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

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  2. Vacation Rentals with Pool
  3.  Sint Maarten
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155 Best Vacation Rentals with Pool in Pelican Key (Starting from $127)

Hilton Vacation Club Flamingo Beach Sint Maarten
Hilton Vacation Club Flamingo Beach Sint Maarten
Resort
Simpson Bay, Sint Maarten (Dutch part)
0.1k from Pelican Key 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
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
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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)
0.2k 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
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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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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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The Villas at Simpson Bay Resort
The Villas at Simpson Bay Resort
Resort
Simpson Bay, Sint Maarten (Dutch part)
0.4k from Pelican Key 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)
0.4k from Pelican Key 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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La Vista Resort
La Vista Resort
Resort
Pelican Key, Simpson Bay, Sint Maarten
0.4k from Pelican Key center

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

50 Bedrooms36 Guests
8.9

Fabulous

261 reviews

$160
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
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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
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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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The Atrium Resort and Spa, Sint Maarten
The Atrium Resort and Spa, Sint Maarten
Resort
Simpson Bay, Sint Maarten (Dutch part)
0.5k from Pelican Key center

Accessibility, Oceanfront, Laundry, Security/Safety, Pool, Child Friendly, Ocean View

66 Bedrooms12 Guests
8.5

Very Good

4 reviews

$175
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
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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 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
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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
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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
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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
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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
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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 with Pool in Pelican Key.

Stay Near Pelican Key's Top Attractions

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Pelican Key Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 155 verified vacation rentals with a pool in Pelican Key. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Pelican Key vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $127 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Pelican Key offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Pelican Key welcome pets. Currently, 7 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Pelican Key often include additional outdoor features such as Pool, Internet, and Balcony/Terrace. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Pelican Key offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.