
Vacation rentals with a pool in Simpson Bay Beach
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Top-rated rentals with a pool in Simpson Bay Beach
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SeaScapes Luxury Condo At Aqualina SXM
Imagine waking up to the sound of rolling waves, stepping onto your private balcony with a cup of coffee at this stunning 2bedroom condo in the exclusive Aqualina Beach Club, every day feels like a dream vacation. The condo opens directly onto Simpson Bay Beach, one of the island’s longest and most beautiful stretches of soft white sand. Spend mornings swimming in crystal-clear waters, afternoons lounging by the pool, and evenings sipping cocktails while the sky turns shades of pink and orange.

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

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
A spacious apt in a great location. This apt is located on the 2nd and 3rd floor in a gated +24/7 secured community of the Simpson Bay Yacht Club. A fully stocked kitchen. Open concept Dining/Living room combination leads to a covered patio for outdoor dining with panoramic bay views. 2 large and spacious bedrooms with private baths. Enjoy morning coffee or afternoon cocktails on one of the 3 patios all overlooking water. This complex offers 2 pools, Tennis, Jacuzzi, security and parking.

2 Bedroom Beachfront Condo with Private Pool D 1.1
Welcome to Kim Sha Beach Front apartment where amazing memories are made! Location is our shining spot! Just mins walking to the beach and located in the busiest area! Surrounded by bars and popular restaurants with local and international food, spas, shops and casinos! Walking distance to Simpson Bay Marina where you have departures to different islands with numerous boat charter and water sports activities. The location assures that you will have an unforgettable holiday!

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.

Private Pool- 5 min DRIVE to Maho Beach & Airport
OUTDOOR AREA (NOT shared with other guests) - Automatic Generator - Private Pool - Private Gazebo - chairs and table - Beach Towels - Grill ONE BEDROOM - Queen Size Bed/ Gel Memory Foam Mattress Topper (Optional) - Smart Samsung TV - High speed WIFI - Storage spaces - Air conditioning TOP FLOOR The upstairs unit is occupied, but we do not use any part of the downstairs guest area. The studio, pool, and outdoor space are fully private for your exclusive use.

The Blue Door Villa - 4 bed ocean view home
At the Blue Door Villa, we offer our guests all the creature comforts of being in a well-equipped vacation home. We are located on the Dutch side, minutes from the French border in a quiet gated community. The Blue Door Villa is a perfect place to relax while you listen to ocean waves and swim in the infinity pool. There are multiple outdoor spaces offering privacy or space to gather. We are now offering our guests an exclusive, free concierge service.

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

Escapes at the Emerald – Airport & Beach Nearby
Welcome to your Soualiga getaway! This bright, beachy studio offers stunning ocean and runway views, perfect for plane spotting or relaxing. Enjoy cozy furnishings, coastal décor, and all the comforts of home. Amenities include a pool with BBQs, fitness center, laundry room, and lounge. Just minutes from beaches, restaurants, and shops, it’s the perfect blend of comfort, convenience, and tropical charm.

Independent apartment at the bottom of the villa – Indigo Bay
The Villa Stella apartment welcomes you in a unique setting with spectacular views of the Caribbean Sea. Located in a 24-hour secure residence, tranquility awaits. You will be just an 8-minute walk to Indigo Bay Beach and close to shops and restaurants in the Dutch side. Composed of 2 bedrooms and 2 bathrooms, you can relax in the pool/jacuzzi overlooking the bay.

Indigo Bay Villa Poolside - Ocean 14
Experience refined Caribbean living in this enchanting 2-bedroom villa, nestled within the exclusive Indigo Bay community of St. Maarten. This beautifully designed villa offers a perfect blend of comfort, style, and outdoor elegance, making it an ideal retreat for those seeking tranquility and luxury.

Villa Dream View Belair Sint Maarten SXM
Embrace the tranquility in a friendly tropical caribbean modern designed private villa with spacious rooms that are sure to keep you comfortable and feeling at home. Enjoy the sunny day with infinity pool overlooking caribbean sea or enjoy the sea view while watching the sailing huge cruise ships.
Popular amenities for Simpson Bay Beach rentals with a pool
House rentals with a pool

Fleur De Lis, Private POOL, 2 bed. 2 bath

Sunrise Over St. Barths

Spacious 3BR with Private Cozy Pool

Blue Palm Estate Townhouse w/ Ocean View

Townhouse Villa LX

The best view on the island!

Préstige - Luxurious 3 bedroom by the Beach

Teresa’s Ocean Paradise
Condo rentals with a pool

Loft Condo - STEPS FROM BEACH!

Oceanfront w Pool | Maho Beach area

Waterfront, beautiful ELBA! 2 to 4 people

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

cosy apartment

Brand New- Maho Condo Studio with Seaview and Pool

Saint Maarten La Terrasse Maho

The Bay Shack
Other vacation rentals with a pool

Waterfront "Bonjour" Beacon Hill St Maarten

New listing! Ocean Vibes Luxury appt ocean front

Penthouse! 3-Bdr. Apartment with Stunning Views!

Modern Bungalow With Pool - 3 Min Walk To Beach

Escape by the Lagoon

Ocean View Villa Little Bay

Tropical Flamboyant Villa with Jacuzzi & Seaview

The Pineapple Suite
Destinations to explore
- Rentals with a washer and dryer Simpson Bay Beach
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- Waterfront rentals Simpson Bay Beach
- Rentals with pools Sint Maarten





