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Apartment vacation rentals in Simpson Bay

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Top-rated apartment rentals in Simpson Bay

Guests agree: these apartments are highly rated for location, cleanliness, and more.

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Rental unit in Point Pirouette

4.92 out of 5 average rating, 100 reviews

Secret View amazing apartment- Private pool

Secret View, amazing apartment directly on the lagoon with private pool. Totally and newly renovated apartment with one separate bedroom, 1,5 bath, full equipped kitchen, huge terrace, private pool, directly on the lagoon. Very quiet and secure location, next to Maho, Mullet Bay , golf course , supermarket, bars, restaurants, casinos. A really relaxing place, it will be the best part of your holidays. Private and free parking. Sint Maarten is currently experiencing some daily power outages

Rental unit in Simpson Bay

5 out of 5 average rating, 19 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.

Rental unit in Simpson Bay

5 out of 5 average rating, 191 reviews

The Beach House Apartment

A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more

Rental unit in Simpson Bay

4.94 out of 5 average rating, 110 reviews

Le Petit Paradis - Beachfront 1 Bedroom Apartment

"Petit Paradis" (Little Paradise), a genuine Caribbean getaway. A spacious one-bedroom Beachfront apartment right on beautiful Simpson Bay Beach and in the center of all the happenings. Relaxing terrace, five stairs away from the Beach, and within walking distance from great Restaurants, Nightlife, Activities, and Watersports. This modern, fully furnished, and equipped apartment has everything you need for a dream vacation, Hope to invite you soon in our Paradise, Elodie

Rental unit in Oyster Pond

4.88 out of 5 average rating, 110 reviews

Lovely Studio Apartment with Pool & Nature Views!

Take a break and unwind at this peaceful studio apartment, perfect for your Caribbean getaway! This fully equipped studio is located just 7-10 minutes away from the capital, Philipsburg, and a few minutes away from several beautiful beaches. It also has gorgeous scenic views and an inviting and relaxing pool! As well as a rooftop terrace with scenic 360 views. Baby crib and grill available upon request for small fee and washer & dryer available on premise for free use.

Rental unit in Simpson Bay

4.97 out of 5 average rating, 178 reviews

Lilly's Beach

This is a very SPECIAL SMAll RESIDENCE known as Ocean Edge . Beach Front located directly on beautiful Simpson Bay Beach! Enjoys one of the best locations on the island . Panoramic sea views with your toes in the sand and balmy Caribbean breezes. A clear turquoise sea dazzles in tropical sun, powdery white sands stretching along one of St. Maarten's longest beaches. New totally refurbished modern apartment with modern amenities and comforts. A perfect vacation spot !

Rental unit in Lowlands

4.97 out of 5 average rating, 117 reviews

Cupecoy Garden Side

Delightful one bedroom appt. Fully furnished with mid century teak furniture. A spacious 70m2 space with large terrace in a mature tropical garden. A brand new fully equipped kitchen was added in October 2022. Located in trendy and safe Cupecoy. CJ1 is a quiet oasis to relax in the luxurious garden, or head for the the renowned beach of Mullet bay within a 3 minute walk. Supermarkets, gym yoga studio very close by. This is the place to be.

Rental unit in Lowlands

4.9 out of 5 average rating, 29 reviews

The Emerald at Maho

Welcome to "Hangar 310W" , a unique and cozy condo located in the heart of Maho with views of Princess Julianna International airport. The condo is in walking distance to all the basics you need for your intended stay. Just a 5 minute walk to Maho village which is full of shops, a variety of restaurants, bars, casinos and nightclubs. The world famous Maho Beach is a 10 minute walk where you can smell the jet fuel up close and personal.

Rental unit in Philipsburg

4.98 out of 5 average rating, 131 reviews

Hibiscus-Large 1 bed Beachfront apartment 1st flr

This modernly decorated apartment home is centrally located in the capital of the Dutch side, Philipsburg. The area is full of life during the day and quiet and relaxing in the evening. This home away from home will make your daydreams of island life a reality. Enjoy the lovely courtyard garden downstairs, relax on the balcony looking out to the beautiful garden and plan your day’s adventure on and around this dual nation Island.

Rental unit in Simpson Bay

5 out of 5 average rating, 114 reviews

Simpson bay beach, spacious, beautiful views!

Amazing spacious 3 bedroom, 2 bathroom apartment with awesome location in the heart of Simpson Bay. location, location, location in the middle of it all. Right across the 2.5 mile beautiful Simpson Bay Beach. All the beach necessities are there to enjoy, beachchairs, snorkeling gear, fishing rod and even 2 kayaks. You can walk to many nearby restaurants, grocery stores and other shops. Public transportation is also steps away.

Rental unit in Little Bay

4.98 out of 5 average rating, 129 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 !

Rental unit in Simpson Bay

4.8 out of 5 average rating, 100 reviews

Apartment on the beach 3

Beach front apartment with beautiful view of Caribbean sea! The white sandy, two miles long Simpson bay beach is right out of the door. It is located walking distance to the tourist area with many restaurants, bars, clubs, grocery stores, spas, night clubs, the marina to watch the large yachts, souvenir shops and much more!!!

Vacation rentals for every style

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Villas

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Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Simpson Bay apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

Rental unit in Lowlands

4.95 out of 5 average rating, 22 reviews

Golden studio in Maho

Rental unit in Rue des Terres-Basses, Baie Nettlé

5 out of 5 average rating, 11 reviews

The Captain's Quarters (1 bedroom)

Rental unit in Lowlands

5 out of 5 average rating, 29 reviews

Gorgeous 2 bedroom-17th floor, Fourteen Mullet Bay

Rental unit in Lowlands

4.79 out of 5 average rating, 29 reviews

B Maho Studio

Rental unit in Simpson Bay

4.94 out of 5 average rating, 16 reviews

Comfy Beachside Vacation I

Rental unit in Simpson Bay

4.83 out of 5 average rating, 6 reviews

Maho Beach Studio Apartment Sunset

Rental unit in Lowlands

4.93 out of 5 average rating, 14 reviews

Villa Spice For Life SXM 2

Rental unit in Koolbaai

4.91 out of 5 average rating, 11 reviews

Beautiful Spacious Studio with spectacular view

Private apartment rentals

Rental unit in Sandy Ground

4.85 out of 5 average rating, 34 reviews

Splendid apartment Le Secret Baie Nettlé!

Rental unit in Collectivité de Saint-Martin

4.98 out of 5 average rating, 44 reviews

"Paradise Beach" - Impressive 2 bedrooms seafront

Rental unit in Lowlands

5 out of 5 average rating, 19 reviews

Gorgeous Beachfront studio

Rental unit in Sint Maarten

5 out of 5 average rating, 12 reviews

CONDOStmaarten by the sea (Adults Only)

Rental unit in Lowlands

5 out of 5 average rating, 5 reviews

Luxury apartment, sea view

Rental unit in Lowlands

4.86 out of 5 average rating, 14 reviews

Condo with stunning sea views and Mullet Bay Beach

Rental unit in Lowlands

5 out of 5 average rating, 28 reviews

Rock Star Gem in Maho with generator

Rental unit in Simpson Bay

4.92 out of 5 average rating, 13 reviews

Beachfront condo with pool

Apartment rentals with a hot tub

Rental unit in Cole Bay

4.75 out of 5 average rating, 4 reviews

Colebay Retro Vibe w Private Outdoor Enclosure

Rental unit in Lowlands

4.86 out of 5 average rating, 7 reviews

Unique 4BR Penthouse,Close to day & night activiti

Rental unit in Lowlands

4.92 out of 5 average rating, 13 reviews

breathtaking apartment with ocean view

Rental unit in Simpson Bay

5 out of 5 average rating, 8 reviews

Studio - Simpson Bay Yacht Club

Rental unit in Simpson Bay

4.96 out of 5 average rating, 96 reviews

Top of the art penthouse

Rental unit in Collectivity of Saint Martin

5 out of 5 average rating, 9 reviews

Le Colibri - Baie Orientale - Private Jacuzzi

Rental unit in St Martin

4.93 out of 5 average rating, 71 reviews

The Perch - A unique jungle experience.

Rental unit in Indigo bay

4.94 out of 5 average rating, 82 reviews

Independent low villa apartment - Indigo Bay

Quick stats about apartment rentals in Simpson Bay

Total rentals
120 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
3.2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
60 properties have a pool

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