
Villa vacation rentals in Simpson Bay
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Top-rated villa rentals in Simpson Bay
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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

Indigo Oceanfront Condo Poolside - Unit 1
Welcome to Indigo Bay Oceanview Villa, in Indigo Bay, Sint Maarten. This spacious condo offers stunning ocean views, modern amenities, and easy access to pristine beaches. With 3 elegant bedrooms, each featuring en-suite bathrooms, an open-concept living area with plush seating, and a gourmet kitchen equipped with state-of-the-art appliances, you’ll find everything you need for a perfect stay. Step outside to your private pool, sun deck, and shaded patio for alfresco dining.

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.

Villa Indigo Dream, Indigo Bay SXM
Prepare to de-stress and to be mesmerized by the continuous influence of the sunlight and the sea throughout the villa. The villa offers a spectacular indoor-outdoor living experience which opens onto the infinity pool deck and boasts breathtaking views of the islands Saba, St. Eustatius and St.Kitts. The home defines true tranquility. Listen to the surf as sip your coffee in the morning or make a sunset toast watching nature's greatest light show over the sea.

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.

Luxury Villa, Pool, Jacuzzi, Pinel View 3 Bedroom
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 Île Pinel, Petite Clef, Orient Bay, Tintamarre and Saint Barthélemy. It overlooks the incredible and famous nature reserve of Cul de Sac Bay, 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"......

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.

Infinity Ocean Edge - Luxury Oceanfront Penthouse
✨ Infinity at Ocean Edge with IRE Vacations✨ 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.

Villa Crystal Clear - Luxury Villa w/ Private Pool
Imagine waking up every morning in paradise from the comfort of your own private villa. Lounge by your pool while enjoying the view of the ocean and neighboring islands without ever leaving the comfort of your villa. 2 Bedrooms, 2.5 Bathrooms, perfect for a group of up to 6 guests, or an intimate getaway for two. The ultimate in luxury Caribbean living. *Inquire about our available vehicle for rent*

SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay
Sea View Luxury Villa Perfect for Girls Getaways & Birthday Celebrations Maho Village Celebrate in style at this stunning Sea True villa, custom designed with high end finishes and built for an unforgettable immersive sensorial experience. With 5.8 meter vaulted ceilings a private pool and every amenity you could dream of. It’s the ultimate escape for groups and special occasions.
Popular amenities for Simpson Bay villa rentals
Private villa rentals

Luxury 1 bedroom at VILLA KIMON + AMAZING PATIO!

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

Ultra Modern Tropical Villa with stunning sea view

Villa Sea Forever @ Pelican Key - Paradise Awaits!

Secret Harbor Villa, Amazing place in Anse Marcel

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

3 Bed & 3 Bath Villa Domila with Private Pool SXM

Infinity Views Indigo Bay SXM
Luxury villa rentals

Marewa - Breathtaking sea view luxury villa 4hp

Oceanview Oasis - Villa Del Sol W/Generator

Villa Zabricot with pool- sxm island vacation

OOF architect's villa, sea view facing Pinel Island

Villa Livity 5 Bed Luxury Sea view boutique oasis

Sea Haven Villa - Breathtaking Views of Dawn Beach

Villa Azur Pinel Cul de Sac

Reflection Z 5 Star Villa
Villa rentals with a pool

Ocean Breeze B

Villa Paradis - Unbeatable views!

Luxury villa, swimming pool and panoramic sea view

Villa Mumbai - Beach Access - 3 Bedrooms

Villa Marant - Elegant Luxury Caribbean Escape

Oceanfront Villa with Private Pool

Modern Bungalow With Pool - 3 Min Walk To Beach

Villa KALYA -3 br - Orient Bay - SXM
Quick stats about villa rentals in Simpson Bay
Total rentals
30 properties
Nightly prices starting at
$150 before taxes and fees
Total number of reviews
310 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
30 properties have a pool
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