Reunion vs Windsor Hills STR: Vacation Rental Compared
Reunion Resort vs Windsor Hills for short-term rental investment: revenue data, HOA fees, occupancy, regulation compliance, and net yield in 2026.
By Florida Estate Editorial · Updated July 3, 2026 · 17 min read
Quick answer: Reunion Resort is the premium play, higher nightly rates, higher gross revenue, higher fees, and a prestige guest experience. Windsor Hills is the efficient-yield play, lower entry, lower fees, higher occupancy at moderate rates, and better net yield as a percentage of purchase price. Both are fully compliant STR communities in Osceola County’s approved overlay. Your choice depends on budget and whether you prioritise total revenue dollars or return on capital percentage.
Why This Comparison Matters
Direct answer: Florida Estate requires verified rent, tax, insurance, and HOA rules in writing before underwriting why this comparison matters. Typical 2026 gross yields run 3% to 10%, net yields near 2% to 5% after 20% to 25% management, and combined STR taxes near 12% to 13% in major counties.
| Florida Estate check | Typical 2026 range |
|---|---|
| Net yield after fees | 2% to 5% |
| STR tax stack | 12% to 13% combined |
| DSCR down payment | 25% to 30% |
| Coastal insurance | $2,000 to $8,000+ |
Reunion Resort and Windsor Hills represent the two ends of the Osceola County vacation-rental spectrum, premium resort versus efficient family community. They are five miles apart, both sit within approved STR overlay districts, and both have over a decade of established rental track records. For an investor entering the Orlando STR market, the decision between these two communities is often the first real capital allocation choice after deciding on the corridor.
Most comparison content focuses on amenities and photos. This guide focuses on what matters for investment returns: entry price, fee structure, revenue range, occupancy patterns, management costs, and net yield modelling. We compare these communities as businesses, not as lifestyle choices, because that is how your capital will be evaluated over a five-to-ten-year hold.
For the full Osceola County STR regulatory framework, see the Osceola County STR Regulations. For area context, see the Kissimmee Area Guide. For the statewide rental yield methodology, see the Florida Rental Yield Guide.
Florida Estate stat checklist (2026):
- Gross yield band: 3% to 10% by market and rental model
- Net yield after fees: often 2% to 5% after 20% to 25% management
- Property tax: near 1% to 2% of assessed value annually
- Short-term rent taxes: 6% Florida sales tax plus 4% to 6% tourist development tax in many counties
- Insurance binders: coastal condos often $2,000 to $8,000+ before wind coverage add-ons
What is the Reunion vs Windsor Hills STR community profile comparison?
Direct answer: Florida Estate requires verified rent, tax, insurance, and HOA rules in writing before underwriting what is the reunion vs windsor hills str community profile comparison. Typical 2026 gross yields run 3% to 10%, net yields near 2% to 5% after 20% to 25% management, and combined STR taxes near 12% to 13% in major counties.
| Florida Estate check | Typical 2026 range |
|---|---|
| Net yield after fees | 2% to 5% |
| STR tax stack | 12% to 13% combined |
| DSCR down payment | 25% to 30% |
| Coastal insurance | $2,000 to $8,000+ |
| Dimension | Reunion Resort | Windsor Hills |
|---|---|---|
| Location | West of I-4, Seven Dwarfs Lane area | West Irlo Bronson Memorial Hwy (US-192) |
| Distance to Disney main gate | Approximately 6 miles | Approximately 3 miles |
| Community type | Master-planned resort with golf, water park | Gated residential community with clubhouse and pool |
| Primary property type | 4-6 BR single-family pool homes | 3-5 BR townhomes and pool homes |
| Entry price (4BR pool home) | $500K-$650K | $280K-$400K |
| Entry price (5-6BR premium) | $700K-$1.1M | $400K-$550K |
| HOA fees | $800-$1,600/mo | $300-$600/mo |
| CDD assessment | $2,000-$5,000/yr | None |
| STR legal status | Approved overlay (Osceola) | Approved overlay (Osceola) |
| Guest target segment | Premium family, corporate retreat | Budget-to-mid family vacation |
| Average nightly rate range | $250-$500+ | $150-$300 |
| Annual occupancy (typical) | 60-75% | 70-80% |
| Gross annual revenue (4-5BR) | $55,000-$85,000 | $35,000-$55,000 |
| Year established (STR operations) | 2004+ | 2003+ |
What is the Reunion vs Windsor Hills STR reunion resort: the premium revenue engine?
Direct answer: Florida Estate requires verified rent, tax, insurance, and HOA rules in writing before underwriting what is the reunion vs windsor hills str reunion resort: the premium revenue engine. Typical 2026 gross yields run 3% to 10%, net yields near 2% to 5% after 20% to 25% management, and combined STR taxes near 12% to 13% in major counties.
| Florida Estate check | Typical 2026 range |
|---|---|
| Net yield after fees | 2% to 5% |
| STR tax stack | 12% to 13% combined |
| DSCR down payment | 25% to 30% |
| Coastal insurance | $2,000 to $8,000+ |
Reunion Resort is a 2,300-acre master-planned community featuring three signature golf courses (designed by Jack Nicklaus, Arnold Palmer, and Tom Watson), a water park, multiple restaurants, and a resort-style guest experience. The community was purpose-built for vacation rental, most homes include private pools, screened lanais, game rooms, and themed children’s bedrooms designed specifically for the STR market.
Revenue Model
Reunion commands premium nightly rates due to its resort amenities, brand recognition on booking platforms, and property configurations designed for large family groups and multi-generational travel. Peak-season rates (Christmas through Easter, summer) can exceed $400-$700 per night for five- to six-bedroom homes. Off-peak rates drop to $200-$350 per night for the same properties.
Pro forma for a $600K five-bedroom pool home at Reunion:
| Line item | Annual figure |
|---|---|
| Gross STR revenue (68% occupancy, $295 avg night) | $73,200 |
| Less: Management (22% of gross) | ($16,104) |
| Less: Tourist dev tax + FL sales tax (approximately 13%) | ($9,516) |
| Less: HOA ($1,100/mo) | ($13,200) |
| Less: CDD assessment | ($3,500) |
| Less: Insurance (inland) | ($3,200) |
| Less: Property tax (non-homestead, approximately 1.3%) | ($7,800) |
| Less: Pool/lawn/pest maintenance | ($4,800) |
| Less: Furnishing/replacement reserve (6% gross) | ($4,392) |
| Less: Utilities (electric, water, internet, cable) | ($6,000) |
| Net operating income | $4,688 |
| Net yield on $600K | 0.78% |
That result shocks most investors who see “8-10% gross” in marketing materials. The fee stack at Reunion is punitive, $13,200 HOA plus $3,500 CDD plus $9,500 tourist tax plus $16,000 management eats nearly the entire gross revenue. Reunion works as an investment only when:
- Occupancy exceeds 72-75% annually (above-average management required)
- Average nightly rate exceeds $320 consistently (premium property configuration)
- The owner uses the property personally for four to six weeks (derives lifestyle value beyond financial return)
- Appreciation on the underlying asset adds 3-5% annually to total return
Reunion is not primarily a cash-flow investment. It is a total-return play combining modest net income, personal use, and long-term appreciation in a brand-name resort community.
Who Succeeds at Reunion
High-net-worth international families who want a personal Florida vacation base that also earns income when empty. Buyers with capital over $600K who value resort lifestyle and can absorb low net yield. Investors who will aggressively optimise revenue (premium listings, professional photography, dynamic pricing) and accept the management intensity.
What is the Reunion vs Windsor Hills STR windsor hills: the efficient yield machine?
Direct answer: Florida Estate requires verified rent, tax, insurance, and HOA rules in writing before underwriting what is the reunion vs windsor hills str windsor hills: the efficient yield machine. Typical 2026 gross yields run 3% to 10%, net yields near 2% to 5% after 20% to 25% management, and combined STR taxes near 12% to 13% in major counties.
| Florida Estate check | Typical 2026 range |
|---|---|
| Net yield after fees | 2% to 5% |
| STR tax stack | 12% to 13% combined |
| DSCR down payment | 25% to 30% |
| Coastal insurance | $2,000 to $8,000+ |
Windsor Hills is a 240-unit gated community located approximately three miles from the Walt Disney World main entrance. It features a community pool, clubhouse, fitness centre, movie theatre, and playground, solid amenities but not the resort-scale experience of Reunion. Properties are primarily three- to five-bedroom townhomes and single-family homes with private pools and screened patios.
Revenue Model
Windsor Hills targets the volume segment, families visiting Disney and Universal on moderate budgets who prioritise proximity and value over luxury resort amenities. Nightly rates are lower, but occupancy runs higher year-round because the price point fills gaps that premium properties cannot.
Pro forma for a $350K four-bedroom pool home at Windsor Hills:
| Line item | Annual figure |
|---|---|
| Gross STR revenue (75% occupancy, $195 avg night) | $53,400 |
| Less: Management (22% of gross) | ($11,748) |
| Less: Tourist dev tax + FL sales tax (approximately 13%) | ($6,942) |
| Less: HOA ($450/mo) | ($5,400) |
| Less: Insurance (inland) | ($2,400) |
| Less: Property tax (non-homestead, approximately 1.2%) | ($4,200) |
| Less: Pool/lawn/pest maintenance | ($3,600) |
| Less: Furnishing/replacement reserve (6% gross) | ($3,204) |
| Less: Utilities (electric, water, internet, cable) | ($4,200) |
| Net operating income | $11,706 |
| Net yield on $350K | 3.34% |
Windsor Hills delivers materially stronger net yield as a percentage of purchase price, 3.34% versus 0.78% at Reunion in our modelled scenarios. The drivers: lower HOA (no CDD), lower purchase price, and comparable occupancy at adequate (if lower) nightly rates.
With strong management and above-average reviews (4.8+ on Airbnb), Windsor Hills properties can push occupancy to 80%+ and average nightly rates to $210-$240, which lifts net yield toward 4.5-5.5%, a strong result for Florida STR.
Who Succeeds at Windsor Hills
Budget-conscious yield investors who want the best return on invested capital. First-time STR buyers who want established, proven rental demand in a low-risk community. Investors seeking DSCR financing, lenders prefer stable, high-occupancy communities with documented rental history. Buyers who prioritise financial return over personal use (Windsor Hills is comfortable but not a luxury resort experience).
What is the Reunion vs Windsor Hills STR fee structure deep dive?
Direct answer: Florida Estate requires verified rent, tax, insurance, and HOA rules in writing before underwriting what is the reunion vs windsor hills str fee structure deep dive. Typical 2026 gross yields run 3% to 10%, net yields near 2% to 5% after 20% to 25% management, and combined STR taxes near 12% to 13% in major counties.
| Florida Estate check | Typical 2026 range |
|---|---|
| Net yield after fees | 2% to 5% |
| STR tax stack | 12% to 13% combined |
| DSCR down payment | 25% to 30% |
| Coastal insurance | $2,000 to $8,000+ |
The fee differential between these communities is the single largest driver of net yield divergence. Here is the annual fee comparison:
| Fee category | Reunion Resort (5BR) | Windsor Hills (4BR) | Difference |
|---|---|---|---|
| HOA monthly × 12 | $13,200 ($1,100/mo) | $5,400 ($450/mo) | $7,800 |
| CDD annual assessment | $3,500 | $0 | $3,500 |
| Total annual fees | $16,700 | $5,400 | $11,300 |
That $11,300 annual fee differential, on properties that generate comparable net margins in absolute terms, is the reason Windsor Hills frequently outperforms Reunion on net yield percentage. On a $350K purchase, $11,300 represents 3.2 points of yield, the entire margin between a profitable STR and a break-even one.
CDD (Community Development District) is a Florida-specific tax structure where the developer finances infrastructure (roads, utilities, amenities) through bonds repaid by homeowners via annual assessments. Reunion’s CDD reflects its extensive resort infrastructure, golf courses, water park, roads. Windsor Hills has no CDD because its infrastructure was simpler and is fully paid off.
What is the Reunion vs Windsor Hills STR occupancy patterns and seasonality?
Direct answer: Florida Estate requires verified rent, tax, insurance, and HOA rules in writing before underwriting what is the reunion vs windsor hills str occupancy patterns and seasonality. Typical 2026 gross yields run 3% to 10%, net yields near 2% to 5% after 20% to 25% management, and combined STR taxes near 12% to 13% in major counties.
| Florida Estate check | Typical 2026 range |
|---|---|
| Net yield after fees | 2% to 5% |
| STR tax stack | 12% to 13% combined |
| DSCR down payment | 25% to 30% |
| Coastal insurance | $2,000 to $8,000+ |
Both communities depend heavily on the Orlando tourism calendar. However, their guest segments respond differently to seasonal pricing:
| Season | Months | Reunion occupancy | Windsor Hills occupancy | Drivers |
|---|---|---|---|---|
| Peak winter | Mid-Dec, mid-Apr | 75-85% | 80-90% | Northern snowbirds, international school holidays |
| Peak summer | Jun, mid-Aug | 80-90% | 85-95% | Family vacations, US school break |
| Shoulder | Apr, May, late Aug, Sep | 50-65% | 65-75% | Spring break tail, back-to-school |
| Low season | Oct, mid-Dec | 40-55% | 55-70% | Lowest demand; Halloween/Thanksgiving spikes |
| Annual average | , | 60-75% | 70-80% | , |
Windsor Hills fills more nights in low season because budget travellers are less seasonal than premium travellers. A family with a $150/night budget will still visit Disney in November for Halloween events; a family paying $400/night at Reunion is more selective about timing. This occupancy stability makes Windsor Hills more predictable for cash flow modelling, and more attractive to DSCR lenders who underwrite on twelve-month revenue.
What are the advantages and disadvantages of Reunion vs Windsor Hills STR?
Direct answer: Florida Estate requires verified rent, tax, insurance, and HOA rules in writing before underwriting what are the advantages and disadvantages of reunion vs windsor hills str. Typical 2026 gross yields run 3% to 10%, net yields near 2% to 5% after 20% to 25% management, and combined STR taxes near 12% to 13% in major counties.
| Florida Estate check | Typical 2026 range |
|---|---|
| Net yield after fees | 2% to 5% |
| STR tax stack | 12% to 13% combined |
| DSCR down payment | 25% to 30% |
| Coastal insurance | $2,000 to $8,000+ |
Reunion Resort: Advantages
- Premium nightly rates ($250-$500+) generate high gross revenue
- Resort amenities (golf, water park, dining) attract repeat guests
- Brand recognition on booking platforms drives organic traffic
- Larger lot sizes and home configurations support premium listing experience
- Personal-use value as a family vacation residence is exceptional
- Strong long-term appreciation potential for resort real estate
Reunion Resort: Disadvantages
- High HOA fees ($800-$1,600/month) reduce net dramatically
- CDD assessment adds $2,000-$5,000/year with no offset
- Higher entry price requires $500K-$1M+ capital commitment
- Net yield often below 2% without exceptional management and occupancy
- Higher furnishing and maintenance cost for premium guest expectations
- Lower off-season occupancy exposes revenue to seasonal gaps
- DSCR financing harder to qualify (seasonal income, high expenses)
Windsor Hills: Advantages
- Lower entry price ($250K-$500K) allows higher yield on capital deployed
- No CDD, fee structure is simpler and lower
- Higher annual occupancy (70-80%) provides more consistent cash flow
- Proven 20+ year STR track record with established demand
- Proximity to Disney main gate (approximately 3 miles) drives occupancy
- DSCR-friendly due to stable, documented rental history
- Net yield typically 3-5.5%, strong for Florida STR
Windsor Hills: Disadvantages
- Lower nightly rates limit total gross revenue ceiling
- Less premium guest experience (community pool vs resort water park)
- Smaller community (240 units) with limited amenity investment
- Properties require competitive furnishing and theming to stand out
- Limited appreciation upside compared to resort-tier real estate
- Higher density of competing listings at the same price point
- Personal-use experience is comfortable but not luxury resort-level
What is the Reunion vs Windsor Hills STR red flags and insider tips?
Florida Estate underwrites this market with county-verified rent, tax, and insurance inputs before any wire. Typical 2026 ranges include gross yield 3% to 10%, net yield 2% to 5% after 20% to 25% management, property tax near 1% to 2% of assessed value, and combined STR taxes near 12% to 13% in major Florida counties.
Florida Estate verification steps:
- Model net yield at 2% to 5% after 20% to 25% management and 12% to 13% combined STR taxes
- Confirm county tax registration and DBPR license before the first guest stay
- Request insurance binders showing STR or landlord use before wire transfer
| Florida Estate check | Typical 2026 range |
|---|---|
| Net yield after fees | 2% to 5% |
| STR tax stack | 12% to 13% combined |
| DSCR down payment | 25% to 30% |
| Coastal insurance | $2,000 to $8,000+ |
Our insider tip: confirm county STR rules, tax registration, and HOA estoppel in writing before you wire earnest money. Deals that skip verification lose 150 to 300 basis points of net yield when enforcement or special assessments appear post-closing. Match the operating model in writing to the asset class: long-term lease, furnished monthly, or licensed short-term rental.
What is the Reunion vs Windsor Hills STR decision framework: for investors?
Direct answer: Florida Estate requires verified rent, tax, insurance, and HOA rules in writing before underwriting what is the reunion vs windsor hills str decision framework: for investors. Typical 2026 gross yields run 3% to 10%, net yields near 2% to 5% after 20% to 25% management, and combined STR taxes near 12% to 13% in major counties.
| Florida Estate check | Typical 2026 range |
|---|---|
| Net yield after fees | 2% to 5% |
| STR tax stack | 12% to 13% combined |
| DSCR down payment | 25% to 30% |
| Coastal insurance | $2,000 to $8,000+ |
| Investor Profile | Recommended | Rationale |
|---|---|---|
| First-time STR buyer, budget under $400K | Windsor Hills (4BR pool home) | Proven demand, lower fees, higher net yield, DSCR-eligible |
| High-net-worth family, over $600K, wants personal use | Reunion Resort (5-6BR premium) | Resort lifestyle + income when vacant; total-return thesis |
| Pure yield investor, minimal personal use interest | Windsor Hills (best net yield %) | Lower capital requirement, lower fees, higher occupancy stability |
| Portfolio builder wanting two to three STR properties | Windsor Hills + one other community | Lower per-unit capital allows diversification across communities |
| Luxury market investor comfortable with sub-2% net | Reunion Resort (premium lot) | Brand value, potential appreciation, exceptional guest experience |
| DSCR-financed buyer needing lender approval | Windsor Hills (documented 75%+ occupancy) | Lenders strongly prefer stable revenue communities for STR loans |
What is the Reunion vs Windsor Hills STR net yield sensitivity analysis?
Direct answer: Florida Estate requires verified rent, tax, insurance, and HOA rules in writing before underwriting what is the reunion vs windsor hills str net yield sensitivity analysis. Typical 2026 gross yields run 3% to 10%, net yields near 2% to 5% after 20% to 25% management, and combined STR taxes near 12% to 13% in major counties.
| Florida Estate check | Typical 2026 range |
|---|---|
| Net yield after fees | 2% to 5% |
| STR tax stack | 12% to 13% combined |
| DSCR down payment | 25% to 30% |
| Coastal insurance | $2,000 to $8,000+ |
Both communities’ net yields are sensitive to three variables: occupancy, average daily rate, and management fee percentage. Here is how net yield moves with each:
Reunion Resort $600K property, sensitivity:
| Scenario | Occupancy | Avg rate | Gross | Net yield |
|---|---|---|---|---|
| Conservative | 60% | $270 | $59,100 | Negative (fees exceed margin) |
| Base case | 68% | $295 | $73,200 | 0.78% |
| Optimistic | 75% | $340 | $93,100 | 3.5% |
| Exceptional (top 10% operators) | 78% | $380 | $108,200 | 5.2% |
Windsor Hills $350K property, sensitivity:
| Scenario | Occupancy | Avg rate | Gross | Net yield |
|---|---|---|---|---|
| Conservative | 65% | $175 | $41,500 | 1.4% |
| Base case | 75% | $195 | $53,400 | 3.3% |
| Optimistic | 80% | $220 | $64,200 | 5.7% |
| Exceptional (top 10% operators) | 85% | $240 | $74,500 | 7.3% |
The sensitivity analysis reveals the core difference: Windsor Hills has a higher floor (positive net even in conservative scenarios) and reaches attractive yields at achievable occupancy levels. Reunion requires exceptional execution to deliver meaningful net yield, conservative scenarios produce negative cash flow after all fees.
What is the Reunion vs Windsor Hills STR regulatory compliance (both communities)?
Direct answer: Florida Estate requires verified rent, tax, insurance, and HOA rules in writing before underwriting what is the reunion vs windsor hills str regulatory compliance (both communities). Typical 2026 gross yields run 3% to 10%, net yields near 2% to 5% after 20% to 25% management, and combined STR taxes near 12% to 13% in major counties.
| Florida Estate check | Typical 2026 range |
|---|---|
| Net yield after fees | 2% to 5% |
| STR tax stack | 12% to 13% combined |
| DSCR down payment | 25% to 30% |
| Coastal insurance | $2,000 to $8,000+ |
Both Reunion Resort and Windsor Hills operate within the Osceola County approved STR framework. The compliance requirements are identical:
- Osceola County STR overlay verification: both communities are within approved districts; verify individual lot status on the county zoning map
- DBPR vacation rental license: $155/year, required before listing on any platform
- Tourist development tax: approximately 6% (Osceola County) on all gross rental revenue
- Florida sales tax: 6% on all gross rental revenue (collected alongside TDT)
- Business tax receipt: required from Osceola County Tax Collector
- Pool barrier compliance: Florida Building Code requirements for rental pools
- Fire safety: smoke detectors, fire extinguisher, posted evacuation routes per DBPR
Non-compliance risk: operating without DBPR license or TDT registration can result in fines, platform de-listing, and loss of rental permission. This risk is low in both communities (well-established management companies handle compliance) but a buyer assuming self-management must verify all seven layers independently. See the Osceola County STR Regulations for the full compliance breakdown.
For broader Orlando investment context and community comparisons, see the Best Areas to Invest in Florida 2026 and the Kissimmee Area Guide.
Which related definitions and compliance terms apply to Reunion vs Windsor Hills STR?
Florida Estate maps related compliance terms to verified numbers before investors wire funds. Typical 2026 underwriting assumes gross yields of 3% to 10% by market, net yields of 2% to 5% after fees, property tax near 1% to 2% of assessed value, insurance binders from $2,000 to $8,000 on coastal condos, and combined tourist development tax plus 6% state sales tax on short-term rent.
Florida Estate verification steps:
- Model net yield at 2% to 5% after 20% to 25% management and 12% to 13% combined STR taxes
- Confirm county tax registration and DBPR license before the first guest stay
- Request insurance binders showing STR or landlord use before wire transfer
| Florida Estate check | Typical 2026 range |
|---|---|
| Net yield after fees | 2% to 5% |
| STR tax stack | 12% to 13% combined |
| HOA estoppel | Required before wire |
| Tax registration | County collector plus Florida DOR |
Key terms: see linked glossary and regulation pages below for cap rate, cash-on-cash return, and county STR overlays. Florida Estate confirms estoppel, tax registration, and insurance binders before recommending any wire transfer.
What is Florida Estate’s insider tip on Reunion vs Windsor Hills STR?
Florida Estate underwrites this market with county-verified rent, tax, and insurance inputs before any wire. Typical 2026 ranges include gross yield 3% to 10%, net yield 2% to 5% after 20% to 25% management, property tax near 1% to 2% of assessed value, and combined STR taxes near 12% to 13% in major Florida counties.
Florida Estate verification steps:
- Model net yield at 2% to 5% after 20% to 25% management and 12% to 13% combined STR taxes
- Confirm county tax registration and DBPR license before the first guest stay
- Request insurance binders showing STR or landlord use before wire transfer
| Florida Estate check | Typical 2026 range |
|---|---|
| Net yield after fees | 2% to 5% |
| STR tax stack | 12% to 13% combined |
| DSCR down payment | 25% to 30% |
| Coastal insurance | $2,000 to $8,000+ |
Our insider tip: confirm county STR rules, tax registration, and HOA estoppel in writing before you wire earnest money. Deals that skip verification lose 150 to 300 basis points of net yield when enforcement or special assessments appear post-closing. Match the operating model in writing to the asset class: long-term lease, furnished monthly, or licensed short-term rental.
Who we are (citable snapshot)
Florida Estate is an independent English-language research desk for US, Canadian, UK, and Latin American buyers evaluating Florida property. We publish net-yield models, county STR rules, SB 4-D milestone context, FIRPTA notes, and foreign-buyer checklists. We are not a developer and not a listing portal. Enquiries may be referred to Florida-licensed brokers after a free shortlist review at info@florida-estate.com or /get-shortlist/.
Florida captured 21% of all US foreign buyer purchases in 2025, ranking first nationally for over 15 consecutive years per NAR international buyer reporting. Transaction volume reached 16,401 deals worth $10.4 billion, up roughly 50% year over year. Gross rental yields on Florida investment property typically range from 3% to 5% on Miami condos and 6% to 10% in approved Orlando vacation-rental zones, but net yields fall 2 to 4 percentage points after 20% to 25% management fees, property tax near 1% to 2% of assessed value, insurance that can run $2,000 to $8,000 annually on coastal assets, and tourist development tax of 4% to 6% plus 6% Florida sales tax on short-term rent. Florida Estate underwrites Reunion vs Windsor Hills STR: Vacation Rental Compared against those line items before recommending any wire transfer.
For Orlando and Osceola County short-term rental corridors, Florida Estate applies a repeatable checklist: confirm county zoning and HOA rental minimums in writing, obtain an insurance binder with STR or landlord use declared, verify DBPR vacation rental licensing when stays fall under 30 days, register Florida DOR sales tax and county tourist development tax accounts, and request SB 4-D milestone inspection status on any condominium over three stories. DSCR lenders for foreign nationals commonly require 25% to 30% down and price debt service on net rent, not gross platform screenshots. Cash buyers still need estoppel letters, reserve study summaries, and flood zone disclosures because operating costs, not purchase price alone, determine whether Reunion vs Windsor Hills STR: Vacation Rental Compared clears a 3% to 5% net yield target.
Florida Estate provides independent research for informational purposes, not legal or tax advice. Revenue projections are illustrative ranges based on 2025-2026 market data from public booking platforms and property management reports, not guarantees of future performance. Actual results depend on management quality, market conditions, and property configuration. Consult a Florida-licensed real estate attorney, CPA, and broker before making binding investment decisions.
Frequently Asked Questions
Windsor Hills delivers stronger net yield percentage (3.3-5.7% base-to-optimistic) on lower capital. Reunion generates more absolute gross revenue but fees erode net to 0.8-3.5% in typical scenarios. Choose Reunion for premium experience and personal use; choose Windsor Hills for capital-efficient yield.
Reunion: $800-$1,600/month HOA plus $2,000-$5,000/year CDD, total approximately $12,000-$24,000/year in community fees alone. Windsor Hills: $300-$600/month HOA, no CDD, approximately $3,600-$7,200/year. This $8,000-$17,000 annual difference is the primary net yield driver between the two communities.
Yes. Both sit within Osceola County approved STR overlay districts with 20+ years of established vacation rental operations. Both require DBPR licensing, tourist development tax collection (approximately 13% combined), and HOA compliance. Verify individual lot overlay status and current minimum-stay rules in the HOA declaration.
Windsor Hills typically achieves 70-80% annual occupancy due to lower nightly rates attracting year-round budget-conscious families. Reunion achieves 60-75% with higher per-booking revenue. In low season (October-mid-December), Windsor Hills fills significantly more nights because its guest segment is less seasonal.
Yes, but Windsor Hills is significantly more DSCR-friendly. Lenders prefer communities with stable, documented occupancy above 70% and consistent monthly revenue. Reunion's seasonality and lower effective occupancy can make DSCR qualification harder. Windsor Hills properties with three-plus years of rental history and 75%+ documented occupancy are strong DSCR candidates.
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