Vacation Rentals & Villas in Simpson Bay

/ Home
/ Vacation Rentals
/ Caribbean
/ St. Martin Sint Maarten
/ Sint Maarten
/ Simpson Bay
Book with confidence.

Updating...

age 0-16
52 Results

Relevance

Price: low to high

Price: high to low

Reviews

Why am I receiving these results?

52 villas

Why am I receiving these results?

ATLANTIS... Beachfront on Simpson Bay - totally redone after Irma!

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Cycling trips

All filters match

Price per night from

$272

Match: Cycling trips

All filters match

Price per night from

$1,796

COCO BEACH HOUSE... Charming refurbished 2BR on Simpson Bay Beach

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Cycling trips

All filters match

Price per night from

$390

Villa Ocean Breeze - Private Pool - 2 Masters - Private Courtyard

Simpson Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Cycling trips

All filters match

Price per night from

$745

Great rentals within 20 miles that match your search

Duplex Creole Nettle Bay view and pool

Baie Nettle apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Cycling trips

All filters match

Price per night from

$147

AMBIANCE... Fabulous villa!! 4 Huge equal bedrooms, the PERFECT couples villa!

Terres Basses house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Cycling trips

All filters match

Price per night from

$1,143

LOASIS... Amazing Beachfront Estate, Spa, Gym, Heated Pool!

Terres Basses villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 12

Match: Cycling trips

All filters match

Price per night from

$4,744

CASA SAND... Gorgeous tropical hideaway! Very private and quiet!

Anse Marcel house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Cycling trips

All filters match

Price per night from

$600

ESTHER... charming, new, affordable townhome with private pool, walk to Orient b

Orient Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect!!” We stayed at Villa Esther just last week. It's in a excellent location with walking access to Bikini Beach as well as La Playa which provides a free chair and umbrella, with drink purchase. The plunge pool is perfect for a cooling down after the beach. Wifi keeps you connected with home without massive cell charges, and the entire place is clean and functional. A/C works great on hot nights. Best part is your walking distance to some of the best cuisine on the island. It's all here at Villa Esther, as well as an outstanding staff to welcome you.

Match: Cycling trips

All filters match

Price per night from

$225

MES AMIS...Spectacular Ultra Deluxe cliffside masterpiece! Breathtaking views! A

Terres Basses villa

  • 14 bedrooms
  • 13 bathrooms
  • sleeps 26

Match: Cycling trips

All filters match

Price per night from

$5,000

CORALITA...4 BR casual villa in French St Martin on Oyster Pond

Oyster Pond villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Cycling trips

All filters match

Price per night from

$475

Match: Cycling trips

All filters match

Price per night from

$914

Match: Cycling trips

All filters match

Price per night from

$472

MARINA 360......Porto Cupecoy, overlooking Simpson Bay and the Marina, St Maarte

Cupecoy Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Cycling trips

All filters match

Price per night from

$400

VILLA SKY BLUE... Luxurious 5BR ocean view villa - fabulous water views

Oyster Pond house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Cycling trips

All filters match

Price per night from

$856

BestValue1300/5bd/night. Rent 1 bdr or more, rates adjusted on a sliding scale

Seafeathers villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 11

“A luxurious getaway par excellence” The Villa Gardenia provided the ideal setting for our week in paradise. The villa accommodated three couples (one with young child) with ease. With warm colors and a bright, airy, open layout, we never wanted to leave. Whether lingering in the kitchen after a meal, lounging on the adjoining living room's sofa or (most of all) spending hours by the gorgeous pool, the Villa Gardenia was a delight. We can't wait to return!

Responds fast! avg. 1 hour 43 minutes

Match: Cycling trips

All filters match

Price per night from

$1,638

Between lagoon and Caribbean Ocean, large studio

Marigot apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Cycling trips

All filters match

Price per night from

$144

ST MARTIN LUXURY 4 BEDROOM VILLA MINUTES TO BEACH

Terres Basses villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Cycling trips

All filters match

Price per night from

$1,554

Dawn Beach Club, St.Maarten - Ocean Front, next to JWMarriott property

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Cycling trips

All filters match

Price per night from

$573

Villa Nonza, 5 bedrooms, pool, spa, orient B beach

Orient Bay villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 16

Responds fast! avg. 3 hours 4 minutes

Match: Cycling trips

All filters match

Price per night from

$611

**AMAZING SPECIAL OFFERS PLEASE ENQUIRE** Mumbai - Cupecoy Beach - 3 Bedrooms

Cupecoy Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Cycling trips

All filters match

Price per night from

$814

"PLEASE ENQUIRE ABOUT OUR SPECIALS" Encore - Stunning Villa Rental - 5 Bedrooms

Beacon Hill, Sint Maarten villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Cycling trips

All filters match

Price per night from

$1,264

**AMAZING SPECIAL OFFERS ** Villa Ambiance - Terres Basses - 4 Bedroom

Cupecoy Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Cycling trips

All filters match

Price per night from

$1,143

Match: Cycling trips

All filters match

Price per night from

$858

**PLEASE ASK ABOUT OUR SPECIAL OFFERS** Casa Cervo - Baie Rouge 4 Bedrooms

Cupecoy Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Cycling trips

All filters match

Price per night from

$1,643

Belle Bague - Stunning Sea Views - 4 Bedroom

Colombier villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Cycling trips

All filters match

Price per night from

$2,857

ARTIMINO...3 BR condo, located in Porto Cupecoy, St Maarten

Cupecoy Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Cycling trips

All filters match

Price per night from

$450

Villa Dulcinea - Ocean views, near beach, outdoor space, great for groups!

East End Village house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Cycling trips

All filters match

Price per night from

$573

Gd studio dans résidence Mont Vernon vue montagne

Orient Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Cycling trips

All filters match

Price per night from

$74

CASA DE LA PLAYA... Spectacular Baie Longue beachfront estate with Chef!

Terres Basses house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Cycling trips

All filters match

Price per night from

$3,914

200 m away from the beach! Big villa for 11 ppl. with swimming-pool

Terres Basses villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 3 minutes

Match: Cycling trips

All filters match

Price per night from

$2,655

Amazing appartement 2 km away from the beach for 2 ppl. at La Savane

La Savane apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 3 minutes

Match: Cycling trips

All filters match

Price per night from

$151

House 2 km away from the beach for 6 ppl. with sea view at La Savane

La Savane house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 hours 3 minutes

Match: Cycling trips

All filters match

Price per night from

$198

Enchanting, Family Friendly 3bdr, adjustable fee for more or less bedrooms

East End Village house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 11

Responds fast! avg. 1 hour 43 minutes

Match: Cycling trips

All filters match

Price per night from

$1,260

Match: Cycling trips

All filters match

Price per night from

$296

Spacious villa 2 km away from the beach for 5 ppl. with swimming-pool

Orient Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 3 minutes

Match: Cycling trips

All filters match

Price per night from

$260

Villa ALLAMANDA in Guana Bay

Philipsburg villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Cycling trips

All filters match

Price per night from

$1,374

100 m away from the beach! Nice house for 2 ppl. at Saint-Martin

Baie Nettle house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Responds fast! avg. 3 hours 3 minutes

Match: Cycling trips

All filters match

Price per night from

$118

Viewing 38 of 52
rentals in Simpson Bay

×

Also consider