Distinctive luxury properties for the ultimate trip
Distinctive luxury properties for the ultimate trip
Start-to-finish trip planning
Concierge teams coordinate your arrival, departure, and everything in between.
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Every Luxury Retreats home is personally verified to be in pristine condition.
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29 luxury villas and vacation rentals in Saint John
1 – 16 of 29 Rentals
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Planning a St John vacation? We’re here to help!
When Christopher Columbus stumbled across a group of islands dotting the eastern Caribbean Sea in 1493, he thought them so dazzling that he named them ‘Las Virgenes’, after the 11,000 virgin handmaidens of the legendary St Ursula. The name stuck, and today we know the collection of islands as the US and British Virgin Islands. St John, the smallest of the three US Virgin Islands, remains as close as you could hope to the untouched beauty of the past. Some 60% of the island is designated as the Virgin Islands National Park, and this protection extends to encompass much of the surrounding waters, coral reef, and shoreline. St John has a low-key, laid-back vibe: there are no cruise-ship docks and there is is no airport – you arrive by ferry from neighboring St Thomas. Hiking and snorkeling are the main activities here, though you could of course just keep it super-chilled, kicking back on some of the most gorgeous beaches you’re ever likely to set foot on.
Sand and surf
So, about those beaches. The shore to landmass ratio of this small island means you’ll never have to travel too far to find the perfect stretch of sand, but some of St John’s beaches deserve special mention. The most popular is wide, palm-tree-lined Trunk Bay. The water here is usually calm so it is a great choice if you’re traveling with kids, and the gentle surf and reefs make it a good spot for beginning snorkelers too – a snorkel trail stretching 200 yards is marked by underwater signs to guide you on your below-the-surface discoveries. Top all this off with excellent facilities – a snack bar, bathrooms, a changing room, showers, a picnic area, a gift shop and lockers – and most consider it well worth paying the small entry fee that this beach, unlike others on the island, charges.
Those of you chasing the wave might want to head to Cinnamon Bay, a little further east, where you can swim, snorkel, surf, windsurf, sail, kayak, and paddleboard – your Luxury Retreats concierge can organize gear rentals if you don’t have your own equipment, as well as lessons to help beginners on their way.
To get away from the crowds, head to Salt Pond Beach. The long drive from Cruz Bay and the 15-minute walk down from where you need to park mean that this sheltered bay with crystal-clear water has an off-the-beaten-track appeal. Bring a picnic and sit on the tables in the shade, or grab one of the barbecue pits for a surfside sizzle.
Take a hike
The Virgin Islands National Park is crisscrossed with no fewer than 22 hiking trails, and one of the best is Reef Bay Trail. You can go it alone (with the help of a park service map), but on a guided tour led by a park service ranger, you’ll learn about St John’s tropical forests as they identify the trees, plants and animals – deer, bats, land crabs, termites – along the way. A slight detour takes you to the ancient petroglyph site, where mysterious carvings surround a freshwater pool at the base of a waterfall – archaeologists believe them to be sacred symbols carved by Taino Indians over 1,000 years ago. The trail ends as it passes the remains of an old sugar plantation and you wind up on lovely Reef Bay beach. Don’t forget to pack some sturdy shoes – you may be in the tropics but this 2.5-mile trail is not the place for flip-flops.
If you’re keen to find out more about the history of St John, the place to do it is at the Annaberg Plantation, the most intact sugar plantation ruins in the Virgin Islands and also run by the Virgin Islands National Park Service. This Danish Colonial plantation was built in 1721 to produce sugar, rum, and molasses. Today, it's a museum where you can learn about plantation life and sugar production in the 18th and 19th centuries, with a tour of the old slave quarters, the rum still, and the windmill, following a signposted walking trail.
Luxury Retreats, an expert in St John villa rentals
If you’re looking for a base from where you can explore St John’s natural beauty, we have options including terracotta-tiled villas and striking modern architecture, with room to take the whole family or just that one special person.
Stay close to Cruz Bay
Nicknamed ‘Love City,’ St John’s main town of Cruz Bay has a carefree Caribbean vibe. Streets are lined with shops, restaurants, and bars, and happy hour is a much-loved institution with locals and vacationers alike. Spend afternoons strolling the colorful lanes and soaking up the town’s laid-back charm before settling down to a slap-up dinner – you’ll find many good options to choose from. If you want to stay close to the action (such as it is, on this most chilled-out of islands), then one of our Cruz Bay rentals could be just what you’re looking for – we have rental properties sleeping 6 to 12, with turquoise pools and sun-soaked verandahs. Our Chocolate Hole vacation rentals , a 10-minute drive from town, are another good choice, blessed with sweeping views and plenty of alfresco lounging options – so when you’ve had a busy day hitting the shops or working on your tan, head home for a sundowner on your terrace in the cool ocean breeze.
Chill out in Coral Bay
Sleepy Coral Bay lies tucked away on at the unspoiled southeastern side of the island, and our Coral Bay villas are ideal for a secluded getaway. Choose a villa perched high above the tranquil bay and surrounded with lush tropical grounds full of fruit trees, or perhaps a vacation home right on the beach, so that you can tumble out of bed and almost straight onto the sand.