Guesthouse holiday rentals in St. John

Oceanfront Clifftop Escape Guest Suite

Maridadi Clifftop is perched atop Boatman Point, offering sweeping, south-facing views, and is located just under a 10-minute drive (2 miles) from Cruz Bay. The clifftop boasts a stunning outdoor terrace perched just above the crashing waves, surrounded by lush tropical vegetation. Inside, a modern, air-conditioned unit features a king-size bed, smart TV, ceiling fan, his and hers nightstands, a walk-in closet, a full bathroom, and a living area, creating the perfect romantic Caribbean escape.

Faith

Forget your worries in this spacious and serene space. Enjoy outdoor kitchen and dining area in Faith Cottage. Relax in the shared space that makes up Grateful Grotto Gardens. Our one bedroom/ one bathroom cottage is all you need after a day at the beach. Centrally located off of Centerline Road, Minutes from Cruz Bay and less than 20 minutes from Coral Bay. You can feel at peace in the safe and homely residential setting and enjoy a comfortable and restful nights sleep in Grateful Grotto.

Private Cottage with Ocean Views

You'll have a great time at this comfortable place to stay. Enjoy the trade wind breeze and the sunrise over Fish Bay from the covered porch of your own private cottage. Ayiti cottage is an east-facing cottage located in a quiet Fish Bay neighborhood, an easy 2.9 miles from Cruz Bay and 20 minutes away from the stunning north shore beaches. Ayiti cottage is perfect for any couple that needs a quiet and private escape to enjoy the beautiful island of St. John! We are a non-smoking property.

A House of Open Arms Villa with Pool and AC

House of Open Arms Villa with dazzling pool has 180 degrees of views and white water crashing waves below. Perfect for 2 people. Spoon into a nest of intimacy. Immerse yourself in island breezes. Take in the views of the rising sun and moon as they glisten across the crystalline waters of Hurricane Hole. Settle into the rhythm of Island life with solar energy and purified rainwater, resourceful recommendations, advice and insider tips. Welcome to simple elegance.

Ocean Blue Cottage

Ocean Blue Cottage located in Upper Carolina, 400' above sea level, overlooking Coral Bay harbor, Bordeaux Mt, Carolina valley and a peek of the Caribbean Sea. 23 steps down from the road, it has a bedroom 9'x12', dining/kitchen area 6'x10', bathroom 3'x10', private outdoor shower 4'x5', deck 8'x4' with grill, furniture, umbrella. Pricing is $150 night. There’s also an $90 cleaning fee per reservation. 5 min drive to restaurants, 10 min to beaches.

Island Shackteau

This unique place has a style all its own. Resting in south side of Coral Bay just a short two minute walk from the Johnson Bay Estate private beach. This is a glamping eco style guest house. Hot water shower and toilet are outside. There is a small kitchen with an outdoor grill. This is perfect for a single traveler or couple. The space is small but cozy with AC, Starlink, and the soothing sounds of Caribbean ocean waves and peeper frogs at night.

Blue Aweigh

Our hilltop, chocolate hole location provides fantastic ocean views and the southern exposure catches the cooling trade-winds. This one-bedroom private casita has outdoor balconies that lend itself to tranquil ocean views and amazing sunrises. We are close to town and within walking distance to Hart Bay and Chocolate Hole beach, (rocky beaches great for exploring).

The Guest House of Villa Solare

Upon entering the Villa property, you experience the natural Caribbean artistry of stone & shell archways, brick courtyard and tropical gardens. This accommodation includes access to the upper level of the Guest Cottage with a queen suite (en-suite bath) and attached, separate room with kitchenette, sleeper sofa and second full bath.

Cactus Flower Cottage

Beautiful Cactus Flower Cottage overlooking Fish Bay and the Caribbean. Hike directly out of Fish Bay to the most well known National Park Reef Bay Trail, L'Esperance Trail, Fish Bay Gut, etc! Hikers delight. Close to Cruz Bay. Beautiful, peaceful and friendly area of St John. Quick drive to Cruz Bay and the North Shore Beaches.