Villa in Cruz Bay
6 guests · 3 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this villa rental
Welcome to Castaway Villa, a beautifully renovated private vacation home designed for guests who want the perfect balance of luxury, comfort, convenience, and breathtaking island beauty. Nestled in the desirable Estate Chocolate Hole neighborhood on St. John, this exceptional villa offers sweeping turquoise water views, peaceful surroundings, and an unbeatable location just a short walk to the Westin Resort and a very quick drive to the dining, shopping, and nightlife of Cruz Bay.
Whether you are returning to Castaway Villa or discovering it for the first time, you’ll find a thoughtfully updated property that blends modern upgrades with relaxed Caribbean elegance. Recent renovations and improvements have elevated the entire experience—inside and out—making Castaway Villa a place you truly won’t want to leave.
Prime Location with the Best of St. John at Your Fingertips
Castaway Villa is ideally situated for guests who want both privacy and proximity. The Chocolate Hole neighborhood is known for its tranquility, scenic roads, and stunning harbor views, making it a favorite for morning runs or leisurely walks while soaking in the beauty of the island. At the same time, you are moments away from everything St. John has to offer including;
- Walking distance to the Westin Resort
- Less than a 5-minute drive to Cruz Bay, the heart of St. John, with its boutiques, restaurants, bars, and ferry dock
- Around the corner from the St. John & Dolphin Market, perfect for quick grocery runs, fresh provisions, or last-minute supplies
The location allows you to feel tucked away from the crowds while still enjoying easy access to the island’s most popular destinations.
Extensive Renovations & Modern Comforts
Castaway Villa has recently undergone major renovations, ensuring a fresh, modern, and worry-free stay. Guests returning after previous visits will immediately notice the transformation.
Recent upgrades include:
- A fully renovated driveway
- New exterior lighting
- A beautifully updated saltwater swimming pool and expansive pool deck
- All new outdoor furniture, perfect for lounging, dining, and soaking in the views
- Brand-new windows & ceiling fans throughout the villa
- Renovated kitchen and bathrooms
- Tesla backup battery system, providing uninterrupted power during island outages
These enhancements were designed with guest comfort and peace of mind in mind, so you can relax and fully enjoy your island getaway.
Spacious Layout – Ideal for Families & Couples
Castaway Villa comfortably accommodates guests with three private bedroom suites plus an additional half bath, offering space, privacy, and flexibility for families, couples, or friends traveling together.
The main house features two spacious bedroom and bathroom suites, each designed as a private retreat.
- King-size beds in both suites (one can be converted to two twins if needed)
- Elegant double vanity bathrooms
- Luxurious private outdoor showers, allowing you to bathe under the island sky
- Direct access to ocean breezes and stunning water views
A convenient half bath is also located in the main house for guests and shared living areas.
The third bedroom suite is located in the pool cabana, just steps from the pool deck—perfect for guests who appreciate extra privacy. This includes;
- King-size bed
- Full bathroom
- Sliding glass doors opening to a private water-view deck
- Gorgeous views overlooking Hart Bay
Architectural Charm & Island Ambiance
Both the main house and pool cabana showcase beautiful wood plank cathedral ceilings that add warmth and character while enhancing airflow. Cool stamped concrete floors throughout the villa keep the space comfortable and easy to maintain in the tropical climate.
The villa is equipped with:
- Full central air conditioning throughout all bedrooms and common areas
- Ceiling fans for additional comfort
- Large screened windows that allow you to enjoy cool ocean breezes if you prefer natural airflow
From nearly every angle, you’ll enjoy vibrant views of the Caribbean’s iconic turquoise waters.
Outdoor Living at Its Finest
Outdoor living is at the heart of the Castaway Villa experience. The centerpiece is the stunning 30-foot saltwater pool, surrounded by a large sundeck designed for relaxation and entertainment.
Enjoy:
- Floating on pool rafts with panoramic water views
- Lounging in the sun or shade on brand-new outdoor furniture
- Sipping frozen margaritas made fresh in the blender
- Dining or grilling outdoors with the new gas grill
- Rinsing off in the outdoor shower after long beach days
Whether you’re enjoying a quiet morning swim or a sunset cocktail, the outdoor spaces are designed to make every moment memorable.
Fully Equipped for a Stress-Free Stay
Castaway Villa is thoughtfully stocked so you can focus on enjoying your vacation, not managing logistics. The villa includes everything needed for a comfortable and convenient stay.
Amenities include:
- Fully stocked kitchen with all cookware, utensils, and small appliances
- High-quality linens and towels
- Beach towels, beach chairs, pool floats, and coolers
- Wi-Fi and flat screen TV which includes Apple TV
- Washer and dryer
There’s truly nothing to bring but your clothes and sunscreen. The private driveway comfortably fits two vehicles, making it easy for guests who choose to rent a car.
Local Support & Peace of Mind
A full-time caretaking crew lives on St. John and is available to assist during your stay. Whether you have questions about the villa, the island, or need support during your visit, help is always close by.
The home’s Tesla backup battery system ensures uninterrupted power during outages, offering an added level of comfort and reliability that is especially valuable on an island.
Exploring St. John
While Castaway Villa is a destination in itself, renting a car is strongly recommended to fully experience St. John’s world-famous beaches, scenic overlooks, and hiking trails.
Please note:
- Trash removal is the responsibility of tenants; a fee will apply if caretakers must assist
- Driving is on the left side of the road, and local rental companies provide clear guidance and support
With a car, you’ll have easy access to Trunk Bay, Cinnamon Bay, Maho Bay, and countless other island treasures.
Your Island Escape Awaits
Castaway Villa is more than a place to stay—it’s a private Caribbean retreat designed for unforgettable memories. From the newly renovated interiors and outdoor spaces to the spectacular water views and unbeatable location, every detail has been carefully curated to ensure an exceptional St. John experience.
Whether you’re returning to a favorite getaway or discovering Castaway Villa for the first time, we’re confident you’ll fall in love with this special place—and start planning your next visit before you even leave.
Please note; traveler’s insurance is strongly recommended to protect your investment and provide peace of mind.
Whether you are returning to Castaway Villa or discovering it for the first time, you’ll find a thoughtfully updated property that blends modern upgrades with relaxed Caribbean elegance. Recent renovations and improvements have elevated the entire experience—inside and out—making Castaway Villa a place you truly won’t want to leave.
Prime Location with the Best of St. John at Your Fingertips
Castaway Villa is ideally situated for guests who want both privacy and proximity. The Chocolate Hole neighborhood is known for its tranquility, scenic roads, and stunning harbor views, making it a favorite for morning runs or leisurely walks while soaking in the beauty of the island. At the same time, you are moments away from everything St. John has to offer including;
- Walking distance to the Westin Resort
- Less than a 5-minute drive to Cruz Bay, the heart of St. John, with its boutiques, restaurants, bars, and ferry dock
- Around the corner from the St. John & Dolphin Market, perfect for quick grocery runs, fresh provisions, or last-minute supplies
The location allows you to feel tucked away from the crowds while still enjoying easy access to the island’s most popular destinations.
Extensive Renovations & Modern Comforts
Castaway Villa has recently undergone major renovations, ensuring a fresh, modern, and worry-free stay. Guests returning after previous visits will immediately notice the transformation.
Recent upgrades include:
- A fully renovated driveway
- New exterior lighting
- A beautifully updated saltwater swimming pool and expansive pool deck
- All new outdoor furniture, perfect for lounging, dining, and soaking in the views
- Brand-new windows & ceiling fans throughout the villa
- Renovated kitchen and bathrooms
- Tesla backup battery system, providing uninterrupted power during island outages
These enhancements were designed with guest comfort and peace of mind in mind, so you can relax and fully enjoy your island getaway.
Spacious Layout – Ideal for Families & Couples
Castaway Villa comfortably accommodates guests with three private bedroom suites plus an additional half bath, offering space, privacy, and flexibility for families, couples, or friends traveling together.
The main house features two spacious bedroom and bathroom suites, each designed as a private retreat.
- King-size beds in both suites (one can be converted to two twins if needed)
- Elegant double vanity bathrooms
- Luxurious private outdoor showers, allowing you to bathe under the island sky
- Direct access to ocean breezes and stunning water views
A convenient half bath is also located in the main house for guests and shared living areas.
The third bedroom suite is located in the pool cabana, just steps from the pool deck—perfect for guests who appreciate extra privacy. This includes;
- King-size bed
- Full bathroom
- Sliding glass doors opening to a private water-view deck
- Gorgeous views overlooking Hart Bay
Architectural Charm & Island Ambiance
Both the main house and pool cabana showcase beautiful wood plank cathedral ceilings that add warmth and character while enhancing airflow. Cool stamped concrete floors throughout the villa keep the space comfortable and easy to maintain in the tropical climate.
The villa is equipped with:
- Full central air conditioning throughout all bedrooms and common areas
- Ceiling fans for additional comfort
- Large screened windows that allow you to enjoy cool ocean breezes if you prefer natural airflow
From nearly every angle, you’ll enjoy vibrant views of the Caribbean’s iconic turquoise waters.
Outdoor Living at Its Finest
Outdoor living is at the heart of the Castaway Villa experience. The centerpiece is the stunning 30-foot saltwater pool, surrounded by a large sundeck designed for relaxation and entertainment.
Enjoy:
- Floating on pool rafts with panoramic water views
- Lounging in the sun or shade on brand-new outdoor furniture
- Sipping frozen margaritas made fresh in the blender
- Dining or grilling outdoors with the new gas grill
- Rinsing off in the outdoor shower after long beach days
Whether you’re enjoying a quiet morning swim or a sunset cocktail, the outdoor spaces are designed to make every moment memorable.
Fully Equipped for a Stress-Free Stay
Castaway Villa is thoughtfully stocked so you can focus on enjoying your vacation, not managing logistics. The villa includes everything needed for a comfortable and convenient stay.
Amenities include:
- Fully stocked kitchen with all cookware, utensils, and small appliances
- High-quality linens and towels
- Beach towels, beach chairs, pool floats, and coolers
- Wi-Fi and flat screen TV which includes Apple TV
- Washer and dryer
There’s truly nothing to bring but your clothes and sunscreen. The private driveway comfortably fits two vehicles, making it easy for guests who choose to rent a car.
Local Support & Peace of Mind
A full-time caretaking crew lives on St. John and is available to assist during your stay. Whether you have questions about the villa, the island, or need support during your visit, help is always close by.
The home’s Tesla backup battery system ensures uninterrupted power during outages, offering an added level of comfort and reliability that is especially valuable on an island.
Exploring St. John
While Castaway Villa is a destination in itself, renting a car is strongly recommended to fully experience St. John’s world-famous beaches, scenic overlooks, and hiking trails.
Please note:
- Trash removal is the responsibility of tenants; a fee will apply if caretakers must assist
- Driving is on the left side of the road, and local rental companies provide clear guidance and support
With a car, you’ll have easy access to Trunk Bay, Cinnamon Bay, Maho Bay, and countless other island treasures.
Your Island Escape Awaits
Castaway Villa is more than a place to stay—it’s a private Caribbean retreat designed for unforgettable memories. From the newly renovated interiors and outdoor spaces to the spectacular water views and unbeatable location, every detail has been carefully curated to ensure an exceptional St. John experience.
Whether you’re returning to a favorite getaway or discovering Castaway Villa for the first time, we’re confident you’ll fall in love with this special place—and start planning your next visit before you even leave.
Please note; traveler’s insurance is strongly recommended to protect your investment and provide peace of mind.
Amenities at Poolside Paradise at Castaway Villa with new kitchen, baths, & Tesla batteries !
Non-smoking
No pets allowed
Map of Cruz Bay
Ratings and reviews
10 / 10Outstanding·Feb 2026
House is wonderful. Spotlessly clean, great kitchen and super location. The neighborhood is great for walking and is close to town and amenities. The pool area is lovely as well. We will definitely be back
10 / 10Outstanding·Dec 2025
Fantastic place, one of the best that we’ve ever stayed at. Beautiful view of water and the pool was big and secluded. The owners were very attentive and left a great welcome basket for us when we arrived. Restaurants, groceries, and the car ferry port in Cruz Bay were all very close-by (5-10 minute drives). Would definitely stay there again
10 / 10Outstanding·Dec 2025
We just got back from a wonderful 9 day stay at Castaway! This place was perfect for our family of four. The reviews saying that the place was located in a "quiet area but close to all of the action in Cruz Bay" were spot on with only a five minute drive. We felt well taken care of as the ONLY hiccup we had was the grill was out of propane but a quick text and Elian was able to bring one in what felt like minutes. The rooms and beds were very comfortable and we felt we had everything we needed to cook breakfast, dinner etc. The pool was PERFECT to come home to after exploring the island all day and felt larger than what is depicted on VRBO. Thanks Todd & Steph for hosting..we got so much in during this St. Jean trip that we won't be back for a while but would definitely stay here again!
10 / 10Outstanding·Nov 2025
The villa was beautiful, and we had no problems at all. We would definitely stay there again.
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Top rated by guests
10Outstanding
(146 Ratings)
"House is wonderful. Spotlessly clean, great kitchen and super location. The neighborhood is great for walking and is close to town and amenities. The pool area is lovely as well. We will definitely be..."
Sarah D.Don't miss out! Price and availability may change
