50 Best Vacation Rentals in Sint Maarten - Holiday Lettings - Cabins

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Villas Simpson Bay
148 properties
Philipsburg
129 properties
Oyster Pond
120 properties
Cupecoy Bay
40 properties
Maho
23 properties
Cole Bay
17 properties
Dawn Beach
12 properties
Mullet Bay
9 properties
Beacon Hill, Sint Maarten
5 properties

Sint Maarten

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513 Vacation rentals

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20

Oyster Pond Vacation villa rental

Sint Maarten / Oyster Pond

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Ideal for 1 couple, 2 or 3 couples or a family. Sleeps to maximum of 6 in 3 double beds , a villa that offers all the comforts of a cozy home away from home and is very affordable. Villa Oyster Bay View is very well appointed in its 2 double bed bedrooms ( California …see more

from $211 / night

$1471 - $2980 / week

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from $211 / night

28

Vacation villa with swimming pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Welcome to our beautiful villa Sea Dream located on the hillside in Happy Bay. It is a gorgeous villa and only a 5 minute walk from the beach at Happy Bay. Friar's Bay is also very close and has 2 beach restaurants that are very popular with guests. …see more

from $383 / night

$2681 - $5854 / week

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from $383 / night

(1) Excellent 

23

Vacation villa with swimming pool, golf nearby in Cupecoy Bay

Sint Maarten / Cupecoy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Welcome to The Retreat located in Shore Pointe, one of the newest and most exquisite developments and situated directly on the stunning beach at Cupecoy. This spectacular 4 bedroom ultra luxurious fully air conditioned property with private pool and Jacuzzi off …see more

from $922 / night

$6449 - $18850 / week

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from $922 / night

24

Vacation villa with swimming pool in Cupecoy Bay

Sint Maarten / Cupecoy Bay

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Welcome to Carisa one of the most exquisite villas in St. Martin situated directly on the stunning Baie Rouge Beach. This spectacular beach front property offers the most incredible views of the pristine white sandy beach and sea beyond. Carisa is a luxurious on …see more

from $1347 / night

$9425 - $18850 / week

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from $1347 / night

25

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

Sint Maarten / Beacon Hill, Sint Maarten

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Welcome to La Perla Classic, a lovely one bedroom fully air-conditioned beachfront villa with private swimming pool located directly on Baie Rouge which is one of the most beautiful beaches in St Martin. Baie Rouge one of the most fabulous, intimate and quiet b …see more

from $993 / night

$6945 - $7441 / week

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from $993 / night

76

Vacation villa with swimming pool, golf nearby in Maho

Sint Maarten / Maho

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Welcome to our luxurious Baie Longue Beach House villa. This wonderful villa is tastefully decorated in a West Indian style with lovely arches on the sea side is located directly on Baie Longue Beach. Baie Longue beach is really beautiful with over a mile of shimmering …see more

from $852 / night

$5953 - $11905 / week

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from $852 / night

(2) Excellent 

24

Vacation villa with swimming pool in Beacon Hill, Sint Maarten

Sint Maarten / Beacon Hill, Sint Maarten

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Les Palmiers one of the most exquisite villas in St. Martin situated directly on the beautiful Baie Rouge Beach. This stunning beach front property offers the most incredible views of the pristine white sandy beach and sea beyond. Baie Rouge is one o …see more

from $993 / night

$6945 - $10913 / week

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from $993 / night

24

Vacation villa with golf nearby in Beacon Hill, Sint Maarten

Sint Maarten / Beacon Hill, Sint Maarten

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Villa Encore, a luxury 5 bedroom villa located in the hill side of Terre Basses in St Martin. The villa is tasteful decorated offer a very spacious living area perfect for a large family. The nearest beach is Plum Bay beach which is a 3 minute drive f …see more

from $1114 / night

$7788 - $21826 / week

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from $1114 / night

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24

Vacation villa in Cupecoy Bay

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Welcome to Mumbai located in Shore Pointe, one of the newest and most exquisite developments and situated directly on the stunning beach at Cupecoy. This spectacular 3 bedroom ultra luxurious fully air conditioned property with private offers the most incredible views o …see more

from $808 / night

$5655 - $15377 / week

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from $808 / night

24

Vacation villa with swimming pool, golf nearby in Cupecoy Bay

Sint Maarten / Cupecoy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Casa Cervo, one of the St Martin's most exquisite and luxurious Beach Front Villa. This stunning 4 bedroom ultra luxurious property with private pool has the most incredible views looking out onto Baie Rouge Bay, one of the most beautiful beaches in St M …see more

from $1186 / night

$8299 - $27778 / week

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from $1186 / night

(2) Excellent 

36

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $312 / night

$2183 / week

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from $312 / night

24

Vacation villa with swimming pool, golf nearby in Cupecoy Bay

Sint Maarten / Cupecoy Bay

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Welcome to villa Ambiance, our luxurious 4 bedroom property located on the hillside of Terres Basses overlooking the Caribbean Sea. It is a fantastic family retreat and the perfect villa to spend a special occasion. The pool at Villa Ambiance is simply stunning and is t …see more

from $1064 / night

$7441 - $21826 / week

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from $1064 / night

(1) Excellent 

26

Vacation villa with shared pool, golf nearby in Dutch Lowlands

Sint Maarten / Dutch Lowlands

2 2 3 nights min

  • 2 bedrooms
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
Two lovely Private entrance Suites in waterfront Villa in Sint Maarten . The 2 Suites have private entrance, bath, safe boxes, tv, wifi internet all over the property, BBQ, bar, pool lounge common area, property is on the lagoon with boat accessibility . 5 minutes away …see more

from $99 / night

$688 / week

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from $99 / night

8

Sint Maarten / Oyster Pond

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $135 / night

$863 - $1132 / week

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from $135 / night

(1) Excellent 

43

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $359 / night

$2511 / week

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from $359 / night

6

Sint Maarten / Oyster Pond

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Air conditioning

from $122 / night

$853 / week

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from $122 / night

15

Sint Maarten / Oyster Pond

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

from $247 / night

$1725 - $2199 / week

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from $247 / night

(2) Good 

13

Sint Maarten / Oyster Pond

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $108 / night

$539 / week

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from $108 / night

(2) Excellent 

32

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $416 / night

$2910 - $3018 / week

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from $416 / night

9

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $462 / night

$3233 / week

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from $462 / night

(1) Excellent 

9

Sint Maarten / Oyster Pond

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $65 / night

$453 / week

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from $65 / night

12

Sint Maarten / Dawn Beach

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

from $539 / night

$3772 / week

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from $539 / night

15

Sint Maarten / Oyster Pond

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

from $124 / night

$863 / week

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from $124 / night

13

Sint Maarten / Oyster Pond

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

from $54 / night

$378 - $518 / week

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from $54 / night

10

B&b rental in Oyster Pond

Sint Maarten / Oyster Pond

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Nearest beach 0.5 mi
  • Ask about children
  • Air conditioning
You will love the charm of my house + garden in Oyster Pond, on the quieter aside of the island where everything is more authentic and less touristy. 5 minutes from Captain Oliver Marina and the ferry to St Barth. American Breakfast for 2 included. Nice large room with …see more

from $75 / night

$525 / week

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from $75 / night

11

Sint Maarten / Dawn Beach

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

from $458 / night

$3206 / week

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from $458 / night

(1) Very Good 

9

Sint Maarten / Philipsburg

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

from $301 / night

$2102 / week

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from $301 / night

(1) Excellent 

23

Villa rental in Philipsburg with shared pool

Sint Maarten / Philipsburg

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
Villa #9 on the left edge of "VILLAS ON GREAT BAY" complex, directly on the beach of Philipsburg, the capital of dutch St.Maarten. Being the side villa it offers more privacy and tranquillity. On the ground floor: terrace on the beach with wooden floor, a la …see more

from $334 / night

$2334 - $2681 / week

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from $334 / night

(1) Good 

21

Sint Maarten / Oyster Pond

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $97 / night

$679 / week

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from $97 / night

13

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $348 / night

$2431 - $4584 / week

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from $348 / night

11

Sint Maarten / Oyster Pond

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $130 / night

$906 - $1369 / week

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from $130 / night

(1) Excellent 

11

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Air conditioning
  • Private garden

from $770 / night

$5388 / week

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from $770 / night

20

Sint Maarten / Dawn Beach

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $231 / night

$1617 / week

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from $231 / night

5

Vacation apartment in Cole Bay

Sint Maarten / Cole Bay

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Air conditioning
  • Ask about pets
Located in Almond Grove an upmarket gated community in Cole Bay St Maarten.This spacious 1 bed apartment has everything for a lovely vacation.Guests have use of a 60 foot swimming pool and jacuzzi,barbecue,sauna and gym. Fully equipped kitchen ,Flat screen TV ,Stere …see more

from $100 / night

$700 / week

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from $100 / night

7

Sint Maarten / Cole Bay

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $308 / night

$2156 / week

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from $308 / night

17

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

from $201 / night

$1401 / week

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from $201 / night

13

Vacation apartment in Philipsburg

Sint Maarten / Philipsburg

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
for your holidays rents continued for 8 people at the Westin Dawn Beach Resort and Spa St.Maarten. Apartment 180m2,3 bedrooms, including a master suite with dressing room convertible sofa in the living room. 2 bathrooms, fully equipped kitchen, satellite TV in all bedro …see more

from $185 / night

$1294 / week

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from $185 / night

8

Sint Maarten / Dawn Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $410 / night

$2802 - $3233 / week

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from $410 / night

10

Sint Maarten / Oyster Pond

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly

from $151 / night

$1057 / week

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from $151 / night

23

Simpson Bay / Simpson Bay Beach

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

from $426 / night

$2905 / week

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from $426 / night

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