
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.

Ocean Breeze B
Welcome to unparalleled luxury at Indigo Bay, Sint Maarten. Nestled in one of the island's most sought-after gated communities, this 3-bedroom villa offers modern elegance with breathtaking views of the Caribbean Sea. The villa is thoughtfully designed with an expansive living room, full kitchen, bar, and a TV room for relaxation. Step outside to your private oasis featuring a private pool, BBQ area, and sun-soaked deck, perfect for alfresco dining or unwinding with a cocktail. The master suite

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.

VILLA I LOVE VIEW - villa luxe avec vue mer
Villa I LOVE VIEW est une oasis de tranquillité – avec sa piscine privative (naturisme possible), sa grande terrasse et son espace de cuisine luxueux. Venez découvrir sa vue aux multiples nuances de bleues en vous relaxant sur les transats au bord de la piscine aux reflets pierres naturelles zen Située à Cul de Sac, face à Saint Barth , l'ilet Pinel et la Baie Orientale. A proximité des plus belles plages de l'ile, restaurants, divertissements nautiques, c'est le lieu idéal pour vos vacances.

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"......

Tropical Flamboyant Villa with Jacuzzi & Seaview
Relax in your calm, elegant Kombawa Tropical House set in a garden with a splendid sea view. Enjoy the large covered terrace with the comfortable hot tub or swim in the huge pool with its breathtaking view. Relax in the waxed concrete bathtub with its view of the sea and the island of Saba. Prepare your meal in the fully equipped open kitchen. The rooms are comfortable and restful for a rejuvenating stay. Come and recharge your batteries in this unique place in the heart of Terres Basses

Villa Blue Roc
Cette villa luxueuse , est situee dans une residence securisee avec une vue epoustouflante , face a l ocean et l ile de St Barthelemy, Perchee sur les hauteurs de Dawn Beach, a 15 minutes des fameuses plages/restaurants d Orient Bay et Grand Case en partie francaise. La villa est egalement a 5 minutes de la capital hollandaise , Philipsburg, un incontournable du shopping. Grace aux grands espaces exterieurs et a la piscine a debordement , cette villa vous offrira un sejour inoubliable.

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.

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.
Popular amenities for villa rentals in Simpson Bay
Private villa rentals

Seabreeze beachfront house on Simspon bay beach

Villa Paradis - Unbeatable views!

Ultra Modern Tropical Villa with stunning sea view

Villa Zircon in Pelican Key awaits you - Generator

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

Sea Haven Villa - Breathtaking Views of Dawn Beach

Villa Litchi | Collection Villas Saint-Martin

Infinity Views Private Apartment Indigo Bay
Luxury villa rentals

Villa Tropical Heaven

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

Your Paradise Villa

Marewa - Villa de luxe vue mer époustouflante 4 ch

Secret Harbor Villa, private escape in Anse Marcel

Water access, heated pool, kayaks & snorkeling

Villa Marine les pieds dans l'eau face îlet Pinel

Private Orient Bay Villa with Spectacular Views
Villa rentals with a pool

Villa Sea Forever @ Pelican Key - Paradise Awaits!

[Sunset Place] 3BR Oceanfront Villa, Private Pool

Reflection Y 5 Star Villa

Oceanfront Villa with Private Pool

Villa Tibo

Spacious Villa - Saint Martin - Pool & 4 Bedrooms

Villa Ancre Bleue, magnifique vue sur Ilet Pinel

Villa Crystal Clear - Luxury Villa w/ Private Pool
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £1,495 | £1,152 | £1,152 | £1,003 | £909 | £909 | £909 | £848 | £848 | £848 | £848 | £1,207 |
| 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 £179 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Wifi availability
30 of Simpson Bay holiday rentals include wifi 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!
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