
Holiday 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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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 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.

Panoramic View Terrace Infinity Pool Top Penthouse
Wake up to the magnificent panoramic view of the lagoon on the top floor, rejuvenate your body with a refreshing dip in the private rooftop infinity pool with a coffee or tropical drink. Take a 10 mins stroll to the famous Mullet bay Beach and grab a few freshly French croissants by the Square. After sunset, enjoy the plentiful neighborhood bars and restaurants or take 5 mins drive to Maho where you will find a vast variety of restaurants, casino and clubs or Porto Cupecoy for romance spot.

Beachfront Caribbean Breeze in Paradise, SXM
Caribbean Breeze inviting Beach front home. A few steps to our beach and pool. Walk to mainstream. Amazing views . 2/2.5 with huge Master. Hear the waves flowing in onto the shore for those relaxing days and nights. New kitchen, living room , bathrooms, dining area,etc. Unwind on any balcony, penthouse ocean view, on daybed with a nice drink , looking over the verse tranquil ocean. Take a dip in the soothing crystal clear waters, 1 minute walk away. Amenities enclosed & Wi-Fi included.

Sint 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...

Maho Love Nest: 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.

THE HILL HOUSE, 2 Bdr, pool, panoramic view
Hébergement avec piscine privée et vue à couper le souffle Offrez-vous une parenthèse de rêve dans cette maison élégante, nichée dans le quartier sécurisé Almond Grove Estate. Profitez de 2 chambres climatisées, d’un salon lumineux, d’une cuisine équipée, et surtout d’un espace extérieur idyllique avec piscine et vue panoramique sur Simpson Bay. À seulement 5 min de Marigot, 10 min de l’aéroport et 15 min des plages, c’est l’adresse parfaite pour un séjour inoubliable !

Secret View amazing apartment- Private pool
Welcome to Secret View, a stunning, fully renovated, stylish and modern apartment located directly on the lagoon with a private pool and breathtaking views. Quiet and secure area, next by Maho, Mullet Bay, the golf course, supermarket, bars, restaurants, and casinos. A true sanctuary, it’s sure to be the highlight of your holiday. Private and free parking Your ultimate vacation retreat. Sint Maarten is currently experiencing some daily power outages

Sea Loft, Breathtaking View – Private Pool
* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with deckchairs, garden furniture, outdoor table and BBQ * Office space * 100 Mbps WiFi * 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, shops and other stores * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

Shore Thing - Cosy Condo on Simpson Bay Beach
✨ Shore Thing with IRE Vacations ✨ Welcome to Shore Thing, your beachfront escape in the heart of Simpson Bay, located within the exclusive Coco’s Beach Club complex. Perfect for couples or solo travelers, this elegant oceanfront condo offers the ideal blend of comfort, privacy, and island style. The condo features a king-size bed, a fully equipped kitchen, and a relaxing living area that opens directly to the sea breeze.

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 Beach rentals with a pool
House rentals with a pool

Life's Good

Aman Oceanview

2 Bedroom Ocean Front Villa, Private Infinity Pool

Casa Bisani,2BR 2.5BH Townhouse in Cupecoy Estates

Préstige - Luxurious 3 bedroom by the Beach

Teresa’s Ocean Paradise

Villa Monchal, 1-minute walk to the beach

"Sweet Home on the Beach"
Apartment rentals with a pool

Waterfront, beautiful ELBA! 2 to 4 people

Villa Belharra, amazing view

2BR Beachfront Oasis •Pool + Epic Sunsets @Encanto

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

Beachfront Condo| Pool View + Private Beach Access

Maho Vibes Condo

Ocean Breeze at Las Arenas

Lovely 2 Bedroom Condo With Ocean Views in SXM
Other holiday rentals with a pool

The Captain's Quarters (1 bedroom)

"Black Pearl"

Gorgeous 2 bedroom-17th floor, Fourteen Mullet Bay

NEW 1BR apt lagoon & sunset view 2/3p

Brand new! - Slowlife - Enjoy Villa

Little Spot of Paradise(ground floor, beach, pool)

"Paradise Beach" - Impressive 2 bedrooms seafront

Indigo Bay Villa Poolside - Ocean 14
Destinations to explore
- Rentals with a washing machine and dryer Simpson Bay Beach
- Rentals with a patio Simpson Bay Beach
- Beachfront rentals Simpson Bay Beach
- Rentals with beach access Simpson Bay Beach
- Family-friendly rentals Simpson Bay Beach
- Rentals with outdoor seating Simpson Bay Beach
- Apartment rentals Simpson Bay Beach
- Waterfront rentals Simpson Bay Beach
- Flat rentals Simpson Bay Beach
- Rentals with pools Sint Maarten




