Maho Reef which includes a coastal town, landscape views and a sandy beach

Philipsburg holiday rentals

We found 6,146 holiday rentals — enter your dates for availability

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August 2025

September 2025

Holiday rentals with weekly discounts - Philipsburg (SXM-All Airports)

Showing deals for:21 Nov - 28 Nov

Exceptional

(5 reviews)

Luxury 5 Bedroom Villa

Les Terres Basses, Collectivité de Saint-Martin

9% off

S$1,711 per night

includes taxes & fees

View from porch looking out to patio and sea

Wonderful

(5 reviews)

Beautiful beachfront getaway. Recently updated...air conditioning, through out

Les Terres Basses, St Martin

9% off

S$781 per night

includes taxes & fees

Exceptional

(22 reviews)

Direct Beachfront 6 BDR/en-suite /maid included. Excellent service. Rare gem (H)

Philipsburg, Sint Maarten

8% off

S$1,001 per night

includes taxes & fees

Exceptional

(15 reviews)

DISCOUNTED RATE for a renovated 3 bedroom villa - VILLA HARMONY - Terres Basses

Nettle Bay, Collectivité de Saint-Martin

9% off

S$1,012 per night

includes taxes & fees

Exceptional

(23 reviews)

Direct Beachfront 6 BDR/en-suite /maid included. Excellent service. Rare gem (O)

Philipsburg, Sint Maarten

8% off

S$1,001 per night

includes taxes & fees

Chicken fight in the pool overlooking the Caribbean Sea

Exceptional

(39 reviews)

Beach - Private Heated Pool - 2 Master King Bedrooms - Auto Generator Power

Cole Bay

9% off

S$702 per night

includes taxes & fees

Pool and Sun Deck - you can see for miles, west, north and east!

Exceptional

(38 reviews)

Crème de la Crème: Stunning views of Orient Bay! Grand piano. Kids welcome!

Orient Bay

9% off

S$578 per night

includes taxes & fees

Exceptional

(41 reviews)

Park View Charming 3 bdrs 3 bathrs with amazing view on tintamarre/Pinel island

Cul de Sac, Collectivité de Saint-Martin

9% off

S$427 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Philipsburg

Holiday House in beautiful Cupecoy

Sleeps 5 · 2 bedrooms · 1 bathroom

La Maison de L'Ile, Stylish with Boho Chic Caribbean Flare, 6 Bdrms & 5 Bthrms.

Sleeps 12 · 6 bedrooms · 5 bathrooms

Fully equipped apartment, ideal for remote work, 50 steps from the ocean.

Sleeps 3 · 1 bedroom · 1 bathroom

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Enjoy full kitchens, laundry, pools, gardens and more
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