorter than CG.  New modern houses, much higher prices than CG.  You save a few bucks on the reno as they already come with flex/game rooms instead of having to drywall in the garage like in CG/Windsor.  But your place theming better be awesome here because people are doing these things to the nines.  Also while every neighborhood has it's issues (Windsor has the least), Storey Lake has maybe the most.  I swear the front gate hasn't worked properly in a year and they just don't seem to care to fix it.

Reunion - If you're a baller with $2M+ to spend, this is the place to do it.  You get an actual unique home (not the same thing repeated like the other neighborhoods) and do something special.  But this is a totally different market than all the rest.  If you are looking at the main, real part of Reunion with the $4M custom homes, then you're not considering the other neighborhoods because it may as well be a different city.

Solara - Meh, it's nice.  Small compared to the other behemoths.  Does everything okay, not particularly a standout at anything, so people tend to forget about it.

Solterra - Just don't do it.

Windsor Island/Windsor at Westside - I honestly know less about these resorts than the others, as I only manage one in WI, none at Westside.  My impression is that the returns are not quite as good here, but I don't have hard data on that like many of the other neighborhoods where I own or manage multiple.

Bottom Line - If it were me, I would buy a big place in CG and spend a bunch of money on really really good theming.  Or I would buy in Windsor Hills and try to be one of the top 20 properties there, as location is the one thing you can never change and a thing people will always be looking for.  And don't sleep on the difference in maintenance costs.  These behemoth resorts further from Disney definitely bring in a lot more wear and tear than the kind of visitors typically coming to quiet Windsor.

A place like Storey Lake is really nice, and will do a bit more in revenue, but I don't think enough to justify the cost.  Our themed places in Storey Lake may do 10-15% more in revenue than our themed places in CG/Windsor, but you're talking about a $1M acquisition price on those Storey Lake homes versus $600k-$700k in Champions Gate and Windsor.

Just my $0.02.  I also have a realtor friend (that sold me my house in CG: https://www.airbnb.com/rooms/52612233) that has a lead on a totally different option to get out of the grind of the same home in these resort neighborhoods copied over and over, if you wanted an introduction.