Discover Your Perfect Hollywood Casino Vacation Homes

Best Vacation Homes in Hollywood Casino

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10.0 (21 Reviews)
Apartment
125 m² Apartment ∙ 4 bedrooms ∙ 8 guests
  • 1345 ft² Apartment
  • Air Conditioner
  • Parking
  • Pool
View Availability
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9.0 (3 Reviews)
Villa
55 m² Villa ∙ 3 bedrooms ∙ 6 guests
  • 592 ft² Villa
  • Air Conditioner
  • Parking
  • Pool
View Availability

Why Choose Rent By Owner for your Hollywood Casino 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 Hollywood Casino Vacation Rentals

Where are the best neighborhoods to stay in Hollywood Casino?

When choosing where to stay in the vibrant area surrounding Hollywood Casino in Simpson Bay, Sint Maarten, you'll find a variety of neighborhoods that cater to different preferences and lifestyles. Whether you're seeking a lively atmosphere close to entertainment or a more tranquil setting by the coast, the local neighborhoods offer an authentic Caribbean experience. Exploring these areas will help you discover the perfect vacation rental tailored to your desires, ensuring a memorable stay on this beautiful island.

Pelican Key

This neighborhood offers a tranquil setting with easy access to the vibrant nightlife and beaches, making it an ideal spot for those seeking both relaxation and entertainment in the region. Here, you can enjoy a peaceful retreat while remaining close to the area's popular attractions.

View 100+ Rentals in Pelican Key

Maho

Known for its lively atmosphere and proximity to world-famous airport views, this destination is perfect if you're looking to experience the energetic side of the region. Staying here places you near bustling entertainment options and iconic moments right outside your doorstep.

View 463+ Rentals in Maho

Cay Bay

Offering direct access to beautiful beaches and calm waters, this area is suited for travelers wanting a relaxing seaside escape. It provides a convenient base for exploring the scenic coastlines and enjoying water-based activities.

View 1010+ Rentals in Cay Bay

Almond Grove

Nestled within a lush setting, this neighborhood provides a peaceful environment with close proximity to local amenities. It's an excellent choice for those seeking a serene stay while staying connected to the area's attractions.

View 1024+ Rentals in Almond Grove

Indigo Bay

Positioned near the heart of the city, this location offers convenient access to shopping, dining, and entertainment options. Staying here means being at the center of the region's lively scene while enjoying comfortable accommodations.

View 58+ Rentals in Indigo Bay

Belair

This community combines a quiet residential ambiance with close proximity to the bustling town center. It's well-suited for travelers who want a balance of leisure and accessibility during their visit.

View 33+ Rentals in Belair

St. Peters

Known for its peaceful surroundings and scenic views, this neighborhood offers a relaxed environment just minutes from local attractions. It’s ideal for visitors seeking a calming retreat close to the area's highlights.

View 824+ Rentals in St. Peters

Fort William

With its rich history and picturesque setting, this area provides a charming backdrop for your stay, offering easy access to the city's cultural sites and waterfront activities. It’s perfect for travelers interested in exploring the region’s heritage while enjoying modern comforts.

View 1015+ Rentals in Fort William

Best Times to Visit Hollywood Casino

When should you plan your Vacation Rentals stay?

Timing your visit to this destination can significantly enhance your experience, so consider the most favorable seasons to enjoy ideal weather and local events in the area when booking your vacation rentals here.

Peak Season Highlights

spring
December to April

This is the most popular time to visit, with warm weather and lively events enhancing your experience here.

Average Temperature Daytime: 27°C - Nighttime: 22°C
spring
June to August

During these months, you can enjoy the vibrant atmosphere and bustling activities in the area, making it ideal for lively vacations.

Average Temperature Daytime: 30°C - Nighttime: 24°C

Off-Season Highlights

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May and November

Visit during these shoulder months to enjoy fewer crowds and more relaxed surroundings while still experiencing pleasant weather.

Average Temperature Daytime: 28°C - Nighttime: 21°C
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September to October

This period tends to be quieter, offering a more peaceful stay as the region experiences less tourist traffic.

Average Temperature Daytime: 29°C - Nighttime: 23°C

Weekly Weather Forecast for Hollywood Casino

How to Book Your Hollywood Casino 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 Hollywood Casino

More Top-Rated Vacation Rentals in Hollywood Casino 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 a refreshing outdoor swimming pool to unwind after exploring the area.
  • Take advantage of well-maintained outdoor dining areas perfect for al fresco meals.
  • Relax on private patios or balconies with scenic views of the surrounding landscape.
  • Make the most of lush garden spaces that provide a tranquil setting for relaxation.
  • Utilize available outdoor lounge furniture for sunbathing or casual gatherings.
  • Participate in outdoor recreational activities such as volleyball or other lawn games.
  • Benefit from secure gated entryways and private parking for added convenience during your stay.

Top Attractions Around Hollywood Casino

What attractions are nearby?

While staying nearby, you'll have the opportunity to enjoy a variety of activities in this vibrant destination, from relaxing on beautiful beaches to exploring local dining and entertainment options just moments from your vacation rental.

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Family Activities

  • Hollywood Casino Family Fun Day: Experience an exciting day at the casino with kid-friendly events and entertainment designed for families in this lively area.
  • Beachside Activities: Enjoy a relaxing afternoon building sandcastles or swimming at the pristine beaches just minutes from your vacation rental in the region.
  • Water Sports Adventures: Discover thrilling water sports such as snorkeling or paddleboarding that are perfect for adventurous families visiting here.
  • Local Dining Experiences: Savor delicious cuisine at family-friendly restaurants nearby, offering a variety of local flavors in a welcoming atmosphere.
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Adult Activities

  • Casino Gaming: Test your luck at the local casino, where the excitement of table games and slot machines creates a lively atmosphere perfect for an adult evening out.
  • Putt-Putt Golf: Enjoy a fun-filled round of mini-golf along the scenic course that offers a relaxing way to unwind while taking in the vibrant surroundings.
  • Fine Dining Experiences: Savor exquisite Caribbean cuisine and international flavors at the area’s top restaurants, ideal for memorable dinners during your stay.
  • Nightlife and Bars: Explore the energetic nightlife scene with trendy bars and lounges nearby, providing great venues to socialize and enjoy local entertainment.

Hollywood Casino Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities Early: Take advantage of the area’s vibrant entertainment options by scheduling your favorite activities in advance to make the most of your stay here.
  • Choose a Prime Location: Opt for holiday homes near the key attractions and amenities to enjoy effortless access to the region’s lively scene and beautiful beaches.
  • Experience Local Cuisine: Incorporate visits to nearby dining spots into your itinerary to savor the authentic flavors that highlight this destination's culinary charm.
  • Stay Connected with Reliable Wi-Fi: Select accommodations offering dependable internet service to keep you connected whether you're planning outings or sharing moments from your trip.

Transportation Options

  • Public Transit: Buses serve the area regularly, providing an affordable way to explore Simpson Bay and its surroundings.
  • Taxi Services: Taxis are readily available for quick and convenient transportation around the region, especially from this destination's central location.
  • Car Rentals: Renting a car offers flexibility and comfort, perfect for discovering hidden gems and scenic routes nearby.
  • Private Shuttle Transfers: Private shuttles can be arranged for stress-free transportation between your vacation rentals and popular destinations in the vicinity.

Local Customs Options

  • Respect for Local Customs: Embrace the friendly and welcoming attitude of the area, where politeness and courteous interactions are highly valued by locals.
  • Dress Appropriately: When visiting local establishments or religious sites, it is customary to dress modestly as a sign of respect for the region's cultural norms.
  • Photography Etiquette: Always ask permission before photographing local residents or their properties to honor their privacy and cultural sensitivities.
  • Celebration and Festivals: Participate in community events and festivals with enthusiasm, as they highlight the area's rich cultural traditions and are open to visitors seeking authentic experiences.

Frequently Asked Questions About Hollywood Casino?

What are the top vacation rentals in Hollywood Casino?

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

How many Rentbyowner vacation rentals are available in Hollywood Casino?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1619 in the Hollywood Casino 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 Hollywood Casino. 

Best Vacation Homes in Hollywood Casino

10.0 (4 Reviews)
Apartment
Boheme
  • Air Conditioner
  • Parking
  • Balcony/Terrace
View Availability