
Villa vacation rentals in Simpson Bay
Find and book unique villas on Airbnb
Quick stats about villa rentals in Simpson Bay

Total vacation rentals
Explore 30 vacation rentals in Simpson Bay

Nightly prices starting at
Simpson Bay vacation rentals start at G$37,631 GYD per night before taxes and fees

Verified guest reviews
Over 560 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Wi-Fi availability
30 of Simpson Bay vacation rentals include wi-fi 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.
ValueLocationView
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
LocationValueDecor
5.0 out of 5 average rating, 16 reviews
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.
LocationFamilyLong stay
5.0 out of 5 average rating, 110 reviews
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
ValueLocationLong stay
4.85 out of 5 average rating, 157 reviews
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.
FamilyValueQuiet
4.94 out of 5 average rating, 88 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
LocationFamilyGetting around
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.
LocationFamilyQuiet
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.
ValueLocationDecor
4.87 out of 5 average rating, 89 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.
LocationValueWalkability
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.
ValueLocationBathroom
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.
ValueFamilyBeach
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.
LocationValueLayout
4.98 out of 5 average rating, 47 reviewsPopular amenities for Simpson Bay villa rentals
Private villa rentals

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

Your Paradise Villa
FamilyLocationBathroom
4.99 out of 5 average rating, 106 reviews
Villa Solandra – 3BR Oceanfront Sunset w/ Pool
FamilyLocationWalkability
4.94 out of 5 average rating, 50 reviews
NEW Les Terres Basses- Villa Coco Paillette- Sxm
FamilyValueNearby
4.91 out of 5 average rating, 11 reviews
Villa Kyanéa | Vue océan St Barth · Piscine privée
LocationFamilyAccuracy
4.94 out of 5 average rating, 32 reviews
Sea Haven Villa - Breathtaking Views of Dawn Beach
ValueLocationAccuracy
4.99 out of 5 average rating, 94 reviews
Villa Saint-Tropez Breathtaking Sea Views
LocationFamilyIndoor spaces
4.86 out of 5 average rating, 7 reviews
Water access, heated pool, kayaks & snorkeling
LocationFamilyView
4.98 out of 5 average rating, 46 reviews
Marewa - Villa de luxe vue mer époustouflante 4 ch
FamilyLocationComfort
5.0 out of 5 average rating, 8 reviewsVilla rentals with a pool

Little Paradise 2, piscine privée, vue magnifique
FamilyValueHiking
4.9 out of 5 average rating, 41 reviews
Spacious Villa - Saint Martin - Pool & 4 Bedrooms
FamilyValueBiking
4.97 out of 5 average rating, 66 reviews
Ocean Pearl - Spacious Villa in Dawn Beach
FamilyLocationKitchen
5.0 out of 5 average rating, 18 reviews
Villa Ti Case • Waterfront, water access & kayaks
LocationFamilyGrill
5.0 out of 5 average rating, 42 reviews
villa Koala, piscine chauffée, vue mer, Cul de Sac
FamilyValueAmenities
5.0 out of 5 average rating, 17 reviews
Villa Plum Bay
FamilyLocationCleanliness
4.95 out of 5 average rating, 19 reviews
Belle Lurette • 3BR waterfront with kayaks, pool
LocationFamilyPool
5.0 out of 5 average rating, 16 reviews
Villa Solana in Upscale Indigo Bay w/Private Pool
LocationFamilyNearby
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 | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$419,372 GYD | G$322,996 GYD | G$322,996 GYD | G$277,630 GYD | G$245,226 GYD | G$248,362 GYD | G$255,052 GYD | G$237,909 GYD | G$237,909 GYD | G$237,909 GYD | G$237,909 GYD | G$338,675 GYD |
| 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 |
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