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Holiday Lettings
> North America
> Caribbean
> St. Maarten - Saint Martin
> Sint Maarten
> Villas and Houses in Simpson Bay

Holiday Rentals in Simpson Bay - Holiday Lettings - Villas

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  • Apartment (5)
  • Villa (179)
  • House (55)
  • Penthouse (1)
  • Condo (1)

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5 Holiday homes

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Great rentals within 20 miles that match your search

Holiday apartment in Maho

Maho apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £626 / night

£4,374 - £11,103 / week

1 / 57

Great rentals within 20 miles that match your search

Holiday apartment in Cupecoy Bay

Cupecoy Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £361 / night

£2,522 - £6,163 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday apartment with swimming pool in Philipsburg

Philipsburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4
31 reviews

from £207 / night

£1,444 / week

1 / 23

Great rentals within 20 miles that match your search

Oyster Pond holiday apartment rental

Oyster Pond apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £190 / night

£1,326 / week

1 / 32

Great rentals within 20 miles that match your search

Oyster Pond holiday apartment rental

Oyster Pond apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £257 / night

£1,797 / week

1 / 23

Great rentals within 20 miles that match your search

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Philipsburg holiday villa rental

Philipsburg villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 filter does not match: Property type

from £204 / night

£1,423 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday villa rental

Philipsburg villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £688 / night

£4,470 / week

1 / 46

Great rentals within 20 miles that match your search

Maho holiday penthouse accommodation

Maho penthouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £561 / night

£3,634 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday villa in Terres Basses

Terres Basses villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £580 / night

£3,880 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Terres Basses

Terres Basses villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 filter does not match: Property type

from £550 / night

£3,849 - £10,970 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday villa in Simpson Bay

Simpson Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

1 review

from £230 / night

£1,604 / week

1 / 17

Great rentals within 20 miles that match your search

Cupecoy Bay holiday home let

Cupecoy Bay house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 filter does not match: Property type

2 reviews

from £734 / night

£5,132 / week

1 / 36

Great rentals within 20 miles that match your search

Philipsburg holiday villa rental

Philipsburg villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

1 filter does not match: Property type

7 reviews

from £1,100 / night

£7,698 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Pelican Key

Pelican Key villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

1 filter does not match: Property type

from £801 / night

£5,603 - £9,605 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday home rental

Terres Basses house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £579 / night

£4,050 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday villa in Terres Basses

Terres Basses villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

from £777 / night

£5,435 / week

1 / 43

Great rentals within 20 miles that match your search

Maho holiday villa rental

Maho villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 filter does not match: Property type

from £1,100 / night

£9,165 / week

1 / 12

Great rentals within 20 miles that match your search

Terres Basses holiday villa rental

Terres Basses villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

1 review

from £523 / night

£3,657 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday villa with swimming pool, golf nearby in Maho

Maho villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £687 / night

£4,807 - £9,609 / week

1 / 76

Great rentals within 20 miles that match your search

Terres Basses holiday villa rental

Terres Basses villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

1 filter does not match: Property type

from £758 / night

£5,306 / week

1 / 44

Great rentals within 20 miles that match your search

Cupecoy Bay holiday villa rental

Cupecoy Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £633 / night

£4,426 / week

1 / 38

Great rentals within 20 miles that match your search

Holiday villa in Terres Basses

Terres Basses villa

  • 1 bedroom
  • 5 bathrooms
  • sleeps 8

1 filter does not match: Property type

from £1,830 / night

£12,808 / week

1 / 58

Great rentals within 20 miles that match your search

Villa rental in Terres Basses with swimming pool

Terres Basses villa

  • 1 bedroom
  • 5 bathrooms
  • sleeps 10

1 filter does not match: Property type

from £825 / night

£5,771 / week

1 / 34

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Terres Basses

Terres Basses villa

  • 1 bedroom
  • 6 bathrooms
  • sleeps 10

1 filter does not match: Property type

from £3,039 / night

£21,274 / week

1 / 52

Great rentals within 20 miles that match your search

Holiday villa rental

Cupecoy Bay villa

  • 1 bedroom
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Property type

from £854 / night

£5,978 / week

1 / 40

Great rentals within 20 miles that match your search

Villa letting in Terres Basses with swimming pool

Terres Basses villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Property type

from £1,359 / night

£9,514 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Terres Basses

Terres Basses villa

  • 1 bedroom
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £733 / night

£5,127 / week

1 / 47

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Cupecoy Bay

Cupecoy Bay villa

  • 1 bedroom
  • 4 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £707 / night

£4,948 / week

1 / 48

Great rentals within 20 miles that match your search

Holiday villa in Terres Basses

Terres Basses villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

1 filter does not match: Property type

from £1,553 / night

£10,869 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday villa rental

Terres Basses villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 filter does not match: Property type

from £888 / night

£6,214 / week

1 / 41

Great rentals within 20 miles that match your search

Terres Basses holiday villa rental

Terres Basses villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Property type

from £684 / night

£4,785 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Terres Basses

Terres Basses villa

  • 1 bedroom
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £544 / night

£3,805 / week

1 / 38

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Terres Basses

Terres Basses villa

  • 1 bedroom
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Property type

from £866 / night

£6,062 / week

1 / 47

Great rentals within 20 miles that match your search

Villa rental in Terres Basses with swimming pool

Terres Basses villa

  • 1 bedroom
  • 5 bathrooms
  • sleeps 8

1 filter does not match: Property type

from £777 / night

£5,435 / week

1 / 41

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Terres Basses

Terres Basses villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £666 / night

£4,662 / week

1 / 39

Great rentals within 20 miles that match your search

Terres Basses holiday villa rental

Terres Basses villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 filter does not match: Property type

from £600 / night

£4,197 / week

1 / 33

Great rentals within 20 miles that match your search

Villa rental in Terres Basses with swimming pool

Terres Basses villa

  • 1 bedroom
  • 4 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £638 / night

£4,466 / week

1 / 41

Great rentals within 20 miles that match your search

Terres Basses holiday villa rental

Terres Basses villa

  • 1 bedroom
  • 5 bathrooms
  • sleeps 8

1 filter does not match: Property type

from £2,735 / night

£19,145 / week

1 / 52

Great rentals within 20 miles that match your search

Holiday villa in Terres Basses

Terres Basses villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

from £311 / night

£2,174 / week

1 / 32

Great rentals within 20 miles that match your search

Terres Basses holiday villa rental

Terres Basses villa

  • 1 bedroom
  • 4 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £777 / night

£5,435 / week

1 / 33

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