Holiday rentals - Holiday homes to rent - Book direct

View larger map

Price per night

£337 Average

Price per night

to

Bedrooms

Bathrooms

Location

  • St. Maarten - Saint Martin
  • Sint Maarten
  • Simpson Bay

Location

  • All locations

More

Less

Property type

More

Less

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

50 Holiday homes

Filters applied: Pets allowed (3)

1 / 24

Holiday villa in Cole Bay

Sint Maarten / Cole Bay

5 10 Min stay varies

Villa / 5 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £449 / night

£3138 / week

Book

from £449 / night

1 / 5

Holiday apartment in Cole Bay

Sint Maarten / Cole Bay

1 3 Min stay varies

Apartment / 1 bedroom / sleeps 3 / Min stay varies

Add to shortlist

from £70 / night

£490 / week

Book

from £70 / night

1 / 14

Holiday villa with swimming pool in Cole Bay

Sint Maarten / Cole Bay

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £493 / night

£3447 - £4828 / week

Enquire

from £493 / night

More results near

Distance approx 0.52 miles from Cole Bay Show on Map

1 / 8

Simpson Bay holiday villa rental

Sint Maarten / Simpson Bay

3 6 5 nights min stay

Villa / 3 bedrooms / sleeps 6 / 5 nights min stay

Add to shortlist

from £173 / night

£1207 / week

Enquire

from £173 / night

Distance approx 0.57 miles from Cole Bay Show on Map

1 / 23

Holiday villa with swimming pool in Simpson Bay

Sint Maarten / Simpson Bay

6 12 5 nights min stay

Villa / 6 bedrooms / sleeps 12 / 5 nights min stay

Add to shortlist

from £592 / night

£4138 - £8207 / week

Enquire

from £592 / night

Distance approx 0.58 miles from Cole Bay Show on Map

1 / 15

Holiday condo in Simpson Bay

Sint Maarten / Simpson Bay

2 6 4 nights min stay

Condo / 2 bedrooms / sleeps 6 / 4 nights min stay

Add to shortlist

from £221 / night

£1545 / week

Book

from £221 / night

Distance approx 0.64 miles from Cole Bay Show on Map

(1) Excellent 

1 / 18

Apartment rental in Simpson Bay

Simpson Bay / Simpson Bay Beach

1 4 Min stay varies

Apartment / 1 bedroom / sleeps 4 / Min stay varies

Add to shortlist

from £96 / night

£672 - £845 / week

Book

from £96 / night

Distance approx 0.64 miles from Cole Bay Show on Map

1 / 8

Simpson Bay holiday apartment rental

Sint Maarten / Simpson Bay

2 4 5 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 5 nights min stay

Add to shortlist

from £207 / night

£1380 / week

Book

from £207 / night

Distance approx 0.66 miles from Cole Bay Show on Map

1 / 28

Holiday villa in Simpson Bay

Sint Maarten / Simpson Bay

5 10 5 nights min stay

Villa / 5 bedrooms / sleeps 10 / 5 nights min stay

Add to shortlist

from £425 / night

£2966 - £3932 / week

Enquire

from £425 / night

Distance approx 0.67 miles from Cole Bay Show on Map

1 / 49

Holiday villa with swimming pool in Simpson Bay

Sint Maarten / Simpson Bay

7 14 5 nights min stay

Villa / 7 bedrooms / sleeps 14 / 5 nights min stay

Add to shortlist

from £1035 / night

£7242 - £15932 / week

Enquire

from £1035 / night

Distance approx 0.68 miles from Cole Bay Show on Map

1 / 40

Holiday villa with swimming pool in Simpson Bay

Sint Maarten / Simpson Bay

5 10 5 nights min stay

Villa / 5 bedrooms / sleeps 10 / 5 nights min stay

Add to shortlist

from £533 / night

£3725 - £7932 / week

Enquire

from £533 / night

Distance approx 0.7 miles from Cole Bay Show on Map

1 / 28

Holiday villa with swimming pool in Simpson Bay

Sint Maarten / Simpson Bay

6 12 Min stay varies

Villa / 6 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £444 / night

£3105 - £8207 / week

Enquire

from £444 / night

Distance approx 0.74 miles from Cole Bay Show on Map

1 / 25

Simpson Bay holiday villa rental

Sint Maarten / Simpson Bay

5 10 4 nights min stay

Villa / 5 bedrooms / sleeps 10 / 4 nights min stay

Add to shortlist

from £1380 / night

£9656 / week

Enquire

from £1380 / night

Distance approx 0.75 miles from Cole Bay Show on Map

1 / 9

Simpson Bay holiday villa rental

Sint Maarten / Simpson Bay

3 6 5 nights min stay

Villa / 3 bedrooms / sleeps 6 / 5 nights min stay

Add to shortlist

from £173 / night

£1207 / week

Enquire

from £173 / night

Distance approx 0.79 miles from Cole Bay Show on Map

(3) Very Good 

1 / 43

Simpson Bay holiday villa rental

Sint Maarten / Simpson Bay

5 10 5 nights min stay

Villa / 5 bedrooms / sleeps 10 / 5 nights min stay

Add to shortlist

from £582 / night

£4069 - £9656 / week

Enquire

from £582 / night

Distance approx 0.79 miles from Cole Bay Show on Map

1 / 10

Villa rental in Simpson Bay with swimming pool

Sint Maarten / Simpson Bay

4 8 5 nights min stay

Villa / 4 bedrooms / sleeps 8 / 5 nights min stay

Add to shortlist

from £641 / night

£4483 - £6207 / week

Enquire

from £641 / night

Distance approx 0.79 miles from Cole Bay Show on Map

(1) Very Good 

1 / 39

Holiday villa rental

Sint Maarten / Simpson Bay

6 12 5 nights min stay

Villa / 6 bedrooms / sleeps 12 / 5 nights min stay

Add to shortlist

from £444 / night

£3104 - £6690 / week

Enquire

from £444 / night

Distance approx 0.81 miles from Cole Bay Show on Map

1 / 24

Holiday villa with swimming pool in Simpson Bay

Sint Maarten / Simpson Bay

6 12 4 nights min stay

Villa / 6 bedrooms / sleeps 12 / 4 nights min stay

Add to shortlist

from £2759 / night

£19311 / week

Enquire

from £2759 / night

Distance approx 0.88 miles from Cole Bay Show on Map

1 / 30

Holiday villa in Simpson Bay

Sint Maarten / Simpson Bay

6 12 5 nights min stay

Villa / 6 bedrooms / sleeps 12 / 5 nights min stay

Add to shortlist

from £1282 / night

£8966 - £19311 / week

Enquire

from £1282 / night

Distance approx 0.89 miles from Cole Bay Show on Map

1 / 4

Holiday villa with swimming pool in Simpson Bay

Sint Maarten / Simpson Bay

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £463 / night

£3240 - £4485 / week

Enquire

from £463 / night

Distance approx 0.89 miles from Cole Bay Show on Map

1 / 22

Holiday home with shared pool in St. Maarten - Saint Martin

Caribbean / St. Maarten - Saint Martin

3 8 7 nights min stay

House / 3 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £641 / night

£4483 - £13794 / week

Enquire

from £641 / night

Distance approx 0.89 miles from Cole Bay Show on Map

1 / 17

St. Maarten - Saint Martin holiday home rental

Caribbean / St. Maarten - Saint Martin

2 6 7 nights min stay

House / 2 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £473 / night

£3311 - £8276 / week

Enquire

from £473 / night

Distance approx 1.07 miles from Cole Bay Show on Map

(2) Very Good 

1 / 28

Simpson Bay holiday apartment rental

Sint Maarten / Simpson Bay

1 4 Min stay varies

Apartment / 1 bedroom / sleeps 4 / Min stay varies

Add to shortlist

from £97 / night

£676 / week

Book

from £97 / night

Distance approx 1.25 miles from Cole Bay Show on Map

1 / 11

Simpson Bay holiday apartment rental

Sint Maarten / Simpson Bay

1 4 3 nights min stay

Apartment / 1 bedroom / sleeps 4 / 3 nights min stay

Add to shortlist

from £89 / night

£623 / week

Book

from £89 / night

Distance approx 1.27 miles from Cole Bay Show on Map

1 / 21

Home accommodation in Terres Basses

Saint-Martin / Terres Basses

3 6 5 nights min stay

House / 3 bedrooms / sleeps 6 / 5 nights min stay

Add to shortlist

from £372 / night

£2597 / week

Enquire

from £372 / night

Distance approx 1.27 miles from Cole Bay Show on Map

1 / 19

St. Maarten - Saint Martin holiday villa rental

Caribbean / St. Maarten - Saint Martin

3 6 5 nights min stay

Villa / 3 bedrooms / sleeps 6 / 5 nights min stay

Add to shortlist

from £444 / night

£3104 / week

Enquire

from £444 / night

Distance approx 1.27 miles from Cole Bay Show on Map

1 / 11

Terres Basses holiday villa rental

Saint-Martin / Terres Basses

6 12 5 nights min stay

Villa / 6 bedrooms / sleeps 12 / 5 nights min stay

Add to shortlist

from £424 / night

£2966 / week

Enquire

from £424 / night

Distance approx 1.27 miles from Cole Bay Show on Map

1 / 24

Holiday villa in Terres Basses

Saint-Martin / Terres Basses

2 4 5 nights min stay

Villa / 2 bedrooms / sleeps 4 / 5 nights min stay

Add to shortlist

from £276 / night

£1932 / week

Enquire

from £276 / night

Distance approx 1.27 miles from Cole Bay Show on Map

(1) Excellent 

1 / 12

St. Maarten - Saint Martin holiday home rental

Caribbean / St. Maarten - Saint Martin

2 6 7 nights min stay

House / 2 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £183 / night

£1276 / week

Book

from £183 / night

Distance approx 1.33 miles from Cole Bay Show on Map

1 / 30

Villa rental in Philipsburg with swimming pool

Sint Maarten / Philipsburg

4 8 Min stay varies

Villa / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £285 / night

£1989 / week

Book

from £285 / night

Distance approx 1.75 miles from Cole Bay Show on Map

(1) Excellent 

1 / 16

Holiday apartment rental

Marigot / Nettle Bay Beach Club

1 4 7 nights min stay

Apartment / 1 bedroom / sleeps 4 / 7 nights min stay

Add to shortlist

from £78 / night

£543 - £698 / week

Book

from £78 / night

Distance approx 1.87 miles from Cole Bay Show on Map

(1) Excellent 

1 / 24

Philipsburg holiday villa rental

Sint Maarten / Philipsburg

5 10 5 nights min stay

Villa / 5 bedrooms / sleeps 10 / 5 nights min stay

Add to shortlist

from £513 / night

£3587 - £6897 / week

Enquire

from £513 / night

Distance approx 1.9 miles from Cole Bay Show on Map

1 / 26

Marigot holiday home rental

Saint-Martin / Marigot

5 10 7 nights min stay

House / 5 bedrooms / sleeps 10 / 7 nights min stay

Add to shortlist

from £2956 / night

£20690 - £89656 / week

Enquire

from £2956 / night

Distance approx 1.91 miles from Cole Bay Show on Map

1 / 20

Apartment rental in Anse aux Cajoux

Saint-Martin / Anse aux Cajoux

2 6 Min stay varies

Apartment / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £73 / night

£504 - £679 / week

Book

from £73 / night

Distance approx 2.03 miles from Cole Bay Show on Map

(1) Very Good 

1 / 30

St. Maarten - Saint Martin holiday villa rental

Caribbean / St. Maarten - Saint Martin

3 6 5 nights min stay

Villa / 3 bedrooms / sleeps 6 / 5 nights min stay

Add to shortlist

from £316 / night

£2207 - £4345 / week

Enquire

from £316 / night

Distance approx 2.04 miles from Cole Bay Show on Map

1 / 15

Holiday condo in Simpson Bay

Sint Maarten / Simpson Bay

1 3 Min stay varies

Condo / 1 bedroom / sleeps 3 / Min stay varies

Add to shortlist

from £145 / night

£1014 / week

Book

from £145 / night

Distance approx 2.04 miles from Cole Bay Show on Map

1 / 9

Holiday condo in Simpson Bay

Sint Maarten / Simpson Bay

1 3 Min stay varies

Condo / 1 bedroom / sleeps 3 / Min stay varies

Add to shortlist

from £112 / night

£778 / week

Book

from £112 / night

Distance approx 2.05 miles from Cole Bay Show on Map

1 / 24

Simpson Bay holiday villa rental

Sint Maarten / Simpson Bay

5 12 Min stay varies

Villa / 5 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £376 / night

£2632 / week

Book

from £376 / night

Distance approx 2.05 miles from Cole Bay Show on Map

1 / 20

Holiday villa in Beacon Hill, Sint Maarten

Sint Maarten / Beacon Hill, Sint Maarten

4 8 Min stay varies

Villa / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £373 / night

£2607 - £7449 / week

Book

from £373 / night

Distance approx 2.05 miles from Cole Bay Show on Map

1 / 4

Apartment rental in Guadeloupe

Caribbean / Guadeloupe

1 1 3 nights min stay

Apartment / 1 bedroom / sleeps 1 / 3 nights min stay

Add to shortlist

from £42 / night

£294 - £348 / week

Book

from £42 / night

Distance approx 2.06 miles from Cole Bay Show on Map

1 / 25

Holiday villa with swimming pool in Simpson Bay

Sint Maarten / Simpson Bay

5 12 5 nights min stay

Villa / 5 bedrooms / sleeps 12 / 5 nights min stay

Add to shortlist

from £395 / night

£2762 / week

Book

from £395 / night

Distance approx 2.06 miles from Cole Bay Show on Map

1 / 30

Villa rental in St. Maarten - Saint Martin with swimming pool

Caribbean / St. Maarten - Saint Martin

5 10 5 nights min stay

Villa / 5 bedrooms / sleeps 10 / 5 nights min stay

Add to shortlist

from £454 / night

£3173 - £5449 / week

Enquire

from £454 / night

Distance approx 2.07 miles from Cole Bay Show on Map

1 / 19

Marigot holiday apartment rental

Saint-Martin / Marigot

1 3 3 nights min stay

Apartment / 1 bedroom / sleeps 3 / 3 nights min stay

Add to shortlist

from £43 / night

£299 - £597 / week

Book

from £43 / night

Distance approx 2.07 miles from Cole Bay Show on Map

(1) Excellent 

1 / 15

Holiday villa in Simpson Bay

Sint Maarten / Simpson Bay

5 10 5 nights min stay

Villa / 5 bedrooms / sleeps 10 / 5 nights min stay

Add to shortlist

from £375 / night

£2621 - £4000 / week

Enquire

from £375 / night

Distance approx 2.15 miles from Cole Bay Show on Map

(1) Good 

1 / 36

Holiday villa with swimming pool in Marigot

Saint-Martin / Marigot

8 16 5 nights min stay

Villa / 8 bedrooms / sleeps 16 / 5 nights min stay

Add to shortlist

from £1173 / night

£8207 - £21725 / week

Enquire

from £1173 / night

Distance approx 2.17 miles from Cole Bay Show on Map

1 / 23

Simpson Bay holiday home rental

Simpson Bay / Simpson Bay Beach

3 6 1 night min stay

House / 3 bedrooms / sleeps 6 / 1 night min stay

Add to shortlist

from £299 / night

£2090 / week

Book

from £299 / night

Distance approx 2.22 miles from Cole Bay Show on Map

(2) Excellent 

1 / 28

Holiday apartment with shared pool in Baie Nettle

Saint-Martin / Baie Nettle

1 4 7 nights min stay

Apartment / 1 bedroom / sleeps 4 / 7 nights min stay

Add to shortlist

from £70 / night

£489 - £1086 / week

Book

from £70 / night

Distance approx 2.31 miles from Cole Bay Show on Map

1 / 33

St. Maarten - Saint Martin holiday villa rental

Caribbean / St. Maarten - Saint Martin

3 6 5 nights min stay

Villa / 3 bedrooms / sleeps 6 / 5 nights min stay

Add to shortlist

from £375 / night

£2621 - £5173 / week

Enquire

from £375 / night

Distance approx 2.35 miles from Cole Bay Show on Map

(7) Excellent 

1 / 18

Holiday apartment with shared pool in Baie Nettle

Saint-Martin / Baie Nettle

1 2 7 nights min stay

Apartment / 1 bedroom / sleeps 2 / 7 nights min stay

Add to shortlist

from £119 / night

£828 - £1000 / week

Book

from £119 / night

Distance approx 2.4 miles from Cole Bay Show on Map

1 / 16

Holiday villa with swimming pool in Maho

Sint Maarten / Maho

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £444 / night

£3105 - £5518 / week

Enquire

from £444 / night

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page