Discover Your Perfect Pineapple Beach Vacation Homes

Best Vacation Homes in Pineapple Beach

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10.0 (42 Reviews)
Apartment
139 m² Apartment ∙ 2 bedrooms ∙ 6 guests
  • 1496 ft² Apartment
  • Air Conditioner
  • Parking
  • Pool
View Availability
10.0 (24 Reviews)
Apartment
139 m² Apartment ∙ 2 bedrooms ∙ 6 guests
  • 1496 ft² Apartment
  • Air Conditioner
  • Parking
  • Pool
View Availability

Why Choose Rent By Owner for your Pineapple Beach Vacation Rental Homes?

What makes our Vacation Rentals 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 Pineapple Beach Vacation Rentals

Where are the best neighborhoods to stay in Pineapple Beach?

When planning your stay in Pineapple Beach, St. Thomas, U.S. Virgin Islands, you'll find that the neighborhood offers a tranquil and picturesque setting perfect for relaxation. Located along the island’s stunning coastline, this area provides easy access to pristine beaches and breathtaking ocean views. Whether you're seeking a peaceful retreat or convenient proximity to local amenities, staying in Pineapple Beach ensures an authentic Caribbean experience. Explore the variety of vacation rentals available nearby to enjoy a seamless and dependable booking process, making your tropical getaway both memorable and hassle-free.

Green Cay Plantation

Located in the scenic region near Pineapple Beach, Green Cay Plantation offers a tranquil retreat with easy access to vibrant local attractions, making it an ideal spot for those seeking relaxation and convenience.

View 126+ Rentals in Green Cay Plantation

Contant Farms

Nestled within the lush surroundings of this area, Contant Farms provides an authentic island experience with close proximity to beautiful beaches and outdoor activities, perfect for exploring here.

View 33+ Rentals in Contant Farms

Rosendal

This peaceful neighborhood is just a short drive from the coast, offering quiet accommodations amidst stunning tropical scenery, ideal for unwinding during your stay in the region.

View 168+ Rentals in Rosendal

Havensight

As a bustling port area nearby, Havensight is perfect for travelers who want convenient access to shopping, dining, and cruise excursions while staying close to the waters here.

View 1073+ Rentals in Havensight

Bellevue

Set atop scenic hills, Bellevue provides breathtaking views and easy access to the area's most popular beaches, making it a desirable choice for exploring the best of this destination.

View 1030+ Rentals in Bellevue

Contant Hill

Perched in a peaceful part of the island, this area offers elevated views and proximity to natural parks, ideal for visitors seeking a serene getaway in the region.

View 1260+ Rentals in Contant Hill

Rendezvous & Ditleff

Known for its charming ambiance, this neighborhood combines privacy with easy access to hiking trails and beaches, perfect for an immersive island experience here.

View 1259+ Rentals in Rendezvous & Ditleff

Point Rendezvous

Offering stunning waterfront vistas, this area is favored for its scenic tranquility and proximity to the island’s natural beauty, suitable for memorable stays in the region.

View 1268+ Rentals in Point Rendezvous

Best Times to Visit Pineapple Beach

When should you plan your Vacation Rentals stay?

To make the most of your stay here, consider visiting during the shoulder seasons when the weather is delightful and the area offers fewer crowds, ensuring an optimal experience with your chosen vacation rentals in Pineapple Beach, St. Thomas, U.S. Virgin Islands.

Peak Season Highlights

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Winter (December to April)

During the winter months, you'll experience the region's busiest season with warm, inviting weather that attracts many visitors seeking a tropical escape. The area’s vibrant atmosphere and lively events make it an ideal time for booking your vacation rental here.

Average Temperature Daytime: 78°F to 85°F - Nighttime: 70°F to 75°F
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Summer (June to August)

The summer season draws travelers looking to enjoy the warmest weather and longer daylight hours. Expect more activity and a bustling vibe, perfect for those who want to immerse themselves in the local culture while booking a comfortable vacation rental in this destination.

Average Temperature Daytime: 88°F to 90°F - Nighttime: 77°F to 80°F

Off-Season Highlights

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Late Spring (May)

In late spring, visitation slows slightly, providing a more relaxed experience without sacrificing great weather. Booking your vacation rental during this period allows you to enjoy the tranquility of the area before the summer rush begins.

Average Temperature Daytime: 82°F to 86°F - Nighttime: 72°F to 76°F
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Fall (September to November)

Autumn offers fewer crowds and lower rates, making it a desirable time for your getaway. You can still expect warm temperatures and pleasant evenings while enjoying a more peaceful atmosphere at your vacation rental here.

Average Temperature Daytime: 81°F to 84°F - Nighttime: 73°F to 77°F

Weekly Weather Forecast for Pineapple Beach

How to Book Your Pineapple Beach Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. 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 Pineapple Beach

More Top-Rated Vacation Rentals in Pineapple Beach Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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 the stunning ocean views from your private outdoor space at your vacation rental in the area.
  • Relax by the outdoor swimming pool if your property offers one, perfect for cooling off under the sun.
  • Take advantage of spacious patios or decks to dine al fresco with the scenic surroundings as your backdrop.
  • Make the most of lush, landscaped gardens that provide a peaceful ambiance right outside your door.
  • Participate in outdoor recreational activities such as beach volleyball or paddleboarding available nearby.
  • Benefit from convenient outdoor parking facilities to easily explore this tropical region at your own pace.
  • Use outdoor grilling areas, ideal for hosting casual cookouts and enjoying local flavors with family and friends.

Top Attractions Around Pineapple Beach

What attractions are nearby?

In this charming destination, you can enjoy a variety of nearby activities such as relaxing on the pristine beaches, exploring vibrant local markets, or taking scenic boat tours along the coast—all just moments from your Pineapple Beach vacation rental.

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Family Activities

  • Snorkeling Adventures: Explore the vibrant coral reefs just off the coast, offering families a memorable underwater experience in this tropical paradise.
  • Beach Picnics and Relaxation: Enjoy a day of lounging on the pristine sands while savoring a picnic with locally sourced treats, perfect for relaxing with loved ones.
  • Water Sports Activities: Engage in fun-filled activities such as paddleboarding or kayaking, providing exciting ways to explore the calm waters here as a family.
  • Nature Walks and Scenic Viewing: Discover scenic trails and lookout points that showcase the area's natural beauty, ideal for easy hikes suitable for all ages.
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Adult Activities

  • Sailing Tours: Explore the crystal-clear waters with a sailing excursion that offers stunning views and a relaxing way to experience the region's maritime beauty.
  • Snorkeling Adventures: Discover vibrant marine life and colorful coral reefs just off the coast of this destination, perfect for underwater exploration.
  • Beachside Dining: Indulge in local cuisine at beachfront restaurants, enjoying fresh seafood while soaking in scenic ocean vistas.
  • Sunset Cruises: Unwind on a sunset cruise that provides an unforgettable perspective of the area's breathtaking sunsets over the water.

Pineapple Beach Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities Early: Booking outdoor excursions and water activities in advance ensures you make the most of your time in this tropical destination.
  • Choose a Prime Location: Select vacation rentals near the beach or main attractions to maximize your relaxation and exploration opportunities here.
  • Respect the Local Environment: Practice eco-friendly habits to help preserve the natural beauty that makes this area a sought-after getaway spot.
  • Enjoy Authentic Local Cuisine: Take advantage of nearby dining options to experience the regional flavors that add to your memorable stay in the region.

Transportation Options

  • Taxis and Ride-Sharing Services: Conveniently available for quick trips around the area, allowing you to explore the region without the hassle of driving yourself.
  • Car Rentals: Offering flexibility and independence, local car rental agencies enable you to discover all that this destination has to offer at your own pace.
  • Public Transportation: Buses provide an economical transportation option connecting key points within the region, ideal for budget-conscious travelers.
  • Ferries and Water Taxis: Accessible for scenic crossings and day trips between nearby islands or coastal destinations, enhancing your island experience here.

Local Customs Options

  • Greetings and Farewells: When visiting this Caribbean destination, it’s customary to greet locals with a warm "Good morning" or "Good afternoon" to show respect and friendliness.
  • Respect for the Environment: Maintaining cleanliness and respecting the natural beauty of the area is highly valued by residents and visitors alike.
  • Local Market Interactions: Engaging in friendly conversations and bargaining politely at markets enhances your experience and reflects appreciation for local culture.
  • Celebrating Festivals: Participating or observing traditional festivals and events offers insight into the region’s rich history and customs, creating meaningful memories during your stay.

Frequently Asked Questions About Pineapple Beach?

What are the top vacation rentals in Pineapple Beach?

There are a lot of options in Pineapple Beach. If you plan on staying in the Pineapple Beach area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pineapple Beach:

How many Rentbyowner vacation rentals are available in Pineapple Beach?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1947 in the Pineapple Beach 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 Pineapple Beach. 

Best Vacation Homes in Pineapple Beach