If you’re coming all the way to St. John, you shouldn’t be sharing a pool or fighting for a lounge chair. The properties below all deliver what most travelers are really looking for: a private pool, real ocean views, and enough outdoor space that “going back to the villa” feels like the best part of the day.
Every villa here is available through Vacation VI, with on-island support, vetted homes, and a team that actually knows these properties, not just a booking calendar.
1. Marea – Secluded Ditleff Point Estate with Dramatic Pool
Tucked behind the gates of Ditleff Point, Marea is a serious showpiece villa, wrapped in water views on a private peninsula. The outdoor living is anchored by a large ocean-facing pool, surrounded by expansive stone terraces, shaded lounging areas, and lush landscaping with a waterfall feature that adds to the resort feel.
Multiple bedroom suites open straight to the pool deck or view terraces, so you wake up to the Caribbean every morning. This is a strong choice for groups who want ultra-privacy, high-end finishes, and very little reason to leave the house.
2. The Last Resort – Peninsula Pool Deck with 270° Water Views
Perched in Chocolate Hole, The Last Resort sits with water on three sides and a massive infinity-edge pool that seems to spill straight into the bay. Many stays here revolve around that pool deck: loungers, shaded seating, and wide open views that capture both sunrise and sunset depending on the season.
With multiple king suites and generous indoor common areas, it works well for extended families or groups of friends who want a private-compound feel just a short drive from Cruz Bay dining and charter docks.
3. Villa Carlota – North Shore Views from the Infinity Pool
Villa Carlota overlooks St. John’s legendary North Shore from Upper Peter Bay, with an infinity-edge pool that takes in the curve of shoreline and the British Virgin Islands in the distance. The pool terrace is wrapped with stonework, loungers, and covered outdoor living spaces, so you can be outside all day without baking in the sun.
Inside, classic Caribbean architecture (arched stone, mahogany, high ceilings) meets modern comfort. If you want that “postcard St. John” view from your pool, this is exactly that.
4. Isla Vista – 35-Foot Pool Above Cruz Bay
Isla Vista sits on a private estate road above Cruz Bay, behind a security gate, with a 35-foot swimming pool at the center of the property and commanding views across the water toward St. Thomas and the out-islands.
The main living areas and gourmet kitchen open out toward the pool and ocean, with outdoor dining and grilling that make it easy to keep everyone on-site in the evenings. With its mix of king suites, ocean views, and proximity to Cruz Bay, Isla Vista is ideal if you want privacy at the villa but quick access to restaurants, ferries, and day trips.
5. Mare Blu – 48-Foot Infinity Pool Over Rendezvous Bay
If your non-negotiable is a serious pool, Mare Blu over Rendezvous Bay is hard to beat. The outdoor living area flows from covered veranda to sun deck to a 48-foot infinity-edge pool.
Six en-suite bedrooms are spread across multiple pavilions, all tied together by the pool, gardens, and huge outdoor kitchen/dining area. This layout works extremely well for multi-family trips: everyone gets privacy, but the pool and terrace pull the group together.
6. A La Mer – Beachfront Estate with a Resort-Style Pool & Swim-Up Bar
On the shoreline of Great Cruz Bay, A La Mer feels more like a boutique resort than a private home. The aquamarine pool is enormous, bordered by a strip of white sand, loungers, and a fire pit, and features a true swim-up bar with underwater stools at the pool cabana.
You’re right on the water with a private sandy beachfront area and views of yachts anchored in the bay, plus easy access into Cruz Bay. For groups that want “all-day-by-the-pool” with every box ticked (bar, cabana, shaded seating, sunset fire pit), this is exactly that experience.
7. Tennis Villa & Cottage – 43-Foot Lap Pool in Great Cruz Bay
Tennis Villa & Cottage is built around a 43-foot lap pool that runs the length of the terrace, giving you plenty of room for lap swimming as well as lounging with a view of Great Cruz Bay and the surrounding hillside.
Multiple bedroom configurations between the main villa and cottage make this a flexible choice for families or mixed groups. The pool terrace has sun and shade, outdoor dining, and sightlines that let you keep an eye on kids in the water while you relax with a drink.
8. Paraiso Azul – Sunrise Pool Deck over Klein & Rendezvous Bays
At Paraiso Azul (Caribe Villa) on Boatman Point, the pool sits on a 25’ x 85’ deck overlooking the ocean, Klein Bay, and Rendezvous Bay. The 12’ x 22’ pool is framed by teak furniture and two covered areas for shade, with the deck specifically called out as a spot for watching the sunrise while you enjoy the trade winds.
If you’re an early riser or planning a trip where quiet mornings at the villa matter as much as afternoons on the beach, this sunrise-facing pool deck is a real asset.
9. Tre Vista Estate – Double Infinity-Edge Pool and Serious Entertaining Space
Tre Vista Estate in Great Cruz Bay is all about outdoor living. The villa features a double infinity-edge pool with sweeping views over Great Cruz Bay, Chocolate Hole, and Hart Bay, plus a large patio with a 10-seat dining table, bar seating, sectional sofa, and upgraded lounge furniture.
Add in a fully equipped chef’s kitchen, Sonos sound throughout the great room and pool deck, and a rare grassy lawn, and you have a property that’s built for big groups who actually plan to use the house—dinners in, pool days, and sunset cocktails without ever leaving the estate.
10. Casa Del Sol – Classic Caribbean Villa with Pool and Hot Tub Views
Casa Del Sol overlooks Rendezvous Bay from a hillside position and pairs a private pool with a hot tub, both facing a sweeping view of Rendezvous Bay, Ditliff Point, and Fish Bay.
The classic open Caribbean design—local blue stone, vaulted ceilings, and wide decks—keeps everything airy, with each bedroom featuring its own deck seating so everyone gets their own private slice of the view. It’s a strong option if you want a traditional-feeling St. John villa with modern comforts and a very photogenic pool-and-view combo.
Ready to Dive In?
All of these villas combine what most travelers are really searching for on St. John: a private pool, real ocean views, and layouts that work for groups who want to spend time together without sacrificing comfort.
Vacation VI curates this portfolio and backs every stay with concierge support, from helping you choose the right villa and lining up private chefs and charter boats, to coordinating jeeps and airport transfers.
If you’re ready to turn this short list into your actual vacation, head to VacationVI.com, pull up these properties, and check your dates. Or reach out to the Vacation VI team with your group size and travel window, and let them match you with the best fit.
Book your next stay in the Virgin Islands through Vacation VI and make that private-pool, ocean-view villa your reality, not just a daydream on your screen.
