10 communities compared. Real MLS data. From 7 bedrooms to priced out.
10
Communities Compared
7
In Budget
7 bed
Max at $500K
3
Priced Out
Half a million dollars sounds like a lot until you start shopping for an Orlando vacation rental. Some communities hand you a 7-bedroom pool home with change left over. Others won’t even let you through the gate.
I compared real MLS listings across the 10 most popular short-term rental communities near Disney World to answer one question: what does $500,000 actually buy in Orlando’s vacation rental communities? The differences are bigger than most investors expect. Finding the best Orlando vacation rental community for your budget starts here.
Every community below allows short-term rentals and sits in Osceola or Polk County zoning. All prices reflect active listings as of September 2026.
Best Value
Where $500K Goes Furthest
Solara Resort
Kissimmee • 8 miles to Disney
Best Value
| BEDS | PRICE | SQ FT | POOL |
|---|---|---|---|
| 5–7 | $450K–$535K | 2,400–4,100 | Private |
The most bedrooms per dollar in Orlando. A 7-bed/7-bath at $515,000. Even 9-bedroom homes at $535,000. Built by Mattamy Homes, with a FlowRider surf simulator and resort pools. More bedrooms means more revenue: 7-bed homes in STR communities near Orlando can gross $70,000-$90,000 annually. HOA: ~$663/mo.
Solterra Resort
Davenport • 12 miles to Disney
In Budget
| BEDS | PRICE | SQ FT | POOL |
|---|---|---|---|
| 5 | $495K–$530K | 2,800–3,100 | Private |
101 homes on the market. Average asking $535K, average selling $514K. Sellers are negotiating. Median hit $500K in June 2026 (down 6.1% YoY). The lowest HOA of all 10 communities at $350-$500/mo. Lower carrying costs mean better cash flow from day one.
Windsor at Westside
Kissimmee • 4 miles to Disney
In Budget
| BEDS | PRICE | SQ FT | POOL |
|---|---|---|---|
| 5 | $499K–$510K | 2,260–2,490 | Private |
Median sale $505K. One of the closest affordable vacation rental communities to Disney (4 miles). The 10,000 sqft clubhouse, lazy river, and tiki bar check every amenity box guests filter for. Fewer bedrooms than Solara, but proximity to the parks commands higher nightly rates.
Storey Lake
Kissimmee • 8 minutes to Disney
In Budget
| BEDS | PRICE | SQ FT | POOL |
|---|---|---|---|
| 4–5 | $420K–$530K | 1,800–2,600 | Private |
Buyer’s market in 2026. Median sale price dropped to $430K (down 11.2% YoY) while occupancy holds at 70-80%. Homes are selling 4% below asking. That combination of lower prices and strong occupancy is exactly what top investors look for. 105 homes available. Room to negotiate.
Tight Fit
Tight Fit at $500K
Windsor Hills
Kissimmee • 2 miles to Disney
Tight Fit
| BEDS | PRICE | SQ FT | POOL |
|---|---|---|---|
| 4 | $480K–$520K | 1,800–1,900 | Private |
The closest short-term rental community near Disney at just 2 miles. That proximity is Windsor Hills’ superpower. A 4-bed runs $480K-$520K. Five bedrooms start at $570K+. Older homes (mid-2000s) may need updating. But the location drives $28,000-$90,000 in annual rental income. Buyer’s market with 45-50 active listings.
ChampionsGate (The Retreat)
Davenport • minutes from Disney off I-4
Tight Fit
| BEDS | PRICE | SQ FT | POOL |
|---|---|---|---|
| 4–5 | $450K–$525K | 2,000–2,800 | Private |
Over 900 acres with a water park, lazy river, movie theater, golf, and dining. The Retreat section is the vacation home near the Disney zone. Broader ChampionsGate median: $368K (pulled down by condos). Brand name recognition helps with bookings and resale. One of the best Orlando vacation rental communities for short-term rental investors who want resort-scale amenities.
Reunion Resort
Kissimmee • 6 miles to Disney
Limited Options
| BEDS | PRICE | SQ FT | POOL |
|---|---|---|---|
| 3–4 | $467K–$495K | 1,800–2,200 | Some |
$500K gets you into Reunion, but not the Reunion most people picture. At this budget: condos, townhomes, or small detached homes. Luxury estates start at $800K+. HOA: $815-$1,790/mo (highest on this list). A 3-bed condo at $470K with $1,000/mo HOA needs $50K+ gross to break even. Know your CDD fees in Orlando before buying.
Priced Out
Priced Out at $500K
Windsor Island
Davenport • 10 miles to Disney
Over Budget
Average selling price: $583K. Cheapest 5-bed listings start at $520K-$535K. Built by Pulte Homes with a 6,500 sqft resort pool, lazy river, and mini golf. Great community, but you need $530K+ to get in.
Encore Resort
Kissimmee • adjacent to Reunion
Over Budget
Entry price: ~$545K. Average selling: $823K. Luxury 4-13 bedroom villas with private waterpark access. Premium product at a premium price. Budget $550K minimum.
Margaritaville
Kissimmee • 3 miles to Disney
Over Budget
$500K buys only a small 2-bedroom cottage. A rentable 3-bedroom starts at $619K+. Guests also pay a nightly resort fee of $34-$59 per night, which reduces your booking competitiveness. Need $620K+ for a viable rental unit.
Where I’d Put $500K Right Now
I own 10 vacation rentals across these communities and manage roughly 100 through FunStay Florida. Here’s what I tell investors with a $500K budget:
Bedroom count drives revenue. A 7-bedroom home at Solara grosses more than a 4-bedroom at Windsor Hills, even though Windsor Hills is closer to Disney. The math usually favors more bedrooms.
Lower HOA means better cash flow. Solterra’s $350-$500/month versus Reunion’s $815-$1,790/month is the difference between positive cash flow and feeding the property every month.
Buyer’s markets don’t last. Storey Lake prices are down 11%, with occupancy holding at 70-80%. That spread between price and performance is exactly when smart investors buy.
$500,000 can absolutely work as an Orlando short-term rental investment in 2026. The key is matching your budget to the best Orlando vacation rental community for your goals, not stretching into a premium resort where carrying costs eat your returns.
Explore All 10 Communities
Browse current listings in each Orlando vacation rental community:
Find Your Orlando Vacation Rental
$500K is enough to get into 7 of the top short-term rental homes near Disney World. Let’s find the right Orlando vacation home for your investment goals.
Mike Chen | La Rosa Realty Celebration | 503-888-8070
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