Discover Your Perfect Hollywood Casino Rentals by Owner

Hollywood Casino Rentals by Owner

10.0 (4 Reviews)
Apartment
Boheme
  • Air Conditioner
  • Parking
  • Balcony/Terrace
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10.0 (3 Reviews)
Apartment
The Lady Bug
  • Air Conditioner
  • Parking
  • View
View Availability
More Top-Rated Rentals by Owner in Hollywood Casino Area

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

Where are the best neighborhoods to stay in Hollywood Casino?

When choosing where to stay in the vibrant area of Hollywood Casino in Simpson Bay, Sint Maarten, you'll find a variety of neighborhoods that cater to different preferences. Whether you prefer the lively atmosphere close to entertainment and dining options or a more tranquil retreat with scenic views, the local neighborhoods provide excellent options for a comfortable and convenient stay. Booking your rental by owner through Rent By Owner ensures you enjoy a seamless experience, trusted accommodations, and easy access to the best parts of this beautiful region. Explore the neighborhood options to find the perfect home base for your Caribbean getaway.

Pelican Key

Set just a short drive from Hollywood Casino, Pelican Key offers a tranquil retreat with easy access to the region’s vibrant activities. Here, you can enjoy a peaceful atmosphere while remaining close to popular attractions and amenities.

View 111+ Rentals in Pelican Key

Maho

Located nearby, Maho is renowned for its lively atmosphere and proximity to famous beaches, making it an ideal base for exploring the region's bustling nightlife and stunning coastal scenery.

View 456+ Rentals in Maho

Cay Bay

Just a short distance away, Cay Bay provides a convenient location with scenic views and close proximity to key points of interest in the area, perfect for travelers seeking both relaxation and accessibility.

View 1010+ Rentals in Cay Bay

Almond Grove

Nestled in a quiet part of the region, Almond Grove offers a serene environment while remaining within reach of central attractions and entertainment options.

View 1024+ Rentals in Almond Grove

Indigo Bay

This neighborhood provides a blend of beachside tranquility and city convenience, making it an excellent choice for those who want to explore both the natural beauty and lively areas nearby.

View 64+ Rentals in Indigo Bay

Belair

Located close to the heart of the area, Belair offers easy access to local shopping, dining, and entertainment, ideal for visitors wanting to immerse themselves in the regional culture.

View 32+ Rentals in Belair

St. Peters

Situated slightly away from the busiest spots, St. Peters presents a quieter setting that still keeps you within convenient reach of the region’s main attractions.

View 824+ Rentals in St. Peters

Fort William

Offering a strategic location near major sites, Fort William is suited for travelers who prefer to stay close to the area's historical and cultural highlights.

View 1015+ Rentals in Fort William

Best Times to Visit Hollywood Casino

When should you plan your Rentals by Owner stay?

Choosing the optimal time to visit here can enhance your experience, allowing you to enjoy the local climate and vibrant atmosphere at its best while exploring vacation rentals in Hollywood Casino, Simpson Bay, Sint Maarten.

Peak Season Highlights

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December to April

During this peak season, you can enjoy the warm and sunny weather, making it an ideal time to explore the area’s attractions and relax at your rental property.

Average Temperature Daytime: around 80°F (27°C) - Nighttime: around 70°F (21°C)
spring
June to August

This period sees a surge of visitors attracted by the lively atmosphere and perfect beach weather, perfect for making the most of your stay in the region.

Average Temperature Daytime: about 85°F (29°C) - Nighttime: about 75°F (24°C)

Off-Season Highlights

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May and November

These months tend to be quieter, offering you a more relaxed experience and better rental deals while still enjoying pleasant weather in the area.

Average Temperature Daytime: around 82°F (28°C) - Nighttime: around 72°F (22°C)
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September and October

As the region transitions out of peak tourist season, you’ll find fewer crowds and favorable prices, with warm weather lingering here.

Average Temperature Daytime: approximately 83°F (28°C) - Nighttime: approximately 73°F (23°C)

Weekly Weather Forecast for Hollywood Casino

How to Book Your Hollywood Casino 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 Hollywood Casino

More Top-Rated Rentals by Owner in Hollywood Casino 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 access to private or shared outdoor swimming pools with scenic views of the region's surroundings.
  • Relax in beautifully landscaped gardens or courtyards that offer a peaceful outdoor retreat.
  • Take advantage of spacious patios, decks, or verandas perfect for outdoor dining or lounging.
  • Make the most of outdoor grilling facilities to enhance your culinary experience here.
  • Explore nearby walking paths or trails that showcase the natural beauty of the area.
  • Utilize on-site outdoor sports amenities such as tennis courts, volleyball, or other recreational facilities.
  • Cap off your days with outdoor seating arrangements designed for unobstructed sunset or ocean views.

Top Attractions Around Hollywood Casino

What attractions are nearby?

Within this vibrant destination, you can enjoy a variety of nearby activities such as relaxing on the beautiful beaches, exploring local culture, and discovering exciting water sports—all just moments from your rental by owner in Hollywood Casino, Simpson Bay, Sint Maarten.

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Family Activities

  • Dolphin Discovery St. Maarten: Engage in a memorable family experience by swimming with dolphins or enjoying interactive shows at this popular marine park nearby.
  • Simpson Bay Lagoon Yacht Charters: Explore the scenic waters on a family-friendly boat tour that offers a fun and relaxing way to see the region's natural beauty from the sea.
  • Maho Beach: Enjoy a day of sun, sand, and watching airplanes land just overhead at this iconic beach close to your accommodation in the area.
  • Fort Louis Ground Tour: Discover the history and stunning views of the region while wandering through the historic fort suitable for family exploration and photos.
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Adult Activities

  • Casino Gaming Experience: Test your luck at the popular gaming tables and slot machines that attract visitors seeking entertainment in the region.
  • Spa and Wellness Treatments: Pamper yourself with luxurious spa services available nearby, perfect for relaxation after a day of exploring this lively destination.
  • Fine Dining Options: Enjoy exquisite local and international cuisine at the upscale restaurants within the area, offering an authentic taste of Sint Maarten's culinary scene.
  • Nightlife and Live Entertainment: Experience vibrant nightlife with live music, DJs, and themed events designed to entertain adult visitors in this energetic hub.

Hollywood Casino Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities Early: Take advantage of the region’s vibrant entertainment options by scheduling your casino visits and excursions in advance to maximize your time here.
  • Choose a Strategic Rental Location: Opt for a rental near the main attractions and transportation hubs within the area for convenience and easy access to everything on your itinerary.
  • Explore Local Dining and Nightlife: Immerse yourself in the region’s culinary scene and lively nightlife to enrich your stay beyond the casino experience.
  • Prioritize Comfort and Safety: Select well-reviewed rentals with modern amenities to ensure a relaxing and secure environment during your trip here.

Transportation Options

  • Taxi Services: Reliable local taxis provide convenient transportation for exploring the region and reaching Hollywood Casino with ease.
  • Car Rentals: Numerous car rental agencies in the area allow you to explore Simpson Bay and its surroundings at your own pace, offering flexibility and comfort.
  • Public Buses: Affordable public bus options connect the casino district to other parts of Sint Maarten, making budget-friendly travel straightforward.
  • Private Transfers: Customized private transfer services can be arranged for a seamless and comfortable journey directly to or from Hollywood Casino.

Local Customs Options

  • Respect for Local Customs: You’ll find that embracing the region's warm hospitality involves understanding and honoring local customs at gatherings and events in this vibrant area.
  • Dress Modestly for Religious Sites: When visiting any religious sites nearby, it’s appreciated to wear modest clothing as a sign of respect for local traditions.
  • Participate in Cultural Celebrations: Engaging in regional festivals and traditional ceremonies offers a meaningful way to connect with the area's rich cultural heritage during your stay.
  • Mind Local Etiquette: Maintaining polite social interactions and observing customary greetings enhances your experience and shows respect within the local community here.

Frequently Asked Questions About Hollywood Casino Rentals by Owner

1. 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:

2. 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 1248 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. 

3. What is the cancellation policy for a rental by owner in this area?

Cancellation policies vary by property, so it is recommended to review the specific listing details or contact the owner directly for the most accurate information.

4. How do I confirm the availability of a rental by owner in this destination?

Availability can be checked through the listing calendar on the booking platform. For real-time confirmation, reaching out to the property owner is advised.

5. Are there any additional fees I should be aware of when booking a rental by owner here?

Additional fees such as cleaning, service charges, or deposits are typically outlined in the listing details. Contact the owner if you need clarification about any extra costs.

6. What amenities are typically included in a rental by owner in this region?

Most rentals come with essential amenities like Wi-Fi, air conditioning, and kitchen facilities. Specific inclusions are detailed in each listing, so review the property description carefully.

7. How do I contact the owner if I have questions about my booking?

You can communicate directly with the owner through the messaging system provided on the booking platform. For urgent inquiries, ensure to use the contact details specified in the listing.

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More Top-Rated Rentals by Owner in Hollywood Casino Area