
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 €157 per night before taxes and fees

Verified guest reviews
Over 560 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!
Top-rated villa rentals in Simpson Bay
Guests agree: these villas are highly rated for location, cleanliness and more.

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.
4.95 out of 5 average rating, 81 reviews
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
5.0 out of 5 average rating, 16 reviews
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
4.97 out of 5 average rating, 92 reviews
SeaBreeze Luxury Villa Pool & Hot Tub Indigo Bay
The SeaBreeze Villa combines modern architectural design with expansive views of the sky at Indigo Bay, the top-tier gated community in St. Maarten. With four bedrooms and a convenient location just a brief stroll from the beach, this residence features sliding glass walls that lead to a spacious sun terrace and a private pool with stunning vistas of the Caribbean Sea. Offering all the amenities for luxurious island living, The Villa epitomizes upscale coastal lifestyle.
4.91 out of 5 average rating, 87 reviews
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.
4.87 out of 5 average rating, 89 reviews
VILLA I LOVE VIEW – Luxury villa with sea view
Villa I LOVE VIEW is an oasis of tranquility – with its private pool (naturism possible), large terrace and luxurious kitchen area. Come and discover its view with multiple shades of blue while relaxing on the deckchairs by the pool with zen natural stone reflections Located in Cul de Sac, facing Saint Barth, Pinel Island and the Eastern Bay. Close to the most beautiful beaches of the island, restaurants, water sports, it is the ideal place for your vacation.
5.0 out of 5 average rating, 110 reviews
Villa Blue Roc
This luxurious villa is located in a secure residence with a breathtaking view, facing the ocean and the island of St Barthelemy, perched on the heights of Dawn Beach, 15 minutes from the famous beaches/restaurants of Orient Bay and Grand Case in the French part. The villa is also 5 minutes from the Dutch capital, Philipsburg, a must for shopping. Thanks to the large outdoor spaces and the infinity pool, this villa will offer you an unforgettable stay.
4.94 out of 5 average rating, 88 reviews
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
4.85 out of 5 average rating, 157 reviews
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.
4.93 out of 5 average rating, 73 reviews
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.
5.0 out of 5 average rating, 27 reviews
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.
4.77 out of 5 average rating, 154 reviews
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.
4.98 out of 5 average rating, 47 reviewsPopular amenities for villa rentals in Simpson Bay
Private villa rentals

Ocean View Villa Little Bay
5.0 out of 5 average rating, 19 reviews
Seabreeze beachfront 3bedroom on Simpsonbay beach
5.0 out of 5 average rating, 8 reviews
Sea view 3BR Spring Sea Villa w/ pool, St Maarten
4.85 out of 5 average rating, 33 reviews
Villa Indigo Dream, Indigo Bay SXM
4.81 out of 5 average rating, 94 reviews
Villa Elysian in Indigo Bay
4.91 out of 5 average rating, 55 reviews
Caribbean View Villa - Sea - Sunset - Location#1
4.96 out of 5 average rating, 27 reviews
Sunset View – Steps from Friar’s & Happy Bay
5.0 out of 5 average rating, 14 reviews
A heavenly Sint Maarten's retreat
4.7 out of 5 average rating, 46 reviewsLuxury villa rentals

Your Paradise Villa
4.99 out of 5 average rating, 106 reviews
Villa Solandra – 3BR Oceanfront Sunset w/ Pool
4.94 out of 5 average rating, 50 reviews
NEW Les Terres Basses - Villa Coco Paillette - Sxm
4.91 out of 5 average rating, 11 reviews
Villa Kyanéa | Ocean View, St Barth · Private Pool
4.94 out of 5 average rating, 32 reviews
Sea Haven Villa - Breathtaking Views of Dawn Beach
4.99 out of 5 average rating, 94 reviews
Villa Saint-Tropez Breathtaking Sea Views
4.86 out of 5 average rating, 7 reviews
Water access, heated pool, kayaks & snorkeling
4.98 out of 5 average rating, 46 reviews
Marewa - Breathtaking sea view luxury villa 4hp
5.0 out of 5 average rating, 8 reviewsVilla rentals with a pool

Little Paradise 2, private pool, beautiful view
4.9 out of 5 average rating, 41 reviews
Spacious Villa - Saint Martin - Pool & 4 Bedrooms
4.97 out of 5 average rating, 66 reviews
Ocean Pearl - Spacious Villa in Dawn Beach
5.0 out of 5 average rating, 18 reviews
Villa Ti Case • Waterfront, water access & kayaks
5.0 out of 5 average rating, 42 reviews
Villa Koala, heated pool, sea view, Cul de Sac
5.0 out of 5 average rating, 17 reviews
Villa Plum Bay
4.95 out of 5 average rating, 19 reviews
Belle Lurette • 3BR waterfront with kayaks, pool
5.0 out of 5 average rating, 16 reviews
Villa Solana in Upscale Indigo Bay w/Private Pool
4.95 out of 5 average rating, 22 reviewsWhen is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €1,748 | €1,346 | €1,346 | €1,157 | €1,022 | €1,035 | €1,063 | €991 | €991 | €991 | €991 | €1,411 |
| 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 |
Destinations to explore
- Family-friendly rentals Simpson Bay
- Beach apartment rentals Simpson Bay
- Rentals with pools Simpson Bay
- Pet-friendly rentals Simpson Bay
- Rentals with beach access Simpson Bay
- Flat rentals Simpson Bay
- Rentals with a hot tub Simpson Bay
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- Waterfront rentals Simpson Bay
- Villa rentals Sint Maarten





