Search 105,200+ Vacation Rentals

Sint Maarten Waterfront Vacation Rentals, Homes & More - 316 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

316 Vacation rentals

Filters applied: Waterfront

(19)

1 / 22

Philipsburg Apartment

  • 1
  • 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Air conditioning

$85

Excellent (19 reviews)

Book

from $85 / night

(10)

1 / 18

Simpson Bay Apartment

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$358

Excellent (10 reviews)

Book

from $358 / night

1 / 29

Philipsburg Apartment

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$167

Book

from $167 / night

(7)

1 / 86

Philipsburg Villa

  • 9
  • 26
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“My entire family stayed at this property from August 1-8, 2015. We had a wonderful time. This is an amazing vacation rental. The owner [Hans] greeted us upon arrival, and he is an incredibly accommodating and helpful soul. The first thing that...”
- Review left on 08/13/2015

$199

Very Good (7 reviews)

Inquire

from $199 / night

(4)

1 / 56

Philipsburg Villa

  • 4
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This is a breathtaking property. The ocean views are incredible. We would wake up every morning to a spectacular sunrise coming over the ocean onto our deck. Your vacation will start with the owner, Hans, meeting you at his villa. Hans is an...”
- Review left on 08/19/2015

$285

Very Good (4 reviews)

Inquire

from $285 / night

(4)

1 / 15

Philipsburg Apartment

  • 1
  • 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

$96

Excellent (4 reviews)

Book

from $96 / night

(1)

1 / 16

Philipsburg Villa

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“First off, Marlene is a very responsive owner who obviously wants to insure that your stay is as good as it possibly can be. Her notes were very helpful. Marcella did a fantastic job coming in each day to clean (who wants to do dishes while on...”
- Review left on 03/21/2016

$172

Excellent (1 reviews)

Inquire

from $172 / night

1 / 20

Sint Maarten Villa

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $839 / night

1 / 20

Cupecoy Bay Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $322 / night

(6)

1 / 40

Oyster Pond Apartment

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$550

Excellent (6 reviews)

Inquire

from $550 / night

1 / 37

Philipsburg Apartment

  • 3
  • 6
  • Min stay varies
  • Child friendly
  • Air conditioning

from $450 / night

1 / 23

Oyster Pond Villa

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $459 / night

(2)

1 / 22

Oyster Pond Villa

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$200

Excellent (2 reviews)

Inquire

from $200 / night

1 / 24

Simpson Bay House

  • 2
  • 6
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning

from $258 / night

1 / 25

Philipsburg House

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $394 / night

(1)

1 / 18

Sint Maarten Villa

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$643

Excellent (1 reviews)

Inquire

from $643 / night

(3)

1 / 24

Oyster Pond Farmhouse

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$358

Excellent (3 reviews)

Inquire

from $358 / night

(1)

1 / 45

Oyster Pond Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$572

Excellent (1 reviews)

Inquire

from $572 / night

(2)

1 / 19

Oyster Pond Villa

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$286

Excellent (2 reviews)

Inquire

from $286 / night

(3)

1 / 19

Simpson Bay Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$315

Excellent (3 reviews)

Inquire

from $315 / night

(1)

1 / 24

Oyster Pond Villa

  • 3
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$328

Very Good (1 reviews)

Inquire

from $328 / night

(2)

1 / 18

Philipsburg Apartment

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$240

Excellent (2 reviews)

Inquire

from $240 / night

1 / 18

Simpson Bay Apartment

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $400 / night

1 / 26

Simpson Bay Villa

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $858 / night

(1)

1 / 30

Oyster Pond House

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$495

Excellent (1 reviews)

Inquire

from $495 / night

1 / 25

Simpson Bay Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $258 / night

1 / 13

Simpson Bay Villa

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $358 / night

(3)

1 / 19

Oyster Pond Apartment

  • 3
  • 1
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$450

Excellent (3 reviews)

Inquire

from $450 / night

1 / 48

Simpson Bay Villa

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $750 / night

1 / 22

Simpson Bay Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $258 / night

1 / 20

Oyster Pond House

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $429 / night

1 / 10

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $787 / night

(1)

1 / 20

Simpson Bay Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$272

Excellent (1 reviews)

Inquire

from $272 / night

(1)

1 / 29

Simpson Bay Villa

  • 3
  • 6
  • Min stay varies
  • Child friendly
  • Air conditioning

$258

Excellent (1 reviews)

Inquire

from $258 / night

(1)

1 / 24

Simpson Bay Apartment

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$215

Very Good (1 reviews)

Inquire

from $215 / night

(3)

1 / 16

Oyster Pond Apartment

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$358

Excellent (3 reviews)

Inquire

from $358 / night

(6)

1 / 26

Oyster Pond Villa

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$500

Very Good (6 reviews)

Inquire

from $500 / night

(3)

1 / 20

Oyster Pond Villa

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$379

Excellent (3 reviews)

Inquire

from $379 / night

1 / 34

Oyster Pond Villa

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $365 / night

(3)

1 / 13

Simpson Bay Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$398

Very Good (3 reviews)

Inquire

from $398 / night