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

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

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

The Beach Condo
The Beach Condo, located in Palm Beach Apt. complex is a completely newly renovated 2 bedroom condo right on Simpson Bay Beach. Equipped with all amenities, this is your ideal tropical luxurious getaway. A brand new, fully equipped kitchen, large living and dining area and two king size bed-bedrooms with individual bathrooms give you all the space you need for a retreat in the Caribbean. Lounge on the porch, swim in the pool or live it up on the beach, it's all right there for you to enjoy.

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.

Beach front Condo Simpson Bay beach
Most beautiful beach on the Island (hands down!). Great 3 bedrooms, 2.5 bath condo. Located directly on Simpson Bay beach. You will enjoy amazing views of the ocean, and sunsets from the private patios. This beach condo, equipped with all amenities is the perfect location for your dream vacation with just a few steps away from the beach. Within walking distance from many restaurants, grocery stores and nightclubs. Every second you will enjoy, inside the condo or outside. Simply amazing.

On the Sea - Beachfront 3 bedroom on Simpson Bay
✨Sur Mer with IRE Vacations ✨ Directly on the beach of Simpson Bay, this spacious 3 bedroom, 3 bathroom apartment is the perfect place for your next Sint Maarten vacation. In a private residence Sur Mer is close to the airport, restaurants, shops and night life. Step out onto the white sandy beach, or catch the sunset on your balcony while listening to the crashing waves below. You can admire planes taking off and landing from your back terrace. Shared pool and gym within the residence.

Ocean Breeze at Las Arenas
This Beach Front Modern Condo is located in Simpson Bay, making it central to many of St. Maarten's popular restaurants, bars, stores, supermarkets, casinos and beaches. Comfortable and spacious enough for a family or group of friends, you get to enjoy your privacy and be minutes away from fun activities on the island. Escape from the busy city center of St. Maarten within minutes and relax on your balcony while watching amazing sunsets and listening to the sound of the waves.

4 Bedroom Beachfront Condo with Private Pool D2.1
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!

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

Beachfront condo with pool
This beautiful 2 bedroom - 2 bathroom apartment is located on Simpson bay road with a shared pool and of course it’s right on the most beautiful beach of Sint Maarten. The master bedroom has a king size bed. The second bedroom has a queen size bed. The patio has a dining area and a BBQ for you to enjoy nights overlooking the pool and ocean. Add my listing to your wishlist by clicking the❤️ in the upper right corner.

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.
Popular amenities for Simpson Bay Beach rentals with a pool
House rentals with a pool

Pelican key - BEACH FRONT Villa

Sunrise Over St. Barths

Villa Coral | Collection Villas Saint-Martin

Spacious 3BR with Private Cozy Pool

Blue Palm Estate Townhouse w/ Ocean View

Townhouse Villa LX

Stunning Panoramic Views Of The Ocean & St Barth!

The best view on the island!
Apartment rentals with a pool

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

Indigo~2 KingSuites, Priv Pool, 2 Min Walk 2 Beach

Renovated 2-Level Condo @ Simpson Bay Yacht Club

cosy apartment

Brand New- Maho Condo Studio with Seaview and Pool

Saint Maarten La Terrasse Maho

Studio on the water in the Simpson Bay Yacht Club

Havya Cozy Stays | In Maho, Near Beaches & Airport
Other holiday rentals with a pool

Life's Good

Waterfront "Bonjour" Beacon Hill St Maarten

Aman_Aria

Brand new! - Slowlife - Enjoy Villa

Bella Vista - Pool & sea view, 5 minutes from Grand Case

Modern Bungalow With Pool - 3 Min Walk To Beach

Villa Blue Roc

Tropical Flamboyant Villa with Jacuzzi & Seaview
Destinations to explore
- Apartment rentals Simpson Bay Beach
- Rentals with outdoor seating Simpson Bay Beach
- Rentals with beach access Simpson Bay Beach
- Rentals with a patio Simpson Bay Beach
- Family-friendly rentals Simpson Bay Beach
- Waterfront rentals Simpson Bay Beach
- Rentals with a washing machine and dryer Simpson Bay Beach
- Flat rentals Simpson Bay Beach
- Beachfront rentals Simpson Bay Beach
- Rentals with pools Sint Maarten





