The Unique Orlando Owner Rental Market + Orlando travel plan

A guest post for you to enjoy: I’ve been running several villa rental sites for resort communities in and around the Orlando area for a number of years now. At Windsor Hills Private Rentals we provide a platform for owners in Windsor Hills Resort (2 miles from Disney) to short term rent their properties. We’ve been in the unique position of seeing the rise, fall and rise again of the Orlando rental market. And we’ve had to develop our sites accordingly. In such capricious economic conditions it’s been an interesting experience trying to develop sites that keep pace with the general mood of the market place and ensure we meet the needs of both property owners (sellers) and holidaymakers (buyers).

For many avid fans the annual trip to Disney means scouring holiday rental sites for that most value for money off-site rental property. What ensues after initial contact is usually a lengthy game of email ping pong with several hundred owners, a trade in half-truths followed by the kind of fight to the death Charles Darwin might use as evidence of evolution theory permeating all segments of daily life. The Orlando vacation property rental market bears all the hallmarks of a securities trading floor. At the turn of the millennium property development went into overdrive in and around the Disney area with a subsequent flooding of the market with cheap rental property. With the property crash and ensuing worldwide economic downturn a series of events conspired to reset the rules of the Disney off-site rental market. Many resorts suffered swathes of foreclosures which in several circumstances breached that critical tipping point where resort association fees from non-delinquent owners are able to keep shared facilities operational. In most cases it left owners with properties they couldn’t sell in a market where supply could not satiate demand. From this malaise interesting behaviours developed in holidaymakers who rightly wanted only to get the best rental deal for their family.

Resorts such as Emerald Island and Windsor Hills have held up well given their proximity to Disney and the other major theme parks. Behind the scenes however owners have had to, and still have to, withstand a barrage of what they term “low ballers”. These are holidaymakers who loop round every owner in a resort sometimes with a sob story but always with an offer to rent a property at a rate so low the owner would almost certainly lose money from the transaction. It’s a shared frustration amongst owners in these resorts but it’s something that is very hard to eradicate.

Commonly accepted amongst the owners is the fact that low-ballers are so widespread and outwardly confident in achieving their target rate that someone in the owner community must be renting their property out at these rates. During the boom years many wealthy people such as sports stars had wealth managers buy up chunks of resorts on their behalf. In such circumstances it is likely that property managers have little interest in eating up time negotiating high rates. With no mortgages on the properties managers probably set pretty rudimentary rental rate targets. In this environment owners with big mortgages and electricity rates to cover are overlooked or screwed down to rates so low they struggle to stay afloat. It’s usually these owners however that have adapted their offering to stay solvent. To do this they’ve learned to offer a service; a personal phone call to discuss the initial enquiry, tips and advice for the trip, on call service during your stay where nothing is too much trouble and after care which ensures you’ve enjoyed your stay and any issues are action upon and resolved. Return business is king. And it’s for these reasons why holidaymakers should be careful about making budget their sole focus in planning a Disney vacation trip.

A real challenge when running rental sites in Orlando is to find the balance between allowing holidaymakers the flexibility to quickly enquire across various properties and property ranges while also protecting owners from blanket enquiries which frankly waste everyone’s time. As operators of rental sites for several of the most popular resort communities around Walt Disney World we’ve had to continually tweak our offering. We’ve restricted the ease with which a holidaymaker can submit enquiries to more than one property (instead of all villas, the choices are more granular such as number of bedrooms.) We’ve also encouraged owners to browse the site and really spend time reviewing each property by making the individual enquiry process as slick and simple as possible for holidaymakers; an example would be by pre-populating our enquiry form with the owners details so each individual enquiry becomes a simple one press transaction similar to Amazon’s one-click purchase functionality. Devising and developing functionality which pleases both holidaymakers and owners alike is tough and challenging especially in the Orlando area but it’s an enjoyable experience and always keeps us guessing.

Travel Itinerary – My Last Trip to Orlando

On my last trip to Orlando I rented a villa in Windsor Hills. Having spent several days at Disney and the theme parks in general in the past this trip was focused around the general Orlando area and a road trip north:

Day 1 – Windsor Hills

We spent our early stay in Windsor Hills, relaxing at the clubhouse. In the morning I made sure I arrived early to make full use of the large lagoon style pool, swimming 40 lengths before the holiday throngs arrived. Windsor Hills is a peaceful resort with one of the best community pool areas in Orlando. Most of the day was spent soaking up the sun and making our way back and forth between the clubhouse and our villa (on Teascone Boulevard in the resort), a walk of roughly 2-3 minutes from the main pool. We stayed in a large 6 bed villa with several bathrooms and private pool and Jacuzzi.

Day 2 – Manny’s Steak House

The highlight of day 2 was Manny’s steakhouse. Undoubtedly the best steak I’ve ever had. Think classic American food in classic American surroundings. Huge slabs of marbled meat, which cut like a hot knife through butter they were so tender. The steaks came served with portions of coleslaw that would probably constitute a main meal in themselves back in Europe. The walls were adorned with American memorabilia such as traffic signs and beer logos. Watch out for the desserts. I don’t recall exactly the dish’s official title but I’m sure it involved the word explosion or overload. What arrived was an ice cream sundae served in a glass big enough to bath a small baby. We’d been pre-warned so ordered one between three but even that was too much.

Day 3 – Celebration Golf

Day 3 we golfed at Celebration. Celebration is one of Orlando’s glorious boom time residential follies. The resort was slated to be huge but, begun at the start of the property collapse, Celebration’s large property values collapsed and the resort caved in on itself. When we arrived we found the resort still surviving, just. It is home however to a stunning 18-hole golf course and fantastic clubhouse. These were still running and 18 holes cost a mere $6 per person as the resort attempted to stay solvent. The course was great and we saw a few alligators lounging near the water traps. Not sure what standard Florida protocol is if they begin to take an interest in you but we assumed that run would be the best course of action. Thankfully it didn’t come to that. I actually also made use of the length pool next to the clubhouse to do some swimming.

Day 4 – Kennedy Space Centre

Day 4 we visited Kennedy Space Centre. I’ve always wanted to visit. Kennedy is roughly 65 miles east of Windsor Hills around 1hrs 10mins travel time by car. Seeing the large NASA assembly building loom large on approach made the hairs on the back of my neck stand on end. Having always been a space buff I found the history of the place inspiring and would highly recommend. It is not a visit often considered by holidaymakers to Orlando but it’s a pretty accessible attraction if you use Florida State Highway 528.

Days 5-7 Road Trip to Charlestown and back

For the rest of the holiday we decided to take a road trip north to Charlestown (South Carolina) having always wanted to go. On the way we passed Jacksonville (a larger city than I would have thought with several tall buildings) and Savannah, Georgia (home to some fascinating southern architecture). Florida roads are great and the journey felt a lot shorter than it was. Charlestown is a beautiful place and its small central hub felt not dissimilar to New York’s Greenwich Village possessing an arty student feel. We’re from Scotland so one striking difference between Charlestown and Orlando was the interest in, and identification of, our accents. Charlestown is one of America’s truly historical cities having been home to the British and who fought off various attacks from the French and Spanish. It was later heavily settled by “Scots Irish”, better known as Ulster Scots in the UK. Most locals seemed to have some Scottish or Northern Irish ancestry, most had been to the UK and they all seemed to be able to distinguish not only our accents but also where exactly in Scotland we were from; a refreshing change from Orlando where the locals had us down as everything from Argentinian to Australian. We had a fantastic meal at the Crab Shack on Market Street and several glasses of wine in the roof terrace restaurant. Highly recommended. On the return trip we stopped at St Augustine, the oldest town in the US. In its traditional centre we found some fascinating old buildings from colonial times but outwith that it felt like any other part of small town America, the kind of place you pass through on the way to somewhere else.

We regularly holiday in Florida but a key tip for anyone travelling to Orlando and Florida in general is it’s a very large state, steeped in history and cultural depth which can act as a perfect balance to the theme parks for those who are willing to explore a little.

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