Dolce Dolce Casa - Point Pirouette
Dolce Dolce Casa - Point Pirouette
Dolce Dolce Casa - Point Pirouette
Dolce Dolce Casa - Point Pirouette
Dolce Dolce Casa - Point Pirouette

Dolce Dolce Casa - Point Pirouette

3 bedrooms·3 baths
Sint Maarten

$2,725.00 USD total for 5 nights

Sep 21 – 26, 2026

Sea la Vie - Red Pond Estates
Sea la Vie - Red Pond Estates
Sea la Vie - Red Pond Estates
Sea la Vie - Red Pond Estates
Sea la Vie - Red Pond Estates

Sea la Vie - Red Pond Estates

4 bedrooms·5 baths
Sint Maarten

$3,815.00 USD total for 5 nights

Sep 21 – 26, 2026

Seascapes - Dawn Beach Estate
Seascapes - Dawn Beach Estate
Seascapes - Dawn Beach Estate
Seascapes - Dawn Beach Estate
Seascapes - Dawn Beach Estate

Seascapes - Dawn Beach Estate

4 bedrooms·4 baths
Sint Maarten

$2,802.86 USD total for 5 nights

Sep 21 – 26, 2026

Sky Blue - Dan Beach Estates
Sky Blue - Dan Beach Estates
Sky Blue - Dan Beach Estates
Sky Blue - Dan Beach Estates
Sky Blue - Dan Beach Estates

Sky Blue - Dan Beach Estates

5 bedrooms·5½ baths
Sint Maarten

$4,665.20 USD total for 5 nights

Sep 21 – 26, 2026

Summer Time - Tamarind Hill
Summer Time - Tamarind Hill
Summer Time - Tamarind Hill
Summer Time - Tamarind Hill
Summer Time - Tamarind Hill

Summer Time - Tamarind Hill

5 bedrooms·5 baths
Sint Maarten

$3,114.29 USD total for 5 nights

Sep 21 – 26, 2026

Villa Aqua - Indigo Bay
Villa Aqua - Indigo Bay
Villa Aqua - Indigo Bay
Villa Aqua - Indigo Bay
Villa Aqua - Indigo Bay

Villa Aqua - Indigo Bay

4 bedrooms·4 baths
Sint Maarten

$4,556.20 USD total for 5 nights

Sep 21 – 26, 2026

Diamond Chateau - Cole Bay
Diamond Chateau - Cole Bay
Diamond Chateau - Cole Bay
Diamond Chateau - Cole Bay
Diamond Chateau - Cole Bay

Diamond Chateau - Cole Bay

5 bedrooms·6½ baths
Sint Maarten

$2,335.72 USD total for 5 nights

Sep 21 – 26, 2026

Alizee
Alizee
Alizee
Alizee
Alizee

Alizee

7 bedrooms·7 baths
Sint Maarten

$7,085.00 USD total for 5 nights

Sep 21 – 26, 2026

Villa Paradijs - Hillside
Villa Paradijs - Hillside
Villa Paradijs - Hillside
Villa Paradijs - Hillside
Villa Paradijs - Hillside

Villa Paradijs - Hillside

3 bedrooms·3 baths
Sint Maarten

$1,558.70 USD total for 5 nights

Sep 21 – 26, 2026

Villa Mooi - Red Pond Estate
Villa Mooi - Red Pond Estate
Villa Mooi - Red Pond Estate
Villa Mooi - Red Pond Estate
Villa Mooi - Red Pond Estate

Villa Mooi - Red Pond Estate

3 bedrooms·3 baths
Sint Maarten

$3,698.22 USD total for 5 nights

Sep 21 – 26, 2026

VillaRosa - Red Pond Estates
VillaRosa - Red Pond Estates
VillaRosa - Red Pond Estates
VillaRosa - Red Pond Estates
VillaRosa - Red Pond Estates

VillaRosa - Red Pond Estates

3 bedrooms·3 baths
Sint Maarten

$2,919.64 USD total for 5 nights

Sep 21 – 26, 2026

Windsong - Red Pond Estates
Windsong - Red Pond Estates
Windsong - Red Pond Estates
Windsong - Red Pond Estates
Windsong - Red Pond Estates

Windsong - Red Pond Estates

4 bedrooms·4 baths
Sint Maarten

$3,392.86 USD total for 5 nights

Sep 21 – 26, 2026

Villa BoStar - Tamarind Hill
Villa BoStar - Tamarind Hill
Villa BoStar - Tamarind Hill
Villa BoStar - Tamarind Hill
Villa BoStar - Tamarind Hill

Villa BoStar - Tamarind Hill

3 bedrooms·3½ baths
Sint Maarten

$2,257.86 USD total for 5 nights

Sep 21 – 26, 2026

L'Agua - Oyster Pond
L'Agua - Oyster Pond
L'Agua - Oyster Pond
L'Agua - Oyster Pond
L'Agua - Oyster Pond

L'Agua - Oyster Pond

2 bedrooms·2 baths
Sint Maarten

$2,335.72 USD total for 5 nights

Sep 21 – 26, 2026

Bougainvillea - Dutch
Bougainvillea - Dutch
Bougainvillea - Dutch
Bougainvillea - Dutch
Bougainvillea - Dutch

Bougainvillea - Dutch

5 bedrooms·3 baths
Sint Maarten

$4,671.43 USD total for 5 nights

Sep 21 – 26, 2026

Bella Vita - Pelican Key
Bella Vita - Pelican Key
Bella Vita - Pelican Key
Bella Vita - Pelican Key
Bella Vita - Pelican Key

Bella Vita - Pelican Key

7 bedrooms·7½ baths
Sint Maarten

$8,175.00 USD total for 5 nights

Sep 21 – 26, 2026

Royal Palm Beach Club - Unit 101
Royal Palm Beach Club - Unit 101
Royal Palm Beach Club - Unit 101
Royal Palm Beach Club - Unit 101
Royal Palm Beach Club - Unit 101

Royal Palm Beach Club - Unit 101

3 bedrooms·3 baths
Sint Maarten

$1,863.90 USD total for 5 nights

Sep 21 – 26, 2026

Villa Marisol
Villa Marisol
Villa Marisol
Villa Marisol
Villa Marisol

Villa Marisol

2 bedrooms·3 baths
Sint Maarten

$1,401.43 USD total for 5 nights

Sep 21 – 26, 2026

Royal Palm-5th floor-Amazing OceanViews-1 Bedroom image 1
Royal Palm-5th floor-Amazing OceanViews-1 Bedroom image 2
Royal Palm-5th floor-Amazing OceanViews-1 Bedroom image 3
Royal Palm-5th floor-Amazing OceanViews-1 Bedroom image 4
Royal Palm-5th floor-Amazing OceanViews-1 Bedroom image 5

Royal Palm-5th floor-Amazing OceanViews-1 Bedroom

1 bedroom·1 bath
Simpson Bay • Sint Maarten
4.82(22 reviews)

$1,125.00 USD $1,051.50 USD total for 3 nights

Sep 21 – 24, 2026

Excitement, adventure, and serenity await at this exotic tropical island resort. View from the living room balcony.
Breathtaking view from the living room balcony
Private spa/jacuzzi on a rooftop deck
Resort infinity pool with jacuzzi.
Cozy kitchen for casual dining

Magie Blue at Oyster Pond. Oyster Bay Beach Resort

2 bedrooms·2 baths
Upper Prince's Quarter • Sint Maarten
5(5 reviews)

$1,340.00 USD $1,211.00 USD total for 3 nights

Sep 21 – 24, 2026

On Island Time - St. Martin
On Island Time - St. Martin
On Island Time - St. Martin
On Island Time - St. Martin
On Island Time - St. Martin

On Island Time - St. Martin

3 bedrooms·3 baths
Sint Maarten

$2,608.22 USD total for 5 nights

Sep 21 – 26, 2026

La Mirella - Oyster Pond - Dutch
La Mirella - Oyster Pond - Dutch
La Mirella - Oyster Pond - Dutch
La Mirella - Oyster Pond - Dutch
La Mirella - Oyster Pond - Dutch

La Mirella - Oyster Pond - Dutch

4 bedrooms·4 baths
Sint Maarten

$3,892.86 USD total for 5 nights

Sep 21 – 26, 2026

Summerwinds Villa - Oyster Pond
Summerwinds Villa - Oyster Pond
Summerwinds Villa - Oyster Pond
Summerwinds Villa - Oyster Pond
Summerwinds Villa - Oyster Pond

Summerwinds Villa - Oyster Pond

3 bedrooms·3½ baths
Sint Maarten

$2,725.00 USD total for 5 nights

Sep 21 – 26, 2026

Villa Victoria - Oyster Pond
Villa Victoria - Oyster Pond
Villa Victoria - Oyster Pond
Villa Victoria - Oyster Pond
Villa Victoria - Oyster Pond

Villa Victoria - Oyster Pond

3 bedrooms·3 baths
Sint Maarten

$2,530.36 USD total for 5 nights

Sep 21 – 26, 2026