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Holiday 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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Top guest favourite
A spacious daybed is shaded by a wooden pergola, surrounded by vibrant greenery. The beach and ocean serve as a backdrop, with gentle waves lapping at the shore. Colorful cushions and a soft blanket add comfort, while a small Buddha statue creates a serene ambiance.
Apartment in Simpson Bay
4.97 out of 5 average rating, 95 reviews

Beach front luxury! Huge 2BR that has it all! 😍🤩😍

5 star hotel luxury is yours in this modern beach home! 2 guest rooms with en-suite bathrooms and deck access. Enjoy cooking your own meals and dine inside or on the deck (or beach!). Largest deck on Simpson Bay beach has it all: huge daybed, loungers, living and dining areas for your comfort and pleasure. Unwind in the den and enjoy the big screen there or in either bedroom. Your neighbor is a boutique hotel and will gladly serve you meals and drinks right to your deck! Much more info available

Guest favourite
A cozy living area features a comfortable gray sofa and a wooden coffee table. Two windows offer expansive views of the ocean, with light reflecting off the water. Beams stretch across the ceiling, enhancing the airy feel of the space.
Apartment in Simpson Bay
4.81 out of 5 average rating, 180 reviews

Oceanfront w Pool | Maho Beach area

Location , Location Location ! You can not get any closer to the ocean than in this cliff side apartment. The sound of waves crashing below and incredible ocean views from every room. The sunrise is magical everyday and by night the glowing lights of Simpson bay. This cliff side apartment has everything you need for a dream stay away from the crowds. . Just steps from 4 beaches Simpson bay, Mullet bay, burgeux bay and a 5minute walk to the world famous Maho Beach with its famous plane landings

Top guest favourite
Lounge chairs are placed on sandy ground, facing the vibrant turquoise ocean. Palm trees gently sway in the breeze, adding to the serene beach setting. A white picket fence encloses the area, and distant mountains can be seen along the shoreline.
Apartment in Simpson Bay
5 out of 5 average rating, 20 reviews

Popular Beachfront Property Barefoot /Simpson bay

This Beautiful Beachfront condo in Sint Maarten, Barefoot, is like being on your own little island. 1 min. to shore. The beautiful crystal blue ocean waters you can see and hear from every corner of this condo. This Oasis has such beauty. Mostly private with pure tranquility. . A constant breeze as you open up the doors and windows to let the sea air open up your senses. 8 minute drive from the Dutch airport 16 minutes walking distance from main restaurants casinos and live entertainment.

Top guest favourite
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.
Flat in Simpson Bay
5 out of 5 average rating, 62 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 favourite
The living area offers a spacious layout with a comfortable sofa and armchair, complemented by a wooden coffee table. Large windows display panoramic views of the lush landscape, while natural light highlights the neutral color palette and elegant decor.
Flat in Lowlands
5 out of 5 average rating, 20 reviews

A-504 Cozy unit facing mullet beach

Welcome to Fourteen at Mullet Bay, one of the most exquisite and luxurious beachfront residences in St Maarten located directly on the famous Mullet Bay beach and golf course. <br><br>Welcome to our exquisite one-bedroom apartment, nestled on the fifth floor and offering stunning views of the Simspon bay Lagoon and Mullet Bay golf course. Prepare to indulge in a world of luxury and sophistication, where every detail has been meticulously designed to create an unforgettable coastal retreat.

Top guest favourite
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, 175 reviews

Sea Loft Vue imprenable - piscine privée

* Loft de 200m² * Vue mer exceptionnelle * Piscine privée * A 250 mètres de la petite plage de Galisbay * Terrasse avec chaises longues, salon de jardin, table d'extérieur et BBQ * Espace bureau * Wifi 100 Mbps * TV avec milliers de chaines du monde entier * A 250 m à pied de la marina Fort Louis de Marigot * A 5 min à pied du centre ville de Marigot avec ses restaurants, boutiques et autres commerces * A 5 min de l'embarcadère pour Saint-Barth et Anguilla, et de la station de taxis

Guest favourite
The image depicts a clear blue swimming pool surrounded by lounge chairs and tropical palm trees. In the background, the ocean can be seen alongside a beach area with a white railing, under a bright sky featuring fluffy clouds.
Flat in Simpson Bay
5 out of 5 average rating, 8 reviews

Sunny Outlook - 1-bdr condo - Beachfront Residence

✨ Sunny Outlook with IRE Vacations ✨ This amazing 1 bedroom 1.5 bathroom unit is located at Palm Beach Condo’s, directly on Simpson Bay Beach. Palm beach is very convenient located in Simpson Bay, here you will find beach bars, restaurants and supermarkets within walking distance. Only a 10 minute drive from the airport. Palm beach offers you a large common pool and private access to the beach. Enjoy your day on the beach, at the pool or go on an adventure on our beautiful island!

Top guest favourite
Apartment in Maho
4.91 out of 5 average rating, 225 reviews

Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub

This charming, cozy, and tranquil tropical nest is located where all the action is! The golf course, iconic bars, the unprecedented landing strip, the popular Maho and Mullet bay beaches, Maho market with daily fresh take away breakfast/lunch buffets and a divine selection of exotic restaurants are all in walking distance. If you wish to just lounge and relax by the pool, jacuzzi, and private gazebo bar or enjoy the nightlife; it’s all readily available for you to indulge.

Guest favourite
Flat in Lowlands
4.96 out of 5 average rating, 46 reviews

"Blue Emerald ¤ Studio" piscine & fitness à Maho

Détendez-vous dans ce cocon tropical calme et élégant. Tout les ustensiles de cuisine pour les casaniers, Tv connectée, wifi gratuit, Netflix activé, et aussi la délicieuse piscine juste en face et la salle de musculation high-tech pour les plus motivés. Proche du centre touristique (shopping, restaurants, bars, clubs ...) et de la plage Mullet Bay (800m) ... Venez profiter d'un espace moderne et confortable, idéal pour les couples ou les voyageurs solo. Vous allez adorer …

Guest favourite
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.
Flat in Point Pirouette
4.91 out of 5 average rating, 127 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.

Top guest favourite
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.
Flat in Little Bay
4.99 out of 5 average rating, 164 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 !

Top guest favourite
A panoramic view of the azure ocean is captured, dotted with sailboats. The sandy beach features thatched umbrellas and lounge chairs. Lush palm trees are visible, alongside a beachside bar area with shaded seating, all under a bright sky with fluffy clouds.
Flat in Cole Bay
4.92 out of 5 average rating, 51 reviews

Royal Palm Hilton SXM

This beautiful 2-bedroom 2-bathroom condo is in the heart of Simpson Bay, located inside the Royal Palm Hilton Vacation Club, and offers full resort amenities including a swimming pool, direct beach access, and a gym. This fourth-floor units has dazzling sunset views. Wake up to the beautiful view and then head downstairs where all you have to do is choose between the beach or the pool.

Popular amenities for Simpson Bay rentals with a pool

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$327 SGD$350 SGD$350 SGD$293 SGD$251 SGD$257 SGD$278 SGD$254 SGD$210 SGD$199 SGD$219 SGD$265 SGD
Avg. temp26°C26°C26°C27°C28°C29°C29°C29°C29°C29°C28°C27°C

Quick stats about holiday rentals with a pool in Simpson Bay

  • Total holiday rentals

    Explore 210 holiday rentals in Simpson Bay

  • Nightly prices starting at

    Simpson Bay holiday rentals start at $103 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,510 verified reviews to help you choose

  • Family-friendly holiday rentals

    120 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    210 of Simpson Bay holiday rentals include wifi 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!