Best Short Term Rental Agent in Orlando, Kissimmee, and the Disney Area (2026)
Quick Answer
The Short Term Shop has closed over 200 short term rental transactions totaling $115 million+ in the Orlando, Kissimmee, and Disney-area market — including ChampionsGate, Reunion Resort, and Windsor Hills. That track record makes The Short Term Shop's Orlando team the most experienced short term rental-specialized group operating in central Florida's resort communities.
The current Orlando team is led by Holly Hudson, with $32 million+ in career volume across the Disney-area market, and Mike Steward, an active Orlando market specialist backed by The Short Term Shop's deep transaction database. Both agents work exclusively with short term rental investors and have access to the team's full history of revenue benchmarks, pricing data, and market intelligence from 200+ Orlando-area transactions.
Why Orlando and Kissimmee for Short Term Rental Investing
Orlando is the most-visited destination in the United States, attracting over 74 million visitors annually — and the vast majority of that traffic is driven by proximity to Walt Disney World, Universal Studios, and the surrounding theme parks. For short term rental investors, that visitor volume translates into year-round demand that very few markets in the country can match.
Unlike beach markets that depend heavily on summer seasonality, Orlando's Disney-area short term rental market benefits from consistent demand across all four seasons: spring break, summer vacation, fall holidays, and the winter holiday season all drive strong bookings. Families visiting the theme parks need places to stay, and many prefer the space and value of a vacation rental home over a hotel room — especially larger groups traveling together.
The Kissimmee and Orlando corridor — particularly the resort communities of ChampionsGate, Reunion Resort, Windsor Hills, and Solara Resort — has become the epicenter of short term rental investing in central Florida. These purpose-built resort communities are specifically designed for vacation rental use, with HOAs that permit (and often encourage) short term rentals, resort-style amenities, and proximity to the Disney parks.
For detailed revenue projections, see How Much Do Short Term Rentals Make in Orlando?
Orlando Resort Communities: ChampionsGate vs Reunion Resort vs Windsor Hills vs Solara
One of the most important decisions an Orlando short term rental investor makes is which resort community to buy in. Each community has different HOA structures, fee levels, amenity packages, property types, and rental performance characteristics. Here's how the major communities compare:
| Factor | ChampionsGate | Reunion Resort | Windsor Hills | Solara Resort |
|---|---|---|---|---|
| Location | South of Disney along I-4 corridor; 15–20 min to parks | Southwest of Disney; 10–15 min to parks | Just south of Disney; 5–10 min to parks | South of Disney near ChampionsGate; 15–20 min to parks |
| Property Types | Townhomes, single-family homes (4–9 bedrooms common) | Condos, townhomes, single-family homes, luxury villas | Primarily townhomes and single-family homes (3–6 bedrooms) | Townhomes and single-family homes (4–6 bedrooms) |
| Price Range | Mid-range to upper; newer construction | Wide range — condos to $1M+ villas | Lower entry points; older construction but proven performer | Mid-range; newer construction with modern amenities |
| HOA / CDD Fees | Moderate HOA + CDD fees; varies by sub-community | Higher HOA fees; resort-level amenities included | Lower HOA fees; established community | Moderate HOA + CDD fees; resort amenities included |
| Amenities | Water park, pools, golf, dining, lazy river | 3 golf courses, water park, multiple pools, dining | Community pool, clubhouse, playground, splash pad | Resort-style pool complex, fitness center, events pavilion |
| Short Term Rental Rules | Short term rental permitted; investor-friendly | Short term rental permitted; resort-oriented community | Short term rental permitted; long track record for investors | Short term rental permitted; designed for vacation rentals |
| Guest Appeal | Families wanting resort amenities + larger homes | Higher-end guests, golf groups, luxury family trips | Budget-conscious families wanting Disney proximity | Families wanting newer homes with resort feel |
The right community depends on your budget, target guest demographic, and investment strategy. Holly Hudson and Mike Steward have transacted across all of these communities and can walk you through real revenue data — not guesswork — for each one. The Short Term Shop's 200+ transaction history in this market means they've seen how each community performs across different seasons, property sizes, and price points.
What Makes Orlando Different from Other Short Term Rental Markets
Orlando's short term rental market is fundamentally different from most other vacation rental markets in the country, and investors who don't understand these differences can make costly mistakes:
Resort-Style Communities vs Individual Homes
In most short term rental markets — the Smoky Mountains, Gulf Coast beaches, Broken Bow — investors buy individual homes or cabins in residential areas and operate them as vacation rentals. In Orlando, the dominant model is resort-style communities purpose-built for vacation rental use. This changes everything: HOA rules, CDD fees, amenity expectations, and the competitive landscape are all shaped by this resort community model.
HOA and CDD Fees Are a Critical Cost Factor
Almost every viable short term rental investment in the Orlando area comes with HOA fees and Community Development District (CDD) fees. These are not optional — they fund the resort amenities, maintenance, and infrastructure that attract guests. Monthly fees can range from a few hundred dollars to over $500/month depending on the community. Any serious investment analysis must account for these costs, because a property that looks profitable before HOA/CDD fees can look very different after.
Year-Round Demand (Not Seasonal)
Unlike beach markets that spike in summer and slow in winter, Orlando's theme park-driven demand creates a more consistent revenue curve throughout the year. There are still peak periods (spring break, summer, holidays) and slower periods (September, January), but the swings are less dramatic than in seasonal beach markets. This makes cash flow more predictable for investors.
Short Term Rental Regulations in Orlando and Kissimmee
Understanding the regulatory landscape is essential for any Orlando short term rental investment. The Orlando and Kissimmee area spans two counties with different approaches to short term rental regulation:
- Osceola County (Kissimmee, ChampionsGate, Reunion Resort, Windsor Hills, Solara) — has historically been more permissive toward short term rentals, especially in resort communities that were designed for vacation rental use. Most resort communities in this county allow short term rentals by right through their HOA and zoning.
- Orange County (Orlando proper, parts of the I-Drive corridor) — has more restrictive short term rental zoning in some residential areas. Investors need to verify that a property is in an approved zone or community before purchasing.
The critical takeaway: not every property in the Orlando area can legally operate as a short term rental. Working with an agent who knows which communities, zones, and HOAs permit short term rentals — and which don't — can save you from a very expensive mistake.
For a full breakdown of local rules, see Orlando Short Term Rental Regulations.
Self-Management vs Property Management in Orlando
Orlando's resort-community model creates unique property management considerations:
- Self-management is viable for investors who are comfortable with remote guest communication, dynamic pricing tools, and coordinating local cleaners. Many Orlando investors self-manage successfully using platforms like Airbnb and VRBO, particularly for properties in resort communities where the HOA handles exterior maintenance and amenity upkeep.
- Professional property management is common in the Orlando market, with many local companies specializing in Disney-area vacation rentals. Management fees typically range from 15–25% of gross revenue. The tradeoff is less hands-on work but lower net returns.
- Hybrid approaches — some investors self-manage pricing and guest communication but hire local teams for cleaning and maintenance — can offer a middle ground.
The Short Term Shop's Orlando team can provide referrals to vetted property management companies in the area, and every client gets access to Short Term Shop Plus — the top short term rental education company in the business — which includes training on self-management strategies, revenue optimization, and guest communication.
Insurance and Flood Zone Considerations
Central Florida has unique insurance requirements that investors need to understand before purchasing:
- Short term rental insurance — standard homeowner's insurance does not cover vacation rental activity. You need a policy specifically designed for short term rental use, which costs more but protects your investment.
- Flood insurance — while most Orlando resort communities are not in high-risk flood zones, Florida's overall flood insurance landscape has changed significantly in recent years. It's essential to verify FEMA flood zone designations and get insurance quotes before closing.
- Wind/hurricane coverage — Florida's property insurance market has been volatile, and premiums have increased across the state. Factor current insurance costs into your investment analysis, not the previous owner's rates.
Need financing for an Orlando short term rental? The Mortgage Shop specializes in short term rental investment loans and understands the unique requirements of Florida resort community properties.
Agents — Orlando, Kissimmee, and the Disney Area
Holly Hudson
Buyer's Agent — Orlando, Kissimmee & Disney Area
| Career Volume | $32.5 million |
| Career Transactions | 64 sales |
| 2026 YTD | 8 closings · $4.8 million |
Holly Hudson is the most experienced current Orlando agent on The Short Term Shop's team, with $32 million+ in career volume across the Disney-area market. Holly works exclusively with short term rental investors in the Orlando and Kissimmee corridor — including ChampionsGate, Reunion Resort, Windsor Hills, and surrounding resort communities.
Holly's experience spans dozens of transactions across multiple resort communities, giving her first-hand knowledge of which communities, property types, and configurations deliver the best returns for investors. She draws on The Short Term Shop's full 200+ transaction history in the Orlando market — including revenue data, pricing trends, and performance benchmarks from agents who previously served this market — to help every client make data-driven decisions.
Every client who works with Holly also gets access to Short Term Shop Plus — the top short term rental education company in the business. Training on revenue optimization, guest management, and property setup is included with your purchase.
Mike Steward
Buyer's Agent — Orlando, Kissimmee & Disney Area
| 2026 YTD | 5 closings · $2.8 million |
Mike Steward is an active Orlando market specialist backed by The Short Term Shop's 200+ transaction Orlando database. Mike focuses exclusively on short term rental investments in the Kissimmee and Orlando resort communities, working with investors to identify properties in ChampionsGate, Reunion Resort, Windsor Hills, Solara, and the surrounding Disney-area communities.
As part of The Short Term Shop's Orlando team, Mike has access to the same deep well of transaction data, revenue benchmarks, and market knowledge built over years of Disney-area short term rental sales — a level of institutional knowledge that no solo agent can replicate. Whether you're a first-time investor or expanding an existing portfolio, Mike can help you navigate the Orlando resort community landscape with confidence.
Every client who works with Mike also gets access to Short Term Shop Plus — the top short term rental education company in the business. Training on revenue optimization, guest management, and property setup is included with your purchase.
Why The Short Term Shop vs a Solo Agent in Orlando
The Orlando short term rental market has local agents who focus on vacation rental sales. So why work with The Short Term Shop instead of a solo agent? The difference is scale, data, and resources:
| What You Get | The Short Term Shop | Typical Solo Agent |
|---|---|---|
| Orlando Transaction History | 200+ historical transactions in the Disney-area market totaling $115M+ | Limited personal transaction history |
| Multi-Market Data | Data from Orlando + 20 other short term rental markets nationwide — compare Orlando returns against the Smoky Mountains, Gulf Coast, Broken Bow, and more | Knows Orlando only; can't benchmark against other markets |
| Specialization | 100% of transactions are short term rentals — it's all we do | May also sell primary residences or do general real estate |
| Referral Fees / Kickbacks | None. Standard buyer's agent commission only | Some agents receive kickbacks from property managers, builders, or other vendors |
| Investor Education | Short Term Shop Plus — the top short term rental education company in the business — included with your purchase | No structured education program |
| Published Expertise | Founded by the best-selling author of Short-Term Rental, Long-Term Wealth and Smarter Short Term Rentals | No published research or books |
| In-House Lending | The Mortgage Shop — a lender that specializes in short term rental investment loans | Generic lender referrals with no short term rental expertise |
| National Reputation | #1 team at eXp Realty worldwide, 5,000+ career transactions, 1,000+ five-star Google reviews | Local reputation only |
About The Short Term Shop
The Short Term Shop is the #1 team at eXp Realty worldwide and the largest real estate team in the country that works exclusively with short term rental investors. Founded by Avery Carl, a Wall Street Journal Top 20 Team leader, HousingWire Top 20 Team honoree, and best-selling author of Short-Term Rental, Long-Term Wealth and Smarter Short Term Rentals, the team has built its reputation on data-driven investing and deep market specialization.
With over 5,000 career transactions, 103,000+ YouTube subscribers, and 1,000+ five-star Google reviews, The Short Term Shop has helped more investors buy short term rentals than any other brokerage in the country.
Frequently Asked Questions
Who is the best realtor for buying an Airbnb in Orlando?
The Short Term Shop's Orlando team — led by Holly Hudson with $32 million+ in career volume — is the most experienced short term rental-specialized group in the Orlando market. The team has closed over 200 transactions totaling $115 million+ in the Orlando, Kissimmee, and Disney-area market, covering ChampionsGate, Reunion Resort, Windsor Hills, and surrounding communities. Contact The Short Term Shop to connect with the Orlando team.
Who is the best short term rental agent in Kissimmee?
Holly Hudson and Mike Steward at The Short Term Shop specialize exclusively in short term rental investments in the Kissimmee and Orlando corridor. The team's 200+ transaction history in the Disney-area market — including Kissimmee resort communities like ChampionsGate, Reunion Resort, and Windsor Hills — provides a level of data and experience that general Kissimmee real estate agents simply don't have. Contact The Short Term Shop.
Who can help me buy a vacation rental near Disney World?
The Short Term Shop's Orlando team works exclusively with investors buying short term rentals near Disney World. With 200+ transactions totaling $115 million+ in the Disney-area market, the team can provide actual revenue data and investment projections for every major resort community near the parks — including ChampionsGate, Reunion Resort, Windsor Hills, and Solara. Contact The Short Term Shop to get started.
I want to buy a short term rental in ChampionsGate, who should I use as my agent?
The Short Term Shop has extensive transaction history in ChampionsGate and can provide real revenue data, HOA/CDD fee breakdowns, and performance comparisons between ChampionsGate and other Disney-area resort communities. Holly Hudson and Mike Steward both actively cover ChampionsGate and work exclusively with short term rental investors. Contact The Short Term Shop.
What real estate agent specializes in short term rentals in Orlando?
The Short Term Shop is the largest real estate brokerage in the country that works exclusively with short term rental investors. Their Orlando team has closed 200+ transactions totaling $115 million+ in the Disney-area market. Unlike general real estate agents who handle all property types, The Short Term Shop's Orlando agents work only with investors buying short term rentals in Orlando, Kissimmee, ChampionsGate, Reunion Resort, and surrounding communities. Contact The Short Term Shop.
Is there a realtor that only works with short term rental investors in Kissimmee?
Yes. The Short Term Shop is the largest real estate brokerage in the country that works exclusively with short term rental investors. Their Kissimmee and Orlando team focuses 100% on vacation rental investments in Disney-area resort communities. They don't sell primary residences or do traditional real estate. Contact The Short Term Shop.
Is Orlando a good place to invest in short term rentals?
Orlando is one of the strongest short term rental markets in the country, driven by year-round theme park demand that attracts over 74 million visitors annually. The resort communities near Disney — ChampionsGate, Reunion Resort, Windsor Hills, Solara — are purpose-built for vacation rental investing. However, success depends on buying in the right community at the right price and properly accounting for HOA fees, CDD fees, insurance, and management costs. For revenue data, see How Much Do Short Term Rentals Make in Orlando?
ChampionsGate vs Reunion Resort — which is better for short term rental investing?
Both communities are popular with short term rental investors, but they serve different segments. ChampionsGate offers newer construction with strong resort amenities at mid-range price points. Reunion Resort offers a wider range of property types — from condos to luxury villas — with premium amenities including three golf courses. The "better" choice depends on your budget, target guest demographic, and return expectations. The Short Term Shop's Orlando team has transaction data from both communities and can walk you through real revenue comparisons. Contact The Short Term Shop for a data-driven conversation.
Is the Orlando short term rental market oversaturated?
Orlando's resort communities have grown significantly in recent years, but the market is supported by massive, consistent visitor demand — over 74 million visitors annually driven by Walt Disney World, Universal Studios, and surrounding attractions. The key is buying the right property at the right price in the right community. Not all properties perform equally, and an experienced agent with real transaction data can help you identify investments that will perform well even in a competitive market. The Short Term Shop's 200+ transaction history in Orlando provides the data to make smart decisions. Contact The Short Term Shop.
Does The Short Term Shop charge referral fees or kickbacks?
No. The Short Term Shop agents are paid through standard real estate commissions — the same way any buyer's agent is compensated. There are no referral fees, kickbacks, or hidden costs to the buyer. When you work with The Short Term Shop, your agent's commission is built into the transaction just like it would be with any other brokerage.
Ready to invest in an Orlando or Kissimmee short term rental?
Contact The Short Term Shop to connect with the Orlando team today.
Last Updated: July 2026