Private Beach Vacation Rentals in Flamingo Beach, Simpson Bay: Compare 10+ Sites & Save

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35 Best Private Beach Vacation Rentals in Flamingo Beach (Starting from $94)

The Villas at Simpson Bay Resort
The Villas at Simpson Bay Resort
Resort
Simpson Bay, Sint Maarten (Dutch part)
0.3k from Flamingo Beach center

Luxury, Accommodations, Pools, Resorts, Parking, Spa, 5-star, Lodgings, Beach

249 Bedrooms15 Guests
8.3

Very Good

425 reviews

$402
Average price / night
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Simpson Bay Resort Marina & Spa
Simpson Bay Resort Marina & Spa
Resort
Simpson Bay, Sint Maarten (Dutch part)
0.3k from Flamingo Beach center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, 5-star, Lodgings, Beach

406 Bedrooms20 Guests
8.2

Very Good

974 reviews

$389
Average price / night
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Hilton Vacation Club Flamingo Beach Sint Maarten
Hilton Vacation Club Flamingo Beach Sint Maarten
Resort
Simpson Bay, Sint Maarten (Dutch part)
0.4k from Flamingo Beach center

Accommodations, Pools, Resorts, Parking, Romantic, Hilton , 3-star, Lodgings, Beach

240 Bedrooms32 Guests
8.5

Very Good

1029 reviews

$148
Average price / night
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#1 Beach House on the Ocean with Private Pool, HGTV Villa Incognito
#1 Beach House on the Ocean with Private Pool, HGTV Villa Incognito
Villa
Flamingo Beach, Simpson Bay, Sint Maarten
0.4k from Flamingo Beach center

Laundry, Breakfast, Internet, Private Beach, Balcony/Terrace, View, Kitchen

3 Bedrooms6 Guests
New to Booking
$551
Average price / night
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Ocean front villa, pool, private ocean snorkeling
Ocean front villa, pool, private ocean snorkeling
Villa
Simpson Bay, Sint Maarten (Dutch part)
0.6k from Flamingo Beach center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms6 Guests
8.3

Very Good

7 reviews

$440
Average price / night
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Hilton Vacation Club Royal Palm St Maarten
Hilton Vacation Club Royal Palm St Maarten
Resort
Simpson Bay, Sint Maarten (Dutch part)
0.7k from Flamingo Beach center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, Hilton , 3-star, Lodgings

117 Bedrooms18 Guests
8.8

Fabulous

357 reviews

$225
Average price / night
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Cocos Bechfront Breeze
Cocos Bechfront Breeze
Apartment
Simpson Bay, Sint Maarten (Dutch part)
1.6k from Flamingo Beach center

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

1 Bedroom1 Guest
New to Booking
$366
Average price / night
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Blue Sanctuary
Blue Sanctuary
Villa
Koolbaai, Sint Maarten (Dutch part)
2.2k from Flamingo Beach center

Wellness Facilities, Entertainment, Restaurant, Ocean View, Parking, Air Conditioner, Spa

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$575
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)
2.6k from Flamingo 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 - Grand Ocean Suite - 2 Bedroom
Maho Beach House - Grand Ocean Suite - 2 Bedroom
Apartment
Maho Reef, Sint Maarten (Dutch part)
2.6k from Flamingo Beach center

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

2 Bedrooms6 Guests
9.7

Exceptional

4 reviews

$420
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)
2.7k from Flamingo 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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Emerald Apt at Maho Beach
Emerald Apt at Maho Beach
Apartment
Maho Reef, Sint Maarten (Dutch part)
2.7k from Flamingo 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)
2.7k from Flamingo 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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Maho Beach House - Premier 1-Bedroom, Oceanview Suite
Maho Beach House - Premier 1-Bedroom, Oceanview Suite
Apartment
Maho Reef, Sint Maarten (Dutch part)
2.7k from Flamingo 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 - Petite Studio - Ocean View
Maho Beach House - Petite Studio - Ocean View
Apartment
Maho Reef, Sint Maarten (Dutch part)
2.7k from Flamingo Beach center

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

1 Bedroom3 Guests
7.3

Good

24 reviews

$214
Average price / night
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Maho Beach House - Petite Studio - Beach Access
Maho Beach House - Petite Studio - Beach Access
Apartment
Maho Reef, Sint Maarten (Dutch part)
2.7k from Flamingo Beach center

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

1 Bedroom2 Guests
8.8

Fabulous

47 reviews

$139
Average price / night
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Maho Beach House - Ocean Suite - 2 Bedroom
Maho Beach House - Ocean Suite - 2 Bedroom
Apartment
Maho Reef, Sint Maarten (Dutch part)
2.7k from Flamingo Beach center

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

2 Bedrooms6 Guests
New to Booking
$400
Average price / night
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Fourteen at Mullet Bay
Fourteen at Mullet Bay
Apartment
Cupecoy, Sint Maarten (Dutch part)
3.7k from Flamingo Beach center

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

138 Bedrooms274 Guests
8.7

Fabulous

208 reviews

$390
Average price / night
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B1401 - Fourteen at Mullet Bay, Luxurious and Cosy 2bed apartment with the sea view
B1401 - Fourteen at Mullet Bay, Luxurious and Cosy 2bed apartment with the sea view
Apartment
Cupecoy, Sint Maarten (Dutch part)
4.0k from Flamingo Beach center

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

2 Bedrooms4 Guests
10.0

Exceptional

7 reviews

$445
Average price / night
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Beachfront Serenity
Beachfront Serenity
Apartment
Cupecoy, Sint Maarten (Dutch part)
4.1k from Flamingo Beach center

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

1 Bedroom4 Guests
New to Booking
$333
Average price / night
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Cupecoy Beach Club Condo
Cupecoy Beach Club Condo
Apartment
Lowlands, Sint Maarten (Dutch part)
4.1k from Flamingo Beach center

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

2 Bedrooms6 Guests
New to Booking
$695
Average price / night
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Divi Little Bay Beach Resort
Divi Little Bay Beach Resort
Resort
Flamingo Beach, Simpson Bay, Sint Maarten
4.1k from Flamingo Beach center

Accommodations, Pools, Resorts, Parking, Spa, 4-star, Lodgings, Beach, Hot tubs

134 Bedrooms14 Guests
8.1

Very Good

156 reviews

$332
Average price / night
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Oceanfront Paradise: Penthouse with Peloton
Oceanfront Paradise: Penthouse with Peloton
Apartment
Cupecoy, Sint Maarten (Dutch part)
4.3k from Flamingo Beach center

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

2 Bedrooms6 Guests
New to Booking
$307
Average price / night
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Tranquil Oceanside: Pools & Direct Beach Access
Tranquil Oceanside: Pools & Direct Beach Access
Apartment
Cupecoy, Sint Maarten (Dutch part)
4.3k from Flamingo Beach center

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

2 Bedrooms4 Guests
New to Booking
$733
Average price / night
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Ocean Bliss: Balcony & Pools & Peloton Bike!
Ocean Bliss: Balcony & Pools & Peloton Bike!
Apartment
Cupecoy, Sint Maarten (Dutch part)
4.3k from Flamingo Beach center

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

2 Bedrooms6 Guests
9.3

Superb

3 reviews

$289
Average price / night
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Prive Loft
Prive Loft
Apartment
Cupecoy, Sint Maarten (Dutch part)
4.5k from Flamingo Beach center

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

1 Bedroom3 Guests
9.7

Exceptional

3 reviews

$94
Average price / night
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The Sunset Charm Penthouse
The Sunset Charm Penthouse
Apartment
Cupe Coy, Sint Maarten (Dutch part)
4.9k from Flamingo Beach center

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

3 Bedrooms8 Guests
New to Booking
$450
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 Private Beach Vacation Rentals in Flamingo Beach.

Where to stay in Flamingo Beach? Best neighborhoods & areas

Flamingo Beach Private Beach Vacation Rentals on the Map

Frequently Asked Questions

You can explore 35 verified private beach vacation rentals in Flamingo Beach. These include secluded coastal homes and estates that offer direct beach access with a higher level of privacy.

Prices for private beach rentals in Flamingo Beach vary depending on the property size, location, and level of beach access. Rates typically start from around $94 per night, with higher prices for larger homes or properties located on more exclusive stretches of coastline.

A private beach rental typically provides direct access to a stretch of sand that is limited to guests or nearby residents. Access levels can vary by location, so reviewing property details can help you understand how secluded the beach area is.

Yes, some private beach rentals in Flamingo Beach welcome pets. Currently, 13 listings allow pets, although policies may vary. It’s also important to check local beach regulations for any seasonal or area-specific restrictions.

Private beach properties are often limited in number and in high demand, so booking 90 to 150 days in advance is recommended for the best selection. Planning early increases your chances of securing a more secluded and desirable property.

Private beach rentals in Flamingo Beach often include amenities such as Internet, View, and Ocean View. These features enhance comfort and allow guests to enjoy a more private and relaxing coastal stay.

Yes, there is a difference. "Oceanfront" means the property is located directly by the water, while "Private Beach" typically indicates that access to the beach area is restricted or less crowded. This distinction is important for travelers seeking a quieter and more exclusive beach experience.