Flag before we discuss: Option A's listing explicitly states "Parties and events are not allowed." With 5+ outside vendors cycling through across the weekend, this retreat could be read as an event under the host's terms even though it doesn't feel like one to us. This is the most-favored option, so this needs a direct answer from the host before we can lock it in.
Category Option A: Windsor at Westside Most Favored Option B: Encore Resort at Reunion Next Favored Option C: Kissimmee (Movie/Game/Pool)
Listing Link View on Airbnb → View on Airbnb → View on Airbnb →
Cost $1,324 / 3 nights (Nov 6-9, w/ tax), confirmed $1,933 / 3 nights (Nov 6-9, w/ tax), confirmed $2,074 / 3 nights (Nov 6-9, w/ tax)
Rooms & Layout 8 BR / 6 BA
2 King (private bath) · 2 Queen (private/near-private bath) · 3 twin-share rooms (some shared bath)
8 BR / 8 BA (near 1:1 ensuite) · sleeps 18
3 King · 3 Queen · 2 themed twin rooms · no bunks
10 BR / 9 BA · sleeps 20+
2 King · 5 Queen · 2 themed twin/double rooms · 1 themed bunk room (sleeps 4)
Fits Our 3-Tier Pricing Yes, cleanest tier fit. King private, Queen private, twin-share rooms all distinct. Yes, King/Queen private straightforward. Twin rooms cover shared tier. Yes, King/Queen private easily. "Shared" tier would mean the themed twin rooms.
Retreat-Relevant Amenities Private pool, lake views, resort clubhouse across street (lazy river, spa, fitness ctr). Confirm outside guests/vendors can access. Private pool, movie theater, on-site spa services, wellness/fitness center, meeting/conference rooms, daily breakfast buffet 7-10AM. Pool, hot tub, home gym w/ yoga mat, home theater, game room, complimentary resort pool access.
Brand / Aesthetic Fit "Minimally themed," best neutral fit for the brand's calm, intentional aesthetic. Only 2 rooms themed (Lego, Mickey), mostly neutral, easy to work around. Frozen, Harry Potter, Minions themed rooms. Fun for family vacation, tonally off for a healing/wellness retreat.
Event Policy "Parties and events are not allowed." Needs direct host clarification before booking. No event restriction stated in listing. Should still confirm directly with host to be safe. Events require approval + guest list (for gate security), capped at 30 people. We're well under cap, most transparent path forward.
Notable Fees / Rules Smoking prohibited · early check-in/late check-out fee-based. 21+ to check in (non-issue) · $500 security hold · smoking prohibited. Heated pool +$50/day · quiet hours 10PM-6AM (fine, fire ceremony ends 8:15) · lost key fob $45.
Pros
  • Lowest cost by a wide margin
  • Best aesthetic fit for the brand
  • Cleanest room-tier breakdown
  • Near Publix for supply runs
  • Meeting room could double as Erica's session space
  • Breakfast included, one less thing to coordinate 2 of 3 mornings
  • On-site spa services available
  • Nearly all rooms private ensuite
  • Most bedrooms/flexibility if group grows
  • Clear, known event-approval process
  • Gym w/ yoga mat on-site
Cons
  • Event policy risk, unresolved
  • Furthest from Disney-adjacent amenities (not necessarily relevant to us)
  • Some bathrooms shared
  • Most expensive for 3 nights
  • $500 hold adds friction
  • 2 themed rooms still a minor aesthetic compromise
  • Highest cost of the three
  • Themed kid rooms clash with retreat tone
  • Vibe leans "big group vacation," not "intimate retreat"
Room Tier Revenue Potential
Based on the finalized pricing: Shared/Twin = base ticket price, Queen Private = +$150, King Private = +$200 (Split Queen/King options also exist at +$50/+$100 per person, not reflected in this illustrative mix). Pricing not yet locked, treat as illustrative until confirmed tonight.
Tier Option A: Windsor Option B: Encore Option C: Kissimmee
King Private slots available 2 3 2
Queen Private slots available 2 3 5
Shared slots available 6 (3 twin-share rooms) 4 (2 twin rooms) 6 (2 themed twin rooms + bunk room)
Illustrative 8-guest mix 2 King + 2 Queen Private + 4 Shared 3 King + 3 Queen Private + 2 Shared 2 King + 4 Queen Private + 2 Shared
Illustrative revenue
(GA base $797, for reference only, actual mix of SZC/Early Bird/GA tickets will vary this)
$7,076 $7,426 $7,376
Capacity flag: Ashley and Charlotte are working staff and likely staying overnight after all. Overnight roster is Cindy, Erica, Ashley, Charlotte, Dani, Elyse, plus Chynna if she attends, 6-7 staff on top of 6-8 guests = 13-15 overnight bodies for Friday and Saturday nights, the binding nights.
Overnight Capacity Check
Category Option A: Windsor Option B: Encore Option C: Kissimmee
Bedrooms 8 8 10
1-person-per-room capacity ~11 (2 King + 3 Queen + 3 twin rooms×2) ~10 (3 King + 3 Queen + 2 twin rooms×2) ~15 (2 King + 5 Queen + 2 twin rooms×2 + bunk room sleeps 4)
Fits 13-15 without doubling up Tight, staff likely need to share beds Tight, staff likely need to share beds Yes, comfortably