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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
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.
Condo 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 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, 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 favorite
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.
Apartment 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.

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, 124 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...

Guest favorite
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.
Apartment 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 favorite
A well-maintained outdoor pool is surrounded by lounge chairs, offering a relaxing space for guests. Shade is provided by large umbrellas, and tropical palm trees are visible in the background. The pool area is complemented by modern residential buildings, enhancing the serene environment.
Condo in Lowlands
4.98 out of 5 average rating, 85 reviews

Brand New- Maho Condo Studio with Seaview and Pool

Brand new studio, centrally located in Maho, with 24/7 security, amenity filled and a short distance to beaches, shopping and nightlife. The studio is a 5 minute walk to Maho Village and an 8 minute walk to the famous Maho Beach where you will find a multitude of restaurants, duty-free shopping and Casino Royale. It's also an 10 minute walk to Mullet Bay, one of the most beautiful and popular local beaches on the island. The location is a convenient 5 minute drive to the airport.

Top guest favorite
Condo in Maho
4.91 out of 5 average rating, 226 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.

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, 175 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, 128 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 favorite
Two sun loungers are positioned on a sandy beach, accompanied by a small table holding a bottle of champagne and two glasses. A backdrop of clear blue water and gentle waves is visible, with a few green trees enhancing the tranquil setting.
Condo in Saint Martin,Guadeloupe
5 out of 5 average rating, 57 reviews

Villa Belharra, amazing view

You dream of a vacation in paradise, Villa Belharra will satisfy you. Unique location directly on the beach, breathtaking view day and night. New apartment for 2/4 people. It is located in a private, quiet and secure residence (night guard) which has 4 private swimming pools, 2 tennis courts, and parking lots. Next to all amenities there are food shops (supermarket, bakery, caterer ...), pharmacy, car rental restaurant.

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, 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 favorite
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.
Apartment 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. priceG$53,116 GYDG$56,880 GYDG$56,880 GYDG$47,679 GYDG$40,778 GYDG$41,823 GYDG$45,169 GYDG$41,196 GYDG$34,086 GYDG$32,413 GYDG$35,550 GYDG$43,078 GYD
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 G$16,729 GYD 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!