Discover Your Perfect Estate Chocolate Hole and Great Cruz Bay Rentals by Owner

Estate Chocolate Hole and Great Cruz Bay Rentals by Owner

More Top-Rated Rentals by Owner in Estate Chocolate Hole and Great Cruz Bay Area

Why Choose Rent By Owner for your Estate Chocolate Hole and Great Cruz Bay vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Estate Chocolate Hole and Great Cruz Bay Rentals by Owner

Where are the best neighborhoods to stay in Estate Chocolate Hole and Great Cruz Bay?

When planning your stay on St. John, U.S. Virgin Islands, exploring the neighborhoods of Estate Chocolate Hole and Great Cruz Bay offers you diverse and scenic options for your vacation rental. Estate Chocolate Hole provides a tranquil setting with stunning views and easy access to local beaches, making it ideal for travelers seeking relaxation and natural beauty. Meanwhile, Great Cruz Bay is known for its vibrant community vibe and convenient location close to the bay’s calm waters, perfect for water activities and enjoying island life. Booking through Rent By Owner ensures a seamless experience in these sought-after areas, giving you the comfort and convenience of staying in trusted vacation rentals tailored to your preferences."

Contant Farms

Located within the region, Contant Farms offers a tranquil setting ideal for those seeking a peaceful retreat while enjoying the natural beauty of the area. This destination provides convenient access to local amenities and is perfect for travelers looking to experience authentic island living.

View 31+ Rentals in Contant Farms

Best Times to Visit Estate Chocolate Hole and Great Cruz Bay

When should you plan your Rentals by Owner stay?

Choosing the optimal time to visit this destination can enhance your experience, as seasonal weather patterns and local events in the area influence the best periods for enjoying its natural beauty and relaxing atmosphere.

Peak Season Highlights

spring
December to April

During the peak season, you'll experience warm, sunny days ideal for beach outings and outdoor activities. This is when many travelers flock here for their winter escape.

Average Temperature Daytime: 85°F - Nighttime: 75°F
spring
June to August

Summer months bring lively energy and bustling activity, making it the perfect time for exploring the area and enjoying vibrant local events.

Average Temperature Daytime: 88°F - Nighttime: 78°F

Off-Season Highlights

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May and November

In the shoulder months, you can enjoy fewer crowds and more relaxed surroundings, perfect for a peaceful retreat in the region.

Average Temperature Daytime: 83°F - Nighttime: 73°F
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September and October

These months typically see lower visitor numbers, offering a tranquil environment with occasional showers, ideal for those seeking solitude and quiet beaches.

Average Temperature Daytime: 86°F - Nighttime: 76°F

Weekly Weather Forecast for Estate Chocolate Hole and Great Cruz Bay

How to Book Your Estate Chocolate Hole and Great Cruz Bay vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Estate Chocolate Hole and Great Cruz Bay

More Top-Rated Rentals by Owner in Estate Chocolate Hole and Great Cruz Bay Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor dining area perfect for alfresco meals under the sun or stars.
  • Relax in a spacious terrace or balcony with stunning views of the surrounding scenery.
  • Take advantage of an inviting swimming pool, ideal for cooling off after a day of exploring.
  • Make use of a well-maintained barbecue grill to host memorable cookouts with family and friends.
  • Benefit from lush landscaped gardens that enhance the natural beauty of your stay.
  • Utilize outdoor lounge furniture designed for unwinding while soaking up the tropical ambiance.
  • Access a perfect spot for outdoor recreation, such as kayaking or paddleboarding, right at the property’s doorstep.

Top Attractions Around Estate Chocolate Hole and Great Cruz Bay

What attractions are nearby?

In this vibrant region, you can enjoy a variety of nearby activities such as relaxing on pristine beaches, exploring scenic marine parks, and discovering local cultural sites, making your stay in Estate Chocolate Hole and Great Cruz Bay an unforgettable experience.

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Family Activities

  • Snorkeling at Great Cruz Bay Beach: Discover vibrant marine life just off the shores of this scenic area, perfect for a family adventure in the region.
  • Relaxing Beach Days: Enjoy family-friendly beaches in the area where you can lounge, build sandcastles, and soak up the Caribbean sun.
  • Hiking on the Reef Bay Trail: Embark on an easy trail suitable for families that offers stunning views and a chance to explore the natural beauty of the island's backcountry.
  • Kayaking and Paddleboarding: Rent equipment locally and explore calm waters around Estate Chocolate Hole, making it an ideal activity for family bonding on the water.
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Adult Activities

  • Sailing and Sunset Cruises: Experience breathtaking views of the coastline by joining a sunset cruise that offers a tranquil escape along the waters surrounding the area.
  • Snorkeling Adventures: Discover vibrant marine life and coral reefs just off the coast, making it an ideal activity for exploring the region's underwater beauty.
  • Private Beach Picnics: Relax on secluded beaches with a catered picnic, enjoying the scenic surroundings of this popular vacation destination.
  • Luxury Spa Treatments: Indulge in rejuvenating spa services at nearby resorts, perfect for unwinding after a day of exploring the region’s natural attractions.

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Estate Chocolate Hole and Great Cruz Bay Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local beaches: Take advantage of the region's beautiful beaches to relax and enjoy water activities right outside your rental, ensuring a true island experience.
  • Opt for a rental close to essentials: Choose accommodations near markets and dining options to make your stay more convenient and maximize your time exploring this destination.
  • Engage with the community: Connect with local guides or hosts to uncover hidden spots and insider tips that will enrich your visit to the area.
  • Plan outdoor excursions early: Schedule boat trips or hikes during the cooler parts of the day to make the most of the scenic beauty here while staying comfortable.

Transportation Options

  • Car Rentals: Renting a car is one of the most convenient ways to explore the region, offering flexibility to visit nearby beaches and attractions at your own pace.
  • Taxi Services: Reliable taxi services are readily available for quick trips around the area, making your travel between rental properties and local sites effortless.
  • Shared Shuttle Services: Shared shuttles provide an affordable, eco-friendly transportation option connecting you to popular spots within the destination.
  • Water Taxis: For scenic and quick access across the water, water taxis are an excellent choice to enjoy the stunning coastline and nearby islands.

Local Customs Options

  • Respect for the local environment: You’ll find that eco-friendly practices and conservation efforts are highly valued here, reflecting the community’s commitment to preserving the natural beauty of this destination.
  • Celebration of Caribbean culture: Engaging with local music, food, and festivals allows you to connect authentically with the region’s vibrant cultural traditions.
  • Greeting and social customs: Warm welcomes and friendly interactions are customary, emphasizing the community’s hospitality and openness toward visitors.
  • Respect for local laws and traditions: Observing community guidelines and customs ensures you honor the area's rich heritage while enjoying your stay in this region.

Frequently Asked Questions About Estate Chocolate Hole and Great Cruz Bay Rentals by Owner

1. What are the top vacation rentals in Estate Chocolate Hole and Great Cruz Bay?

There are a lot of options in Estate Chocolate Hole and Great Cruz Bay. If you plan on staying in the Estate Chocolate Hole and Great Cruz Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Estate Chocolate Hole and Great Cruz Bay:

2. How many Rentbyowner vacation rentals are available in Estate Chocolate Hole and Great Cruz Bay?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 359 in the Estate Chocolate Hole and Great Cruz Bay area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Estate Chocolate Hole and Great Cruz Bay. 

3. What is the cancellation policy for vacation rentals in Estate Chocolate Hole and Great Cruz Bay?

Cancellation policies vary depending on the owner and listing. You should review the specific rental's policy details on the listing page or contact the owner directly to understand refund terms and any applicable fees.

4. How do I find available rental properties by owner in this area?

You can easily browse available rentals through Rent By Owner by filtering your search based on travel dates, preferences, and amenities. Each listing provides detailed information to help you choose the perfect property here.

5. Are there any additional fees I should expect when booking a rental by owner in the region?

Additional fees such as cleaning charges, security deposits, or service fees may apply. These details are typically outlined in the listing, so it's advisable to review them carefully or reach out to the owner for clarification before booking.

6. What amenities are commonly included in vacation rentals on this destination?

Most rentals offer amenities like Wi-Fi, air conditioning, fully equipped kitchens, and outdoor spaces. Specific amenities vary by property, so check each listing for the features that suit your needs.

7. How do I communicate with the property owner during the booking process?

The platform facilitates direct communication with owners through messaging features. You can ask questions about the property, confirm details, or request special arrangements before finalizing your reservation.

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More Top-Rated Rentals by Owner in Estate Chocolate Hole and Great Cruz Bay Area