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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.

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Guest favorite
An outdoor terrace features a wooden deck, complemented by various potted plants. A glass table is surrounded by light-colored chairs. In the background, a sparkling blue pool is visible, alongside a lush green area and a view of the coastline and sky.
Home in Les Terres Basses
5 out of 5 average rating, 15 reviews

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

Top guest favorite
The private patio features a saltwater pool with ocean views, complemented by lounge chairs and tropical plants. Soft clouds drift overhead, enhancing the serene atmosphere. Nearby, a dining area offers an inviting space for meals while overlooking the lush garden and the expansive sea.
Home in Cole Bay
4.81 out of 5 average rating, 21 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.

Top guest favorite
An outdoor dining area is set for a meal with an expansive table that accommodates eight or more guests. The space features sleek chairs and offers unobstructed views of the ocean and horizon, framed by clear skies. The surrounding area reflects a serene coastal ambiance.
Home in Sint Maarten
5 out of 5 average rating, 53 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!*

Top guest favorite
A bright living area features large glass doors that open to a private outdoor space. A comfortable sofa and a coffee table are positioned on a light-toned rug. A TV is mounted on a sleek white cabinet, while wooden accents add warmth to the design.
Apartment in Simpson Bay
5 out of 5 average rating, 66 reviews

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.

Guest favorite
Home in Pelican
5 out of 5 average rating, 6 reviews

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.

Top guest favorite
A scenic view reveals a large swimming pool surrounded by lounge chairs and colorful flower gardens. The sparkling blue ocean and a distant boat can be seen, under a bright sky with fluffy clouds. Palm trees gently sway in the breeze, adding to the tropical ambiance.
Condo in Lowlands
4.95 out of 5 average rating, 125 reviews

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...

Superhost
A bright studio apartment is depicted with a spacious bed adorned with neutral-toned bedding. Natural light streams through large windows, illuminating a cozy seating area with a couch. A television is mounted on the wall above a stylish shelving unit, offering storage and decor.
Apartment in Lowlands
4.8 out of 5 average rating, 171 reviews

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.

Top guest favorite
Apartment in Upper Prince's Quarter
5 out of 5 average rating, 15 reviews

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.

Top guest favorite
An outdoor terrace features comfortable white lounge furniture arranged around a coffee table. Sun loungers are positioned beside a private infinity pool, overlooking the ocean and distant boats. The scene is framed by tropical plants and a clear blue sky, enhancing the serene coastal environment.
Loft in Marigot
4.99 out of 5 average rating, 180 reviews

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

Guest favorite
A bright living area features large glass doors opening to a waterfront view. Neutral-toned furnishings include a comfortable sofa and a unique wooden coffee table atop a circular area rug. Decorative greenery and modern art elements provide subtle accents against the white walls.
Apartment in Point Pirouette
4.91 out of 5 average rating, 133 reviews

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.

Guest favorite
A wooden deck overlooks the sandy beach and crystal-clear sea. Two loungers are positioned for relaxation, complemented by a small table and chairs. The vibrant blue water meets a clear sky, enhancing the scenic views of the tranquil surroundings.
Apartment in Collectivité de Saint-Martin
4.94 out of 5 average rating, 51 reviews

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.

Top guest favorite
A private heated pool is featured at the edge of the terrace, offering views of the ocean and nearby islands. The clear blue water contrasts with the light-colored stone surrounding the pool, while lush greenery can be seen in the background against a clear sky.
Apartment in Little Bay
4.99 out of 5 average rating, 168 reviews

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

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ933ﺩ.ﺇ999ﺩ.ﺇ999ﺩ.ﺇ837ﺩ.ﺇ716ﺩ.ﺇ735ﺩ.ﺇ793ﺩ.ﺇ723ﺩ.ﺇ599ﺩ.ﺇ613ﺩ.ﺇ716ﺩ.ﺇ1,065
Avg. temp26°C26°C26°C27°C28°C29°C29°C29°C29°C29°C28°C27°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!