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Vacation Rentals & Villas in Simpson Bay

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1,186 villas

2BR-Oceanfront-Royal Palm

Simpson Bay condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$452

Sapphire Ruby Suite - Unforgettable Getaway!

Simpson Bay condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$212

BEACHFRONTBLISS

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$343

Blue Pelican Luxury Villas - Featured on HGTV!!!!!

Simpson Bay apartment

1 bedroom / 1 bathroom / sleeps 2

“Excellent place to stay.” The pre-trip information was perfect and the welcome "meet and greet" was perfect and thorough too. We stayed in Villa #2. Essentially, you couldn't wish for more on the inside - serious attention has been paid to detail and amenities, and the extra finishing touches are the icing on the cake. We did not use the pool, but it is a nice neighborhood and quiet residence. We used it as a base to explore the island and beaches on both the French and Dutch sides.

Price per night from

$208

Le Papillon - Modern Luxurious Beachfront Unit, extra clean, stunning view

Simpson Bay apartment

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 23 minutes

Price per night from

$366

The Sapphire: Pearl Suite - Peace of mind!

Simpson Bay condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$197

TARA... Affordable oceanfront villa, walk to beach

Simpson Bay villa

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$657

PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW

Simpson Bay apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$141

1 Bed Luxury Condo

Simpson Bay condo

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$172

Simpson Bay Beach Modern Luxury Ocean View Private Roof Deck 360° views WIFI

Simpson Bay apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$143

COCO BEACH CLUB #5.... Located on the soft white powdery sand of Simpson Bay be

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$272

Steps to Caribbean, pool and 2 mile-long beach

Simpson Bay apartment

1 bedroom / 2 bathrooms / sleeps 2

Price per night from

$258

The Sapphire: Aquamarine Suite- Breathtaking views!

Simpson Bay condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$212

Studio in Pelican Key Paradise

Simpson Bay apartment

/ 1 bathroom / sleeps 2

Price per night from

$172

TOP OF THE ART PENTHOUSE - luxury on the beach

Simpson Bay apartment

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 23 minutes

Price per night from

$560

CARIBBEAN BLUE... 5BR beachfront home in Pelican Key

Simpson Bay villa

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$914

Beautiful Studio in Pelican Key /Simpson Bay

Simpson Bay apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$103

15 steps away from the beach

Simpson Bay apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$148

Beachfront gated Condo directly on Simpson Bay

Simpson Bay apartment

2 bedrooms / 3 bathrooms / sleeps 5

“Right on the beach. Best location on Simpson Beach” On our 7th trip to St. Maarten, my husband and I decided to break free from the typical hotel experience, we booked a week at this condo on Simpson Bay Beach... and I'm so glad we did! The condo itself is well appointed, with everything you could possibly need. Washer/Dryer, wi-fi, cable, grill on the patio, dishwasher (who wants to do dishes on vacation, right?), even a speaker system for our iPod... so we were well taken care of from a practical perspective. But let me tell you, the condo itself is just beautiful... completely modern, beautifully decorated, with an open concept with 3 patios to choose from... two overlooking the oceanfront pool. Most days we would open all of the doors and just let the tropical air breeze through the condo... sit back and listen to the waves with a glass of wine... and it's just heavenly. The location is just awesome... close to everything, but located on (in my opinion) the most beautiful beach on the island... great for exploring... great waves... and really pretty quiet thanks to the private residences along the beach. If you're looking for people, head down the beach to Karakters, a great beach bar built in a renovated school bus right on the south end of the beach... great food and lots of fun. We tried quite a few of the restaurants Bob & Sue recommended and they were all really cool. What we liked best was that they recommended places that were casual and fun! We probably wouldn't have found some of them on our own, so we appreciated that personal touch. Bob was great throughout our booking process and even helped us secure our rental car through angela on the island. They're nice folks and really went out of their way to make sure my husband and I had a good experience. We plan to come back and stay again, as soon as we can!

Price per night from

$290

2 BEDR townhouse overlooking OCEAN ST- MAARTEN

Simpson Bay house

2 bedrooms / 1 bathroom / sleeps 4

“Fabulous resort living with a tropical breeze!” A most wonderful place to enjoy all St Maarten has to offer! Beautiful, airy, spotless accommodations with a contemporary Carribean decor and all the amenities you need for a wondrous vacation! Centrally located; walk to local French bakery , intimate Piano Bar, beautiful white sand beaches, beachside coctail bars, restaurants, shopping, etc! Parking for a rental car so you can hop all around the island. We enjoyed an absolutely fabulous time here..and at the end of the day a relaxing time gazing out at the turquoise ocean from our veranda!

Price per night from

$245

SOL Y MAR... fabulous beachfront penthouse on Kimsha Beach! Private pool, Walk t

Simpson Bay villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$557

Beachfront Condo

Simpson Bay condo

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$589

Pearl on the Beach

Simpson Bay condo

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$589

MARISOL... Light and airy townhouse at Point Blue in Pelican Key Estate

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$329

The Sapphire: Turquoise Suite - Tranquility!

Simpson Bay condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$212

BISOU DU SOLEIL... beautiful, immaculate, affordable villa in Pelican Key

Simpson Bay villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$671

CASA DE BELLA... Great location at a great price!!

Simpson Bay house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$400

PROVENCE... Affordable villa, gorgeous views, close to dining, shopping, casinos

Simpson Bay villa

6 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$643

Ocean Front with Private Pool

Simpson Bay villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$290

WITENBLAUW... Magical Beach Front Estate on Pelican Key

Simpson Bay villa

6 bedrooms / 7 bathrooms / sleeps 12

Price per night from

$2,072

1Bedroom in Pelican Key

Simpson Bay apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$315

COCO BEACH CLUB 6...walk out onto the sand of Simpson Bay Beach

Simpson Bay condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$229

Modern Luxury Directly on the Beach

Simpson Bay condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$315

RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit on a great beach!

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$643

IL PUNTO BLUE...Located right on the beach in prestigious Pelican Key

Simpson Bay apartment

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$336

Amazing View Penthouse apartment on Simpson Bay Beach WE ARE BACK AFTER IRMA

Simpson Bay apartment

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$342

WOW WOW WOW, STUNNING INSIDE AND OUT! VILLA LIBRE`

Simpson Bay villa

3 bedrooms / 3 bathrooms / sleeps 6

“Incredible ! Definiately five star 5* Accomdations” This villa is incredible. It exceeded my expectations. It was immaculate. It is beautiful inside and out. All three of the bedrooms are very spacious with their own large, modern bathrooms. The kitchen is also large for those who want to cook inside, plus there is a new BBQ on the patio, with a table beside. The grocery store and numerous restaurants are within walking distance. The panoramic view was spectacular. You can watch the boats go by all day and evening, and listen to the sound of the surf, just below. There is lots of sun or shade, whichever you prefer, from morning until night on the lovely patio. I would highly recommend this villa. It's first class accommodation in every way. I/we hope to spend more time at this villa next year. We loved it.

Price per night from

$458

ST TROPEZ... amazing views of the Caribbean Sea from this lovely villa in Pelica

Simpson Bay villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$557

Viewing 38 of 1,186
rentals in Simpson Bay

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About Simpson Bay

The beach at Simpson Bay is wide, and over a mile long—a stretch of glorious, uninterrupted sand. The blue waters of the Caribbean lap the shore, providing the perfect backdrop for a relaxing vacation.

But it’s not all relaxation—the main streets of Simpson Bay are bustling hives of activity with bars, restaurants and stores. Why not start searching FlipKey for the perfect vacation rental and plan your perfect trip?

About Simpson Bay, St. Maarten-St. Martin

Many years ago, Simpson Bay was home to the fishermen of the island and their families. Now, it's a popular tourist destination, although the fishermen still ply their trade. The first inhabitants of Simpson Bay and the surrounding area were the Arawaks, from the Amazon basin.

Named after St Martin of Tours, it first appeared on a map in 1516 as Sam Mtim. It was already a Spanish territory by then, though it wasn't a colony. The island has been in the hands of the Spanish, Dutch and French. Today, the island is shared by the Dutch and French whose cultures still influence life on the island.

The cuisine on the island is international, but you can find some traditional food if you look hard enough. Ask a local for their recommendations to discover some authentic places to eat.

Simpson Bay has a vibrant nightlife which contrasts with the peace you can find on Simpson Bay beach. You'll get the best of both worlds here!

What to do in Simpson Bay, St. Maarten-St. Martin

As Saint Maarten-St Martin is an island, water sports are very popular. Why not try some?

If you're looking for a more calming vacation, swim in the clear blue waters, or relax on the beach.

Try a Rhino Safari excursion on a Rhino Rider—an inflatable motorboat. Pilot your own craft and go snorkeling with a guide.

Charter a yacht for a sunset cruise, or hire a 4x4 and go in a guided convoy to see the sights on both the French and Dutch side of the island. This tour will take you to Oyster Pond, Maho Beach and you'll have two hours to laze on Orient Beach.

Traveling with the kids? If the beach is too hot for them, head to the Butterfly farm—it's a great day out.

Happy Bay Beach is for nudists. If you're feeling adventurous, go there for an all-over tan.

Top travel tips for St. Marteen-St. Martin

It's best to rent a car on St. Maarten-St Martin as you'll have the freedom to explore the island in our own time. That being said, there are taxis and local buses if you don't want to bother.

If you do drive, watch out for potholes! If you can find an all-terrain vehicle to rent, do. It'll definitely be worth it!

You will probably find, on both the French and Dutch sides of the island, that a service charge is included in your restaurant bills. Of course, if the service was very good, you can leave an extra cash tip.

There's plenty to do and see on St. Maarten-St. Martin, whichever side of the island you visit, the Dutch or French. Go around the island and see it all!

For a wide choice of accommodation, search the rental properties available here on FlipKey and book your next trip. You won’t be disappointed!

Top Destination reviews

CARIBBEAN BLUE... 5BR beachfront home in Pelican Key
Best time of our lives!!

Love, Love the house and it's location. Claudette was great and a big help. There is restaurants and stores within walking distance. The house has satellite TV so you get alot of music channels and the sound system is Bose. You can use the phone to call the states for free. The house has pretty much everything you need. The only thing we didn't like was not having enough remotes for the gates and the number pads for the gates didn't work,no hair dryer, and the pots and pans could use an upgrade. We would definitely come back, had a hard time leaving!!see more
FAJA LOBIE... 3 BR Offers Great rates for a beachfront villa
Faja Lobie is a beautiful villa with a fantastic view.

We stayed at Villa Faja Lobie for 2 weeks in February and we loved it! It had a million dollar view, beautiful villa with 3 bedrooms and bathrooms. We stayed with our adult children and had the best time ever. The Wifi was a little spotty as we needed to reset it alot. The housekeeper Leslie did a wonderful job. We loved cooking our own dinners in this beautiful villa. Overall, one of our best vacations ever!!see more
Beachfront gated Condo directly on Simpson Bay
Incredible

My husband and I have been back 5 times already and will be returning again this March with more friends. The condo is located on one of St Maarten's finest beaches. Stroll down the beach to Karakters for an incredible mojito and appetizers. Grab a lounge chair,listen to music and enjoy. Take a dip in the crystal blue waters of Simpson Bay or at the pool back at the complex. Sit out on the balcony and enjoy some wine and cheese while listening to the waves. Need a car, Bob will put you in touch with angela who can have a car waiting for you at the airport. Looking for great places to eat and explore, ask Bob and Sue for their recommendation. Whether you book a sun set cruise, dive in the clear waters, snorkel, or shop, there are plenty of thing to do. We had an incredible time, loved where we stayed and will keep going back.see more
Cool Bay Villa St Maarten
Very good first Time in st marteen

Nothing else to say but excellent!! Valérie and Philippe are so kind with their tourists. Everything was so easy with them. Lovely Island and so many beaches "We will go again and again" according to my kids!! … see more
WOW WOW WOW, STUNNING INSIDE AND OUT! VILLA LIBRE`
Sometimes Things are as awesome as They Seem

Just spent a week at this amazing view and I can't begin to say how great a value you are getting. The view is over 180 degrees...the sunsets are literally in your backyard. There is nothing like spending a day at the beach, coming back to the villa, hoping in the pool and watching the sun set before heading out for dinner. The bedrooms were spacious and so tastefully decorated. Each room had its own flatscreen (although who wants to watch TV in St. Maarten?!) and amazing bathrooms with skylights. The housekeeper was fantastic and cared for our group so well all week. I loved my week at the Villa and I will definitely be back! The theme of the vacation for the week "Worth Every Penny!"see more
Blue Pelican Luxury Villas - Featured on HGTV!!!!!
We're Back!

This was our fourth vacation at the Blue Pelican alway staying in Garo's unit. It feels like a home away from home. The furnishings and decor are lovely; lots of towels, beach chairs and umbrella. You can cook up a storm and eat inside or on the patio. You are also a shorty walk or drive to a great assortment of restaurants. A large grocery store is also very close by. Although you can manage without a car we always prefer to rent one giving us the option to go to beaches all over the island. The unit also has an upper deck with loungers to catch some sun as well as tropical gardens on the property that are beautifully maintained surrounding a small pool with more lounge chairs. The property is gated and secure and also very quiet. It is spotless inside and there is a dishwasher as well as a washer and dryer which are handy for longer vacations. Jane, the property manager, greeted us with a basket with wine, fresh fruit and other goodies. She also lives close by should you need any assistance. We will come back to St. Maarten again and most certainly will stay here again and again! I highly recommend staying here.see more

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