When you’re traveling with a big family or a group of friends, you need more than a couple of hotel rooms. You need space, privacy, a real kitchen, and a pool everyone can actually enjoy at the same time. Vacation VI’s St. John portfolio checks all those boxes, with large villas built for multi-generation trips, reunions, retreats, and milestone celebrations.
Below are 10 standout St. John villas with room to spread out, private pools, and the ocean views you came for, all available to book through Vacation VI.
1. The Last Resort – Sleeps Up to 19 With a Bunk/Game Room Kids Love
For groups that want both style and a bit of extra personality, The Last Resort really delivers. This St. John villa offers six bedrooms and 6.5 baths, sleeping up to 19 guests across king suites and a game-room bunk space that can handle up to seven on its own.
Every bedroom has its own private shower and balcony, and the main social spaces open to a large pool deck with ocean views. You’re a short drive from Cruz Bay’s restaurants and the North Shore beaches, so the group can split up easily for different plans without turning logistics into a headache.
2. A La Mer – Beachfront Showpiece on Great Cruz Bay
If you want the “this is insane” reaction the minute everyone walks in, A La Mer is it. This waterfront estate sits directly on its own stretch of Great Cruz Bay and is built for large, multi-generation gatherings. With seven bedroom suites, 8 bathrooms, and over 13,000 square feet of living space, it comfortably hosts up to 16 guests without anyone feeling packed in.
Outside, you get a sprawling pool with a swim-up bar, terraces, private cabana, and a faux-sand beach area for lounging between dips. You’re minutes from Cruz Bay for dinners out, but you could just as easily stay put all week and never feel like you’re missing anything.
3. Tennis Villa + Cottage – Court, Pool, and Space to Spread Out
Tennis Villa + Cottage sits in Great Cruz Bay and is exactly what it sounds like: a 7-bedroom, 7-bath compound with its own tennis court and a large pool-focused courtyard. The main house includes three bedrooms and a gourmet kitchen plus living/dining, while additional bedrooms and a pool house are set around the 43-foot pool and garden courtyard.
For groups that want built-in activity without leaving the property; tennis, swimming, sunning, and quick access to town, it’s a very efficient base.
4. Gardenia Villa – Newly Renovated, Views and Community Amenities
Gardenia is a 4-bedroom, 4.5-bath villa at The Hills St. John, a gated community perched above Cruz Bay. Sleeping up to 8 guests, it’s a strong pick for one or two families traveling together. Floor-to-ceiling windows frame wide views over Cruz Bay and Pillsbury Sound, and the open-plan living area is fitted out with a large sectional and dining space that actually works for game nights and group meals.
The kitchen and baths were recently renovated with new cabinetry, appliances, and quartzite counters. Guests also have access to The Hills’ clubhouse, community pool, fitness center, and fitness center, handy when no one wants to cook but you don’t feel like going all the way into town.
5. Bethel Vista – Flexible 4-Bedroom in The Hills
Also on St. John, Bethel Vista offers 4 bedrooms, 4.5 baths, and space for up to 8 guests in a multi-level layout that balances privacy and togetherness. Like Gardenia, it overlooks Cruz Bay with big-water and island views, and benefits from the same gated setting, community pool, fitness room, and quick drive into town.
This is a good fit for two families traveling together or a group of couples who want large bedrooms, modern finishes, and the option to walk up to the clubhouse for a drink, a workout, or a swim in the shared pool.
6. Papaya Villa – Ideal for One or Two Young Families
Papaya is a 3-bedroom villa at The Hills that sleeps up to 6, but it still belongs in a “spacious for groups” round-up because it’s a clean, functional choice for a smaller family group that doesn’t want to feel crammed into a condo. Bedrooms come with en-suite baths, and the open-plan living/kitchen area opens to a private terrace with big views over St. John and neighboring islands.
You get all the usual Hills perks, gated entry, clubhouse, fitness room, and community pool, plus an easy drive to Cruz Bay and the North Shore beaches. It’s a smart match when you’re bringing kids and maybe a set of grandparents, but don’t need a 7-bedroom estate.
7. Jasmine Villa – Lofted Layout with Room to Breathe
Jasmine Villa is another Hills property that works well for families or groups of friends who value both space and modern finishes. With 4 bedrooms and 4.5 baths, it sleeps up to 8 and gives everyone proper beds and bathrooms, no one gets stuck on a pull-out in the living room.
Large windows and balconies make the most of the hillside location, and the shared infrastructure (pool, gym, clubhouse) helps simplify downtime: older kids can hit the fitness room or pool while adults decompress on the terrace or at the Clubhouse.
8. Sand Dollar Estate – When You Need a Full-On Estate (St. Thomas)
Sand Dollar Estate is on St. Thomas, on the famous Magens Bay, but it absolutely belongs on any list of spacious USVI villas for big groups. This oceanfront compound offers nine bedrooms, 8.5 baths, and a separate 2,300-square-foot guest cottage, accommodating up to 24 guests.
You get extensive indoor–outdoor living space, “private” beach access, and event capacity that works for weddings, milestone birthdays, or full-scale reunions. It’s minutes from Magens Bay Beach and close to Mahogany Run Golf Course and downtown Charlotte Amalie, making it an easy base for guests flying in and out of STT who still want a private villa experience rather than a resort.
9. Tre Vista Estate – Double-Infinity-Pool Drama Near Cruz Bay
Tre Vista Estate is a 5-bedroom, 5.5-bath villa that punches above its weight for big groups thanks to smart design. All five bedrooms are king suites (one with a sofa bed), and all have their own balcony or patio for some breathing room.
Outside, the double infinity-edge pool overlooks Great Cruz Bay, Chocolate Hole, and Hart Bay, with a large dining table, bar seating, and shaded lounge areas that actually fit the whole crew. The kitchen is built for volume, with double dishwashers, double sinks, and premium cookware, so cooking for 10 doesn’t feel like a punishment. And you’re still just a short drive from Cruz Bay for dinners, boat charters, and grocery runs.
Ready to Plan Your Group Trip to St. John?
The right villa makes or breaks a group trip. The homes above give you what crowded resorts can’t: multiple true bedrooms, real communal spaces, private pools and courts, and the flexibility to set your own pace without worrying about closing times or towel cards.
Vacation VI specializes in exactly this kind of travel—pairing groups with the right property, coordinating arrivals from multiple flights, lining up chefs and boat days, and stocking the kitchen before you land.
If you’re planning a family reunion, wedding week, or friends’ getaway in the Virgin Islands, skip the hours of open-tab searching. Explore these villas on VacationVI.com, then connect with the team to talk dates, headcount, and budget. Book your next USVI villa stay through Vacation VI and turn “getting everyone together” into the easiest part of the trip.

3. Tennis Villa + Cottage – Court, Pool, and Space to Spread Out
4. Gardenia Villa – Newly Renovated, Views and Community Amenities
5. Bethel Vista – Flexible 4-Bedroom in The Hills
6. Papaya Villa – Ideal for One or Two Young Families
7. Jasmine Villa – Lofted Layout with Room to Breathe












