
Villa holiday rentals in Simpson Bay
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Top-rated villa rentals in Simpson Bay
Guests agree: These villas are highly rated for location, cleanliness and more.

Villa Sea Forever @ Pelican Key - Paradise Awaits!
Experience a piece of paradise at "Villa Sea Forever" in Pelican Key, Simpson Bay, Sint Maarten! This top floor, 2-bedroom, 2.5-bathroom haven offers mesmerizing, panoramic ocean & sunset views. Dive into pure bliss with a pool, gated community, private parking space, and all the comforts you need, including a full size washer & dryer, and fully stocked kitchen. Feel the breeze from your huge double balcony. Your dream escape awaits at "Villa Sea Forever" where breathtaking moments are endless!

Villa Litchi | Collection Villas Saint-Martin
Cette villa de 2 chambres entièrement rénovée, au design moderne et rafraîchissant, est désormais disponible. Admirez les couchers de soleil spectaculaires sur la mer des Caraïbes depuis la terrasse ou le salon. Parfaite pour un couple ou une petite famille, elle offre également la possibilité de se connecter avec la Villa Kiwi grâce à son jardin communicant. Ainsi, 2 familles ou groupes d’amis peuvent partager des moments mémorables tout en profitant pleinement des équipements de ces 2 villas.

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 Solandra – 3BR Oceanfront Sunset w/ Pool
Welcome to Villa Solandra, a western facing ocean front luxury 3BR/3BA home with a private pool in Indigo Bay. Enjoy romantic & epic sunsets, this cliffside escape blends indoor-outdoor living with sweeping Sea & Bay views, two large oceanfront balconies, and designer interiors. Enjoy a chef inspired kitchen, luxury king suites w/ ensuite baths, private garden just minutes from beaches, dining, Simpson Bay and Maho’s iconic plane spotting. Perfect for families, friends, or romantic getaways.

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 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....

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

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.

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.

Brand new! - Slowlife - Enjoy Villa
Completely NEW Villa!! Enjoy is a beautiful house that we «placed» on the sand. Thinking on every detail for your greatest comfort, you will appreciate its unique location, an exceptional interior design, and its extraordinary outdoor spaces. In the very exclusive and secure residence of Terre Basses, very close to the beach of Baie Longue, experience an incomparable holiday.
Popular amenities for Simpson Bay villa rentals
Private villa rentals

NEW Les Terres Basses - Villa Coco Paillette - Sxm

Villa Tropical Heaven

Luxury 1 bedroom at VILLA KIMON + AMAZING PATIO!

Oceanview Oasis - Villa Del Sol W/Generator

Villa Zircon in Pelican Key awaits you - Generator

Water access, heated pool, kayaks & snorkeling

Sea Haven Villa - Breathtaking Views of Dawn Beach

Villa Indigo Dream, Indigo Bay SXM
Luxury villa rentals

VILLA I LOVE VIEW – Luxury villa with sea view

Ultra Modern Tropical Villa with stunning sea view

Secret Harbor Villa, private escape in Anse Marcel

Villa Plum Bay

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

Villa Marant - Elegant Luxury Caribbean Escape

Villa Elé, 4 bedrooms, tropical garden and pool

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

** New ** VILLA ZAMI, magnificent villa of 1500 sq ft on the second line of Orient Bay beach !

Cheerful 2BR Villa, Stunning Ocean Views

Oceanfront Villa with Private Pool

Baie Nettle Beach Villa 2160

Villa Azur, great view of the Orient Bay

Villa Sonrisa, Beachfront and stunning ocean view

Villa Crystal Clear - Luxury Villa w/ Private Pool

Oceanfront Villa-Breathtaking Views in Pelican Key
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $2,853 NZD | $2,853 NZD | $2,733 NZD | $2,238 NZD | $2,030 NZD | $2,030 NZD | $2,030 NZD | $1,893 NZD | $1,893 NZD | $1,893 NZD | $1,893 NZD | $2,695 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 |
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 $416 NZD per night before taxes and fees

Verified guest reviews
Over 460 verified reviews to help you choose

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

Pet-friendly accommodation
Find 10 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, Wi-Fi and Pool across Simpson Bay rentals

4.8 Average rating
Simpson Bay stays are highly rated by guests—averaging 4.8 out of 5!
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