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Holiday rentals in Philipsburg

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Top-rated holiday rentals in Philipsburg

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A table with two chairs is set on a tiled balcony, offering a panoramic view of the turquoise waters and distant hills. The serene waterfront scene is enhanced by a clear blue sky dotted with white clouds.
Flat in Little Bay
4.93 out of 5 average rating, 27 reviews

Great Bay view charming Apt!

This special place with a Beautiful view of Great Bay! Watch the cruise ships come in with coffee and leave at night with a cocktail! . View Phillipsburg boardwalk from your deck. A short walk down the hill to Little Bay Beach.A mile from Front Street boardwalk shopping. Easy free parking on site. Starlink Wi-fi with a smart Tv and Netflix plus A DVD player with many free DvD’s on site.. Nice Caribbean breezes. 7 night minimum . We suggest renting a car for full enjoyment of touring the island.

Top guest favourite
A bright living area features a spacious sectional sofa, a wooden coffee table, and a light-colored area rug. Large windows allowing natural light create an open ambiance, while artwork adorns the walls. A staircase is visible in the background, leading to an upper level.
Flat in Simpson Bay
5 out of 5 average rating, 65 reviews

The Loft at Simpson Bay Yacht Club

Welcome to The Loft at SBYC. Located in the heart of Simpson Bay in walking distance to the beach, great restaurants, grocery stores, shopping, salons/spas and more. In this fully renovated loft-style apartment, you will find high quality amenities throughout including a European kitchen and an amazing rainfall shower. The SBYC property offers 3 swimming pools, a hot tub, tennis courts and plenty of outdoor space for relaxing, all under 24-hour gated security. Free concierge service included.

Guest favourite
A vibrant blue gate opens to reveal a sandy beach and calm waters. Decorative pots with blooming pink flowers frame the entrance, accompanied by lush green leaves. In the distance, sailboats can be seen on the horizon under a cloudy sky.
Flat in Simpson Bay
4.88 out of 5 average rating, 230 reviews

Apartment on the beach

Let this tranquil, centrally located, 1 bedroom apartment become your home away from home. This beachfront property is located on the BEST and WIDEST stretch of Simpson Bay beach with gentle waves and no rocks, which makes it a perfect spot for swimming. Although this property is tucked away, and there are never many people on this part of the beach, it is in a heart of Simposn Bay. Simpson Bay beach offers one of the longest stretches of uninterrupted sandy, white coastline on Sint Maarten.

Top guest favourite
A dining area features a modern table with four chairs, positioned near large windows showcasing panoramic views of the turquoise sea and sandy beach. A wall mirror reflects the inviting atmosphere, while lush greenery can be seen outside, enhancing the coastal ambiance.
Flat in Simpson Bay
4.96 out of 5 average rating, 215 reviews

Lilly's Beach

This is a very SPECIAL SMAll RESIDENCE known as Ocean Edge . Beach Front located directly on beautiful Simpson Bay Beach! Enjoys one of the best locations on the island . Panoramic sea views with your toes in the sand and balmy Caribbean breezes. A clear turquoise sea dazzles in tropical sun, powdery white sands stretching along one of St. Maarten's longest beaches. Apartment with modern amenities and comforts. A perfect vacation spot ! Back up system installed to insure electricity.

Top guest favourite
The outdoor deck features two lounge chairs positioned for ocean views, surrounded by palm trees and tropical foliage. The crystal clear waters of the beach are visible in the background, and the sky reflects a mix of clouds and sunlight.
Flat in Simpson Bay
5 out of 5 average rating, 228 reviews

The Beach House Apartment

A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more

Guest favourite
A serene terrace area is furnished with wooden chairs and a dining table, shaded by a canopy. The clear waters of Simpson Bay are visible in the background, dotted with sailboats and framed by lush greenery, inviting relaxation and enjoyment of the beachfront setting.
Flat in Simpson Bay
4.93 out of 5 average rating, 139 reviews

Le Petit Paradis – Beachfront 1 Bedroom Apartment

"Petit Paradis" (Little Paradise), a genuine Caribbean getaway. A spacious one-bedroom Beachfront apartment right on beautiful Simpson Bay Beach and in the center of all the happenings. Relaxing terrace, five stairs away from the Beach, and within walking distance from great Restaurants, Nightlife, Activities, and Watersports. This modern, fully furnished, and equipped apartment has everything you need for a dream vacation. Hope to invite you soon in our Paradise, Elodie

Top guest favourite
A patio area is visible, featuring a private pool beside comfortable loungers, adorned with orange towels. A shaded dining space with a table is positioned near the water's edge, with picturesque views of the bay and surrounding landscape.
Villa in Cul-de-Sac
4.99 out of 5 average rating, 166 reviews

VILLA JADE 1: FEET IN THE WATER/POOL SUITE

VILLA JADE is located in the bay of "FRENCH CUL DE SAC". It is a beachfront complex consisting of 3 private villas. VILLA JADE 1 is a suite for 2 people with a private pool. The villas are quiet and private... your only view is the sea. The bay of "FRENCH CUL DE SAC" is 5 minutes from ORIENT BAY, touristy with restaurants, bars, water activities, but also a few minutes from GRAND CASE, our typical little village with gourmet restaurants by the sea....

Top guest favourite
An outdoor terrace features comfortable white lounge furniture arranged around a coffee table. Sun loungers are positioned beside a private infinity pool, overlooking the ocean and distant boats. The scene is framed by tropical plants and a clear blue sky, enhancing the serene coastal environment.
Loft in Marigot
4.99 out of 5 average rating, 179 reviews

Sea Loft, Breathtaking View – Private Pool

* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with lounge chairs, garden furniture, outdoor table and BBQ * Office area * 100 Mbps Wi-Fi * TV with thousands of channels from around the world * 250 m walk to Fort Louis de Marigot Marina * 5 min walk to Marigot city center with its restaurants, boutiques and other shops * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

Guest favourite
A panoramic view of the ocean is showcased through expansive glass walls. The open space features modern white furniture and a seamless transition from indoor to outdoor. Illuminating sunlight pours in, enhancing the bright, airy atmosphere of the terrace overlooking the tranquil water.
Flat in Little Bay
4.94 out of 5 average rating, 140 reviews

Stunning Ocean View - 2 / 3 Brm Terraces Lt. Bay

Treat yourself to the stylish and modern ocean view apartment . This spacious environment, is designed to be enjoyed as a family, has a terrace with stunning sea view, climatized private pool, two master suites (one w/Japanes king bed and walking closet), the other with two double size beds (you can join them and make a king bed) and closet and a third room with daybed. All of them with their own bathroom and ocean view. Welcome!

Top guest favourite
The infinity pool is visibly stretching towards the horizon, blending with the calm turquoise waters of the Caribbean Sea. Palm trees frame the scene, while a cruise ship can be seen cruising in the distance under a clear blue sky.
Flat in Philipsburg
4.97 out of 5 average rating, 35 reviews

Studio Ocean Front, Infinity Pool

Clearwater is a cliffside waterfront property with one of the most spectacular views on the island! Overlooking Great Bay, Philipsburg, Divi Little Bay, the turquoise Caribbean Sea and the magnificent cruise ships, this one of its kind location will be sure to put you at awe. It is perfectly situated for easy access to all SXM has to offer; restaurants, beaches, grocery stores, downtown shopping, bars and entertainment.

Top guest favourite
An inviting outdoor space features a private pool surrounded by lush greenery and sea views. Comfortable lounge chairs are positioned nearby, providing a serene spot to relax. Sunlight reflects off the water's surface, creating a tranquil atmosphere.
Flat in Indigo bay
4.94 out of 5 average rating, 120 reviews

Independent apartment at the bottom of the villa – Indigo Bay

The Villa Stella apartment welcomes you in a unique setting with spectacular views of the Caribbean Sea. Located in a 24-hour secure residence, tranquility awaits. You will be just an 8-minute walk to Indigo Bay Beach and close to shops and restaurants in the Dutch side. Composed of 2 bedrooms and 2 bathrooms, you can relax in the pool/jacuzzi overlooking the bay.

Top guest favourite
A private hot tub is positioned on a balcony, surrounded by white lattice. The crystal-clear water reflects the sunlight, while panoramic views of the turquoise sea and lush hills are visible in the background under a clear blue sky.
Villa in Little Bay
4.99 out of 5 average rating, 81 reviews

Barefoot Villas GreatBay View in Hot Tub & Balcony

Wake up to stunning panoramic views of Philipsburg and Great Bay. Sip your morning coffee as cruise ships glide into port, all while soaking in the refreshing ocean breeze. This centrally located property puts you just minutes away from Philipsburg’s vibrant shopping scene, local supermarkets, restaurants, and some of the island’s best beaches.

Popular amenities for Philipsburg holiday rentals

Frequently Asked Questions

  • What are the most popular amenities for Apartment Rentals in Philipsburg?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do apartment rentals in Philipsburg have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Philipsburg. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Philipsburg?

    Philipsburg has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Philipsburg have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Philipsburg. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Philipsburg?

    Yes! Work meets play with ease at over 10 vacation rentals in Philipsburg featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in apartment rentals in Philipsburg?

    Experience the best of Philipsburg with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Quick stats about holiday rentals in Philipsburg

  • Total holiday rentals

    Explore 10 holiday rentals in Philipsburg

  • Nightly prices starting at

    Philipsburg holiday rentals start at $76 SGD per night before taxes and fees

  • Verified guest reviews

    Over 480 verified reviews to help you choose

  • Wifi availability

    10 of Philipsburg holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Philipsburg rentals

  • 4.8 Average rating

    Philipsburg stays are highly rated by guests – averaging 4.8 out of 5!