Vacation Rentals & Villas in Simpson Bay

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

1,600 villas

(4) Excellent 

10

2BR-Oceanfront-Royal Palm

Simpson Bay / Simpson Bay Beach

Simpson Bay condo

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$401

Price per night from

$401

(2) Excellent 

23

Sapphire Ruby Suite - Unforgettable Getaway!

Sint Maarten / Simpson Bay

Simpson Bay condo

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$212

Price per night from

$212

(1) Excellent 

15

BEACHFRONTBLISS

Sint Maarten / Simpson Bay

Simpson Bay apartment

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Ask about children
  • Ask about pets

Price per night from

$344

Price per night from

$344

(2) Excellent 

22

The Sapphire: Pearl Suite - Peace of mind!

Sint Maarten / Simpson Bay

Simpson Bay condo

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Child Friendly

Price per night from

$197

Price per night from

$197

(5) Excellent 

26

Le Papillon - REOPENED AFTER IRMA - Modern Beachfront Unit with great view

Simpson Bay / Simpson Bay Beach

Simpson Bay apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.01 mi
  • Child Friendly

Price per night from

$372

Responds fast!
avg. 1 hour 55 minutes

Price per night from

$372

(26) Excellent 

Certificate of Excellence

22

Carisma on the beach

Sint Maarten / Simpson Bay

Simpson Bay villa

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Certificate of Excellence

Price per night from

$247

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$247

(29) Excellent 

14

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

Sint Maarten / Simpson Bay

Simpson Bay apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“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
…see more

Price per night from

$217

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$217

(1) Excellent 

14

1 Bed Luxury Condo

Sint Maarten / Simpson Bay

Simpson Bay condo

1 2 4 nights min

  • 1 bedroom
  • sleeps 2
  • 4 nights min

Price per night from

$172

Price per night from

$172

47

TARA... Affordable oceanfront villa, walk to beach

Sint Maarten / Simpson Bay

Simpson Bay villa

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$843

Price per night from

$843

(1) Excellent 

17

Unrivaled Luxury Villa with beach access

Sint Maarten / Simpson Bay

Simpson Bay house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.7 mi
  • Swimming pool

Price per night from

$739

Price per night from

$739

(3) Very Good 

32

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

Sint Maarten / Simpson Bay

Simpson Bay apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$165

Responds fast!
avg. 1 hour 3 minutes

Price per night from

$165

(7) Excellent 

34

Le Papillon Penthouse - The most amazing beachfront property

Sint Maarten / Simpson Bay

Simpson Bay apartment

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.01 mi
  • Child Friendly

Price per night from

$548

Responds fast!
avg. 1 hour 55 minutes

Price per night from

$548

(4) Very Good 

12

PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW

Simpson Bay / Simpson Bay Beach

Simpson Bay apartment

1 2 4 nights min

  • 1 bedroom
  • sleeps 2
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 mi
  • Air conditioning

Price per night from

$137

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$137

(1) Excellent 

34

Caribbean Sun

Simpson Bay / Simpson Bay Beach

Simpson Bay condo

2 4 6 nights min

  • 2 bedrooms
  • sleeps 4
  • 6 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$344

Responds fast!
avg. 2 hours 24 minutes

Price per night from

$344

(1) Excellent 

14

SIMPSON BAY BEACH CONDO #3...right on the beach at Simpson Bay

Sint Maarten / Simpson Bay

Simpson Bay apartment

2 4 14 nights min

  • 2 bedrooms
  • sleeps 4
  • 14 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great location in paradise, will all the comforts of home” This condo was in the perfect location for a family. Directly by the pool and beach. Very clean and great updates. Gated parking, plenty of room! Can't say enough good things about our tim
…see more

Price per night from

$514

Price per night from

$514

39

BEAU RIVAGE... Comfortable home on Burgeoux Bay beach, walk to Maho or Simpson B

Sint Maarten / Simpson Bay

Simpson Bay villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$857

Price per night from

$857

25

Villa Sunshine

Sint Maarten / Simpson Bay

Simpson Bay villa

5 12 5 nights min

  • 5 bedrooms
  • sleeps 12
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$687

Responds fast!
avg. 2 hours 42 minutes

Price per night from

$687

29

COCO BEACH CLUB #5.... step out the door on to the soft white powdery sand of S

Sint Maarten / Simpson Bay

Simpson Bay apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$400

Price per night from

$400

(1) Excellent 

11

Studio in Pelican Key Paradise

Sint Maarten / Simpson Bay

Simpson Bay apartment

2 3 nights min

  • sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children

Price per night from

$172

Price per night from

$172

(1) Excellent 

22

The Sapphire: Aquamarine Suite- Breathtaking views!

Sint Maarten / Simpson Bay

Simpson Bay condo

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Nearest beach 1 mi
  • Child Friendly
  • Air conditioning

Price per night from

$212

Price per night from

$212

33

Steps to Caribbean, pool and 2 mile-long beach

Sint Maarten / Simpson Bay

Simpson Bay apartment

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Car not necessary

Price per night from

$258

Price per night from

$258

13

SAPPHIRE... A casual, comfortable villa with ocean views in Pelican Key!

Sint Maarten / Simpson Bay

Simpson Bay villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$571

Price per night from

$571

(1) Excellent 

46

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

Sint Maarten / Simpson Bay

Simpson Bay villa

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,271

Price per night from

$1,271

(2) Excellent 

18

Anchorage Apartment

Simpson Bay / Simpson Bay Beach

Simpson Bay apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly

Price per night from

$160

Responds fast!
avg. 2 hours 17 minutes

Price per night from

$160

9

Beautiful Studio in Pelican Key /Simpson Bay

Sint Maarten / Simpson Bay

Simpson Bay apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

Price per night from

$103

Price per night from

$103

(2) Excellent 

20

2 BEDR townhouse overlooking OCEAN ST- MAARTEN

Sint Maarten / Simpson Bay

Simpson Bay house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
“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
…see more

Price per night from

$245

Price per night from

$245

22

Beach Front Property - Spectacular Sunset

Sint Maarten / Simpson Bay

Simpson Bay villa

5 16 min stay varies

  • 5 bedrooms
  • sleeps 16
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$973

Price per night from

$973

25

LA CASITA...charming, comfortable oceanfront villa in Beacon Hill, St Maarten

Sint Maarten / Simpson Bay

Simpson Bay villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$543

Price per night from

$543

13

Condo Danielle

Sint Maarten / Simpson Bay

Simpson Bay condo

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$148

Responds fast!
avg. 23 minutes

Price per night from

$148

17

Pearl on the Beach

Simpson Bay / Simpson Bay Beach

Simpson Bay condo

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$590

Price per night from

$590

50

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

Sint Maarten / Simpson Bay

Simpson Bay villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Air conditioning

Price per night from

$671

Price per night from

$671

11

15 steps away from the beach

Sint Maarten / Simpson Bay

Simpson Bay apartment

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$148

Responds fast!
avg. 1 hour 11 minutes

Price per night from

$148

(5) Excellent 

16

Beachfront gated Condo directly on Simpson Bay

Sint Maarten / Simpson Bay

Simpson Bay apartment

2 5 5 nights min

  • 2 bedrooms
  • sleeps 5
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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 itse
…see more

Price per night from

$287

Responds fast!
avg. 1 hour 40 minutes

Price per night from

$287

32

Barefoot Oceanfront Condo St Maarten

Simpson Bay / Simpson Bay Beach

Simpson Bay villa

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$350

Price per night from

$350

9

Beachfront Condo

Simpson Bay / Simpson Bay Beach

Simpson Bay condo

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$590

Price per night from

$590

(1) Excellent 

26

Vacation Villa at Simpson's bay and Marina

Simpson Bay / Simpson Bay Beach

Simpson Bay villa

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

Price per night from

$155

Responds fast!
avg. 1 hour 33 minutes

Price per night from

$155

25

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

Sint Maarten / Simpson Bay

Simpson Bay apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$329

Price per night from

$329

30

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

Sint Maarten / Simpson Bay

Simpson Bay villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$729

Price per night from

$729

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!