
Vacation rentals with a pool in Simpson Bay
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Simpson Bay
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Modern Bungalow with Stunning Seaview & Pool
Découvrez notre Luxueux & Cosy Bungalow Kombawa, chambre séparée, cuisine tout équipée, canapé lit à disposition dans le salon, grand placard, douche à l'italienne, idéal à 2 ou 3, ou en famille. Il est situé à quelques minutes à pied de la très belle plage de Baie aux Prunes, la vue époustouflante vous permettra d'admirer les couchers de soleil sur la mer. Venez vous ressourcer au coeur de cet écrin de verdure à la douce mélodie du chant des oiseaux idéalement situé entre les 2 parties de l'île

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.

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!*

The Loft at Simpson Bay Yacht Club
Welcome to The Loft at SBYC. Located in the heart of Simpson Bay in walking distance to the beach, great restaurants, grocery stores, shopping, salons/spas and more. In this fully renovated loft-style apartment, you will find high quality amenities throughout including a European kitchen and an amazing rainfall shower. The SBYC property offers 3 swimming pools, a hot tub, tennis courts and plenty of outdoor space for relaxing, all under 24-hour gated security. Free concierge service included.

4 bedroom villa + 2bedr apt (sleeps 12) in Pelican
This 4 bedroom/ 4bathroom villa with separate 2 bedroom / 2 bathroom apartment is ideal for a group or family vacation. Enjoy time together while having enough space to relax as well. On the large deck you will find the gorgeous pool with stunning views where you can enjoy dinner, drinks or lounge time. The house is located on a hill overlooking the bay, the lagoon and you can see the planes coming in and Anguilla in the distance. The apartment has a separate entrance with 2 bdr, 2 bath.

Saint Maarten La Terrasse Maho
It's a cozy large studio with a king size bed, a queen size sleeper sofa and a big balcony, it is at the second floor at Royal Islander Club Resort La Terrasse in Maho, fully equipped and furnished. Located just in front of Maho Bay beach and few minutes walk from Mullet bay beach. There are few restaurants and boutiques like cigar shops, jewelers and beauty store. Casino Royale is right next door. There are also a supermarket for grocery shopping, a pharmacy, a clinic and more...

Paradise Studio steps from Mullet Beach
Bright and charming studio 5 minutes from the airport and just steps from Mullet Bay in a safe, gated community. The apartment features amenities such as 24/7 security, included wifi, TV with Netflix, A/C, Full kitchen, 3 Piece Bathroom, Queen bed, with an outdoor pool , gazebo and grill. Laundry service available for a fee.Just a 3 minute walk from local restaurants and bars, supermarket, and the AUC medical school. Beach chairs and pool toys are also in the apartment for use.

Aman_Aria
This unique place has a style all its own, newly built, contemporary retreat features two elegant master bedrooms, each with its own private bathroom, a spacious living area seamlessly connected to a fully equipped kitchen, an inviting outdoor terrace. Every bedroom and the living room offer uninterrupted vistas of the mesmerizing ocean. The heart of Aman is its spectacular infinity pool and sun-drenched deck, inviting you to relax while soaking in breathtaking panoramas.

Sea Loft, Breathtaking View – Private Pool
* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with lounge chairs, garden furniture, outdoor table and BBQ * Office area * 100 Mbps Wi-Fi * TV with thousands of channels from around the world * 250 m walk to Fort Louis de Marigot Marina * 5 min walk to Marigot city center with its restaurants, boutiques and other shops * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

Secret View amazing apartment- Private pool
Welcome to Secret View! An elegant and intimate retreat with a private pool and a spacious terrace set directly on the lagoon. Designed for couples seeking calm, romance and discretion, just minutes from vibrant Maho with its restaurants, bars and casinos, and Mullet Bay Beach, one of the island’s finest beaches with stunning turquoise waters. Free private parking. This hidden gem is the perfect setting for unforgettable moments together.

New, a dream on the beach!
Villa "Malaka" is located in a unique and quiet complex called Nettlé Bay Beach Club, 4 swimming pools, 2 tennis courts, secure parking, breathtaking sea views, ideally located on Nettlé Bay between the French and Dutch sides, close to useful amenities: supermarket, bakery, 4 restaurants, water sports. The "Malaka" villa can accommodate up to 4 people, it will be the ideal place for a dream stay by the water.

Stunning 2 BD Ocean View - Terraces Lt Bay
Treat yourself to the utmost stylish and modern ocean view apartment located in the exclusive Little Bay Hill . This spacious environment, is designed to be enjoyed as a family, has a terrace with stunning sea views, private pool, one master suites ( Japanese king bed and a walking closet), one bedroom suite with two twin size beds ( could be converted to king size bed ) . Welcome to Terraces Little Bay !
Popular amenities for Simpson Bay rentals with a pool
House rentals with a pool

Pelican key - BEACH FRONT Villa

Blue Palm Estate Townhouse w/ Ocean View

Townhouse Villa LX

Slowlife - Villa Wellness 4 beds

Villa Carib sxm piscine.

5B Oceanview villa near Philipsburg

Préstige - Luxurious 3 bedroom by the Beach

Teresa’s Ocean Paradise
Condo rentals with a pool

Oceanfront w Pool | Maho Beach area

Awesome view : Condo with lagoon view !

Beachfront Escape with Pool & Stunning Sunsets

"SeaBird" studio, feet in the water on the beach

Princess Anouk, Orient Bay, pool, on the beach

cosy apartment

Premium studio with Caribbean sea view & swimming pool - Marigot

The Beach Condo
Other vacation rentals with a pool

Waterfront "Bonjour" Beacon Hill St Maarten

Sunny Marina Residence

Gorgeous 2 bedroom-17th floor, Fourteen Mullet Bay

Pelican Sea View 1bdrm Maison Mazu

Beachfront/6 bdrs en-suite/Maid included (J)

Villa Tibo

CondoSTmaarten panoramic (Adults Only)

Duplex Aloe Vera vue ST Barth
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ933 | ﺩ.ﺇ999 | ﺩ.ﺇ999 | ﺩ.ﺇ837 | ﺩ.ﺇ716 | ﺩ.ﺇ735 | ﺩ.ﺇ793 | ﺩ.ﺇ723 | ﺩ.ﺇ599 | ﺩ.ﺇ613 | ﺩ.ﺇ716 | ﺩ.ﺇ1,065 |
| 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 vacation rentals with a pool in Simpson Bay

Total vacation rentals
Explore 210 vacation rentals in Simpson Bay

Nightly prices starting at
Simpson Bay vacation rentals start at ﺩ.ﺇ294 per night before taxes and fees

Verified guest reviews
Over 4,510 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
210 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!
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