
House holiday rentals in Simpson Bay
Find and book unique houses on Airbnb
Quick stats about house rentals in Simpson Bay

Total holiday rentals
Explore 20 holiday rentals in Simpson Bay

Nightly prices starting at
Simpson Bay holiday rentals start at $89 SGD per night before taxes and fees

Verified guest reviews
Over 620 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Holiday rentals with a pool
10 properties feature pools

Wifi availability
20 of Simpson Bay holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Simpson Bay rentals

4.9 Average rating
Simpson Bay stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated house rentals in Simpson Bay
Guests agree: these houses are highly rated for location, cleanliness and more.

Endless Views @ Acqua Bleu
Nestled in the heart of Saint Martin, Acqua Bleu offers breathtaking views of turquoise waters and pristine beaches. You'll have direct access to some of the most gorgeous spots on the island, ensuring endless fun in the sun. You’ll enjoy access to various amenities, including a fully equipped kitchen, spacious living areas, a refreshing swimming pool, and much more! Acqua Bleu features two king bedrooms, each accompanied by a private bathroom. Get ready to enjoy a truly rejuvenating vacation!
ValueLocationHospitality
4.99 out of 5 average rating, 107 reviews
Luxury Villa Turquoise Heaven in Pelican Key
Welcome to Villa Turquoise Heaven- Modern Luxury in Pelican Key, SXM Experience the pinnacle of Caribbean elegance at Villa Turquoise Heaven, the newest luxury villa in the exclusive Tepui Residence. Designed for relaxation and style, this modern retreat offers a seamless blend of indoor-outdoor living with unparalleled views of the turquoise Caribbean Sea. From waking up to the gentle sound of waves to savoring sunsets from your private infinity pool, Villa TH offers an unforgettable escape.
FamilyValueView
4.88 out of 5 average rating, 48 reviews
Townhouse Villa LX
Superbe Maison mitoyenne, faisant partie d’une petite copropriété sécurisée dans le quartier de Beacon Hill. Située à 5 minutes de l’aéroport, vous pourrez admirer le ballet unique des avions au dessus de la plage de Maho, sans nuisances sonores, depuis la piscine partagée installée sur un rooftop. Très spacieuse avec ses 3 belles chambres, 2 salles de bain, entièrement climatisée, terrasse arborée et cuisine équipée. Située à proximité des restaurants et clubs. Accès plage direct en 1 minute.
LocationFamilyCheck-in
4.81 out of 5 average rating, 26 reviews
Ocean View Villa-Indigo Bay W/Private Pool/0 Steps
Welcome to paradise in Indigo Bay, St. Maarten! Our brand new property offers ultimate indoor-outdoor living with sliders opening to breathtaking sea views. Open-concept layout, fully-equipped kitchen, private pool and courtyard, NO STEPS, and three ocean-view bedrooms. Experience luxury and comfort at our oceanfront villa. Book now for an unforgettable vacation! *There is construction of a new hotel in the bay. Noise has been minimal but is subject to change. Contact us with any questions!*
FamilyLocationQuiet
4.99 out of 5 average rating, 75 reviews
ALMOND BLUE ...Pinel bay view - caribbean feeling
Relaxez-vous aux Caraïbes dans cette superbe maison avec sa vue extraordinaire sur la baie de Pinel, élue 3ème plus belle destination des Caraïbes. Au milieu d'une réserve naturelle avec vue sur St Barthélémy, vous nagerez avec les tortues et les poissons exotiques. Avec un accès à la mer en contre-bas de la maison, vous profiterez des kayaks mis à disposition pour aller déguster une langouste ou un cocktail dans l'un des 2 restaurants sur l'ilet Pinel. St Martin - La perle des Caraïbes !
LocationFamilyWifi
4.89 out of 5 average rating, 100 reviews
Luxurious villa with magnificent view ALSO 6bedr!
This gorgeous 4 bedroom - 4 bath villa is the best place to stay for your next vacation. The villa is also available as 6 bedroom. please reach out to us. The views are the best on the island as you will be overlooking Simpson Bay, the airport, the lagoon, the bridge and of course Anguilla. You are minutes away from restaurants, bars, shops and activities. This luxurious villa with teak furniture inside and outside has a beautiful pool with stunning ocean views and sleeps up to 8 people.
LocationValueBeach
5.0 out of 5 average rating, 19 reviews
Blue Palm Estate Townhouse w/ Ocean View
Welcome to Blue Palm Estate! Sint Maarten/Saint Martin is a very small island owned by the Netherlands and France. This 2 bedroom 3 bathroom is located in Pelican Key. It is a beautiful, safe and private area in a gated 4 unit villa. It is walking distance to many restaurants on the main street which is a very popular area with tons of delicious restaurants and wonderful shops to peruse. You will also see a beautiful sandy beach within 5 minute walking distance to the unit!
FamilyLocationGetting around
4.96 out of 5 average rating, 23 reviews
Sweet Home on the Beach rdc
SITUATION Exceptionnelle. Vue sur la baie de Marigot Pieds dans l’eau Face à la Mer des Caraïbes Superbe plage de sable blanc, cocotiers, mer turquoise ATOUTS Maison sur la plage Situation idéale pour visiter 4 Piscines 1 tennis Un beau jardin Résidence sécurisée 24H/24H Parking gratuit A côté : supermarché, boulangerie, restaurants Idéal pour Couple BON A SAVOIR A 2 kms de Marigot Voiture location conseillée Wifi, forfait ménage, serviettes, draps inclus dans le prix.
LocationSleep qualityComfort
5.0 out of 5 average rating, 8 reviews
La Pearle - Luxurious 1 Bedroom Condo By the Beach
Nestled on the hills of Indigo Bay, La Pearle is located midway between Philipsburg and the Simpson Bay touristic hang out. La Pearle exudes relaxation the minute you walk through the door! Awake to watching the Allure of the Seas make its way into the harbor. La Pearle, elegant, sophisticated and distinguished! The 1- bedroom spacious condo sleeps two! Experience luxury with a huge verandah overlooking the Indigo beach, Caribbean living, yours to enjoy!
FamilyLocationKitchen
4.79 out of 5 average rating, 220 reviews
CoCo Signature Luxurious Villa & Exceptional View
Renovated in 2022 and located in Terres Basses (French side), Villa CoCo Signature features 4 spacious bedrooms and offers breathtaking 180˚ views of the lagoon and the island of Saint-Martin. The warm Mediterranean-style ambiance and the outdoor kitchen the opens onto a private infinity-pool are perfect for enjoying the stunning scenery while relaxing, swimming or cooking.
FamilyLocationView
4.95 out of 5 average rating, 62 reviews
3BR Townhouse in Pelican Key
Escape to your family's perfect Sint Maarten retreat! This bright 3-bedroom, 2.5-bath townhouse in Pelican Key comfortably hosts 8 with king beds & a fun bunk room. Enjoy a modern kitchen, two private balconies, and a shared pool just steps away. With beach access, parking, and nightlife nearby, it's the ideal home base for your unforgettable Caribbean adventure!
LocationValueParking
4.79 out of 5 average rating, 39 reviews
Préstige - Luxurious 3 bedroom by the Beach
Nestled on the hills of Indigo Bay, Préstige is located midway between Philipsburg and the Simpson Bay touristic hangout. Préstige exudes relaxation the minute you walk through the door, elegant and distinguished! The 3-bedroom spacious residence sleeps six! Overlooking Indigo Beach with private swimming pool! Caribbean living, yours to enjoy!
LocationValueCondition
4.83 out of 5 average rating, 215 reviewsPopular amenities for house rentals in Simpson Bay
House rentals with a pool

Sunrise Over St. Barths
LocationCleanlinessAccess
4.98 out of 5 average rating, 46 reviews
3 Bed 3 Bath Villa | Private Pool | Pelican | SXM
LocationValueWalkability
4.83 out of 5 average rating, 23 reviews
SeaRenity Villa With Private Pool Indigo Bay
FamilyLocationQuiet
4.97 out of 5 average rating, 37 reviews
Villa Josefa SXM · Ocean View Above Friar’s Bay
ValueFamilySleep quality
5.0 out of 5 average rating, 29 reviews
Villa ELIOS 2BR SeaView
DecorViewCondition
5.0 out of 5 average rating, 6 reviews
Slowlife! Blooming Villa! Freshly Renovated
FamilyLocationAmenities
4.92 out of 5 average rating, 72 reviews
Fun times ahead! Devine in You Cupecoy is calling.
LocationValueCleanliness
4.9 out of 5 average rating, 60 reviews
Teresa’s Ocean Paradise
FamilyValueAccess
4.96 out of 5 average rating, 77 reviewsWeekly house rentals

Villa Kansha | 3BR Wellness Escape & Hot Tub
LocationFamilyBack garden
4.94 out of 5 average rating, 17 reviews
Macassi Beach Paradise, villa 3 chambres
LocationFamilyView
5.0 out of 5 average rating, 14 reviews
Villa Amber - Spectacular Sea View - Terres Basses
LocationFamilyView
5.0 out of 5 average rating, 5 reviews
Atypik Villa
ValueLocationCondition
4.97 out of 5 average rating, 37 reviews
Nouveau "La maison sur la plage"
LocationFamilyView
4.91 out of 5 average rating, 11 reviews
3-Bedroom Home In Philipsburg, Near the Beach
ValueFamilyCheck-in
4.93 out of 5 average rating, 85 reviews
ALOHA penthouse
LocationFamilyComfort
4.85 out of 5 average rating, 74 reviews
Villa Louisiana, Orient Bay
FamilyLocationGetting around
4.93 out of 5 average rating, 40 reviewsPrivate house rentals

Bungalow luxueux avec piscine privée
ValueLocationHospitality
4.96 out of 5 average rating, 85 reviews
Villa.lalabay Mont Vernon 3, st. martin
FamilyLocationAccuracy
4.81 out of 5 average rating, 16 reviews
Upscale Villa Hideaway in Orient Bay
LocationFamilyBathroom
4.93 out of 5 average rating, 28 reviews
2 Bedroom Ocean Front Villa, Private Infinity Pool
ValueFamilyView
5.0 out of 5 average rating, 32 reviews
Prestigious Villa with Breathtaking Ocean View
LocationFamilyView
5.0 out of 5 average rating, 22 reviews
Coconut Villa, Vue mer, piscine, 6 personnes
FamilyLocationView
4.92 out of 5 average rating, 12 reviews
Villa Tamarind | Luxury | Spectacular Views | 4BDR
ValueFamilyPool
4.96 out of 5 average rating, 83 reviews
Villa Cataleya jacuzzi & piscine à Orient Bay
LocationNearbyOutdoor spaces
5.0 out of 5 average rating, 9 reviewsWhen is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $382 SGD | $297 SGD | $351 SGD | $351 SGD | $383 SGD | $498 SGD | $378 SGD | $379 SGD | $159 SGD | $255 SGD | $255 SGD | $351 SGD |
| 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
- Beach apartment rentals Simpson Bay
- Rentals with pools Simpson Bay
- Pet-friendly rentals Simpson Bay
- Flat rentals Simpson Bay
- Rentals with a hot tub Simpson Bay
- Apartment rentals Simpson Bay
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- Serviced apartment rentals Simpson Bay
- Villa rentals Simpson Bay
- Beachfront rentals Simpson Bay
- House rentals Sint Maarten





