
Villa holiday rentals in Simpson Bay
Find and book unique villas on Airbnb
Quick stats about villa rentals in Simpson Bay

Total holiday rentals
Explore 30 holiday rentals in Simpson Bay

Nightly prices starting at
Simpson Bay holiday rentals start at $406 NZD per night before taxes and fees

Verified guest reviews
Over 510 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Wi-Fi availability
30 of Simpson Bay holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Simpson Bay rentals

4.8 Average rating
Simpson Bay stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated villa rentals in Simpson Bay
Guests agree: These villas are highly rated for location, cleanliness and more.

Las Brisas Penthouse A
Welcome to this stunning 3-bedroom penthouse located in the prestigious gated community of Las Brisas, Cole Bay, St. Maarten. This luxurious residence offers an unmatched living experience with breathtaking views and modern amenities. The penthouse features three spacious bedrooms, each designed with elegance and comfort in mind. The master suite boasts an en-suite bathroom and private balcony, perfect for soaking in the serene surroundings. The open-concept living and dining areas flow seamles

Villa Ocean - Indulge Yourself in Paradise
A three-bedroom, two-bathroom beauty overlooking beach/vast views of the ocean in Indigo Bay. Sunset viewing on the deck, private pool or down to the beach 10 min by walking. 10 min to airport, night life, other popular beaches. Close to town. groceries, restaurants. All the bedrooms have a view of beach and the ocean. There is free wireless internet, TV, air conditioning, a dishwasher, refrigerator, microwave, wine refrigerator, coffee maker, washer dryer, outdoor gas grill and private parking.

Ocean View Villa Little Bay
🌴 Villa Little Bay – Oceanview Bliss With 360° Views Enjoy the peaceful sound of the waves and a serene, private atmosphere that’s still close to everything. We’re located within walking distance to Philipsburg, the vibrant heart of SXM—Front Street, top shopping, restaurants, and the island’s best casinos. The beach is just 5 minutes away, Step outside to your private patio for sunbathing, and shimmering ocean‑view pool. Villa offers the perfect blend of tranquility and convenience.

Waterfront "Bonjour" Beacon Hill St Maarten
This stunning 4-bedrooms, 4 bathrooms villa overlooks Maho Bay and provides a front row seat to beautiful SXM sunsets, and over the famous Maho Beach. Enjoy the views while taking a dip in the home’s infinity pool overlooking the ocean or from its multiple outdoor dining and seating options conveniently and securely located minutes from restaurants, bars, nightlife, Maho Market and more, steps away from direct beach access to Simpson Bay Beach. Back up Diesel Generator

Modern 2 bedroom luxury beachside villa with pool
Your own private paradise. Modern 2 bedroom luxury villa in safe gated community with security. New appliances with air conditioning, WIFI, security cameras, and secured free parking including Smart TV with free NetFlix, HBO Max, and Prime access. Private pool with adjacent outdoor dining/lounge area. Perfect for families or couples. Maid and private chef service available if needed. Walking distance from dining, night clubs, and shopping. Steps away from the beach.

The Blue Door Villa - 4 bed ocean view home
At the Blue Door Villa, we offer our guests all the creature comforts of being in a well-equipped vacation home. We are located on the Dutch side, minutes from the French border in a quiet gated community. The Blue Door Villa is a perfect place to relax while you listen to ocean waves and swim in the infinity pool. There are multiple outdoor spaces offering privacy or space to gather. We are now offering our guests an exclusive, free concierge service.

Villa Bella sea view pool and jacuzzi 3 bedrooms
Wake up every morning facing Pinel Island, in a modern villa bathed in light, with a private pool and a quiet and green environment. The Villa is located in the Horizon Pinel residence overlooking Îlet Pinel, Petite Clef, Orient Bay, Tintamarre and Saint Barthélemy. It overlooks the incredible and famous Cul de Sac Bay Nature Reserve, known for its population of turtles, rays and pelicans. The shallow and always calm bay is ideal for snorkeling

VILLA JADE3: 2 BEDROOMS & POOL FEET IN THE WATER
VILLA JADE is a complex of 3 villas, on the waterfront. VILLA JADE 3, our 2 bedroom villa is located in Cul de Sac Bay, facing PINEL Island and the turquoise water nature reserve. Life is peaceful there, kayaking, relaxing, BBQ... You are 5 minutes from the fabulous Baie Orientale, its restaurants, bars and water activities... The 3 villas are adjoining but very private and quiet, your only view is the sea... your only goal is to "enjoy"......

Infinity Ocean Edge - Luxury Oceanfront Penthouse
✨ Infinity at Ocean Edge with IRE Vacations✨ 15% Discount on select dates* Come take advantage of this luxury property located on the end of the Beacon Hill peninsula, ensconced on all sides by the inviting Caribbean Sea! This spectacular waterfront property is one of a kind. Located just minutes from several of St. Maarten’s most popular beaches and beach bar hangouts, a great day is always guaranteed. This property is not kid friendly.

Beach-Private Pool-2 Master King Bedrooms
Get away from your everyday stress and let the breathtaking views of the Caribbean Sea wash it all away as you enjoy the incomparable blue hues of the sea. Unwind in two sublime master suites, each boasting an inviting king-size bed and private bathrooms where you can melt away your worries like never before. Slip into total relaxation with every dip in a heated pool within a breathtaking courtyard—all at your own leisure!

Ocean Dream Villa
Indulge in luxury at a two-bedroom villa in Indigo Bay, Sint Maarten. Enjoy modern elegance, a private pool, and ocean views. Relax indoors or outdoors, savor gourmet meals, and unwind under starlit skies. Luxurious bedrooms offer ocean vistas. Whether for romance or family, this villa promises a memorable Caribbean escape at Ocean Dream, where luxury meets natural beauty. Book now for an extraordinary island retreat.

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 Simpson Bay villa rentals
Private villa rentals

Villa Pure • 3BR waterfront with kayaks, Wi-Fi, AC

Villa Sea Forever @ Pelican Key - Paradise Awaits!

Marewa - Breathtaking sea view luxury villa 4hp

Villa Plum Bay

Sea Haven Villa - Breathtaking Views of Dawn Beach

Villa Pineapple - Grand Case Area -5mn Orient Bay

Bella Vista-Piscine & vue mer a 5' de Grand Case

Caribbean View Villa - Sea - Sunset - Location#1
Luxury villa rentals

VILLA I LOVE VIEW – Luxury villa with sea view

Villa Tropical Heaven

Sea breeze Villa right on Simspon bay beach

Villa SEA VIEW, 5' from Grand Case beach, privacy

Villa Azur, great view of the Orient Bay

Villa Marine, waterfront, facing Îlet Pinel

Private Orient Bay Villa with Spectacular Views

Villa Seascapes, Stunning 180° Ocean view
Villa rentals with a pool

Reflection Y 5 Star Villa

Modern Bungalow With Pool - 3 Min Walk To Beach

Charming 3-Bed Villa in Maho

Little Paradise 2, private pool, beautiful view

Spacious Villa - Saint Martin - Pool & 4 Bedrooms

Classic Caribbean villa in safe Terres Basses

Villa Sunset : very close to two beaches !

A heavenly Sint Maarten's retreat
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $2,901 NZD | $2,901 NZD | $2,780 NZD | $2,275 NZD | $2,064 NZD | $2,064 NZD | $2,064 NZD | $1,925 NZD | $1,925 NZD | $1,925 NZD | $1,925 NZD | $2,741 NZD |
| Avg. temp | 26°C | 26°C | 26°C | 27°C | 28°C | 29°C | 29°C | 29°C | 29°C | 29°C | 28°C | 27°C |
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