Anyone evaluating a Bears Den Reunion Resort investment will hit the same question within five minutes of research: is the premium justified?
Homes start at $1.2 million. HOA dues run $1,000 per month. Club membership costs $15,000 upfront. But Bears Den properties also command $400 to $1,100+ per night and gross $85,000 to $200,000+ annually. At FunStay, we manage properties across Reunion Resort and have watched Bears Den consistently outperform every other neighborhood on a per-night basis.
High revenue, though, does not automatically mean high returns. This guide breaks down the actual costs, the Bears Den Reunion Resort Airbnb income data from our managed portfolio, and the ROI math so you can decide whether the premium is justified for your investment goals.
What Is Bears Den at Reunion Resort?
Bears Den is a 73-homesite luxury enclave within Reunion Resort, the 2,300-acre master-planned community in Kissimmee, Florida. Developed by Encore Capital Management (CEO Arthur Falcone), Citicommunities, and Americrest Custom Homes, it holds a distinction no other neighborhood in Central Florida can claim: it’s the first residential community worldwide to carry the Jack Nicklaus brand.
When Nicklaus broke ground on Bears Den in December 2016, the concept was straightforward: build the best homes in an already premium resort, position them on the 17th and 18th holes of the Nicklaus Tradition Course, and wrap the whole community in a second layer of gating and its own private clubhouse.
The homes themselves are serious. Nine standard floor plans range from 3,883 square feet (the Arlington II, 4 bedrooms) to 5,628 square feet (the Pine Valley, 8 bedrooms). Custom builds go even larger, with some exceeding 14,500 square feet. All homes include private pools, Sub-Zero/Wolf kitchens, home theaters, and game rooms, and they’re sold fully furnished.
Bears Den operates as a resort within a resort: double-gated with 24-hour security, its own Jack Nicklaus Grand Clubhouse (full-service restaurant, fitness center, pro shop), and Golden Bear Park with a playground, dog park, and practice putting green. Residents also have access to Reunion Resort’s broader amenities, which include three championship golf courses (Nicklaus, Palmer, Watson), a 5-acre water park with a 1,000-foot lazy river, 10 community pools, 7 restaurants, a full-service spa, and tennis and pickleball courts.
Phase 1 vs. Phase 2: A critical distinction for investors. Bears Den’s original 52 homesites (Phase 1) permit short-term rentals. Phase 2 lots are deed-restricted as residential only, meaning no Airbnb, no VRBO, no short-term rental income of any kind. This is the first such restriction in Reunion Resort’s history. If you’re buying Bears Den as an STR investment, confirm the lot is in Phase 1 before writing an offer.
What Bears Den Actually Costs to Own
This is where Bears Den separates from every other Reunion neighborhood. The cost structure has four layers, and the total carrying cost is significantly higher than what you’d pay anywhere else in the resort.
Layer 1: Purchase price
Active listings as of September 2026 range from $1,245,000 to $7,994,900. Recent closed sales tell a clearer story:
| Address | Sale Price | Date |
|---|---|---|
| 510 Muirfield Loop | $6,000,000 | Feb 2025 |
| 350 Muirfield Loop | $5,200,000 | 2025 |
| 460 Muirfield Loop | $2,000,000 | Feb 2026 |
| 624 Muirfield Loop | $1,925,000 | Dec 2025 |
| 374 Muirfield Loop | $1,300,000 | Mar 2024 |
Average price per square foot is approximately $451. List-to-sell ratio sits at 96%, and the average home sells in 53 days. Bears Den also charges a 1.5% royalty fee at closing, unique to this community, attributed to the Nicklaus branding license. On a $2.5 million purchase, that’s an additional $37,500.
Layer 2: HOA dues
Bears Den’s HOA runs $1,000 per month ($12,000 per year), making it the highest single-family HOA in Reunion Resort. For context, here’s how it compares:
| Neighborhood | Monthly HOA | Annual |
|---|---|---|
| Heritage Crossing | $395 | $4,740 |
| Homestead / Patriots Landing | $496-$550 | $5,952-$6,600 |
| Carriage Pointe / Centre Court Ridge | $550-$650 | $6,600-$7,800 |
| Eagles Trace | $678 | $8,136 |
| Bears Den | $1,000 | $12,000 |
That’s 2.5x Heritage Crossing’s fee. The Bears Den HOA covers 24-hour guard-gated security, cable TV, internet, trash, grounds maintenance, pest control, common area taxes, and pool access.
Layer 3: Club membership
This is the layer that catches new buyers off guard. Club membership is not included with your home purchase, but without it, your rental guests can’t access the resort’s marquee amenities: the water park, the pools, the golf courses, the restaurants, and the spa. That makes club membership effectively mandatory for any STR investor.
| Fee | Amount |
|---|---|
| Initiation (one-time) | $15,000 + tax |
| Gold Membership (monthly) | $500/month ($6,000/year) |
| Platinum Membership (monthly) | $925/month ($11,100/year) |
The 60-day window: New buyers have exactly 60 days after closing to accept or decline club membership. If you miss this window, the membership is forfeited permanently. You cannot join later. For an STR investment, this is non-negotiable: close on Monday, submit your membership application on Tuesday.
Layer 4: Taxes, insurance, and CDD assessments
- Property taxes: Approximately 13-15 mills ($13-$15 per $1,000 of assessed value). No homestead exemption for STR properties.
- CDD assessments: Bears Den falls in Reunion West CDD. Estimated $1,500-$4,000+ per year depending on lot size.
- STR income taxes: 6% Florida sales tax + 1.5% discretionary surtax + 6% Osceola County tourist development tax = 13.5% total on gross rental revenue.
- Insurance: STR policies in Florida run $6,000-$10,000+ per year for homes in this price range.
Revenue: What Bears Den Properties Actually Earn
We manage Bears Den properties across multiple bedroom configurations. The revenue numbers consistently exceed broader market averages.
Revenue by bedroom count
| Bedrooms | Avg Nightly Rate | Peak Season Rate | Est. Annual Revenue |
|---|---|---|---|
| 5-Bedroom Villa | $400-$550 | $650-$850 | $85,000-$110,000 |
| 6-Bedroom Villa | $500-$700 | $800-$1,100 | $100,000-$140,000 |
| 7-Bedroom Estate | $650-$900 | $1,000-$1,400 | $130,000-$175,000 |
| 8-Bedroom Estate | $750-$1,100 | $1,200-$1,600 | $150,000-$200,000+ |
To put those numbers in context: the median annual STR revenue in Kissimmee (34747 ZIP code) is $45,155, with an average ADR of $237 and occupancy hovering around 52%. Bears Den properties are grossing 2x to 4x the area median, with occupancy at Reunion running 75-80% compared to approximately 52% in the 34747 ZIP code.
What drives the premium? Three factors compound:
- Home size and configuration. An 8-bedroom estate sleeping 18 guests replaces three hotel rooms at $300+ per night each. At $1,100/night for the house, guests save money while getting a private pool, game room, and full kitchen.
- The Nicklaus brand and exclusive amenities. Golf groups booking 3-4 night stays at $3,000-$8,000 per booking are drawn specifically by the Nicklaus association and the Grand Clubhouse. This guest segment fills shoulder-season gaps that other communities can’t reach.
- Reunion Resort’s amenity stack. Three championship golf courses (the only place in the world with Nicklaus, Palmer, and Watson courses in one resort), the water park, 10 pools, and 7 restaurants give every listing a value proposition that standalone homes in Kissimmee can’t match.
Guest demographics
Bears Den properties attract four distinct guest segments, each with different booking patterns and revenue profiles:
| Segment | Stay Length | Lead Time | Peak Season |
|---|---|---|---|
| Multi-generational families | 5-7 nights | 60-90 days | Spring break, summer, holidays |
| Golf groups | 3-4 nights | 30-45 days | Fall, spring |
| Celebration/event groups | 3-5 nights | 45-60 days | Year-round |
| Snowbirds/extended stay | 14-28 nights | 60-120 days | January through March |
The golf segment is particularly valuable for Bears Den specifically. These groups of 8-16 golfers book midweek stays during September and October (the lowest-demand period for family-oriented properties), paying $3,000-$8,000 per booking. That seasonal gap-filling is one reason Bears Den properties maintain higher occupancy than communities that rely solely on the family travel market.
The ROI Math: Does the Premium Pay for Itself?
Here’s a worked example using a 7-bedroom estate purchased at $2.5 million, which sits in the middle of recent closed sales for this floor plan.
Estimates based on FunStay managed portfolio data. Year 1 costs are higher: add $15,000 club initiation + $37,500 royalty fee (1.5% of $2.5M). Mortgage payments not included in NOI calculation.
A cap rate under 2% tells you this is not a cash-flow investment. If you’re buying Bears Den with a mortgage, the property will likely be cash-flow negative in years 1-3. Monthly mortgage payments on a $1.875 million loan (25% down) at 7% run approximately $12,475 per month, or $149,700 per year, which alone exceeds projected gross revenue at the low end.
Who should buy Bears Den? Investors in one of two positions:
- All-cash buyers who view STR income as a return on an asset they’d own anyway, treating the $21,000-$45,000 net income as a bonus that offsets carrying costs while the property appreciates.
- High-equity buyers with 50%+ down payments who can tolerate thin margins in exchange for a luxury asset in a supply-constrained community (only 52 STR-eligible homes exist, and that number will never increase).
The appreciation argument is worth examining. Bears Den’s average price per square foot is roughly $451, compared to $200-$300 in mid-tier Reunion neighborhoods. The Nicklaus branding, the finite supply, and the quality of construction create a floor under resale values that standard-construction resort homes don’t have. The 96% list-to-sell ratio and 53-day average time on market suggest strong demand even at premium pricing.
For context on the real cost to run a short-term rental in Orlando, our full breakdown of operating expenses covers properties across all price points, from $300K condos to $2M+ estates. The cost stack is similar in structure but the percentages shift as you move into luxury properties where fixed costs (HOA, club dues) represent a larger share of gross revenue.
Bears Den vs. Other Reunion Neighborhoods
Bears Den isn’t the only investment option in Reunion Resort. Reunion’s 11 neighborhoods offer different risk and return profiles depending on your investment goals.
| Neighborhood | Entry Price | Monthly HOA | Est. Revenue | Investment Profile |
|---|---|---|---|---|
| Heritage Crossing 3-4 BR condos/townhomes | $300K-$500K | $395 | $28K-$55K | Cash-flow entry point. Lowest barrier, steady returns. |
| Homestead / Patriots Landing 4-5 BR single-family | $450K-$700K | $496-$550 | $50K-$85K | Balanced. Moderate cost, solid family rental demand. |
| Eagles Trace 5-7 BR single-family | $600K-$1.2M | $678 | $70K-$120K | Mid-tier luxury. Better per-night rates, larger homes. |
| Bears Den 4-8 BR custom estates | $1.2M-$8M+ | $1,000 | $85K-$200K+ | Luxury appreciation play. Premium brand, finite supply. |
The takeaway: if your primary goal is cash-on-cash return, Heritage Crossing or Homestead will outperform Bears Den on a percentage basis. A $400K townhome generating $45K on $4,740 in HOA produces a very different cap rate than a $2.5M estate generating $150K on $12,000 in HOA plus $6,000 in club dues. For investors building their first Orlando STR portfolio, those lower-entry neighborhoods offer a more forgiving cost structure.
But if your goal is owning a luxury asset that generates significant gross income, appreciates in a supply-constrained market, and carries a globally recognized brand, Bears Den is the only option in Reunion that checks all three boxes. Investors still evaluating the broader corridor can compare options in our Kissimmee resort communities guide.
How FunStay Florida Helps Bears Den Owners Protect Their Investment
A property with $12,000 in annual HOA, $6,000 in club dues, and $32,000+ in taxes does not leave room for management mistakes. At FunStay, we manage Bears Den estates with the same attention we give every property in our portfolio, but the stakes are higher here. Every vacant night costs $400-$1,100 in lost revenue. A single bad guest review on an 8-bedroom estate can suppress bookings for weeks.
Our approach is built around filling all four guest segments year-round: multi-generational families in summer and holidays, golf groups in shoulder season, celebration bookings throughout the year, and snowbirds in January through March. We handle dynamic pricing across all platforms, coordinate with the Grand Clubhouse for guest access, and manage the property to the standard that luxury guests expect and that protects your Airbnb ranking.
If you are evaluating a Bears Den purchase or already own and want to compare your current returns, we will run a free revenue projection based on your specific property.
100+properties
78%avg occupancy
4.9guest rating
2,600+5-star reviews
Risk Factors Every Investor Should Know
Bears Den carries risks proportional to its premium positioning.
HOA fee escalation
Bears Den’s HOA has risen from approximately $607 per month when the community opened to $1,000 per month in 2026, a 65% increase in roughly seven years. There’s no cap on future increases, and as the community ages and infrastructure needs grow, this trend is likely to continue. Budget for 5-8% annual HOA increases in your long-term projections.
Supply growth in the broader market
Kissimmee’s active STR listings grew 53.7% year-over-year through mid-2026. While Bears Den itself has a fixed supply (52 STR-eligible homes), the broader market dilution puts downward pressure on ADR and occupancy for all properties in the region. The question is whether Bears Den’s luxury positioning insulates it from commodity-market trends.
The financed buyer’s math
At 7% interest with 25% down, monthly mortgage payments on a $2.5M purchase run approximately $12,475. Add $10,000+ in monthly operating costs, and you need roughly $22,500 per month in gross revenue just to break even, or about $270,000 per year. That’s above the top end of even 8-bedroom projections. If you’re financing with less than 50% down, the cash flow math is difficult at current rates.
Florida insurance market
Florida’s property insurance market remains volatile. STR policies in this price range currently run $6,000-$10,000+ per year, but rates have spiked 30-50% in some areas following recent hurricane seasons. A single major storm could push premiums significantly higher.
Developer-to-owner HOA transition
When the developer still controls the HOA (common in newer communities), they often subsidize fees to keep them attractive for sales. When control transfers to homeowners, fees can jump 30-40% as the actual maintenance costs surface. Confirm where Bears Den sits in this transition before purchasing. Our vacation rental due diligence checklist covers how to verify HOA governance status, CDD obligations, and other items that should be resolved before closing.
Downside scenario: what happens at 50% occupancy?
If occupancy drops from 75% to 50% (which some Kissimmee communities experienced during the post-COVID supply surge), a 7-bedroom Bears Den estate might gross $87,000-$117,000 instead of $130,000-$175,000. Against $108,000-$130,000 in operating costs, that puts you at breakeven or slightly negative on NOI, before any mortgage payment. Bears Den’s cost structure leaves little room for revenue underperformance.
Seasonal Calendar and Pricing Strategy
Understanding Bears Den’s seasonal revenue patterns is essential for projecting annual income. The demand curve follows Orlando’s tourism calendar, but Bears Den’s guest mix shifts the peaks compared to standard vacation rental communities.
| Season | Months | Strategy |
|---|---|---|
| Peak | March through April | Premium pricing. Spring break drives back-to-back family bookings. 5-7 night minimums. |
| High | June through August | Highest volume. Multi-generational families filling 6-8 BR estates. Extended stay discounts for 7+ nights. |
| High | November through December | Holiday premium pricing. Thanksgiving and Christmas/New Year’s command the highest nightly rates of the year. |
| Shoulder | January through February | Snowbird season. 14-28 night extended stays at lower ADR but near-full occupancy. |
| Shoulder | September through October | Golf groups fill Bears Den specifically. 3-4 night midweek stays at $3,000-$8,000 per booking. |
| Lowest | Early September | Aggressive pricing, relaxed minimum nights. Average Bears Den gross in September drops to roughly $3,074. |
The key insight for Bears Den owners: golf groups and event bookings make September and October significantly less painful than they are for family-only communities. A 4-bedroom townhome in Heritage Crossing might sit empty most of October, while an 8-bedroom Bears Den estate can fill midweek with golfers drawn by the Nicklaus courses.
Location: How Close Is Bears Den to Everything?
Reunion Resort sits in Kissimmee along the I-4 corridor, positioned between Disney’s southern gates and the growing development along US-192. Bears Den’s location within the resort puts it closer to Disney’s Animal Kingdom than almost any other gated STR community.
| Destination | Distance | Drive Time |
|---|---|---|
| Disney’s Animal Kingdom | ~6 mi | 10-14 min |
| Disney’s Hollywood Studios | ~8 mi | 12-16 min |
| EPCOT | ~10 mi | 14-18 min |
| Magic Kingdom | ~12 mi | 15-20 min |
| SeaWorld Orlando | ~15-17 mi | 18-22 min |
| Universal Studios / Islands of Adventure | ~18-20 mi | 20-25 min |
| Epic Universe | ~20-22 mi | 25-35 min |
| Orlando International Airport (MCO) | ~27-30 mi | 25-35 min |
Frequently Asked Questions
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