St. John USVI Vacation Villa Rentals and Property Management

trunk bay on st john usvi

Carefree Getaways is located right here on Sunny St. John!

We provide that extra personalized care to our guests.

Our agents 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!

Jump to a St. John Villa:

Last Minute Vacation Specials
bongo bongo villa pool

Bongo Bongo

Last Minute Special! March 24 - April 9 Low Season rates! As low as $485.71 per night / $3400 per week.
st john villa rental

Inn Paradise

Ready for the Beach? 10% Discount! Dates open March 22 - 30 & April 8 - 15. As low as $360 per night! 7 night minimum.

Leeward St. John

Leeward St John Available March 18 - 25!
st john vacation villa dining with a view

Morgan Point

From the Carefree Getaways staff; We wish to thank everyone for their well wishes and support. We did lose Morgan Point and Paradise Revisited but the owners are rebuilding! We are taking reservations for our other villas! St John is recovering from Hurricanes Irma & Maria quickly. St John Island update Feb. 2, 2018; At this time no phones - but internet and email work fine and expect those to be up shortly. St John is recovery quickly with 170+ wire crews quickly replacing the downed poles. Our villas have power have welcomed some guests for the past Holidays. Roads are clear, trees, palm trees and foliage have sprouted and bloomed, beaches have been cleared of debris and the water is crystal clear - although Maho Bay took a beating. Restaurants, shops, grocery stores, gas stations are already opened or are opening. St John is looking real inviting. We welcome your emails with any questions. Weather is great! Hope to see you!

St. John Villa Guest Services by Carefree

From your initial call or e-mail, host Cindy Ward will help you choose the St. John villa best suited to your needs.
To make your Caribbean vacation at our St. John villa rentals as Carefree as possible, we provide the following services:

  • Reserve a RENTAL CAR for you, right here on St. John
  • Reserve PRIVATE TAXI SERVICE to take you from the St. Thomas airport to the Ferry Dock in Red Hook.
  • Cindy or one of our friendly staff will GREET YOU AT THE ST. JOHN FERRY DOCK, take you to your rental car agency and lead you to your St. John villa.
  • WE ARE ON CALL DURING BUSINESS HOURS FOR ADVICE on where to dine, swim, snorkel, hike, rent kayaks, powerboats, windsurfers, etc.
  • GROCERY / PROVISIONING DELIVERY: We recommend St. John Provisions

Carefree Getaways on St. John welcomes you to our lovely island of St. John in the United States Virgin Islands. Enjoy the Caribbean Tropics from a US Territory. St. John villa rentals are some of the most beautiful and varied in the Caribbean. Our St. John villas are located on an island which is two thirds National Park and therefore pristine and uncrowded. All of our St. John villa rentals have sparkling sea views, most have A/C in the bedrooms, a pool and/or spa.

Carefree Getaways St. John Villa Rentals
All of our St. John villa rentals are privately owned and fully equipped for your vacation relaxation and pleasure. Each St. John villa provides linens, paper products, cookware, microwave and the usual kitchen appliances; ceiling fans, telephones with answering machines, irons and ironing boards, gas or charcoal grills, coolers, beach towels and chairs, cable TV, VCR or DVDs and CD stereo systems. With few exceptions, each St. John villa rental offers washer/dryers and dishwashers, as well. **Please note: Any gatherings larger than the number of guests confirmed and paying for their stay at our villas are subject to Carefree Getaways and the home owner's approval. Additional fees will apply if the gathering is approved. Please inquire for further details.

Real estate info from our associate, AMERICAN PARADISE REAL ESTATE