Owner Direct Vacation Rentals in Flamingo Beach

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203 Flamingo Beach Vacation Homes From $109

Looking for the ideal vacation rental in Flamingo 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.

Pelican Key Hideaway
Pelican Key Hideaway
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.1k from Flamingo Beach center

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

2 Bedrooms4 Guests
New to Booking
$442
Average price / night
Check Availability
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)
0.3k from Flamingo 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)
0.3k from Flamingo 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
Check Availability
villa de charme vue mer superbe
villa de charme vue mer superbe
Villa
Simpson Bay, Sint Maarten (Dutch part)
0.4k from Flamingo Beach center

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

4 Bedrooms6 Guests
New to Booking
$276
Average price / night
Check Availability
Island Bliss Condo
Island Bliss Condo
Apartment
Koolbaai, Sint Maarten (Dutch part)
0.4k from Flamingo Beach center

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

1 Bedroom2 Guests
New to Booking
$218
Average price / night
Check Availability
Beach Front Condos
Beach Front Condos
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.4k from Flamingo Beach center

Security/Safety, Parking, Child Friendly

2 Bedrooms14 Guests
New to Booking
$300
Average price / night
Check Availability
#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
Check Availability
Villa Zircon in Pelican Key awaits you
Villa Zircon in Pelican Key awaits you
Villa
Koolbaai, Sint Maarten (Dutch part)
0.4k from Flamingo Beach center

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

4 Bedrooms10 Guests
New to Booking
$770
Average price / night
Check Availability
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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Newly renovated studio
Newly renovated studio
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.7k from Flamingo Beach center

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

1 Bedroom2 Guests
New to Booking
$145
Average price / night
Check Availability
Villa Cleavage
Villa Cleavage
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.7k from Flamingo Beach center

Guest Services, Laundry, Ocean View, View, Sports/Activities, Balcony/Terrace, Internet

1 Bedroom3 Guests
8.4

Very Good

16 reviews

$109
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)
0.8k from Flamingo 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
Check Availability
Charming 3BR Villa w Private Pool in Pelican Key
Charming 3BR Villa w Private Pool in Pelican Key
Villa
Simpson Bay, Sint Maarten (Dutch part)
0.8k from Flamingo Beach center

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

1 Bedroom8 Guests
10.0

Exceptional

1 reviews

$571
Average price / night
Check Availability
3 Bedroom Condo in Simpson Bay
3 Bedroom Condo in Simpson Bay
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.8k from Flamingo Beach center

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

3 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$320
Average price / night
Check Availability
Sunset Heaven Villa
Sunset Heaven Villa
Villa
Flamingo Beach, Simpson Bay, Sint Maarten
0.8k from Flamingo Beach center

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

3 Bedrooms6 Guests
New to Booking
$400
Average price / night
Check Availability
Blue Sky apartment with lagoon view
Blue Sky apartment with lagoon view
Apartment
Koolbaai, Sint Maarten (Dutch part)
0.8k from Flamingo Beach center

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

1 Bedroom2 Guests
7.0

Good

1 reviews

$219
Average price / night
Check Availability
Luxurious 1 bedroom Apt with pool in Simpson Bay
Luxurious 1 bedroom Apt with pool in Simpson Bay
Apartment
Koolbaai, Sint Maarten (Dutch part)
0.8k from Flamingo Beach center

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

1 Bedroom2 Guests
8.6

Fabulous

5 reviews

$127
Average price / night
Check Availability
1 bedroom apt with pool in Simpson Bay
1 bedroom apt with pool in Simpson Bay
Apartment
Koolbaai, Sint Maarten (Dutch part)
0.8k from Flamingo Beach center

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

1 Bedroom2 Guests
9.0

Fabulous

8 reviews

$172
Average price / night
Check Availability
Blue Sky 1 bedroom apartment in Simpson Bay
Blue Sky 1 bedroom apartment in Simpson Bay
Apartment
Koolbaai, Sint Maarten (Dutch part)
0.8k from Flamingo Beach center

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

1 Bedroom2 Guests
9.0

Fabulous

1 reviews

$193
Average price / night
Check Availability
Blue Sky 2 bedr apartment with pool in Simpson bay
Blue Sky 2 bedr apartment with pool in Simpson bay
Apartment
Koolbaai, Sint Maarten (Dutch part)
0.8k from Flamingo Beach center

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

2 Bedrooms4 Guests
7.5

Good

2 reviews

$219
Average price / night
Check Availability
The luxe 1 bedroom apartment
The luxe 1 bedroom apartment
Apartment
Koolbaai, Sint Maarten (Dutch part)
0.8k from Flamingo Beach center

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

1 Bedroom2 Guests
8.0

Good

3 reviews

$193
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 Flamingo Beach.

Flamingo Beach Vacation Rentals on the Map

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Frequently Asked Questions

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

You can explore 203 verified vacation rentals in Flamingo 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 Flamingo 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 Flamingo 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 Flamingo Beach welcome pets. Currently, 5 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 Flamingo Beach often include amenities such as Internet, Balcony/Terrace, 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.