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.

Sunrise Cottage - Secluded, Romantic, Private

Sunrise cottage is located on the cool & breezy north side of St. Thomas. A relaxing 1 bedroom cottage with a full kitchen & living area. You can soak up the sun on the sundeck or hang out in your private soaking pool, while appreciating the breath taking view during the day & the abundance of stars at night. When venturing out you are 20 mins to Magen’s Bay Beach, 15 mins to Town, 30 mins to Red Hook. Note: The hosts live on property with 2 dogs and this cottage is adult only 18 or older.

Darling Palms: Solar Tree House Studio

Solar powered, battery back up! Our spacious studio apartment is nestled among a paradise of palm trees, with a ‘tree house' atmosphere. Just a short stroll away, discover the allure of a nearby beach and resort, offering two restaurants, a market, and a pool bar for ultimate relaxation. Embrace the outdoor ambiance on our patio, complete with comfortable seating and a grill, perfect for alfresco dining. Please note that the studio shares a wall with another rental unit. Parking available!

SEASIDE 2 BEDROOM VILLA- Cena's Beach Rental

This Newly renovated 2 bedroom Villa at Cena's Beach Rental, sits right at the shores edge with beautiful seaside views and access to crystal blue waters just a few steps from the back door. You are certain to sleep well to the soothing sounds of the calming waves and the cool summer breeze. The sunset view is the perfect backdrop for a romantic evening sitting out on the back patio. This gem will certainly help you understand why the BVI is nicknamed Natures Little Secret.

St. John Oceanview Stone Villa, 4BR w/King Suite

Enjoy stunning ocean views of nearby islands from this beautiful stone villa, situated on a steep hillside near the main road. The top floor unit offers a peaceful retreat just 8 minutes from Cruz Bay, with easy access to beaches, restaurants, and grocery stores perfect for families or small groups. • Master suite w/Kg bed & Patio • 2 Bedrooms w/Queen beds • 1 Bedroom w/2 Full beds • 2 Bathrooms • Living area • Kitchen with workstation • Dining area • A/C • Smart TVs • Wifi

OMAJELAN CASTLE (A)

Welcome to the Omajelan Castle. Set amongst the lush mountain canopy of Santa Maria, on the North Western side of St. Thomas, with a view that is befitting of a king and queen. About 5 minutes from the beach and 15 minutes from downtown, Charlotte Amalie, The Omarjelan Castle's regal architecture is further enhanced by a breathtaking yet tranquil view of the Atlantic ocean. These small yet comfortable efficiencies afford you a unique experience you'll not soon forget

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.

Long Bay Surf Shack

"Location, location, location!" This rustic yet charming guest studio is nestled on a hillside above one of the most sought-after and beautiful resorts in the Virgin Islands. Just a two-minute walk to Long Bay Beach and Resort, which offers an amazing spa, beach bar and restaurant. This guest studio is perfect for a couple or a family of three. Hosts have lived in the BVI for 30 years and love to share local insights.

La Brisa: Peaceful Oceanview Retreat

Escape to La Brisa, a serene oceanview retreat perched 1,100 feet above sea level on Skyline Drive. This luxurious one-bedroom suite offers breathtaking Caribbean views, modern coastal decor, and thoughtful amenities for a tranquil island getaway. Perfectly located near Magens Bay and vibrant Red Hook, La Brisa is ideal for relaxation, exploration, or a romantic escape. Your paradise awaits!