Holiday rentals with a pool in Road Town

Periwinkle Cottage in Coral Bay w/Pool, and Views🏝

Periwinkle Cottage of Coral Bay is a perfect rendition of a traditional West Indian cottage with modern amenities. 🌴 Ceiling fans, large screened in porch and open air porch areas. Located at the end of a private road, Periwinkle has a Million Dollar view of Coral Bay! Located only minutes from grocery stores, shopping & dining in Coral Bay. This cottage offers privacy & sits on over a half acre lot! You are right near the Virgin Islands National Park and some of the best beaches in the world

Sweet Spice: A Nifty Little Cottage. With A Pool!

This very small 1 BR cottage lives BIG with a screened porch, SOLAR POWER, valley views, ac, dishwasher, outdoor fitness, and plunge pool. With a clean modern vibe, Sweet Spice is more laidback getaway than luxury villa. It’s an ideal HQ for 2 active STJ adventurers - but with a few extra amenities! Located off the beaten path on the quiet side of STJ, it feels secluded but is only a 5 minute drive to the shops of Coral Bay. Note: road is rough and requires a 4WD and there are LOTS of stairs.

Peaceful 1 bed/Lush gardens/Plunge pools

Experience ocean views, AC-cooled comfort, solar power and a spacious deck in this new solar-powered cottage. Part of a unique collection, it shares an infinity waterfall plunge pool with "Caribbean" cottage (two more cottages coming in 2026). Enjoy constant breezes, afternoon shade, and magical moonrises from the “Ocean” cottage. Guests have 24/7 on-site concierge service and assistance, with full vacation planning by a Superhost experienced in welcoming first-timers to St. John.

Rockroom One Bedroom Condo at The Hills Saint John

"The Rockroom" is a one bedroom apartment located within The Hills Saint John. This large space with amazing views of Cruz Bay and St Thomas features a large bedroom with King bed, two full baths, a large living area and a full kitchen. There is also a large private patio with a gas grill and patio furniture. Guests staying at Rockroom will also have access to The Clubhouse Bar (open seasonally and located on the property) as well as a 24 hour fitness center and community pool.

Lloyd Hill Villas Holiday Suite

Welcome to your new sanctuary! This fully furnished two-bedroom, two-bath suite is located at the Lloyd Hill Villas and offers the ideal blend of sea breeze and sun, and quiet comfortable living. With the added luxury of a swimming pool and a view of nearby Guana Island a lifetime trip awaits you. Step into a space designed for relaxation and functionality. The suite is enhanced with Internet, Satellite Dish, and TV. Washing facilities available. Book your stay today!

Into the Mystic Lower Suite with POOL and VIEWS!

Into the Mystic Lower Suite is a beautifully finished suite located in peaceful Coral Bay, St. John. Offering every amenity you need for a perfect vacation - Salt water pool, high speed Wi-Fi, DISH TV, electric grill, solar with back up batteries & more. Our lower-level suite is your own private escape after a day exploring St. John's beaches and hiking trails. We offer a beautiful indoor living space & a peaceful balcony which showcases our view of Coral Bay & beyond.

Paradisea 2 Bedroom w/ Pool & Backup Solar Power

2 cozy bedrooms, fully equipped kitchen, large decks, pool, solar and backup battery power. Everything you need for a day at the beach: chairs, umbrella, coolers, toys, towels all provided. Close to Coral Bay restaurants and shops. North Shore beaches and hiking trails are only a short drive away. Quiet setting in the hills above Coral Bay. Close to it all with a far away feel. good for couples, solo adventurers, and families with children over the age of 8.

Sol~Azul Cozy Studio Cottage w/ Pool & Ocean View

Fully equipped, spacious studio with full kitchen. Beautiful view of the sea and St Thomas in a peaceful neighborhood near Cruz Bay. Easy to navigate roadways with flat driveway and plenty of parking. Enjoy a nice evening on the pool deck to watch the sunset. Conveniently located 10 min from beaches and shopping. Beach Chairs & Towels provided. Laundry on-site. Shared Grill and Pool area w/ the Main Villa on property. Perfect for a couples getaway.

Esperance~Pool~New~National Park

Spacious 2BR, 2BA luxury apartment in Fish Bay Skytop with full kitchen and washer/dryer. Both bedrooms feature Loom & Leaf memory foam mattresses. King bedroom with en-suite bath, second bedroom with queen bed and bathroom across the hallway. Smart TV with Netflix and streaming apps (no cable). 10 min drive to Cruz Bay dining, shopping, groceries, 25 min to North Shore beaches. 4 ft shared pool and BBQ with two other apartments.

Winter’s Nook - Caribbean Escape

Welcome to Winter’s Nook—a cozy studio in a secure Road Town enclave, perfect for solo travelers or couples. Steps from the financial district and walking distance to shops, banks, and restaurants. Enjoy a shared pool, coin laundry, and designated parking. With security cameras on-site and a peaceful vibe, it’s your ideal Caribbean base for work or play. Comfort, convenience and charm all in one.

Villa Matija

Villa Matija is nestled comfortably into the hillside overlooking Brewers Bay on Tortola in the British Virgin Islands. Allow yourself a little luxury and be eco-friendly at the same time! Villa Matija (pronounced ma-TEE-ya) sits above Brewers Bay with an outstanding view of Jost Van Dyke and several other smaller cays & islands. On a clear day you can see Puerto Rico (about 70 miles away)!

Kerensa Villa

Stylish, secluded villa with pool and stunning views. Kerensa is close to gorgeous beaches and has panoramic views of the North coast and surrounding islands. You’ll love it because of the beautiful natural setting, the seclusion, the high end equipment and the quirky antiques and decor. It is ideal for romantic couples but can sleep up to 4 with a pull-out sofa-bed if required.