Vacation Rentals in Pelican Key, Simpson Bay: Compare 10+ Sites & Save

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  4.  Simpson Bay
  5.  Pelican Key

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203 Best Vacation Rentals in Pelican Key (Starting from $109)

Island Bliss Condo
Island Bliss Condo
Apartment
Koolbaai, Sint Maarten (Dutch part)
0.1k from Pelican Key center

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

1 Bedroom2 Guests
New to Booking
$218
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
Pelican Key, Simpson Bay, Sint Maarten
0.1k from Pelican Key center

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

3 Bedrooms6 Guests
New to Booking
$551
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)
0.2k from Pelican Key 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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villa de charme vue mer superbe
villa de charme vue mer superbe
Villa
Simpson Bay, Sint Maarten (Dutch part)
0.2k from Pelican Key center

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

4 Bedrooms6 Guests
New to Booking
$276
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)
0.2k from Pelican Key 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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Newly renovated studio
Newly renovated studio
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.2k from Pelican Key center

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

1 Bedroom2 Guests
New to Booking
$145
Average price / night
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Blue Dream Apartments
Blue Dream Apartments
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.2k from Pelican Key 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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Villa Zircon in Pelican Key awaits you
Villa Zircon in Pelican Key awaits you
Villa
Koolbaai, Sint Maarten (Dutch part)
0.2k from Pelican Key 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
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Villa Cleavage
Villa Cleavage
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.3k from Pelican Key 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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La Villa Salee
La Villa Salee
Villa
Simpson Bay, Sint Maarten (Dutch part)
0.4k from Pelican Key center

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

8 Bedrooms16 Guests
New to Booking
$3509
Average price / night
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Beach Front Condos
Beach Front Condos
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.4k from Pelican Key center

Security/Safety, Parking, Child Friendly

2 Bedrooms14 Guests
New to Booking
$300
Average price / night
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Sunset Heaven Villa
Sunset Heaven Villa
Villa
Pelican Key, Simpson Bay, Sint Maarten
0.4k from Pelican Key center

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

3 Bedrooms6 Guests
New to Booking
$400
Average price / night
Check Availability
Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea
Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea
Villa
Pelican Key, Simpson Bay, Sint Maarten
0.4k from Pelican Key center

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

3 Bedrooms6 Guests
New to Booking
$725
Average price / night
Check Availability
Puerta al Mar
Puerta al Mar
House
Simpson Bay, Sint Maarten (Dutch part)
0.5k from Pelican Key center

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

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$805
Average price / night
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Oceanfront Villa
Oceanfront Villa
Villa
Simpson Bay, Sint Maarten (Dutch part)
0.5k from Pelican Key center

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

1 Bedroom4 Guests
New to Booking
$450
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)
0.5k from Pelican Key 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
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Pelican Key Hideaway
Pelican Key Hideaway
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.5k from Pelican Key center

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

2 Bedrooms4 Guests
New to Booking
$442
Average price / night
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Pelican Pearl
Pelican Pearl
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.5k from Pelican Key center

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

1 Bedroom2 Guests
8.6

Fabulous

21 reviews

$127
Average price / night
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The Hills Residence
The Hills Residence
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.6k from Pelican Key center

Apartments, Cheap, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Vacation rentals, Hot tubs

66 Bedrooms152 Guests
8.8

Fabulous

196 reviews

$226
Average price / night
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3 Bedroom Condo in Simpson Bay
3 Bedroom Condo in Simpson Bay
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.6k from Pelican Key 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
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The Hills Residence at Simpson Bay
The Hills Residence at Simpson Bay
Apartment
Simpson Bay, Sint Maarten (Dutch part)
0.6k from Pelican Key center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Hot tubs, Places to stay, Family

43 Bedrooms96 Guests
6.0

Review score

1 reviews

$251
Average price / night
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Blue Sky apartment with lagoon view
Blue Sky apartment with lagoon view
Apartment
Koolbaai, Sint Maarten (Dutch part)
0.6k from Pelican Key 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)
0.6k from Pelican Key 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)
0.6k from Pelican Key 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)
0.6k from Pelican Key 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)
0.6k from Pelican Key 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)
0.6k from Pelican Key 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:
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 Vacation Rentals in Pelican Key.

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Frequently Asked Questions

You can explore 203 verified vacation rentals in Pelican Key. 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 Pelican Key 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 Pelican Key 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 Pelican Key welcome pets. Currently, 3 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 Pelican Key often include amenities such as Internet, Balcony/Terrace, and Pool. 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.