Owner Direct Vacation Rentals in Simpson Bay Beach

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203 Simpson Bay Beach Vacation Homes From $109

Looking for the ideal vacation rental in Simpson Bay Beach? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.

Cocos Bechfront Breeze
Cocos Bechfront Breeze
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.3k from Simpson Bay Beach center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Beach, Places to stay

1 Bedroom1 Guest
New to Booking
$366
Average price / night
Check Availability
The Horny Toad Guest House
The Horny Toad Guest House
Apartment
Simpson Bay Beach, Simpson Bay, Sint Maarten
0.4k from Simpson Bay Beach center

Apartments, Accommodations, Parking, Serviced apartments, Lodgings, Vacation rentals, Beach, Places to stay, Self-catering

8 Bedrooms16 Guests
9.6

Exceptional

109 reviews

$344
Average price / night
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Sunnydays Condo
Sunnydays Condo
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.7k from Simpson Bay Beach center

Apartments, Accommodations, Pools, Parking, Lodgings, Beach, Places to stay, Condos

2 Bedrooms4 Guests
New to Booking
$436
Average price / night
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2-Bedroom Condo With Marina Views In Simpson Bay
2-Bedroom Condo With Marina Views In Simpson Bay
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.8k from Simpson Bay Beach center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering, Condos

2 Bedrooms6 Guests
8.8

Fabulous

4 reviews

$236
Average price / night
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Tradewinds Apartments Simpson Bay
Tradewinds Apartments Simpson Bay
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.9k from Simpson Bay Beach center

Apartments, Cheap, Accommodations, Pools, Lodgings, Vacation rentals, Beach, Places to stay, Family

12 Bedrooms30 Guests
9.3

Superb

168 reviews

$250
Average price / night
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Hamaka condo a beachfront retreat on Simpson Bay Beach
Hamaka condo a beachfront retreat on Simpson Bay Beach
House
Simpson Bay, Sint Maarten (Dutch part)
0.9k from Simpson Bay Beach center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom3 Guests
9.2

Superb

5 reviews

$210
Average price / night
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Beacon Hill Hideaway Luxury Condo in Simpson Bay
Beacon Hill Hideaway Luxury Condo in Simpson Bay
Apartment
Simpson Bay, Sint Maarten (Dutch part)
1.1k from Simpson Bay Beach center

Apartments, Luxury, Accommodations, Pools, Parking, Lodgings, Beach, Places to stay, Condos

1 Bedroom6 Guests
New to Booking
$379
Average price / night
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New* Tropical Modern Townhouse in SXM
New* Tropical Modern Townhouse in SXM
Villa
Simpson Bay, Sint Maarten (Dutch part)
1.2k from Simpson Bay Beach center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Self-catering

4 Bedrooms8 Guests
8.0

Good

3 reviews

$276
Average price / night
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SXM Spotters Paradise
SXM Spotters Paradise
Apartment
Simpson Bay Beach, Simpson Bay, Sint Maarten
1.2k from Simpson Bay Beach center

Sports/Activities, Parking, Smoking, View, Air Conditioner, Internet, Security/Safety

6 Bedrooms12 Guests
8.1

Very Good

18 reviews

$189
Average price / night
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Studio Sleeps 2 with Free Parking
Studio Sleeps 2 with Free Parking
Apartment
Simpson Bay Beach, Simpson Bay, Sint Maarten
1.2k from Simpson Bay Beach center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

1 Bedroom2 Guests
9.6

Exceptional

10 reviews

$115
Average price / night
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Pelican Key Hideaway
Pelican Key Hideaway
Apartment
Simpson Bay, Sint Maarten (Dutch part)
1.3k from Simpson Bay Beach center

Apartments, Accommodations, Parking, Serviced apartments, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$442
Average price / night
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SURFSONG VILLA-NEW LUXURY WATER FRONT VILLA-6 BEDS also available in 4 and 5 beds
SURFSONG VILLA-NEW LUXURY WATER FRONT VILLA-6 BEDS also available in 4 and 5 beds
Villa
Maho Reef, Sint Maarten (Dutch part)
1.3k from Simpson Bay Beach center

Internet, View, Air Conditioner, Ocean View, Pet Friendly, Oceanfront, Balcony/Terrace

6 Bedrooms12 Guests
New to Booking
$1574
Average price / night
Check Availability
Reflection Z 5 Star Villa
Reflection Z 5 Star Villa
Villa
Simpson Bay Beach, Simpson Bay, Sint Maarten
1.3k from Simpson Bay Beach center

Transportation/Shuttle, Child Friendly, View, Smoking, Parking, Security/Safety, Breakfast

3 Bedrooms6 Guests
9.4

Superb

8 reviews

$700
Average price / night
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Ocean&airport view condo with pool&gym in Maho, walk to Maho Beach and Mullet Bay
Ocean&airport view condo with pool&gym in Maho, walk to Maho Beach and Mullet Bay
Apartment
Philipsburg, Sint Maarten (Dutch part)
1.4k from Simpson Bay Beach center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom2 Guests
8.5

Very Good

21 reviews

$109
Average price / night
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Cozy Maho Studio w Pool Gym & Nearby Beaches
Cozy Maho Studio w Pool Gym & Nearby Beaches
Apartment
Maho Reef, Sint Maarten (Dutch part)
1.4k from Simpson Bay Beach center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay

1 Bedroom2 Guests
8.0

Good

2 reviews

$115
Average price / night
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Emerald Apt at Maho Beach
Emerald Apt at Maho Beach
Apartment
Maho Reef, Sint Maarten (Dutch part)
1.5k from Simpson Bay Beach center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Beach, Places to stay, Self-catering

1 Bedroom2 Guests
8.6

Fabulous

9 reviews

$126
Average price / night
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Emerald Upscale Studio in Maho-Walking distance to beach
Emerald Upscale Studio in Maho-Walking distance to beach
Apartment
Maho Reef, Sint Maarten (Dutch part)
1.5k from Simpson Bay Beach center

Apartments, Accommodations, Pools, Parking, Lodgings, Beach, Places to stay, Self-catering

1 Bedroom2 Guests
7.4

Good

9 reviews

$130
Average price / night
Check Availability
Paraiso in St Maarten- Steps away from Bars & Restaurants and Beach!
Paraiso in St Maarten- Steps away from Bars & Restaurants and Beach!
Apartment
Simpson Bay, Sint Maarten (Dutch part)
1.5k from Simpson Bay Beach center

Parking, Ocean View, Guest Services, Internet, Balcony/Terrace, Barbecue/Outdoor Cooking, Security/Safety

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$369
Average price / night
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Beach Front Condos
Beach Front Condos
Apartment
Simpson Bay, Sint Maarten (Dutch part)
1.5k from Simpson Bay Beach center

Security/Safety, Parking, Child Friendly

2 Bedrooms14 Guests
New to Booking
$300
Average price / night
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villa de charme vue mer superbe
villa de charme vue mer superbe
Villa
Simpson Bay, Sint Maarten (Dutch part)
1.6k from Simpson Bay Beach center

Balcony/Terrace, Pool, Air Conditioner, Parking, Internet, Child Friendly

4 Bedrooms6 Guests
New to Booking
$276
Average price / night
Check Availability
Maho Beach House - 2 Bedroom Corner Ocean Suite
Maho Beach House - 2 Bedroom Corner Ocean Suite
Apartment
Simpson Bay, Sint Maarten (Dutch part)
1.6k from Simpson Bay Beach center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

1 Bedroom6 Guests
New to Booking
$484
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Simpson Bay Beach.

Simpson Bay Beach Vacation Rentals on the Map

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Frequently Asked Questions

There are a lot of options in Simpson Bay Beach. If you plan on staying in the Simpson Bay 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 Simpson Bay Beach

You can explore 203 verified vacation rentals in Simpson Bay Beach. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Simpson Bay Beach vary depending on the season, property size, and location. Rates typically start from around $109 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Simpson Bay Beach include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Simpson Bay Beach welcome pets. Currently, 29 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it's recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Simpson Bay Beach often include amenities such as Internet, Child Friendly, and Security/Safety. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.