Large group vacation rentals in British Virgin Islands

Explore 131 large group vacation rentals, homes, and villas in British Virgin Islands for your next getaway or business trip. With space for everyone, enjoy the comfort and privacy of a home designed for gathering, alongside premium amenities such as Air Condition Homes, Homes with Free Parking and Best Affordable Homes. Throughout your stay, spend time together, share meals, and relax in spacious living areas that make group travel feel cohesive. With options starting as low as $160 per night and homes offering up to bedrooms and bathrooms, it's easy to book a stay that fits your group. And with 24/7 local support and high-speed Wi-Fi, everyone stays connected and protected. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, making each trip more rewarding than the last. Book your next group getaway with Homes & Villas by Marriott.

131 Great for Groups in British Virgin Islands

Beneath the Mango Tree | Pool & Ocean Views

Cruz Bay, St. John, VI
3 Bedrooms 6 Guests
Sep 30 - Oct 4
$712 night

Beneath the Mango Tree Villa is an immaculate island retreat showcasing beautiful stonework and classic Caribbean indoor-outdoor living. Enjoy a spacious covered veranda, sunny pool deck, and sweeping views of Great Cruz Bay and St. Thomas—the perfect setting for breathtaking sunsets and tropical breezes. Due to the layout and for safety considerations, the villa welcomes guests aged 16 and older. The villa is also equipped with a battery backup power system that will seamlessly activate during power outages so guests can continue to enjoy a comfortable stay. For extended battery life during outages, we do suggest limiting AC use when possible. 🌴 Beautiful mahogany French doors connect the stunning veranda to the open-concept, fully air-conditioned great room. Inside, you’ll find a well-appointed kitchen with counter seating, a charming dining area, and a comfortable living room—perfect for relaxing or entertaining indoors. The primary bedroom, located on the main level, is elegantly appointed and features a unique island stone outdoor garden shower, soaring cypress ceilings, custom mahogany wardrobes, and French doors that open to the veranda with beautiful ocean views. Just steps from the pool deck, the lower level offers two identical, thoughtfully designed bedrooms with private entrances, en-suite bathrooms, and air conditioning. Large sliding doors frame lovely ocean views and lead to a covered deck—an inviting spot to enjoy your morning coffee or a quiet afternoon with a good book. 🌴 Property Manager will arrange for a personal greeter to meet you at the villa for check-in, provide a brief tour of the property, answer any questions about the home, and share helpful insights about the island. Check-in arrangements are tailored to your party size, arrival time, and familiarity with the area to ensure a smooth arrival. Property Manager highly recommends renting a 4-wheel drive vehicle to comfortably navigate the terrain on St. John. We are happy to provide a list of trusted local rental companies, and we also have a few villa vehicles available for guests when available. Current villa vehicle options may include: • New Custom Toyota Land Cruiser – Full-Time Four-Wheel Drive – 5 Passenger • Lexus GX – Full-Time Four-Wheel Drive – 6 Passenger • Jeep Wrangler Islander (4-door) – Four-Wheel Drive – 5 Passenger • Toyota Highlander – AWD – 6 Passenger • Chevy Trax – AWD – 4 Passenger Please inquire with the Property Manager Team to check availability and explore the best option for your stay. 🚙🌴 If you prefer not to drive, we are also happy to arrange taxi service during your stay. All Guests will receive a contract for signature for terms and conditions. Once your flight is booked, we ask that you please provide your flight information so we can help plan a smooth arrival and transfer from the airport on St Thomas. We can assist with arranging private transportation from the airport to the villa, private taxi service, boat charters, private chefs, and spa services. Guests can expect a few emails to help with your vacation planning. We look forward to welcoming you to St. John!

Arc Du Soleil- Ultimate Island Living, Refreshing Salt Water Pool, Stunning Views!

Cruz Bay, St. John, VI
3 Bedrooms 6 Guests
Sep 1 - 5
$951 night

ARC DU SOLEIL was designed for Guests to experience outdoor living on St. John and perfectly emulates the Caribbean lifestyle. The beauty of the island’s natural surroundings are the most prominent feature and enduring allure. An experience which can only be found in the tropics; one that brings the outdoors in, and entices you to become more in tune with nature. This is an experience that is unique to the islands. We cordially invite you to come, relax, and enjoy the Arc. True Caribbean open air living featuring magnificent native stone arches, framing the picture perfect view of the Caribbean sea for dramatic sunsets and star gazing. Polished concrete floors, a large and modern gourmet kitchen, master bath offers his and her vanities, and a soaking tub for unwinding after a fun filled day. Master bedroom with new Tempur-Pedic king bed, en-suite bath with soaking tub, and on open hanging area for clothes in the bathroom. There are two guest bedrooms with en-suite baths. One on the main floor with Tempur-Pedic king bed and one on the lower level with 2 twin beds that can be made into a King bed. Property Manager will arrange for a Greeter to meet you at the villa for check-in, provide a tour, address any questions about the property, and offer insights about the island. Check in arrangements will be tailored to your party size, arrival time, and familiarity with the area. Property Manager highly recommends renting a 4-wheel drive vehicle for navigating St. John’s terrain. We can provide a list of trusted local rental companies and have a few villa vehicles available.. Please inquire with the Property Manager Team about options! Guests will receive a contract for signature in order to finalize your booking. Once your flight is booked, please provide your flight information to help us plan your arrival. We can assist with arranging private transportation from the airport to the villa, private taxi service, boat charters, private chefs, and spa services. Guests can expect a few emails to help with your vacation planning. We look forward to welcoming you to St. John!

Mystic Ridge

Cruz Bay, St. John, VI
4 Bedrooms 8 Guests
Sep 1 - 6
$747 night

Mystic Ridge is a magical Villa with outstanding views of Coral Bay and beyond to the British Virgin Islands. The Villa is surrounded by lush greenery. With 4 bedrooms. 4.5 baths and a large living room/kitchen area, this home is perfect for family gatherings. The pool area and outdoor dining table expand your living space options to include being immersed in the tropical Caribbean paradise of this magical location. Mystic Ridge 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 the 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. Enter into the mystic, to the spectacular Mystic Ridge Villa. From the driveway down stone steps you enter through two stately wrought iron gates. Surrounded by the lush tropical forest this private setting is one with nature. The entry courtyard area includes a large round table with barrel bench seating for four and a white wood bench with bright blue pillows. This shaded area is the perfect spot for a game of cards, dominos or whatever suits your need. The remodeled gourmet kitchen, with bar seating for four, includes all stainless steel appliances and a side by side refrigerator/freezer with filtered water and ice dispensers. An antique dining table with rattan chairs with padded cushions comfortably seats eight. The comfortable sitting area has two large white cushioned chairs with small table and lamp, the perfect location to converse with the chef on duty or relax before or after dinner. 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 and formal dining area. The large living space includes a complete entertainment center including 60″ TV,with streaming services, DVD player, Tuner/Amplifier with Ipod/Mp3 hookup. Indoor and Outdoor speakers, and wireless DLS complete this electronics package. Nestled high in the trees, bordered by the National Park, this peaceful setting puts you at one with nature. Enjoy spectacular views of Coral Bay, the British Virgin Islands and the unspoiled East End of St. John from the pool or Jacuzzi. The view will take your breath 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. For toddler safety, a nylon mesh barrier may be installed around the pool by advance request. Our newest amenity is a fire pit situated on the edge of the deck. The natural stone wall is the perfect back drop with floor cushions and bar stools that give plenty of seating for all to enjoy this cozy space. Allow St. John to seduce you with her natural beauty and Mystic Ridge to enrapture you with class and elegance. ● 4 bedrooms, 4.5 baths ● Dream & Serenity Master Suites with king beds ● Bliss Suite with queen bed ● Heaven Suite with two twins or a king ● Swimming Pool 32X12- 3-5ft deep ● Split system A/C units in all four bedrooms ● Luxury Linens ● Hair Dryers in each Bathroom ● Toddler Pool Safety Net ● Pack and Play Crib ● Fully equipped kitchen ● Triple water filtration ● Weber Gas Barbecue Grill ● Laundry room with Washer/dryer ● Iron/Ironing board in all four bedrooms ● Sleeper sofa ● Great Room includes a 60" TV with Streaming Services ● DVD Player, Receiver Tuner/Amplifier with ipod hook up ● Indoor & Outdoor Speakers ● Wireless DSL ● Binoculars ● Selection of Books & Board Games ● Beach chairs, beach towels & coolers ● Safe in great room for your valuables ● Electronic Security Gate ● Welcome snack basket upon arrival ● Child safety net is available for the pool - additional cost to set up and remove On Island Villa Managers, Julie and David, are available anytime during your stay for questions, concierge services and they love to share their knowledge of all the wonderful beaches and hiking trails and restaurants on St John. Mystic Ridge is located half way between Cruz Bay and Coral Bay, making it the perfect location to explore the entire island of St John. It is a short 10 minute drive to the North Shore beaches of the USVI National Park. A rental vehicle is required for this property due to its location.

True Story Ocean View | Private Pool | Generator

Cruz Bay, St. John, VI
3 Bedrooms 6 Guests
Oct 2 - 6
$887 night

Experience the essence of Caribbean living at True Story. This stunning residence offers breathtaking ocean views stretching from Little St. James to Rendezvous and Ram Head. The Great Room, with pocket sliding doors, seamlessly connects to the pool terrace, enhancing the indoor-outdoor flow. This Villa has battery back up power that will automatically kick on if the power goes out so guests can continue to enjoy a comfortable stay. This 3-bedroom, 4-bath oasis is designed for ease and accessibility, featuring a level driveway and lush entry plaza up a few steps. Every detail has been thoughtfully curated for island life, including a full house automatic generator and back up power. True Story embodies the ultimate Caribbean lifestyle—perfect for vacations amidst tranquil views of the Caribbean Sea. As you enter the Villa’s pathway, you will be greeted views that will transport you to paradise with all the modern conveniences you would desire and expect in a luxury resort. From the plush furnishings to the St. John stone walls in the outdoor showers, and the pool overlooking the sparkling turquoise ocean beneath you, True Story will bring you to a place of happiness and peace. High-end window treatments, luxurious bedding, and custom furnishings accompany the exquisite guest rooms. Each private terrace has seating and tables to enjoy the magnificent beauty of the turquoise Caribbean water below. Property Manager will arrange for a greeter to meet you at the villa for check-in, provide a tour, and address any questions about the property, as well as offer insights about the island. Arrangements will be tailored to your party size, arrival time, and familiarity with the area. Alternatively, Property Manager offers a virtual check-in via FaceTime to review the villa and answer any questions. Property Manager highly recommends renting a 4-wheel drive vehicle for navigating St. John’s terrain. We can provide a list of trusted local rental companies and have a few villa vehicles available. You will receive a contract to finalize your booking. Once your flight is booked, please provide your flight information to help us plan your arrival. We can assist with arranging private transportation from the airport to the villa, water service, taxi service, boat charters, private chefs, and massages. Expect a few emails to help with your vacation planning. We look forward to welcoming you to St. John. Please let us know if you have any questions.

Maria Bluff Cottage | 2BR | Pool | Generator

Cruz Bay, St. John, VI
2 Bedrooms 4 Guests
Sep 19 - 23
$807 night

This newer two-story cottage features ocean views, a private pool, and an exquisite kitchen. Ideal for a couple, small group, or family, it offers easy access from its private driveway. The cottage includes a full kitchen, living room, laundry area, coral stone deck, outdoor dining, plunge pool, and two bedrooms with en-suite bathrooms. Multiple zones of air conditioning ensure comfort for everyone in the group. This Villa has a generator that will automatically kick on if the power goes out so guests can continue to enjoy a comfortable stay. The first floor bedroom is the Seabreeze Suite while the second story bedroom is called the Sunset Suite and has a deck to take in the sweeping views. The Cottage connects to the Great House via a short walkway. You can rent both villas together.  There is a landscaping for privacy between the two villas. Property Manager will arrange for a Greeter to meet you at the villa for check-in, provide a tour, address any questions about the property, and offer insights about the island. Check in arrangements will be tailored to your party size, arrival time, and familiarity with the area. Alternatively, Property Manager offers a virtual check-in via FaceTime to review the villa and answer any questions. Property Manager highly recommends renting a 4-wheel drive vehicle for navigating St. John’s terrain. We can provide a list of trusted local rental companies and have a few villa vehicles available. Please inquire with the Property Manager Team about options! All Guests will receive a contract for signature in order to finalize the booking. Once your flight is booked, please provide your flight information to help us plan your arrival. We can assist with arranging private transportation from the airport to the villa, private taxi service, boat charters, private chefs, and spa services. Guests can expect a few emails to help with your vacation planning. We look forward to welcoming you to St. John!

Maria Bluff Main House | 5BR | Pool | Generator

Cruz Bay, St. John, VI
5 Bedrooms 10 Guests
Sep 19 - 23
$2,027 night

Perched high atop Maria Bluff, Maria Bluff Main House offers some of the best views in the Caribbean, with Tradewinds and panoramic vistas in every direction. As you descend the entrance stairs, you’re welcomed by lush landscaping, with swaying palms and vibrant blooms that provide year-round tropical beauty. The crisp white and soft pallet of the interior design perfectly compliments the Caribbean surroundings providing a modern and sophisticated island aesthetic. Famous North Shore beaches- Trunk Bay, Cinnamon Bay and Maho Bay- are just a few miles away and the convenience of town is just a short 7 minute drive all making this the perfect location for your stay. This Villa has a generator that will automatically kick on if the power goes out so guests can continue to enjoy a comfortable stay. This Villa offers a variety of outdoor spaces designed for relaxation and entertainment. Enjoy the lounge area with an outdoor kitchen and plush seating, a covered al fresco dining area, two full sun decks, and a veranda ideal for cocktail hour-all surrounding an expansive pool that overlooks the Caribbean Sea. The Main House features five bedrooms with distinct personalities and each embodies a particular aspect of the island aesthetic. Each room is spacious with en suite bathrooms and air conditioning. Designer furnishings, as well as incredibly soft bed linens, pillowtop mattresses, and rich cooling down comforters, invite the most restful of sleeps. The state of the art kitchen has all stainless steel appliances - a Wolf gas stove and oven, SubZero refrigerator, ice-maker, microwave and two Bosch dishwashers - and custom imported granite countertops. It is the ultimate chef’s kitchen. A 10 person mahogany dining table sits just off the kitchen which also features an island with seating for six. Two living rooms offer plenty of comfortable space for lounging and family night. A state of the art entertainment system including Sonos sound system will delight with indoor and outdoor speakers. The lower living room features a pool table. Wireless high speed internet access is available throughout the house and bedrooms.  Whether you seek relaxation or entertainment, Maria Bluff Main House provides an exceptional experience with its thoughtful design and stunning views. Property Manager will arrange for one of our hosts to meet you at the villa for check-in, provide a tour, address any questions about the property, and offer insights about the island. Once your travel arrangements have been made, let us know the details and we can assist with options for getting to the Villa. Arrangements will be tailored to your party size, arrival time, and familiarity with the area. Property Manager is committed to making your arrival as smooth as possible! Property Manager highly recommends renting at least one 4-wheel drive vehicle for navigating St. John’s terrain. We can provide a list of trusted local rental companies and we have a few villa vehicles available. Having a vehicle at your fingertips allows for large groups to choose separate activities, run to the grocery store, and overall have flexibility during your stay. In addition,. Property Manager can provide assistance in setting up private rides for dinner reservations and trips to town at any time. Reach out to our team to curate the perfect itinerary for your group! All Guests will receive a contract for signature in order to finalize the booking. Once your flight is booked, please provide your flight information to help us plan your arrival. We can assist with arranging private transportation from the airport to the villa, private taxi service, boat charters, private chefs, and spa services. Guests can expect a few emails to help with your vacation planning. We look forward to welcoming you to St. John!

Maria Bluff Estate | 7-Bedroom Villa | Generator

Cruz Bay, St. John, VI
7 Bedrooms 14 Guests
Sep 19 - 23
$2,386 night

The ultimate private retreat, Maria Bluff Estate sits atop a secluded bluff in a private cul-de-sac, with panoramic Caribbean views stretching in every direction. This 7-bedroom, 10,000+ square foot estate includes a main house and cottage, linked by a private walkway. Each has its own pool and kitchen for added privacy. A backup generator ensures uninterrupted comfort, just 5 minutes from Cruz Bay. Maria Bluff Estate features seven distinctively designed suites, each with its own en-suite bathroom, incredible view, luxury furnishings, and plush bedding and towels. Five suites are in the Great House, and two are in the two-story Cottage, each positioned for privacy. There is an additional powder room in the living area of the Great House. Whatever your group size, Maria Bluff Estate has the space to accommodate you. Following a multi-million dollar renovation, this supremely luxurious estate sits high above the Caribbean, with panoramic views to the North, South, East, and West, and refreshing breezes day and night. The Great House includes a chef’s eat-in kitchen, a dining area for 12, two living rooms, a full entertainment surround sound system, a Disney+ suite of streaming (Disney+, Hulu, and ESPN Ultimate), a game area with a pool table, and a guest laundry area. Off the main kitchen is a large covered outdoor dining and seating area for up to 12. The lower living room opens onto a veranda with exquisite ocean views and seating for up to 20. Across the expansive coral stone deck, the Sleep House holds four of the five bedrooms, all with en-suite bathrooms; one on the upper level and one on the lower level each open onto a private deck. The coral stone deck and pool area connecting the two spaces offer ample room to enjoy the sun, along with a full outdoor kitchen. The Two-Story Cottage is an entirely new structure with its own private driveway large enough to hold 2 Jeeps. The Cottage is equipped with all the amenities: a full kitchen, living room, laundry area, coral stone deck, outdoor dining, a private pool, and 2 bedrooms with en-suite bathrooms. The second story bedroom has a deck to take in the sweeping views. The Cottage connects to the Great House via a short stone walkway. There is a landscaped privacy hedge between the two buildings so the Cottage can be rented as part of the full Estate or separately. Property Manager will arrange for one of our hosts to meet you at the villa for check-in, provide a tour, address any questions about the property, and offer insights about the island. Once your travel arrangements have been made, let us know the details and we can assist with options for getting to the Villa. Arrangements will be tailored to your party size, arrival time, and familiarity with the area. Property Manager is committed to making your arrival as smooth as possible! For the Christmas and New Years holidays, we require a 7 day bookings. If you are wanting to cross both holidays, then a 10 booking is required. Property Manager highly recommends renting at least one 4-wheel drive vehicle for navigating St. John’s terrain. We can provide a list of trusted local rental companies and we have a few villa vehicles available. Having a vehicle at your fingertips allows for large groups to choose separate activities, run to the grocery store, and overall have flexibility during your stay. In addition,. Property Manager can provide assistance in setting up private rides for dinner reservations and trips to town at any time. Reach out to our team to curate the perfect itinerary for your group! All Guests will receive a contract for signature in order to finalize the booking. Once your flight is booked, please provide your flight information to help us plan your arrival. We can assist with arranging private transportation from the airport to the villa, private taxi service, boat charters, private chefs, and spa services. Guests can expect a few emails to help with your vacation planning. We look forward to welcoming you to St. John! Interested in hosting an event? Reach out to our team to discuss pricing and details!

Oceanview Apt: Walk to Beach & Pet-Friendly Retreat

Cruz Bay, St. John, VI
2 Bedrooms 3 Guests
Sep 1 - 3
$600 night

🔹 Prime Location – 5-min walk to Cruz Bay & ferry 🌅 Breathtaking Ocean Views – Private balcony retreat 🛌 Luxury Beds & Linens – Sleep like royalty 📶 Fast WiFi + Dedicated Workspace – Work & relax 🏝 Beach Gear Provided – Towels, snorkel, & chairs 🚗 Free Parking – Hassle-free island living 💦 On-site Washer/Dryer – Convenient & easy 🔑 Self Check-in – Smart lock for a seamless arrival 🐾 Pet-Friendly – Bring your furry friend! ($100 fee) 🏡 Modern, stylish, and ultra-comfortable getaway! 🔹 The Space: 🛋️ Open-concept living area w/ ocean views 🍽️ Fully stocked kitchen w/ modern appliances 🛏️ Bedroom 1: Queen bed + en-suite bath 🛏️ Bedroom 2: Cozy single bed w/ private access 🌅 Private balcony – unwind w/ morning coffee & sea breeze 🔹 Guest Amenities: 📺 Smart TV & high-speed WiFi ❄️ A/C in bedrooms for ultimate comfort 🏖️ Beach towels & snorkel gear included 🚗 Free parking on premises 🔑 Keyless self check-in for flexibility 🔹 Location Perks: 🚶‍♂️ 5-min walk to Cruz Bay restaurants & shops 🏝️ Short stroll to stunning beaches ⛴️ 8-min walk to ferry dock for island hopping 🎉 Book now – this top-rated villa fills fast! Please note: From August 3–23, 2026, scheduled exterior work will take place at the property during daytime hours (when you are at the beach!). Guests can expect some daytime noise and partial view obstruction from scaffolding, which we’ve priced into the exceptional rate for these dates. ⚠️ House Rules: 🚭 No smoking | 🐶 Pet fee applies | ⏳ Quiet hours after 10 PM Self-check-in with Smart Lock – Hassle-free arrival!

Tradewinds Villa! Wrap Around Balcony with Amazing Views!

East End, St. Thomas, VI
1 Bedrooms 4 Guests
Sep 5 - 8
$330 night

Forget all worries and relax in this spacious 1BR/1BA condo with breathtaking views of the Caribbean. From the moment you walk in, the large wrap around balcony invites you to the best views on the highly sought-after East End of St. Thomas. Sitting on the hilltop of Point Pleasant, you will enjoy the nice Caribbean trade winds breeze. Our villa is ideal for couples or a small family of 4 with the available sofa bed. Minutes from Red Hook and ferry, Coki Point, Lindquist & Sapphire Beaches. Tradewinds Villa is a 1 bedroom and 1 bathroom condo located in one of the hilltop buildings of the Point Pleasant Resort in the East End of St. Thomas, away from the bustle of downtown Charlotte Amalia and cruise ship traffic. As you step inside, you will be welcomed by a fresh interior, designed to be uncluttered and maximize the space for you and your family, and stunning views of the Caribbean Sea through the large wrap-around balcony glass doors. This condo isn’t just a place to stay... it’s a destination in itself! In the bedroom, you will enjoy the comfort of a king size bed, with a sofa bed available in the living room. The bedroom has a small closet available for you to use, as well as chest of drawers. The split-system AC unit is located in the bedroom, which contains a big shutter-style window that opens up to the living room. Both the shutters and bedroom door can be closed for privacy. The bathroom is located adjacent to the bedroom, across the hallway. It has a bathtub shower, single sink, and water closet (toilet area). Our kitchen contains most of the basic items necessary for you to enjoy your meals if you choose to prepare your own. A standard fridge with top freezer, microwave, oven with ceramic flat top are available. A TV is available in the bedroom and in the living room. The TVs are internet-connected with Roku devices, so you are welcome to use your own streaming services with the equipment. We have two non-portable Bluetooth speakers available in the unit for you to enjoy listening to the music of your choice, paired with your devices. One of the speakers is capable of tuning to FM radio. Please be mindful of our neighbors and use volume moderation, as well as respect quiet hours. On the wrap-around balcony, you will relax and appreciate the sweeping views down the island with plentiful turquoise water. The island of St. John, Water Bay, Thatch Cay, and the British Virgin Islands can be seen from here! A brand-new set of Polywood furniture that includes chairs, loungers, and a 4-seat dining table are part of this amenity. Whether you are having a cup of coffee, a few drinks, or a meal outside, this is the best place to hang out and appreciate while relaxing at the condo. A dining table is available inside the unit as well as 4 bar seats at the counter bar. While we hope you don’t have to work while staying with us, an office desk and chair are available. For your outing adventures, two beach chairs, towels, and a cooler are available to use. Please note that furniture and other amenities provided in our villa may be updated or replaced from time to time. As things need replacement and/or renovation, we will do our best to update the pictures to match. We will always update our listing if for any reason one or more amenities are no longer available to our guests.

Windsong-Stunning Views, Pool, Generator!

Cruz Bay, St. John, VI
5 Bedrooms 10 Guests
Oct 1 - 5
$911 night

This stunning private luxury villa in St. John, overlooking the Caribbean Sea and Fish Bay, is the perfect retreat for a vacation with friends and family. Relax with a cool drink on a chaise lounge by the pool, enjoying views of the deep blue sea. Explore the unspoiled beauty of St. John and its magnificent, pristine beaches, then return to WindSong Villa for luxurious relaxation. This Villa has a generator that will automatically kick on if the power goes out so guests can continue to enjoy a comfortable stay. As you enter WindSong Villa’s custom brick and stone pathway, you will be greeted by arched, custom mahogany doors that will transport you back in time, yet have all the modern conveniences you would desire and expect in a luxury resort. From the plush furnishings to the St. John stone walls with seashells, and the pool overlooking the sparkling turquoise ocean beneath you, WindSong Villa will bring you to a place of happiness and peace. Newly renovated in 2022, WindSong Villa sleeps 10 guests in five KING SUITES and has 5.5 bathrooms. This luxury villa offers 3 air-conditioned King Suites on the main floor of the villa, each with its own ensuite bath and a beautiful private outdoor terrace with sweeping views of the crystal blue Caribbean. Additionally, there is a 4th King Suite that is accessible via outdoor staircase below the main level. Finally, there is a separate fully air-conditioned King apartment with a kitchenette and ensuite bath-perfect for guests seeking additional privacy or needing extra amenities. High-end window treatments, luxurious bedding, and custom furnishings accompany the exquisite guest rooms. Each private terrace has seating and tables to enjoy the magnificent beauty of the turquoise Caribbean water below. Property Manager will arrange for a greeter to meet you at the villa for check-in, provide a tour, and address any questions about the property, as well as offer insights about the island. Arrangements will be tailored to your party size, arrival time, and familiarity with the area. Alternatively, Property Manager offers a virtual check-in via FaceTime to review the villa and answer any questions. To make the villa more affordable for smaller groups, the base price covers up to six guests and includes the three-bedroom main house. Additional bedrooms (4th and 5th) can be added for $150 per room per night. If the extra rooms are not required, they will locked for your stay. For 4 bedrooms, please select 8 guests. For 5 bedrooms, please select 10 guests. This will automatically adjust your quote accordingly. Please note that during the Christmas and New Year holidays, there is a minimum stay of seven days, and the dates cannot overlap both holidays. A ten-day minimum is required for bookings that cover both holiday periods. Property Manager highly recommends renting a 4-wheel drive vehicle for navigating St. John’s terrain. We can provide a list of trusted local rental companies and have a few villa vehicles available. You will receive a contract to finalize your booking. Once your flight is booked, please provide your flight information to help us plan your arrival. We can assist with arranging private transportation from the airport to the villa, water service, taxi service, boat charters, private chefs, and massages. Expect a few emails to help with your vacation planning. We look forward to welcoming you to St. John. Please let us know if you have any questions.

’Sea La Vie’ - Waterfront St Thomas Escape w/ Pool

St Thomas, VI
2 Bedrooms 4 Guests
Sep 17 - 20
$512 night

Fly south for the winter to your own slice of island paradise! Don't hesitate to book this stunning 2-bedroom, 2-bathroom St.Thomas vacation rental villa for 4. Facing west, this unbeatable property is the perfect spot to watch the sunset and grill out after a day of adventures. With an infinity pool, breathtaking views, and only a short distance to Red Hook's attractions and the marina boasting ferry access to St. John and more, there's plenty of entertainment for everyone! -- THE PROPERTY -- Ocean Views | Ground-Floor Unit | 1,000 Sq Ft Boasting panoramic views and a private sparkling infinity pool, this St. Thomas villa is a perfect home base for exploring paradise. Bedroom 1: Queen Bed | Bedroom 2: 2 Twin Beds OUTDOOR LIVING: Infinity pool, lounge seating, outdoor grill INDOOR LIVING: Flat-screen TV, iPod/MP3 docking station, ceiling fans, large windows KITCHEN: Fully equipped, dishwasher, drip coffee maker, toaster, refrigerator, stove/oven GENERAL: Stairs required, air conditioning, free WiFi, washer/dryer, new linens, cribs not provided -- THE LOCATION -- OUTDOOR ADVENTURE: American Yacht Harbor (1.6 miles), Smith Bay Beach (2.8 miles), Coki Point Beach (4.5 miles), Coral World Ocean Park (4.7 miles), Magen’s Bay Park (8.5 miles), Darke’s Seat (8.5 miles), Tree Limin’ Extreme Zipline St. Thomas (10.1 miles), fishing, snorkeling, sailing charters THINGS TO DO: Urman Victor Fredericks Marine Terminal - Red Hook (1.8 miles), Pirates Treasure Museum (7.6 miles), Skyride to Paradise Point (8.4 miles), Downtown Charlotte Amalie (8.8 miles), Blackbeard’s Castle (9.2 miles) DINING: Sunset Grille at Secret Harbour (1.3 miles), Duffy’s Love Shack (1.6 miles), XO Bistro (1.6 miles), Bernie’s Bar & Grill (1.6 miles), Senor Pizza (1.7 miles), Sapphire Beach Bar (2.5 miles) AIRPORT: Terrance B. Lettsome International Airport (27.8 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties or large gatherings - Additional fees and taxes may apply - NOTE: The USVI does not require safety fencing around private pools. Children must be monitored at all times - NOTE: Your safety matters. An exterior security camera is located at the front door and stairs, facing out. The camera does not look into any interior spaces - NOTE: Stairs are required for access

Maria Breeze Villa | Stunning Views | 5-BR | Pool

St. John, St. John, VI
5 Bedrooms 10 Guests
Oct 1 - 5
$1,070 night

Maria Breeze is a stunning 5-bedroom, 5.5-bath villa located in St. John, US Virgin Islands, equipped with a whole house generator. Ideal for large families and groups, the property is perched atop Maria Bluff, offering sensational 180-degree ocean and mountain views with beautiful breezes. This expansive home is perfectly positioned just minutes from Cruz Bay, boat charters, and the National Park. Maria Breeze features three separate living areas on the main level, connected by covered decks and stairways. The decor reflects traditional island living with stone masonry, pitched ceilings, white-washed walls, and breezy colors, combined with modern appliances. All five bedrooms are air-conditioned, each with a private bath and ceiling fan. The main level includes three king bedrooms, while the lower level has two king bedrooms, all with full baths. There is also a separate half bath on the main level. Outdoors, the villa boasts an expansive horseshoe-shaped deck with a roof for all-weather enjoyment, generous outdoor furniture, a BBQ, and a large dining table. Below the deck, a sun-drenched pool offers a perfect spot for sunbathing and cooling off. Property Manager will arrange for a greeter to meet you at the villa for check-in, provide a tour, and address any questions about the property, as well as offer insights about the island. Arrangements will be tailored to your party size, arrival time, and familiarity with the area. Alternatively, Property Manager offers a virtual check-in via FaceTime to review the villa and answer any questions. Property Manager highly recommends renting a 4-wheel drive vehicle for navigating St. John’s terrain. We can provide a list of trusted local rental companies and have a few villa vehicles available. You will receive a contract to finalize your booking. Once your flight is booked, please provide us with your flight information to help plan your arrival. We can assist with arranging private transportation from the airport to the villa, private water service, taxi service, boat charters, private chefs, and massages. Expect a few emails to help you plan your vacation. We look forward to welcoming you to St. John. Please let us know if you have any questions.

Cielo Vista | Pool | Sunsets | Generator

Cruz Bay, St. John, VI
4 Bedrooms 8 Guests
Oct 1 - 5
$653 night

Cielo Vista is a hilltop villa with two king suites, a queen loft, and a queen apartment sleeping up to 8 guests. The home blends Latin-style flooring, white plaster walls, and rich mahogany accents. Enjoy AC throughout the villa, including the living room, loft, and kitchen, plus a whole-house generator for added comfort. Relax on the pool deck with breathtaking Caribbean Sea views and unforgettable sunsets. 🌴 Upon entering the villa, you’ll find the central hub of the home: a two-story lofted Great Room designed to capture gentle Caribbean breezes and abundant natural light. The space features multiple seating areas, A/C, and a seamless connection between indoor and outdoor living. The loft includes a queen bed and catwalk leading to a private second-story deck. Loft guests share a bathroom with one of the king bedrooms, as the loft does not have its own en-suite. The Great Room is flanked by two private king bedrooms, each with A/C, king beds, and en-suite bathrooms with dual vanities and spacious spa-style showers. The lower-level studio apartment offers an additional private retreat with a kitchen, living area, queen bed, and screened patio. The heart of the home is a fully equipped kitchen which opens to the Great Room, allowing guests to enjoy the views and conversation while meals are prepared. Across from the kitchen, a large screened veranda provides a comfortable space for relaxing, dining, or reading while overlooking the private pool and lush tropical gardens—perfect for sunsets and evening cocktails.🌴 Property Manager will arrange for a personal greeter to meet you at the villa for check-in, provide a brief tour of the property, answer any questions about the home, and share helpful insights about the island. Check-in arrangements are tailored to your party size, arrival time, and familiarity with the area to ensure a smooth arrival. Property Manager highly recommends renting a 4-wheel drive vehicle to comfortably navigate the terrain on St. John. We are happy to provide a list of trusted local rental companies, and we also have a few villa vehicles available for guests when available. Current villa vehicle options may include: • New Custom Toyota Land Cruiser – Full-Time Four-Wheel Drive – 5 Passenger • Lexus GX – Full-Time Four-Wheel Drive – 6 Passenger • Jeep Wrangler Islander (4-door) – Four-Wheel Drive – 5 Passenger • Toyota Highlander – AWD – 6 Passenger Please inquire with the Property Manager Team to check availability and explore the best option for your stay. 🚙🌴 If you prefer not to drive, we are also happy to arrange taxi service during your stay. All Guests will receive a contract for signature for terms and conditions. Once your flight is booked, we ask that you please provide your flight information so we can help plan a smooth arrival and transfer from the airport on St Thomas. We can assist with arranging private transportation from the airport to the villa, private taxi service, boat charters, private chefs, and spa services. Guests can expect a few emails to help with your vacation planning. We look forward to welcoming you to St. John!

Oceanview Cottage w/ Balcony – Steps to Cruz Bay

Cruz Bay, St. John, VI
2 Bedrooms 4 Guests
Sep 1 - 3
$257 night

🔹 Prime Location – Walk to dining, shopping & ferry 🌅 Private Balcony – Stunning ocean & sunset views 🚿 Outdoor Bamboo Shower – Refresh in nature ❄️ Full AC – Cool, comfortable retreat 🛏️ Spacious 2BR – Ultra-comfy beds for restful sleep 🍽️ Fully Equipped Kitchen – Cook with ease 🚶‍♂️ No Car Needed – Save on rentals, everything is nearby 📺 High-Speed WiFi & Smart TV – Work & relax seamlessly 🎉 Book now—your island retreat awaits! 🐶Pet-Friendly – Bring your furry friend! ($100 fee) 🏡 Welcome to Cruz Bay in St John! This stylish 2-bedroom cottage blends comfort with convenience, offering breathtaking ocean views and easy access to top attractions. 🔹 The Space: 🛋️ Spacious, open-concept living area with plush seating ☕ Fully stocked kitchen – Enjoy home-cooked meals 🛏️ 2 Bedrooms (1 King, 1 Queen) – Ultra-comfy mattresses 🌅 Private Balcony – Watch magical sunsets 🚿 Outdoor Bamboo Shower – Refresh in a tropical setting 📺 Smart TV + High-Speed WiFi for work & entertainment 🌍 Location Perks: 🍹 Steps to Cruz Bay’s best bars & restaurants 🏝️ 5-min walk to the beach – No car needed! 🚕 Close to taxis, ferry, and Virgin Islands National Park 🚗 Free private parking on-site 🎉 Secure your slice of paradise now—dates book fast! Please note: From August 3–23, 2026, scheduled exterior work will take place at the property during daytime hours (when you are at the beach!). Guests can expect some daytime noise and partial view obstruction from scaffolding, which we’ve priced into the exceptional rate for these dates. ⚠️ House Rules: 🚭 No smoking | 🐶 Pet fee applies | ⏳ Quiet hours after 10 PM Self-check-in with Smart Lock – Hassle-free arrival! 🎉 Don’t miss out—reserve your dates today for the ultimate island retreat! While St. John is blissfully quiet and peaceful (seriously, it’s the kind of place where wild donkeys almost outnumber cars), you might hear the occasional road noise. Think of it as the island whispering, "You’re not dreaming, this place really is paradise." 😉

Amazing 3BR private villa with pool & hot tub - all the amenities!

St. Thomas, St. Thomas, VI
3 Bedrooms 10 Guests
Nov 20 - 23
$691 night

The Glass House – Luxury Villa in St. Thomas, USVI Escape to paradise at The Glass House, an exquisite 3-bedroom, 3-bathroom villa in beautiful St. Thomas, USVI. With breathtaking ocean views, modern amenities, and a prime location just minutes from the island’s best attractions, this luxurious retreat is the perfect getaway for families, groups of friends, or couples seeking a tranquil yet conveniently located vacation home. Unparalleled Views & Prime Location Perched on a hillside, The Glass House offers expansive panoramic views stretching from Great Saint James all the way west to Puerto Rico. Watch as superyachts and cruise ships glide into Charlotte Amalie Harbor, a mesmerizing sight from the comfort of your private primary bedroom balcony. Whether you’re sipping coffee at sunrise or enjoying a glass of wine as the sun dips below the horizon, the scenery is truly unforgettable. Just 6 minutes to Havesight and 15 minutes to downtown Charlotte Amalie, The Glass House is ideally located for both relaxation and adventure. Yet, the villa remains a peaceful sanctuary, offering privacy and serenity away from the hustle and bustle. Spacious & Comfortable Accommodations Designed with both comfort and elegance in mind, this three-bedroom villa comfortably accommodates up to 10 guests: Primary Suite – A luxurious retreat with a walk-in closet, ensuite bath, and a private balcony offering breathtaking ocean views. Bedroom 2 & Bedroom 3 – Share a spacious bathroom and feature comfortable sleeping arrangements. Media Room/Office – Located on the ground floor, this versatile space doubles as a fourth sleeping area with a sleeper sofa and has an adjacent full bath for convenience. Additional Sleeping Options – A pullout "sling bed" in Bedroom 2 provides extra space, perfect for two children. Indoor & Outdoor Living at Its Finest The villa’s open-concept living area is bright and inviting, featuring stylish furnishings, a well-appointed kitchen, and a spacious dining area. Whether you’re preparing a gourmet meal or enjoying a family dinner, this space is perfect for gathering and making memories. Step outside to experience island living at its best. The villa boasts a private pool and hot tub, perfect for cooling off after a day of island adventures. Fire up the outdoor kitchen with a BBQ grill and dine al fresco as you take in the spectacular views. Modern Amenities for a Seamless Stay The Glass House is designed to provide all the comforts of home with upscale amenities, including: Fully equipped kitchen with high-end appliances Air conditioning in every bedroom and the media room/office (Note: No AC in the kitchen, dining, or living areas) Washer and dryer for added convenience Spacious indoor and outdoor living areas Fast WiFi Tesla Powerwalls and a backup generator, ensuring uninterrupted comfort and peace of mind during your stay. Your Perfect Island Escape Awaits Whether you’re relaxing in the hot tub under the stars, lounging by the pool with a tropical drink, or exploring the vibrant local culture, this villa is the ultimate home base for your St. Thomas adventure. Book your stay today and experience luxury, comfort, and unforgettable views in the heart of the Caribbean! **Confirmed guests will be required to sign a guest license/rental agreement and may be required to keep a credit card on file for incidentals** ** There are extra guest fees after 6 guests. **All credit card payments are subject to transaction processing fees. In the event of a reservation cancellation, these fees are non-refundable, as the constitute direct costs incurred during the payment transaction. Have questions? Just ask! I’ve been hosting short term rentals in St. Thomas for more than 15 years - so I will make sure we find you the best property to suit your specific needs, plus we have many fantastic options to choose from! Traveling with a larger group? Let us know and we will show you all the units nearby that are available for rental! Why book with Property Manager? 1. All of our properties undergo a 25-point inspection before arrival to make sure everything is working and in perfect order. 2. All of our properties are stocked with the basics, so you don’t have to sweat the small stuff! 3.The Property Manager team is comprised of long time Virgin Island residents and well-seasoned travelers that provide you with accommodations and trip planning to meet your specific needs. We offer all our guests a full-service concierge, free of charge! Whether you’re looking for exhilarating adventure or peaceful relaxation, on land, at sea, or in the air, our complimentary Concierge Service will help ensure you have the Caribbean vacation you’ve been daydreaming about! 4. We represent a large inventory of properties; If there is an emergency issue with your property, chances are you will never be left high and dry. 5. We provide a 24/7 maintenance and an emergency hotline.

Tropical Seabreeze villa-Peaceful Retreat

Cruz Bay, St. John, VI
4 Bedrooms 8 Guests
Sep 1 - 6
$678 night

Welcome to Tropical Sea Breeze Villa — your modern island sanctuary on the breathtaking shores of St. John. Perched above shimmering blue waters and embraced by lush mountainsides, this newly built contemporary escape was designed for travelers who crave style, serenity, and that effortless indoor–outdoor Caribbean lifestyle. From the moment you arrive, the villa invites you to slow down and soak it all in. The pool and wraparound sundeck are perfectly positioned for all-day sunshine, with peaceful shaded spaces nearby for when you want to cool off, curl up with a book, or simply listen to the island breeze. Whether you’re sipping morning coffee from the living room’s cozy couch or unwinding on a lounger with the ocean stretching out before you, this home makes relaxing feel easy and natural. Thoughtful design meets modern comfort. Tropical Sea Breeze Villa is filled with clean lines, open spaces, and warm, minimalist elegance. The home is fully air-conditioned and equipped with high-speed WiFi, smart TVs, a laundry room, a microwave, a barbecue, and plenty of inviting communal areas to gather, dine, and reconnect. Energy-efficient systems — including Tesla Powerwall backup batteries — ensure a smooth and comfortable stay. We chose this location for its peacefulness and beauty: the protected St. John National Park to the east, southern exposure for gorgeous natural light, and refreshing breezes drifting in from the ocean. Explore the Villa The Entry Level: Rest & Retreat Follow a beautifully landscaped tropical pathway lined with flowering plants and young palm trees to reach a sleek staircase leading to the main entry. Step inside, and you’ll find three serene bedrooms on the first level: A spacious master suite with a king bed and ensuite bathroom Two queen bedrooms sharing a well-appointed bath A laundry room conveniently positioned between the rooms to ensure privacy and ease Every bedroom features a smart TV, and WiFi extends seamlessly throughout the entire home — including the pool deck. The Upper Level: Views, Breeze & Island Living Ascend the floating mahogany staircase and enter the heart of the home: an airy open-concept kitchen, dining area, and living room framed by dazzling views of Fish Bay’s blue-green waters. This level was intentionally designed “upside down” so the most spectacular scenery can be enjoyed while cooking, lounging, entertaining, or simply daydreaming. There are two dining spaces to choose from: One indoors, between the kitchen and living room One outdoors on the upper sundeck — perfect for barbecuing, lingering over dinner, or stargazing under Caribbean skies Tucked at the back of this level is a second master suite, complete with a king bed, ensuite bathroom, and private access from either the hallway or the upper deck. A stylish half bath sits just off the kitchen for added convenience. Island Magic, Inside and Out From both levels of the home, you’ll experience glowing partial sunrises, warm pastel sunsets, and the constant soundtrack of gentle ocean breezes. While the villa is fully air-conditioned, most guests find the natural sea breeze keeps the home cool and wonderfully refreshing. Parking is easy, with space for one vehicle in the driveway and additional street parking in front of the villa. Treat yourself to the tranquility, beauty, and modern luxury of Tropical Sea Breeze Villa — where every moment feels like the Caribbean getaway you’ve been dreaming of.

Vessup View - 5BR walk to the beach!

St. Thomas, St. Thomas, VI
5 Bedrooms 11 Guests
Nov 19 - 24
$1,257 night

Welcome to Vessup View, your ultimate Caribbean retreat nestled on the East End of St. Thomas. This spectacular 5-bedroom villa is a haven of tranquility and luxury, perfectly positioned to offer stunning vistas and easy access to the island’s finest attractions. From the moment you arrive, you’ll be captivated by the villa’s exquisite design and serene surroundings. Step inside and discover a spacious, beautifully appointed interior that seamlessly blends comfort and style. The expansive living areas are perfect for relaxing with family and friends, featuring plush furnishings and elegant decor. The fully equipped kitchen boasts modern appliances and ample space, making it a joy to prepare meals or entertain guests. Vessup View’s outdoor spaces are nothing short of spectacular. The highlight is undoubtedly the beautiful pool, and pool deck where you can take a refreshing dip while soaking up the breathtaking views of the Caribbean Sea. The water feature adds a touch of serenity, creating a perfect spot for unwinding under the sun. The covered gazebo provides a shaded retreat for alfresco dining or simply lounging with a good book. Each of the five bedrooms is a private sanctuary, complete with its own air conditioning and comfy linens to ensure a restful night’s sleep. The three full bathrooms and two half bathrooms are designed with comfort in mind, featuring premium fixtures and finishes. Located just minutes from Red Hook, Vessup View offers unparalleled convenience. Red Hook is a vibrant hub where you’ll find a variety of shops, restaurants, and nightlife options, as well as the ferry terminal for excursions to St. John. For those seeking sun and sand, Vessup Beach is a short five-minute walk away, and there are five other beautiful beaches within a mile of the villa. The villa is situated in a secure and quiet residential community, with it’s own automatic security gate, providing peace of mind and privacy. While we recommend renting a vehicle to explore the island at your leisure, we are happy to assist with arranging a driver or taxi service to suit your needs. Why book with Property Manager? 1. All of our properties undergo a 25-point inspection before arrival to make sure everything is working and in perfect order. 2. All of our properties are stocked with the basics, so you don’t have to sweat the small stuff! 3.The Property Manager team is comprised of long time Virgin Island residents and well-seasoned travelers that provide you with accommodations and trip planning to meet your specific needs. We offer all our guests a full-service concierge, free of charge! Whether you’re looking for exhilarating adventure or peaceful relaxation, on land, at sea, or in the air, our complimentary Concierge Service will help ensure you have the Caribbean vacation you’ve been daydreaming about! 4. We represent a large inventory of properties; If there is an emergency issue with your property, you will never be left high and dry. 5. We provide a 24/7 maintenance and an emergency hotline. Have questions? With well over a decade of experience in short-term rentals on St. Thomas, I am dedicated to helping you find the perfect property to suit your needs. If you’re traveling with a larger group, let us know, and we can show you additional nearby properties available for rent. ** There are extra guest fees after 10 guests. **All credit card payments are subject to transaction processing fees. In the event of a reservation cancellation, these fees are non-refundable, as the constitute direct costs incurred during the payment transaction. **Confirmed guests will be required to sign a guest license/rental agreement and may be required to keep a credit card on file for incidentals**

Vacation Rentals in British Virgin Islands by Amenities & Features

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