Great — here are top picks for multi‑generational family stays in Singapore, grouped by type of trip and with the family features that make each hotel a good choice. I’ve included a reliable source for each pick so you can check room types, family packages and facilities.

Best for resort-style, private space on Sentosa (great if you want villas, pools and room to spread out)

• Capella Singapore — luxury villas and multi‑bedroom residences (1–3+ bedrooms, private plunge pools, full kitchens and large living/dining areas). Excellent if you want grandparents, parents and kids under one roof. (capellahotels.com)

• Resorts World Sentosa — Festive Hotel & Hard Rock Hotel — on‑site access to Universal Studios, S.E.A. Aquarium, Adventure Cove; family rooms with loft/extra beds and a dedicated kids’ programme / kids club inside the resort complex. Ideal when your priority is easy access to attractions for kids and teens. (rwsentosa.com)

Best for city-base with big sights nearby (Marina Bay / Downtown)

• Marina Bay Sands — purpose‑built family suites (Sands Family Suite / Paiza Family Suite), easy access to Gardens by the Bay, ArtScience Museum and large shopping/dining options; big suites & kid amenities make it easy for mixed‑age groups. (marinabaysands.com)

• The Ritz‑Carlton, Millenia Singapore — family/“Ritz Kids” programmes, large suites and butler service; good central location for Marina Bay attractions and comfortable for older adults (spacious rooms, concierge services). (ritzcarlton.com)

• Pan Pacific / PARKROYAL COLLECTION Marina Bay — family/interconnecting rooms, dedicated family packages (Urban Jungle family suite, interconnecting room options) and convenient access to shopping/transport — nice middle ground for families wanting space plus central access. (panpacific.com)

Best if you prefer apartment‑style living (best for longer stays, cooks, multi‑bedroom privacy)

• Ascott Orchard (Ascott serviced residences) — 1–3 bedroom serviced apartments with full kitchens, washers/dryers and larger living areas — excellent for families who want to cook, spread out or host a helper/nanny. (silverdoor.com)

• Fraser Suites Singapore — two‑ and three‑bedroom serviced apartments, full kitchens and separate living/dining areas — good for privacy between generations and easy daytime logistics. (frasershospitality.com)

Other strong options (luxury / butler / flexible room layouts)

• Shangri‑La Singapore (Orchard) — dedicated Family Suites & Deluxe Family Rooms, “buds by Shangri‑La” indoor playground and Family Concierge / Family Pantry — an Orchard location that’s great for families with small kids and for guests who want both gardens/pool and city shopping nearby. (shangri-la.com)

• St. Regis Singapore — large suites and signature butler service plus family‑friendly welcome amenities — good if you want high‑service, spacious suites and concierge help coordinating multi‑gen needs. (marriott.com)

Quick selection guide — which to pick

• Want private villas/pools and low‑key island time: choose Capella (Sentosa). (capellahotels.com)
• Bringing young kids who want theme parks and aquariums nearby: stay at a Resorts World Sentosa hotel (Festive / Hard Rock). (rwsentosa.com)
• Want iconic city views + big family suites and attractions on the doorstep: Marina Bay Sands or Ritz‑Carlton. (marinabaysands.com)
• Prefer full kitchen, multiple bedrooms and more independence (especially for longer stays or if you’ll prepare meals): Ascott or Fraser Suites. (silverdoor.com)

Practical tips for multi‑generational bookings

• Book interconnecting rooms or 2–3 bedroom suites/residences well in advance (they’re limited). Many hotels list interconnecting options or family suites on their site — request them when reserving. (panpacific.com)
• Ask about rollaway beds, crib policy and whether breakfast covers children (some hotels include kids’ breakfast). Policies vary by hotel and offer. (shangri-la.com)
• If you travel with elderly relatives, request lower‑floor or lift‑adjacent rooms and check accessibility features (ramps, grab rails, accessible bathrooms). Resorts often list accessible facilities online. (rwsentosa.com)
• Consider a serviced residence if you want a kitchenette, laundry and separate living space to make multi‑day stays simpler. (silverdoor.com)

If you want, I can:

• Narrow these to a shortlist within a specific neighbourhood (Sentosa / Marina Bay / Orchard), or
• Pull current rates and interconnecting‑room availability for specific travel dates (I’ll look up live availability and deals).

(If you want live rates/availability, tell me your travel dates and I’ll look them up.)