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

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Villas Simpson Bay
178 properties
Philipsburg
153 properties
Oyster Pond
131 properties
Cupecoy Bay
42 properties
Maho
29 properties
Cole Bay
18 properties
Mullet Bay
13 properties
Dawn Beach
11 properties
Beacon Hill, Sint Maarten
5 properties

Sint Maarten

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605 Vacation rentals

(3) Very Good 

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 $219 / night

$1530 - $3099 / week

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from $219 / night

(1) Excellent 

43

Vacation apartment rental

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This apartment for 8 persons maximum is rented weekly from Saturday to Saturday. It is a sequel to luxury 5 star 180 m2, 3 bedrooms (1 master suite with dressing room, sofa bed in the living room), 2 bathrooms, fully equipped kitchen, satellite TV in all rooms and the l …see more

from $374 / night

$2612 / week

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from $374 / 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

$693 / week

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from $99 / night

(1) Very Good 

6

Oyster Pond Vacation apartment rental

Sint Maarten / Oyster Pond

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Air conditioning
On the heights of oyster pond, part French, apartment view sea in Homestead, parking space, terrace, panoramic sea view from terrace, stay, kitchen, excellent condition, fully equipped kitchen, bathroom, internet wifi, TV, a nice apartment, it is equipped with air condi …see more

from $127 / night

$887 / week

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from $127 / night

13

Apartment rental in Oyster Pond with shared pool

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
St Maarten – Caribbean: Luxury Sea View Apartment of 190m² (2045 sq ft), 6 to 8 people in a 5 star hotel, the WESTIN, facing St Barth Enjoy a prestige luxury residence to rent all year long for a week, even during Christmas holidays. This is the perfect spot to relax …see more

from $350 / night

$2450 - $4620 / week

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from $350 / night

(1) Good 

21

Oyster Pond Vacation apartment rental

Sint Maarten / Oyster Pond

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Apartment located on the 1st floor, 1 room with king size bed and air conditioning with small balcony lounge with TV, WiFi Internet access, sofa (for 2 people extra) kitchen (microwave, fridge, coffee maker, toaster) lava lingeTerasse with table, magnificent sea view. L …see more

from $101 / night

$707 / week

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from $101 / 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 lanai to enj …see more

from $336 / night

$2352 / week

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from $336 / night

(2) Excellent 

32

Oyster Pond Vacation condo rental

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Loue following 6/8 people at the Westin Dawn Beach Spring & Spa St. Martin. Rental is from Saturday to Saturday for one or two weeks Apartment 180 m2, 3 bedrooms (2 with king size bed), sofa bed in the living room, Wi-Fi. 2 bathrooms, kitchen fully equipped, satellite T …see more

from $401 / night

$2802 - $2914 / week

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from $401 / 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 $858 / night

$6000 - $12000 / week

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from $858 / night

(1) Very Good 

9

Vacation apartment with shared pool in Philipsburg

Sint Maarten / Philipsburg

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Apartment of 180 m2, 3 bedrooms (1 suite with dressing room), sofa bed in the living room, 2 bathrooms, fully equipped kitchen, satellite TV in all rooms and lounge, washing machine and dryer. Linen provided (sheets, duvets, towels ...) Great infinity pool (towels and b …see more

from $313 / night

$2186 / week

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from $313 / night

20

Dawn Beach Vacation hotel apartment rental

Sint Maarten / Dawn Beach

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Westin Dawn Beach Club Resort & Spa St Maarten Hotel 5 * on the sea, apartment of 180 m 2, 3 bedroom with kingsize, (including a master suite with dressing room and ensuite bathroom courtesy-fort), sofa bed in the livingroom, 1 second bathroom, fully equipped kitchen, s …see more

from $241 / night

$1682 / week

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from $241 / night

9

Vacation apartment in Oyster Pond

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Ideal for an unforgettable stay in a high range complex, weekly rental suite of 180 m2 with St Barth, in hotel 5 * (6/8 pers) at the Westin Dawn Beach in Saint Martin (Netherlands part). 3 bedrooms (1 master suite with dressing room), 2 bathrooms including 1 with bathtu …see more

from $481 / night

$3363 / week

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from $481 / night

11

Oyster Pond Vacation b&b rental

Sint Maarten / Oyster Pond

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
2 bed and breakfasts are inside the villa, on a level different from that of the owner, the kitchen is free to access and stay, the swimming pool, the garden room only can be rented for 2 to 3 persons the location is quiet, in a residential area, close to the first beac …see more

from $65 / night

$449 - $572 / week

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from $65 / night

7

Apartment rental in Cole Bay with shared pool

Sint Maarten / Cole Bay

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Loue suite 6/8 personnes au Westin Dawn Beach Ressort & Spa St Maarten Appartement de 180 M2, 3 chambres (dont 1 suite parentale, avec dressing), canapé convertible dans le salon, 2 salles de bain, cuisine américaine toute équipée, télévision satellite dans toutes les …see more

from $321 / night

$2242 / week

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from $321 / night

34

Oyster Pond Vacation apartment rental

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Luxurious Suite 5 * 180 m2 (8 pers) in the Westin Dawn Beach Resort & Spa Hotel complex Saint-Martin (Antilles) for the price of a simple double room 5 * St-Martin. Enjoy the same benefits as the Westin clients and have a real holiday that the small personal belongings …see more

from $265 / night

$1850 / week

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from $265 / 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 Martin …see more

from $1195 / night

$8365 - $28000 / week

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from $1195 / night

(2) Excellent 

36

Vacation apartment with shared pool in Oyster Pond

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Apartment of 180 m2, 3 bedrooms (including a master suite with dressing room), 2 bathroom, fully equipped kitchen, satellite TV in the 3 bedrooms, washing machine, dishwasher, supplied linen (sheets duvet towels) large swimming pool Beach reserved to the customers. …see more

from $265 / night

$1850 / week

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from $265 / 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 $193 / night

$1345 / week

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from $193 / night

21

Beacon Hill, Sint Maarten Vacation villa rental

Sint Maarten / Beacon Hill, Sint Maarten

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
This is a beautiful oceanfront 5 bedroom, 4 bathroom property that is located in a nice quiet area of Beacon Hill overlooking Burgeaux Bay on Dutch St. Maarten.This villa offers amazing colours in the morning and unique sunsets. The villa is located within walking dista …see more

from $494 / night

$3458 / week

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from $494 / night

(2) Good 

13

Oyster Pond Vacation apartment rental

Sint Maarten / Oyster Pond

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
the owners will be happy to move towards best addresses non-standard or unavoidable points of the island. Welcome to sports - surf spot, kyte, diving club, rent a boat less than 10 minutes. and also 10 minutes from the nearest casino. 30 minutes from marigot and 15 minu …see more

from $113 / night

$561 / week

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from $113 / night

11

Vacation hotel apartment in Dawn Beach

Sint Maarten / Dawn Beach

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
IDEAL for holidays on the beach with swimming pool overflowing to SAINT MARTIN rent suite 6/8 people at the Westin Dawn Beach Resort & Spa St Maarten apartment of 180 M2, 3 bedrooms (1 master suite with dressing room), sofa bed in the living room, 2 bathrooms, fully equ …see more

from $477 / night

$3335 / week

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from $477 / night

8

Vacation apartment with shared pool in Oyster Pond

Sint Maarten / Oyster Pond

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
SPACIOUS APARTMENT INDEPENDENT VIEW OF THE POOL. FULLY EQUIPPED. AIR CONDITIONING. FAN. WIRELESS . SEPARATE ROOM WITH SAFE Large bed. PRIVATE TERRACE WITH TABLES AND CHAIRS. PRIVATE GARDEN. IN THE HEART OF OYSTER POND. YOU HAVE ALL MY FOOT FACILITIES. (Restaurants, bar …see more

from $141 / night

$897 / week

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from $141 / night

8

Condo rental in Dawn Beach with shared pool

Sint Maarten / Dawn Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Rent room of 44 m² for 4 people at the Westin Dawn beach St Martin with Seaview (subject to availability) 2 large beds double satellite TV air conditioning/fan ceiling linens provided large pool room 4 people TV iron and ironing board fan wake-up Service janitorial Cloc …see more

from $426 / night

$2914 - $3363 / week

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from $426 / 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

Vacation apartment with shared pool in Oyster Pond

Sint Maarten / Oyster Pond

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
You will be accommodated in a spacious apartment of 90 m 2 approximately composed of a large bedroom on the mezzanine and a second bedroom with its own bathroom. The apartment has all the comfort that we can hope, gazinere, fridge, internet... It is an ideal place for …see more

Pricing unknown

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Pricing unknown

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 $1000 / night

$7000 / week

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from $1000 / night

(2) 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 $930 / night

$6500 - $19000 / week

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from $930 / night

12

Vacation apartment with swimming pool in Dawn Beach

Sint Maarten / Dawn Beach

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
Apartment of 180 M2, 3 bedrooms (1 master suite with dressing room), sofa bed in the living room, 2 bathrooms, fully equipped kitchen, satellite TV in all bedrooms and the living room, washing machine and dryer, Ironing Board and iron ironing. Supplied linen (sheets, du …see more

from $561 / night

$3923 / week

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from $561 / night

11

Oyster Pond Vacation apartment rental

Sint Maarten / Oyster Pond

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
St martin, in the French West Indies, on the heights of oyster pond between phillisburg and East bay, the apartment is located on a plot of 2000 m2 with the (discrete) owners and 2 other studios for rent villa, the place is quiet, residential, secure, with swimming pool …see more

from $135 / night

$942 / week

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from $135 / 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. The …see more

from $386 / night

$2703 - $5900 / week

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from $386 / night

15

Vacation home with swimming pool in Oyster Pond

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
On the heights of oyster pond, this charming villa is very well placed, in a quiet and residential area separate entrance private pool, 3 air-conditioned rooms, 3 bathrooms, you will spend a great holiday with family or friends in the wildest sector of the island on the …see more

from $257 / night

$1794 - $2242 / week

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from $257 / night

17

Vacation apartment in Oyster Pond

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
In secure residence private beach, rents spacious apartment for 6-8 persons. Fully furnished and equipped, you can enjoy relaxing holidays thanks to the quietness of the residence and annex quality service (linen from House, toilet and bath, household). Apartment air-co …see more

from $209 / night

$1457 / week

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from $209 / 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 $1122 / night

$7850 - $22000 / week

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from $1122 / night

(1) Excellent 

11

Vacation hotel apartment in Oyster Pond

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Air conditioning
  • Private garden
Suite 6/8 people at the WESTIN DAWN BEACH Resort & Spa St. Maarten. Apartment of 180 m2, 3 bedrooms (1 master suite with dressing room), sofa bed in the lounge. 2 bathrooms, fully equipped kitchen, satellite TV in all rooms and the lounge, washing machine and dryer. Li …see more

from $801 / night

$5604 / week

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from $801 / night

(3) Very Good 

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 $815 / night

$5700 - $15500 / week

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from $815 / 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 $1072 / night

$7500 - $22000 / week

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from $1072 / night

10

Oyster Pond Vacation apartment rental

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This 180M² condo includes : 2 bedrooms and 1 master suite vith built in closets, 2 bathrooms, pull out bed sofa in living room area, television satellite in all bedrooms including the living room area, an all equipped American style kitchen, a washer and dryer, bed line …see more

from $481 / night

$3363 / week

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from $481 / night

9

Apartment rental in Oyster Pond with shared pool

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
St Maarten – Caribbean: Luxury Sea View Apartment of 190m² (2045 sq ft), 6 to 8 people in a 5 star hotel, the WESTIN, facing St Barth. Enjoy a prestige luxury residence to rent all year long for a week, even during Christmas holidays. This is the perfect spot to relax …see more

from $350 / night

$2450 / week

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from $350 / 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 $1000 / night

$7000 - $11000 / week

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from $1000 / 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 $1357 / night

$9500 - $19000 / week

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from $1357 / night

1