
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 $306 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 20 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

4.8 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.
ValueLocationWalkability

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.
LocationFamilyHiking

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
LocationValueComfort

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.
FamilyValueEV charging

AZUR 4BR 4.5BA Walk to Indigo Beach- Sea Side Dr.
Welcome to AZUR, the newest luxury villa at Indigo Bay, Sint Maarten. Stunning property features 4 BR, 4.5 BA each with a king bed, and en-suite full baths and fitted wardrobes. Guests can enjoy inside and outside dining, each room controlled AC , WiFi, Infinity pool, 3 large terraces, BBQ grill, rooftop lounge, tropical garden, turquoise sea, and sunsets. This captivating spacious villa has gourmet kitchen with island for casual dining. AZUR is your exclusive sanctuary by the sea.
LocationIndoor spacesAccuracy

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

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.
FamilyValueWalkability

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.
FamilyValueGetting around

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.
ValueFamilyCleanliness

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.
FamilyValueWi-Fi

Sol y Mar - Beachfront Penthouse with private pool
✨ Sol y Mar with IRE Vacations ✨ Beautiful beach penthouse Sol Y Mar is located in the heart of Simpson Bay. Sol Y Mar is steps away from the popular Kimsha beach, as well as many restaurants and activities of the area. This beach penthouse sits in the midst of it all. Ideal if you are looking to be within walking distance to supermarkets, restaurants, bars, clubs & watersports.
FamilyLocationAmenities

VILLA JADE 2 : SUITE PIEDS DANS L'EAU / PISCINE
VILLA JADE est un complexe de 3 villas situé dans la baie de CUL DE SAC et ses îlets ... VILLA JADE 2 est une suite spacieuse / vue mer pour 2 personnes les pieds dans l'eau, avec piscine privée. Les 3 villas sont mitoyennes mais très calmes et intimes. Votre unique vue est la mer... Accès direct à la mer par un ponton, et kayaks à votre disposition.
FamilyLocationGetting around
Popular amenities for Simpson Bay villa rentals
Private villa rentals

Seabreeze beachfront 3bedroom on Simpsonbay beach
LocationBeachBathroom

Villa Elysian in Indigo Bay
FamilyLocationBeach

Ocean View Villa Little Bay
LocationFamilyCleanliness

Caribbean View Villa - Sea - Sunset - Location#1
FamilyLocationAir conditioning

Spacious Villa - Saint Martin - Pool & 4 Bedrooms
LocationValueView

Private villa / beautiful View next to La Samanna
FamilyLocationCleanliness

Life's Good
LocationFamilyAccuracy

Villa Kyanéa | Vue océan St Barth · Piscine privée
LocationFamilyPool
Luxury villa rentals

Your Paradise Villa
ValueFamilyHospitality

Sunset View – Steps from Friar’s & Happy Bay
LocationFamilyHiking

Sea Haven Villa - Breathtaking Views of Dawn Beach
LocationValueHospitality

A heavenly Sint Maarten's retreat
ValueLocationAir conditioning

NEW Les Terres Basses- Villa Coco Paillette- Sxm
FamilyValueHospitality

Private Orient Bay Villa with Spectacular Views
ValueLocationPool

Water access, heated pool, kayaks & snorkeling
FamilyValueCleanliness

Villa Magnolia | Collection Villas Saint-Martin
LocationFamilyBeach
Villa rentals with a pool

Bella Vista-Piscine & vue mer a 5' de Grand Case
FamilyLocationSolo travel

Little Paradise 2, piscine privée, vue magnifique
LocationFamilyAir conditioning

Villa Sunset : very close to two beaches !
LocationFamilyAccess

villa Koala, piscine chauffée, vue mer, Cul de Sac
ValueFamilySleep quality

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

Nouveau! Merveilleux 5 chambres, plage, piscines
FamilyLocationCleanliness

Belle Lurette • 3BR waterfront with kayaks, pool
FamilyLocationHospitality

Palm Paradise - Tropical Villa in Oyster Pond
ValueLocationBathroom
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $3,412 NZD | $2,628 NZD | $2,628 NZD | $2,259 NZD | $1,995 NZD | $2,020 NZD | $2,075 NZD | $1,935 NZD | $1,935 NZD | $1,935 NZD | $1,935 NZD | $2,755 NZD |
| 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
- Rentals with beach access Simpson Bay
- Rentals with pools Simpson Bay
- Beach condo rentals Simpson Bay
- Pet-friendly rentals Simpson Bay
- Apartment rentals Simpson Bay
- Rentals with a hot tub Simpson Bay
- Condo rentals Simpson Bay
- House rentals Simpson Bay
- Waterfront rentals Simpson Bay
- Serviced apartment rentals Simpson Bay
- Beachfront rentals Simpson Bay
- Villa rentals Sint Maarten





