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Simpson Bay Holidays & City Breaks - Holiday Lettings

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44 properties suitable for city breaks and holidays

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Holiday villa in Simpson Bay Beach

Simpson Bay villa

1 bedroom • 1 bathroom • sleeps 4

from £130 / night

£909 / week

1 / 26

Holiday villa in Simpson Bay

Simpson Bay villa

6 bedrooms • 6 bathrooms • sleeps 12

from £1,076 / night

£7,526 / week

1 / 35

Holiday condo with shared pool in Simpson Bay

Simpson Bay condo

2 bedrooms • 3 bathrooms • sleeps 4

from £446 / night

£3,119 / week

1 / 9

Holiday condo rental

Simpson Bay condo

2 bedrooms • 3 bathrooms • sleeps 4

from £446 / night

£3,119 / week

1 / 17

Home rental in Simpson Bay with shared pool

Simpson Bay house

2 bedrooms • 3 bathrooms • sleeps 5

from £260 / night

£1,817 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday villa letting

Terres Basses villa

5 bedrooms • 17 bathrooms • sleeps 10

from £881 / night

£6,849 - £14,675 / week

1 / 14

Apartment rental in Dawn Beach with shared pool

Dawn Beach apartment

3 bedrooms • 3 bathrooms • sleeps 8

from £343 / night

£2,397 / week

1 / 10

Terres Basses holiday villa rental

Terres Basses villa

4 bedrooms • 4 bathrooms • sleeps 8

from £1,174 / night

£8,218 / week

1 / 42

Holiday apartment with shared pool, golf nearby in Philipsburg

Philipsburg apartment

3 bedrooms • 2 bathrooms • sleeps 9

from £433 / night

£3,028 / week

1 / 13

Holiday villa with swimming pool in Orient Bay

Orient Bay villa

5 bedrooms • 4 bathrooms • sleeps 16

from £421 / night

£2,544 - £4,550 / week

1 / 20

Holiday apartment rental

Orient Bay apartment

1 bedroom • 1 bathroom • sleeps 4

from £70 / night

£467 / week

1 / 35

Holiday villa with swimming pool, golf nearby in Philipsburg

Philipsburg villa

3 bedrooms • 3 bathrooms • sleeps 6

from £303 / night

£2,120 / week

1 / 39

Holiday apartment rental

Anse Marcel apartment

1 bedroom • 2 bathrooms • sleeps 4

from £98 / night

£685 - £1,096 / week

1 / 17

Home rental in East End Village

East End Village house

4 bedrooms • 4 bathrooms • sleeps 10

from £433 / night

£3,028 / week

1 / 12

Condo rental in Orient Bay

Orient Bay condo

1 bedroom • 1 bathroom • sleeps 3

from £49 / night

£326 - £465 / week

1 / 10

Holiday apartment rental

Orient Bay apartment

1 bedroom • 1 bathroom • sleeps 4

from £130 / night

£909 / week

1 / 20

Holiday apartment in Oyster Pond

Oyster Pond apartment

3 bedrooms • 2 bathrooms • sleeps 8

from £420 / night

£2,935 / week

1 / 9

Holiday apartment rental

Oyster Pond apartment

3 bedrooms • 2 bathrooms • sleeps 8

from £420 / night

£2,935 / week

1 / 8

Apartment rental in Oyster Pond

Oyster Pond apartment

1 bedroom • 2 bathrooms • sleeps 5

from £96 / night

£666 / week

1 / 12

Villa rental in Anse des Cayes with swimming pool, golf nearby

Anse des Cayes villa

2 bedrooms • 2 bathrooms • sleeps 4

from £320 / night

£2,907 - £6,911 / week

1 / 43

Quartier D'Orleans holiday apartment rental

Quartier D'Orleans apartment

1 bedroom • 1 bathroom • sleeps 4

from £108 / night

£685 / week

1 / 20

Holiday studio with shared pool, golf nearby in Bellevue

Bellevue studio

Studio • 1 bathroom • sleeps 2

from £136 / night

£813 / week

1 / 17

Apartment rental in Philipsburg with shared pool

Philipsburg apartment

4 bedrooms • 4 bathrooms • sleeps 12

from £542 / night

£2,708 / week

1 / 28

Baie Nettle holiday studio rental

Baie Nettle studio

Studio • 1 bathroom • sleeps 2

from £109 / night

£761 / week

1 / 19

Holiday apartment rental

Cul de Sac apartment

2 bedrooms • 1 bathroom • sleeps 4

from £108 / night

£754 / week

1 / 7

Marigot holiday villa rental

Marigot villa

4 bedrooms • 4 bathrooms • sleeps 8

from £340 / night

£2,377 / week

1 / 12

Villa rental in Grand Case

Grand Case villa

6 bedrooms • 7 bathrooms • sleeps 12

from £1,174 / night

£8,217 / week

1 / 35

Holiday villa in Cupecoy Bay

Cupecoy Bay villa

3 bedrooms • 3 bathrooms • sleeps 6

from £615 / night

£4,306 - £11,709 / week

1 / 24

Holiday villa with swimming pool, golf nearby in Cupecoy Bay

Cupecoy Bay villa

4 bedrooms • 4 bathrooms • sleeps 8

from £1,080 / night

£7,555 - £22,663 / week

1 / 24

Holiday villa with swimming pool, golf nearby in Cupecoy Bay

Cupecoy Bay villa

4 bedrooms • 4 bathrooms • sleeps 8

from £864 / night

£6,044 - £17,375 / week

1 / 24

Holiday villa with swimming pool, golf nearby in Maho

Maho villa

3 bedrooms • 3 bathrooms • sleeps 6

from £649 / night

£4,537 - £9,069 / week

1 / 76

Holiday villa with golf nearby in Beacon Hill, Sint Maarten

Beacon Hill, Sint Maarten villa

5 bedrooms • 5 bathrooms • sleeps 10

from £955 / night

£6,684 - £18,133 / week

1 / 24

Holiday villa with swimming pool, golf nearby in Beacon Hill, Sint Maarten

Beacon Hill, Sint Maarten villa

1 bedroom • 1 bathroom • sleeps 2

from £1,727 / night

£12,087 - £33,997 / week

1 / 25

Holiday villa with swimming pool in St. Jean

St. Jean villa

2 bedrooms • 2 bathrooms • sleeps 4

from £810 / night

£5,666 - £18,886 / week

1 / 26

Holiday villa with swimming pool in Cupecoy Bay

Cupecoy Bay villa

3 bedrooms • 3 bathrooms • sleeps 6

from £378 / night

£2,644 - £4,913 / week

1 / 28

Holiday villa rental

Colombier villa

4 bedrooms • 4 bathrooms • sleeps 8

from £1,943 / night

£13,598 - £43,815 / week

1 / 23

Holiday apartment in La Savane

La Savane apartment

1 bedroom • 1 bathroom • sleeps 4

from £88 / night

£583 - £760 / week

1 / 12

Holiday home in La Savane

La Savane house

2 bedrooms • 1 bathroom • sleeps 6

from £164 / night

£1,144 / week

1 / 12

Holiday studio in Marigot

Marigot studio

Studio • 1 bathroom • sleeps 3

from £54 / night

£353 / week

1 / 22

Holiday apartment in La Savane

La Savane apartment

1 bedroom • 1 bathroom • sleeps 2

from £65 / night

£453 - £668 / week

1 / 16

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