Family-Friendly Vacation Rentals in Simpson Bay Beach, Simpson Bay: Compare 10+ Sites & Save

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177 Best Family Vacation Rentals in Simpson Bay Beach (Starting from $109)

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
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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
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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
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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
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Specious 2 bedroom in Pelican Key near the beach
Specious 2 bedroom in Pelican Key near the beach
Apartment
Simpson Bay, Sint Maarten (Dutch part)
1.6k from Simpson Bay Beach center

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

2 Bedrooms4 Guests
9.0

Fabulous

1 reviews

$220
Average price / night
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Blue Dream Apartments
Blue Dream Apartments
Apartment
Simpson Bay, Sint Maarten (Dutch part)
1.6k from Simpson Bay Beach center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Hot tubs, Places to stay, Self-catering

25 Bedrooms16 Guests
8.3

Very Good

724 reviews

$161
Average price / night
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Maho Beach House - Luxe 1 Bedroom - Ocean Hideaway
Maho Beach House - Luxe 1 Bedroom - Ocean Hideaway
Apartment
Maho Reef, Sint Maarten (Dutch part)
1.6k from Simpson Bay Beach center

Apartments, Accommodations, Pools, Parking, Spa, Pet-friendly, Lodgings, Vacation rentals, Beach

1 Bedroom4 Guests
7.1

Good

7 reviews

$273
Average price / night
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Maho Beach House - Charming Studio - Beach Access
Maho Beach House - Charming Studio - Beach Access
Apartment
Maho Reef, Sint Maarten (Dutch part)
1.7k from Simpson Bay Beach center

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

1 Bedroom4 Guests
8.6

Fabulous

5 reviews

$165
Average price / night
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Maho Beach House - Modern 1 Bedroom Luxe
Maho Beach House - Modern 1 Bedroom Luxe
Apartment
Maho Reef, Sint Maarten (Dutch part)
1.7k from Simpson Bay Beach center

Apartments, Cheap, Accommodations, Pools, Parking, Spa, Pet-friendly, Lodgings, Beach

1 Bedroom3 Guests
9.3

Superb

4 reviews

$244
Average price / night
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Oceanfront Escape At Aqua Mirage Condo!
Oceanfront Escape At Aqua Mirage Condo!
Apartment
Cupecoy, Sint Maarten (Dutch part)
1.7k from Simpson Bay Beach center

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

1 Bedroom6 Guests
9.5

Superb

2 reviews

$244
Average price / night
Check Availability
Maho Beach House - Premier 1-Bedroom, Oceanview Suite
Maho Beach House - Premier 1-Bedroom, Oceanview Suite
Apartment
Maho Reef, Sint Maarten (Dutch part)
1.7k from Simpson Bay Beach center

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

1 Bedroom3 Guests
9.0

Fabulous

1 reviews

$312
Average price / night
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Maho Beach House - Elegant 1 Bedroom, Beach Level
Maho Beach House - Elegant 1 Bedroom, Beach Level
Apartment
Maho Reef, Sint Maarten (Dutch part)
1.7k from Simpson Bay Beach center

Pool, Security/Safety, Balcony/Terrace, Internet, View, Air Conditioner, Ocean View

1 Bedroom4 Guests
6.5

Good

2 reviews

$187
Average price / night
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Pro Tip:
VacationByOwnerRentals 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 Family Vacation Rentals in Simpson Bay Beach.

Where to stay in Simpson Bay Beach? Best neighborhoods & areas

Simpson Bay Beach Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 177 verified family-friendly vacation rentals in Simpson Bay Beach. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Simpson Bay Beach vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $109 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Simpson Bay Beach offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Simpson Bay Beach are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Simpson Bay Beach often include amenities such as Child Friendly, Internet, and Security/Safety. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.