
Villa holiday rentals in Simpson Bay
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Top-rated villa rentals in Simpson Bay
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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.

Villa Bella vue mer piscine et jacuzzi 3 chambres
Réveillez-vous chaque matin face à l’île Pinel, dans une villa moderne baignée de lumière, avec piscine privée et un environnement calme et verdoyant. La Villa est située dans la residence Horizon Pinel vue sur îlet Pinel, petite Clef, Orient Bay, Tintamarre et Saint Barthélemy. Elle donne vue sur l'incroyable et célèbre réserve naturelle de la baie de Cul de Sac, connue pour sa population de tortues, raies et pélicans. La baie peu profonde et toujours calme est idéale pour le snorkeling

VILLA JADE3: 2 CHAMBRES & PISCINE PIEDS DANS L'EAU
VILLA JADE est un complexe de 3 villas , les pieds dans l'eau. VILLA JADE 3, notre villa 2 chambres est située dans la Baie de Cul de Sac, face à l'Ilet PINEL et la réserve naturelle aux eaux turquoises. La vie y est paisible, sorties kayaks, farniente, BBQ ... Vous êtes à 5 minutes de la fabuleuse Baie Orientale, ses restaurants, bars et activités nautiques... Les 3 villas sont mitoyennes mais très intimes et calmes, votre unique vue est la mer....votre unique but est de " profiter"......

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.

Only Villa with private beach Beach Villa Cala Mar
Optic-fiber wifi, heated swimming pool and private white sand beach! Snorkeling gear and kayaks included. Private Chef, Masseuse & Concierge on demand. Move into this paradise, exclusively designed for your stay to be absolutely perfect. Enjoy every part of it, from the exquisite decoration, the quality of every single component of the Villa, its relaxing white sand beach and all the features included (kayaks, snorkeling gear, beach towels, complimentary drinks & snacks.

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.

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.

Slowlife Harmony - Caribbean Villa Three Bedrooms!
Harmony is your perfect vacation home, will give you the feeling of being at home in the Caribbean, this spacious 3-bedroom Caribbean style villa, we can accommodate a family, couples and friends. Harmony will be your home away from home, and at the same time you will have a personalized service for requests and to guide you with information about all the activities and places that you must experience on our island.

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.
Popular amenities for Simpson Bay villa rentals
Private villa rentals

Luxury 1 bedroom at VILLA KIMON + AMAZING PATIO!

Ultra Modern Tropical Villa with stunning sea view

Villa Zircon in Pelican Key awaits you - Generator

Luxury house 3 Bdr, sea front, private pool, kayak

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

Sea Haven Villa - Breathtaking Views of Dawn Beach

Reflection Z 5 Star Villa

Infinity Views Indigo Bay SXM
Luxury villa rentals

Luxury villa, swimming pool and panoramic sea view

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

Marewa - Villa de luxe vue mer époustouflante 4 ch

Oceanview Oasis - Villa Del Sol W/Generator

OOF villa d’architecte vue mer face à l’îlet Pinel

Villa Livity 5 Bed Luxury Sea view boutique oasis

Villa Azur Pinel Cul de Sac

Plus belle vue de Saint-Martin
Villa rentals with a pool

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

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

Villa Sunset : very close to two beaches !

Ocean front villa, pool, private ocean snorkeling

Little vanille - Sea view & private pool
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $2,608 AUD | $2,608 AUD | $2,498 AUD | $2,045 AUD | $1,855 AUD | $1,855 AUD | $1,732 AUD | $1,732 AUD | $1,857 AUD | $1,732 AUD | $1,730 AUD | $2,608 AUD |
| 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 $228 AUD per night before taxes and fees

Verified guest reviews
Over 310 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

4.9 Average rating
Simpson Bay stays are highly rated by guests—averaging 4.9 out of 5!
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