We have been on-island for 30 years, and can give that personal, detailed information about each villa, call us and chat about your vacation! For nearly three decades, we offer you a delightful variety of St John USVI vacation Villas, Private homes, Cottages and Condos on the most popular island in the US Virgin Islands, with vacation rentals suitable for every size, budget and occasion.
You will find our St. John villa rentals are some of the most beautiful and varied in the USVI. Browse our villas to find the your perfect St John Vacation Rental, or call us and we'll make recommendations to help you decide which one is best for your next memorable St. John vacation! From your initial call or e-mail, host Cindy Ward will help you choose the St. John villa best suited to your needs.
You will find our St. John villa rentals are some of the most beautiful and varied in the USVI. Browse our villas to find the your perfect St John Vacation Rental, or call us and we'll make recommendations to help you decide which one is best for your next memorable St. John vacation! From your initial call or e-mail, host Cindy Ward will help you choose the St. John villa best suited to your needs.
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About Us
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Carefree Getaways has been in business for 20 years, and Cindy Ward, your host, is also a licensed real estate agent. Not only are we a villa management company, but we are here to personally assist all our guests in making their vacation totally carefree! We will help you reserve the villa that fits all of your needs.
Our Villas
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Villa Allesandra has a level floor plan with 2 air-conditioned King Master bedrooms in the main house and a separate air-conditioned Garden cottage with 2 additional bedrooms. Ground level Queen bedroom and a second level small 4th Queen bedroom. 5 flat screen TV's. 20' x 16' pool, lower level has a 20' x 20' covered play area with ping-pong table, games and sky bar.
2 Bedrooms
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A two-bedroom air-conditioned villa in upscale Chocolate Hole North, just five minutes from Cruz Bay, with panoramic views from Hart Bay to Chocolate Hole and the open Caribbean Sea to French Cap with beautiful sunsets and the twinkling lights of St. Thomas at night. This villa features a 75' covered veranda, hot tub and a 40' pool.
3 Bedrooms
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Villa Bijou is a great house for relaxation, great views and comfort with easy access to town, dining and the north shore beaches and is well appointed with your every need in mind. Private 2 bedroom villa with additional sleeping loft, pool, spa, huge views of Coral Bay. Get close to St. John's abundant natural beauty with this secluded and affordable island home.
5+ Bedrooms
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Great Expectations is the perfect villa for families or large groups. This villa features 8 A/C bedrooms, 8 baths, 3 pool, 2 hot tubs, tennis and basketball court and gym. There are 5 bedrooms in the main complex and 3 in the guest house. This villa is centrally located between two bays, Rendezvous and Chocolate Hole, and is a 9 minute drive from Cruz Bay.
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