A coastal town with a marina, mountains in the background, and a clear sky.

Simpson Bay Vacation Rentals

Q: What are some of the best vacation home rentals that Simpson Bay has to offer?

Philips Scott House Calinago : This vacation home rental outside of Simpson Bay is in a shopping district and equipped with air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Amenities like a microwave and free parking are also available for your convenience. Another good choice for your trip to Simpson Bay is Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool .

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Dates

November 2026

December 2026

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Our top choices for Simpson Bay vacation rentals

A resort with a view of sailboats on the water, a beach with palm trees, and a modern building with balconies.

1. Hilton Vacation Club Royal Palm St. Maarten

Simpson Bay

Carmelle,

AED 792 total

includes taxes & fees

11 Nov - 12 Nov

A high-rise hotel with a view of the sunset over a marina.

2. Simpson Bay Suites

Simpson Bay

Manishkumar

AED 555 total

includes taxes & fees

7 Nov - 8 Nov

A modern living room with a large sliding glass door leading to a balcony with a view of a coastal town and mountains.

3. The Hills Residence

Simpson Bay

Harold

AED 1,614 total

includes taxes & fees

6 Dec - 7 Dec

A wooden deck with a staircase leading to a beach view, surrounded by potted plants and colorful beach toys.

4. Maho Beach House Ocean Front Garden Studio

Maho, Sint Maarten

Laura

AED 794 total

includes taxes & fees

7 Nov - 8 Nov

A poolside area with a wooden table, lounge chairs, and a view of the ocean.

5. Blue Sail Apartments - 1-Bedroom Apartments

Pelican Key

AED 689 total

includes taxes & fees

7 Nov - 8 Nov

A compact living space with a kitchenette, a dining area, and a sofa.

6. Beach Front Studio C3

Simpson Bay

Benjamin

AED 529 total

includes taxes & fees

7 Nov - 8 Nov

A modern bathroom with wooden cabinetry, a glass shower enclosure, and a black floor lamp.

7. Beach Front 1 Bedroom Flat D3

Simpson Bay

Christopher

AED 588 total

includes taxes & fees

12 Nov - 13 Nov

A balcony with two white chairs and a view of the ocean.

8. Maho Beach House - Petit Studio Océanique - Charmante Vue

Maho, Sint Maarten

Roy N.

AED 863 total

includes taxes & fees

7 Nov - 8 Nov

9. Blue Sail Apartments - Two-Bedroom Apartments

Pelican Key

Heidi

AED 491 total

includes taxes & fees

7 Nov - 8 Nov

A pool area with a dolphin statue, blue lounge chairs, and a stone wall with greenery.

10. Centrally located Simpson bay 1bdr apt (1-2)

Simpson Bay

AED 859 total

includes taxes & fees

19 Nov - 20 Nov

A pool area with clear blue water, wooden deck, and a view of a marina with boats and a hilly landscape in the background.

11. C314 - Stunning 1 Bedroom Apartment

Sint Maarten

A pool area with a stone wall, palm trees, and lounge chairs.

12. 1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

Simpson Bay

jason l.

AED 700 total

includes taxes & fees

19 Nov - 20 Nov

A swimming pool with lounge chairs and a stone wall.

13. Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

Simpson Bay

A swimming pool with wooden deck, surrounded by greenery, overlooking a coastal town and mountains.

14. C352 - Top view with balcony

Simpson Bay

A balcony with a view of a coastal city and mountains. There are two wicker chairs and a small table with a vase of flowers.

15. C344 - Lagoon view with balcony

Simpson Bay

AED 1,192 total

includes taxes & fees

15 Nov - 16 Nov

A swimming pool with a view of a marina and mountains in the background.

16. B213 - Deluxe 1 Bedroom Apartment

Sint Maarten

AED 1,070 total

includes taxes & fees

13 Nov - 14 Nov

A poolside area with outdoor seating and a view of a hotel building and the sea.

17. Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

Simpson Bay

Douglas T.

AED 1,371 total

includes taxes & fees

19 Nov - 20 Nov

A swimming pool with a view of a marina and mountains.

18. D402 - Beautiful apartment with garden and view

Cole Bay

A rooftop infinity pool with wooden decking and lounge chairs, overlooking a coastal cityscape.

19. B246 - Breathtaking Lagoon View with Balcony

Sint Maarten

AED 1,192 total

includes taxes & fees

24 Nov - 25 Nov

A modern living room with a large TV, a wooden coffee table, a sofa, and a sliding glass door leading to an outdoor patio with a view of mountains.

20. C301 - Beautiful Lagoon View Apartment

Cole Bay

AED 1,192 total

includes taxes & fees

9 Nov - 10 Nov

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Find vacation rentals that suit your style

Top Simpson Bay Hotel Reviews

A glass table with a white mug and a loaf of bread, a decorative vase, and a poolside lounge area with a view of purple flowers and palm trees.

Pomme Cannelle Luxury Suites & Spa

Orient Bay

10/10 Excellent

Pauline & Jeremy!!! Fantastic warm welcome! You can tell that these owners absolutely love their guests. Too many details to mention from the private jacuzzi to concierge services provided by Pauline. Beautiful interiors, comfortable beds. Gated neighborhood 5 minutes on foot to Orient Bay beaches and restaurants. Good old fashioned bed and breakfast atmosphere. Oh!! The amazing, not-to-miss breakfast! Highly recommended.

Lara Abigail

A person sitting at a table with a book, a croissant, and a cup.

Le Martin Boutique Hôtel

Cul de Sac

10/10 Excellent

Elizabeth

A swimming pool with lounge chairs and a table on a wooden deck, surrounded by greenery and a mountain view.

Villa Jwi Lavi Boutique Hotel

Cul de Sac

10/10 Excellent

My wife and I loved this place. It was smaller and quieter than your typical hotel or resort. The hosts provide a nice little breakfast each morning (croissants and baguettes with local jams, plus fresh fruit and juice). The pool is nice, as are the views. The property is a good location on the island, in my opinion. Easy drive to Anse Marcel on the northern tip (phenomenal beach up there). Also easy drive to Grand Case (best food ever) and Orient Beach (great scene in general). The hosts were...

Cameron

A beach resort with palm trees, a pathway, and a view of the ocean.

Orient Beach Hotel

Orient Bay

10/10 Excellent

This is the perfect place to have an ocean view room that is beautifully done. The hotel doesn’t offer a ton of amenities, but it’s in a great location on a beautiful beach. Come here to enjoy time with a partner, have access to beach restaurants and activities and rent a car to explore the island. Our concierge, Junior, was amazing and saved us by getting our passports to us after we had already arrived to the airport!

Anonymous traveler

A modern living room with large windows, a purple sofa, and a view of the beach and ocean.

Mullet Bay Suites: Your Luxury Stay Awaits

Maho

10/10 Excellent

I highly recommend Mullet Bay Suites for its cleanliness, modern amenities, and comfort. The suites offer stunning views, especially in the morning, and feature convenient parking and robust security. The property is just a short walk to the beach, adding to its appeal. The management is excellent, and we received a warm welcome from the property manager, Emmanuel, who greeted us with cold towels and local banana rum—a delightful touch! Emmanuel is attentive, kind, and responsive, providing...

Juanita

A balcony with a view of the sea, a bed with towels, and two white wicker chairs.

Le Temps des Cerises Hotel Beach

Grand Case

10/10 Excellent

The hotel, which is only a few weeks old, and which is owned by the same people who own Sol E Luna nearby, is a classy, first rate property, right on the beach in Grand Case, with a staff that couldn't have been more friendly and helpful. All nine rooms have balconies with full ocean views. The design and styling are very contemporary and absolutely perfect. And, oh, the dining scene in Grand Case can't be beat!

Len

A coastal resort with a swimming pool, beach access, and lush greenery.

Grand Case Beach Club

Grand Case

10/10 Excellent

First time to the island. This resort was absolutely beautiful. Two areas for sun and beach. Beach chairs and umbrellas, water sports… we never had to wake up super early to get a chair which was awesome! We snorkeled around the resort, saw lots of fish, star fish, and found about 10 whole sand dollars! Food was very reasonably priced and delicious. Drinks were good - not watered down. Staff was very helpful and kind, check in was easy and our room was ready when we arrived. Rooms had all the...

Karrie

A narrow pathway flanked by lush greenery and a building with a light-colored facade.

La Villa Hibiscus

Orient Bay

10/10 Excellent

We spent 4 nights at La Hibiscus. Really enjoyed everything about it. Florian gave us a free upgrade to the Jasmine suite. Large, comfortable bed, great shower and bathroom. Great terrace for sunning and looking at the mountains. We had the pool to ourselves which we loved. Very hands off approach by management which meant great privacy which we like. Only 5 minutes to Orient Beach….great choice of restaurants including a couple of breakfast places. Will definitely come back. FYI….renting a car...

Sid

A poolside bar with a view of a pool and lounge chairs.

Hotel L'Esplanade

Grand Case

10/10 Excellent

My wife and I stayed at the Hotel L'Esplanade for a week! And it was out first time here on the French side and we enjoyed it a lot. Very comfortable and spacious accommodations with large bedroom, bathroom and Living/dining room with the full kitchen if you decide to ignore all of the restaurants nearby and decide to make a meal yourself. Big, beautiful terrace to enjoy breakfast or sip wine while watching the sunset. The pool is peaceful, and the food is freshly grilled right before you, while...

Mikhail

A beachfront hotel with a pool, palm trees, and a clear blue sky.

Azure Hotel and Art Studio

Simpson Bay

10/10 Excellent

Mitchell

A swimming pool with clear blue water, a building with balconies, and palm trees.

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key

10/10 Excellent

We rented a two bedroom unit (really two one bedroom units connected by a short hallway) with our 21 year-old triplets. It was a perfect setup for us. My wife and I took one unit, and our kids took the other. The resort is in a very convenient location- also very well-maintained. There are a number of restaurants and bars within walking distance, which our kids really liked because they could go out without waiting for us to drive them somewhere. There is a small grocery store about 100...

John

A resort with a swimming pool, palm trees, and a view of the ocean.

La Samanna, A Belmond Hotel, St Martin

Les Terres Basses

10/10 Excellent

Eduardo

A balcony with a view of a beach and hotel buildings.

Baker's Suites

Simpson Bay

10/10 Excellent

Kathy

A resort with multiple hotel buildings, a marina, and a clear blue ocean.

The Villas at Simpson Bay Resort

Pelican Key

10/10 Excellent

Angelice

A balcony with a view of a beach and ocean.

Holland House Beach Hotel

Downtown Philipsburg

10/10 Excellent

Ellen Wyszynski

A breakfast table with croissants, a watermelon slice, and a glass of orange juice, overlooking the ocean.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

10/10 Excellent

Third stay in St Maarten/Martin since 1993. By far the nicest hotel of my 3 stays. While not directly on a beach, a short drive to Orient, or across the street to Dawn Beach at the Westin. We were on the upper level, building B and had a great view of the ocean across the street. Actually you can drove about anywhere on the island in 30 to 45 minutes depending on traffic. We stayed the first week of November 2015 and full season had not kicked in. The traffic is slow and you have to be...

Island visitor

A swimming pool with a wooden deck, palm trees, and a building with multiple balconies and outdoor seating.

Palm Court Residence & Hotel at Orient Beach

Orient Bay

10/10 Excellent

Great staff! Had trouble with our rental car company and staff arranged to have different company drop car at hotel for us, such a breeze! Awesome morning breakfast, chocolate croissants were very tasty! Great proximity to the beach and a variety of restaurants in Orient Village. You MUST dine at La Table d'Antoine; best onion soup and duck breast w/5 vinegars, to die for!! Hotel has arrangement with Kakoa Beach Bar, so it as easy to get lounge chairs and umbrella each morning. If you're...

Pam

Frequently Asked Questions

Can I find a vacation rental in Simpson Bay?

Yes, we give you a choice of vacation rentals near top attractions in Simpson Bay, or you can choose a secluded option if you'd like a relaxing place to stay. Visitors like the array of shops and popular beaches in Simpson Bay. While you're here, grab a bite or have a drink at the top-notch restaurants and lively bars.

What are some of the best vacation home rentals that Simpson Bay has to offer?

Philips Scott House Calinago: This vacation home rental outside of Simpson Bay is in a shopping district and equipped with air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Amenities like a microwave and free parking are also available for your convenience. Another good choice for your trip to Simpson Bay is Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool .

How many vacation rentals are there in Simpson Bay?

With 38 Expedia vacation rentals, you're sure to find just the right place for your Simpson Bay stay.

What’s there to see and do in Simpson Bay?

Kim Sha Beach and Flamingo Beach are a couple of lovely local spots to get outside and enjoy nature. Hollywood Casino and Simpson Bay Beach are other places to visit while you're in town.

What’s a vacation rental in Simpson Bay like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Simpson Bay. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for families.

Simpson Bay Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Simpson Bay vacation rentals

1. Hilton Vacation Club Royal Palm St. Maarten

2. Simpson Bay Suites

3. The Hills Residence

4. Maho Beach House Ocean Front Garden Studio

5. Blue Sail Apartments - 1-Bedroom Apartments

6. Beach Front Studio C3

7. Beach Front 1 Bedroom Flat D3

8. Maho Beach House - Petit Studio Océanique - Charmante Vue

9. Blue Sail Apartments - Two-Bedroom Apartments

10. Centrally located Simpson bay 1bdr apt (1-2)

11. C314 - Stunning 1 Bedroom Apartment

12. 1 bedroom with pool in Simpson Bay - GENERATOR (1-3B)

13. Blue Sky Apt in the middle of Simpson Bay-GENERATOR(1-3A)

14. C352 - Top view with balcony

15. C344 - Lagoon view with balcony

16. B213 - Deluxe 1 Bedroom Apartment

17. Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

18. D402 - Beautiful apartment with garden and view

19. B246 - Breathtaking Lagoon View with Balcony

20. C301 - Beautiful Lagoon View Apartment

Find vacation rentals that suit your style

Top Simpson Bay Hotel Reviews

Pomme Cannelle Luxury Suites & Spa

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Simpson Bay?

What are some of the best vacation home rentals that Simpson Bay has to offer?

How many vacation rentals are there in Simpson Bay?

What’s there to see and do in Simpson Bay?

What’s a vacation rental in Simpson Bay like?