St. John Villas

If you can’t stay with us, consider these friends on St. John

We have been visiting or living on St John for over thirty years and, have to say, we are still as much in love with it today as we were the day we first stepped foot on our island.  Yes, many things have changed since that first visit, but many of the things that brought us to St John have not changed: the shear beauty of the island, the beaches, the vistas, and the warmth of the people of St John. And, thanks to the Virgin Islands National Park which covers over 2/3’s St John much of our land will be forever green.

Today there are lots (and lots) of choices of wonderful places to stay on St John. Large. Small. Fancy. Basic.Faces east to get a sunrise. Faces west to capture the sunset. High up on a hill. Walking distance to the beach.

We will be the first to admit we are pretty partial (OK, very) to Great Expectations, given that it has been our ‘baby’ since we designed, built, and now manage it. We also understand that it might not be the best villa for every group, and just as frequently Great Expectations is often already reserved for the dates that some people want to come to St John. With the goal of making sure that people find the villa that is right for them and, quite frankly, hoping that those folks might choose our villa for their next trip to St John when we are available, we are happy to help make the match for this trip. With over 500 villas to choose from the decision can be overwhelming.  We work with a few St John property owners and property managers who we know well and know that they care for their properties as we do Great Expectations and, consequently, we have confidence that your expectations will be met and exceeded. Please let us know if you might be interested in any of these options and we will be happy to make the connection for you.

Calypso del Sol

Just down the hill from Great Expectations and capable of sleeping 6 additional people

Small Neighboring Villa

Calypso del Sol is just down the hill from Great Expectations and can accommodate up to 6 guests. We often recommend when we have very large groups that need additional bedrooms. 

Located on Chocolate Hole Bay about 5 minutes from the picturesque town of Cruz Bay, a stay at this new, 3 bedroom, 3 bath, fully air-conditioned villa will be a vacation to remember!

Calypso del Sol has glorious water views from the pool deck and from both large, covered porches, with inviting views of Chocolate Hole and Pillsbury Sound.  Enjoy gazing at the stars while soaking in the hot tub.

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Villa St. John

Our other preferred next door neighbor that sleeps up to 12 guests

One of the very few beachfront vacation rental villas on St. John!

Stunning, warm and welcoming, Villa St. John is available as a six-bedroom villa or, in the low season, can be reserved as two separate villas. The master villa is comprised of four bedroom suites and the guest villa of two bedroom suites. Both the master and guest villas have their own living and dining room areas and newly renovated kitchens with rich mahogany cabinetry and graphite counter tops. One of Villa St. John’s unique features is that all of the six bedrooms are 650 square foot master suites (one of the largest on the island), each with their own balconies, offering panoramic views of Chocolate Hole Bay, the Caribbean and a picturesque inlet that accommodates spectacular yachts, a pristine beach and the rhythmic sound of lapping waves of crystal clear water from the Caribbean.

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Other St John Villa Rental Options

is a spacious 6 bedroom home consisting of 4 bedroom main house with 2 bedroom cottage, just a few steps from the main house, dual security systems, pool, hot tub, a/c in bedrooms, and views galore. Ristaba is in Chocolate Hole North, commanding views of 4 bays: from Hart Bay to the south, Chocolate Hole and Great Cruz Bay to the west all the way to Cruz Bay to the north. On most days you can clearly see St. Croix and the islands of Puerto Rico as well as many numerous cays in between. Ristaba has one of the largest pools on St. John (28x13x12) with plenty of floats and toys. There is a large shaded area as well as full sun decks, with a wet bar, blender, frig and glassware.
Securely snuggled into the verdant green hillside of Bordeaux Mountain, Estate Chateau Margot is situated on Bordeaux's eastern slope, approximately 1,000 feet above sea level. Overlooking the quiet community of Coral Bay, the impressive 4 1/2 acre estate affords majestic views of St. John's East End as well as the British Virgin Islands of Tortola, Virgin Gorda, Norman and several smaller cays along the Sir Francis Drake Channel. This property is only 1½ miles from the turn off Centerline Road that leads straight down to the amazing Maho and Francis Beaches and only 3 miles from the center of Coral Bay. To reach the estate, travel 5 miles from downtown Cruz Bay, halfway through the Virgin Islands National Park, on cool tree-canopied Centerline Road. Only 3/10 of a mile after passing the historic Reef Bay Trail entrance, the road to the estate forks off just to the right of the famous Château Bordeaux restaurant complex. From there, a 1/2 mile paved drive curves around and down to the grand white gates of Chateau Margot.
overlooks Pillsbury Sound and Great Cruz Bay, Oceana is an elegant villa with lots of gathering spaces for your family gathering. This new St John villa has wonderful island stone and vaulted ceilings throughout the property. Fully air-conditioned, Oceana is a villa designed for both large family gatherings and groups of couples vacationing together. There is lots of gathering spaces - both inside and outside - as well as large, private bedrooms. Enjoy the hot tub or lounge in the infinity edged swimming pool. Four Master bedroom suites, each with an ocean view, make this villa a wonderful option for couples vacationing together. One bedroom is fully handicap accessable. Two additional bedrooms make this villa a great villa.
is a first-class luxury villa which overlooks Chocolate Hole harbor to the east and Great Cruz Bay harbor to the west. Total privacy is assured with this 2 acre compound. Its five bedrooms are also configured to assure privacy. This is an ideal villa for a number of couples vacationing together or for an extended family gathering. Its large pool is the central feature of the wrap-around deck area which includes a hot tub and lots of outdoor lounge furniture and dining options.
This beautiful villa boasts over 2,000 square feet of outdoor living space and nearly 5,000 square feet under roof with 5 bedrooms 5 ½ baths. The master suite and three guest suites are in the main house making this an ideal home for families with small children. The Francis Bay Suite with queen bed, sits on the main level, just off the kitchen area. An interior staircase just before, takes you upstairs, where the Master, Maho and Cinnamon Bay guest suites are situated. Both guest suites contain queen beds. The fifth bedroom, below the pool, has a king bed and full kitchen. Located in Rendezvous/Ditliff, gorgeous views of the ocean, Hart Bay, Monte Bay, Klein Bay, Fish Bay, Reef Bay and the island of St. Croix are enjoyed throughout the residence as well as all day sun. The spacious pool deck with comfortable Brown Jordan chaise lounges and snack tables. The chaise lounges recline all the way back for a welcoming afternoon nap. An outdoor case houses toys and floats for lounging in the pool. Outdoor table and chairs by Maya with seating for eight, including two swivel and six stationary chairs. A bistro table with swivel chairs and three high back bar chairs gives ample seating for ten. In addition there is a loveseat glider, recliner with ottoman and end table located on the upper open deck. Visit Villa Tesori >
Located on the southwest end of Hart Bay, this beachfront villa is a perfect villa for newlyweds, families and small groups. Convenient to the main town of Cruz Bay, shopping, dining and the famous North Shore beaches of the National Parks, this 4 bedroom 3 1/2 bath villa located on Hart Bay beach offers a combination of sophistication and romantic tropical charm.The massive 45 X 14 pool, 52" deep with bench seating throughout and 3500 square feet in decking. The beautiful gourmet kitchen features Corian countertops, mahogany cabinets, and ocean-view cooking. Included are refrigerator, gas top range and oven, dishwasher, microwave, and additional gourmet amenities. Ideal for the gourmet chef. The formal mahogany dining table with seating for eight and a large mahogany buffet complete this pleasurable dining experience. The Main Great Room features a comfortable Seagrass loveseat with two large chairs and glass top coffee table. Two plantation style sitting chairs with mahogany accents table to give you plenty of seating for watching tv or the fabulous ocean views of the south to St. Croix and east to Ram's head and the vast Caribbean Sea. The upper and lower outside decks feature glass top dining tables with seating for six. As an added safety feature, a gate as been added at the top of the stairs.
was designed and built with quality lifestyle and love of beauty in mind. Perched high on a mountain ridge on its own private expanse of land surrounded by National Park, this luxurious home offers dramatic and spectacular "down-island" views of the Drake Channel, the British Virgin Islands, St. John's East End, Coral Bay and the National Park mountainsides. Located in the center of our small island means Cruz Bay (15 min), Coral Bay (10 min.), and North Shore Beaches (5 min.) are only brief drives away. Lounge on the large bricked deck, swim in the pool (32'X12') 3 ft shallow 5 ft deep end, or relax in the hot tub, in total privacy. The view will take your breath away!! For toddler safety, a nylon mesh barrier may be installed around the pool, by advance request. Mystic Ridge is 4200 square feet of luxurious living. The villa includes 4 bedroom 4 1/2 baths, an expansive great room (26'X42'), ideal for entertaining, dining and casual living. The split level great room includes a fully equipped gourmet kitchen with countertop seating, a formal dining area and a large living space with a complete entertainment center including RCA 23"TV, Expanded Cable, Sony DVD/VCR Player. Kenwood 5 Disc CD Player with Accurian Receive..
overlooking Chocolate Hole Bay on the beautiful island of St. John, U.S. Virgin islands, Villa IntimaSea is the ultimate in intimate island vacation spots. At Villa IntimaSea you are invited to sit back, kick your feet up and relax where the sky meets the Caribbean Sea while you sit on luxurious Brown Jordan furniture on huge covered decks. The 180 degree panoramic views include sunrise, four Caribbean Bays, and sunset over St. Thomas.