50 Best Vacation Rentals in Philipsburg - Holiday Lettings - Cabins

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4,366 Vacation rentals

(1) Excellent 

23

Villa rental in Philipsburg with shared pool

Sint Maarten / Philipsburg

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $250 / night

$1,750 / week

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Responds fast!
avg. 3 hours 6 minutes

from $250 / 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 $212 / night

$1,482 / week

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from $212 / 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 $344 / night

$2,408 / week

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from $344 / night

33

Vacation villa rental

Sint Maarten / Philipsburg

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 0.3 mi
  • Swimming pool
  • Child friendly
Beautiful new villa in St Martin Dutch side of 200 sqm with 3 air conditioned bedrooms - 3 Bathrooms - 3 toilets - Living room with open kitchen - terrace with pool maintained 2 times a week - 6 chairs and a bioclimatic pergola 2 spaces Parking Maximum 6 people This vil …see more

from $442 / night

$3,087 / week

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from $442 / night

19

Vacation apartment in Philipsburg

Sint Maarten / Philipsburg

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 2 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. Supplied linen (sheets, duvet, towels...) Large swimming …see more

from $529 / night

$3,705 / week

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from $529 / night

25

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Sea La Vie is a wonderful, new 4 bedroom/5 bathroom villa located in the gated community of Red Pond Estates on St. Maarten. The villa offers breathtaking views of the ocean and the neighboring island of St. Barths in the distance. The villa’s two-level spac …see more

from $700 / night

$4,900 - $8,505 / week

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from $700 / night

24

Vacation apartment in Philipsburg

Sint Maarten / Philipsburg

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden
Guests can arrange to stay in my studio which is equipped for 2 persons. My studio is equipped with: - Security windows and doors - 4 poster French Queen size bed - Kitchen with fridge, microwave, coffee & tea maker, and kitchen utensils - Closet, iron board & iron, h …see more

from $60 / night

$400 / week

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from $60 / night

(1) Excellent 

25

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
On Island Time is a wonderful new, stylish, modern villa located in the gated Oyster Pond Hillside. The villa is very unique in its architecture and offers stunning views of the ocean, surrounding hillsides and Orient Bay. The villa is set on two levels. The villa is de …see more

from $479 / night

$3,353 - $6,006 / week

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from $479 / night

18

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Please inquire about lower rates offered for less than full occupancy. Caribella is located on the Dutch side of the island, close to the French border. Experience these two unique worlds as they blend together, offering the best of both diverse cultures. Nestled in the …see more

from $700 / night

$4,900 - $6,500 / week

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from $700 / night

(9) Excellent 

19

Apartment rental in Philipsburg with shared pool

Sint Maarten / Philipsburg

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Welcome to the Atlantica Beach Club. Our Condo, Unit 15 B, is the perfect place to experience the amazing Dawn Beach area and the beautiful island of St. Maarten. The fantastic panoramic views will take your breath away, along with the tropical island breezes. This exqu …see more

from $182 / night

$1,275 - $1,975 / week

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from $182 / night

15

Philipsburg Vacation apartment rental

Sint Maarten / Philipsburg

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Atlantica Beach Club Condo - Unit 4, is one of the newer St Maarten Condos on the island and is located in a secured subdivision. This is a premier location, just a few minutes from a great assortment of fine restaurants and beachfront attractions. This beautiful Condo …see more

from $239 / night

$1,675 - $2,075 / week

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from $239 / night

20

Vacation apartment with shared pool in Philipsburg

Sint Maarten / Philipsburg

3 10 7 nights min

  • 3 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The arrival at the Dawn Beach Club are on Saturday only. Beautiful condo for rent in the Carabbean on the beautiful island of St. Maarten/St Martin , located in Oyster Pond, on the site of the Westin Hotel (Dawn Beach Club) the condo can accommodate up to 8 peop …see more

from $429 / night

$3,000 / week

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from $429 / night

(3) Very Good 

31

Philipsburg Vacation apartment rental

Sint Maarten / Philipsburg

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
NO AVAILABILITY FOR 2016. AVAILABLE 2017 Newly Completed 3 LARGE bedroom Condo is within the Dawn Beach Club on Dawn Beach in St. Maarten, Dutch side (for week 7 February break, all other weeks aren't guaranteed any particular building or floor, depends on availabilit …see more

from $572 / night

$4,000 / week

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from $572 / night

(5) Excellent 

50

Condo rental in Philipsburg with shared pool

Sint Maarten / Philipsburg

1 3 6 nights min

  • 1 bedroom
  • Sleeps 3
  • 6 nights min
  • Swimming pool
  • Air conditioning
Sugar Bird town house is your tropical home away from home nestled in a quiet corner of Pointe Blanche Bay. Perfectly suited for those interested in a longer stay, this extremely large, bright and airy one bedroom town home is well appointed with every detail right down …see more

from $89 / night

$595 - $763 / week

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Responds fast!
avg. 3 hours 51 minutes

from $89 / night

(6) Excellent 

28

Philipsburg Vacation apartment rental

Sint Maarten / Philipsburg

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Pet friendly
Surf's Up is a newly renovated immaculate & cozy apartment and is located right on Pointe Blanche Bay. Walk right out to the beach and search for treasures or watch the sunrise over St Barth's. Easy maintenance and coastal style is what Surf's Up is all about ! Time t …see more

from $89 / night

$595 / week

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Responds fast!
avg. 3 hours 51 minutes

from $89 / night

(1) Excellent 

21

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Air conditioning
Villa Caribella is located on the Dutch side of the island, close to the French border. Experience these two unique worlds as they blend together, offering the best of both diverse cultures. Nestled in the prestigious and elegant Tamarind Hill Estates, a 24-hour gated c …see more

from $558 / night

$3,906 - $6,503 / week

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from $558 / night

(2) Excellent 

28

Vacation apartment in Philipsburg

Sint Maarten / Philipsburg

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Air conditioning
Located in the quiet seaside neighbourhood of Pointe Blanche, this charming, comfortable, cozy, ocean view efficiency apartment is perfect for those looking for bright, airy, clean and affordable accommodations. Affectionately called "the treefrog apartment" the high v …see more

from $75 / night

$525 / week

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Responds fast!
avg. 3 hours 51 minutes

from $75 / night

19

Vacation villa in Philipsburg

Sint Maarten / Philipsburg

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Moondance is located on the Dutch side of the islands within a short three-minute drive of Dawn Beach. Set hillside, it overlooks the ocean and the beach and offers wonderful views of the neighboring island of St. Barth in the distance. Newly constructed, the home offer …see more

from $236 / night

$1,652 - $3,500 / week

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from $236 / night

(18) Excellent 

44

Vacation villa with shared pool in Philipsburg

Sint Maarten / Philipsburg

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This two bedroom, two and a half bath villa is situated right on Great Bay Beach in a small complex of twelve individual villas with a lovely beach front swimming pool and breath-taking ocean views. This gated complex with on-site management is the perfect place to rela …see more

from $200 / night

$1,400 - $2,450 / week

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Responds fast!
avg. 2 hours 33 minutes

from $200 / night

39

Vacation home in Philipsburg

Sint Maarten / Philipsburg

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Please inquire about lower rates offered for less than full occupancy...Le Rocher is a private oasis within one of the exclusive gated communities of Terres Basses, on the French side of St-Martin. High on a hill, the setting, with its manicured grounds and view, is spe …see more

from $1,572 / night

$11,000 - $21,000 / week

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from $1,572 / night

(26) Excellent 

23

Vacation apartment in Philipsburg

Sint Maarten / Philipsburg

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
Luxury vacation rental getaway for 2-4 guests. Also perfect for honeymoons and anniversaries. Private infinity pool for your exclusive use. Breathtaking panoramic view overlooking Great Bay, Philipsburg and the Caribbean Sea, spectacular by day and by night. Conveni …see more

from $200 / night

$1,575 / week

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from $200 / night

13

Vacation apartment with shared pool, golf nearby in Philipsburg

Sint Maarten / Philipsburg

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
A lovely 3-Bedroom, 2-Bathroom apartment, easily sleeping 8 guests, 1800sq ft, perfect for families. This is a luxurious residence, steps from the famous Dawn Beach (perfect sunrises) and only 4 miles from the island's capital Philipsburg. You will have spectacular ocea …see more

from $800 / night

$5,600 / week

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from $800 / night

17

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The Arches is Oyster Pond at its finest. The villa sits high on the hillside with beautiful views of Oyster Pond and the surrounding islands in the Atlantic Ocean. The Arches is immaculately appointed with beautiful, sturdy, Caribbean wicker furniture throughout. With t …see more

from $422 / night

$2,954 - $4,956 / week

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from $422 / night

(1) Excellent 

29

Villa rental in Philipsburg with shared pool

Sint Maarten / Philipsburg

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Windsong is a spectacular, 4 Bedroom, 4 Bathroom villa located in the gated community of Red Pond Estates on St. Maarten. The villa is perched on the hillside with stunning views of the ocean and St. Barths in the distance. The villa’s multi-level space, rooms, ou …see more

from $679 / night

$4,753 - $8,001 / week

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from $679 / night

15

Vacation villa in Philipsburg

Sint Maarten / Philipsburg

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
Villa Gianna on St Martin is a gorgeous waterfront beach house overlooking and thus offering exceptional views of the beautiful Dawn Beach, one of St Martin's loveliest beaches.  Freshly renovated, it gives off a great tropical vibe with all the new Tekalu wind …see more

from $495 / night

$2,765 - $5,950 / week

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from $495 / night

24

Vacation villa rental

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Crystal is an amazing 3 bedroom, 3 1/2 bath private villa located in Red Pond Estates (Gibbs Bay)- Tamarind Hill area, close to Dawn Beach on the eastern side of St. Maarten. The villa has fantastic views of the Atlantic Ocean and of the neighboring French Island …see more

from $500 / night

$3,500 - $4,500 / week

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from $500 / night

48

Vacation apartment in Philipsburg

Sint Maarten / Philipsburg

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Air conditioning
OCEAN'S on Great Bay Beach has the best of both worlds! We are on Front Street and the beach! Ocean's is a 5 story, privately owned, building. Once you are there, 'you belong'. The units are fully loaded and very suitable for people who like to cook. The trade winds blo …see more

from $300 / night

$2,000 / week

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Responds fast!
avg. 1 hour 53 minutes

from $300 / night

25

Vacation villa in Philipsburg

Sint Maarten / Philipsburg

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Alizee is an impressive 7 bedroom, 7 bathroom luxurious villa is located in Guana Bay, within walking distance of Guana Bay Beach. The spectacular views, the back-drop of Sky, sea and the villa is absolutely stunning! The villa has been furnished with contemporary desi …see more

from $1,000 / night

$7,000 - $13,503 / week

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from $1,000 / night

21

Villa rental in Philipsburg with shared pool

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Bell'mare is Italian for "beautiful sea" and that will be your view from this wonderful three bedroom, three bath beachfront villa. The home sits overlooking Dawn beach, one of the nicest beaches on the island. Bell'mare is the only home in the gated community of Dawn B …see more

from $400 / night

$2,800 - $6,300 / week

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from $400 / night

29

Vacation villa rental

Sint Maarten / Philipsburg

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Alizée is an impressive 7 bedroom, 7 bathroom luxurious villa is located in Guana Bay, within walking distance of Guana Bay Beach. The spectacular views, the back-drop of Sky, sea and the villa is absolutely stunning… The villa has been furnished with contemporary …see more

from $1,000 / night

$7,000 - $13,503 / week

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from $1,000 / night

29

Vacation villa with shared pool in Philipsburg

Sint Maarten / Philipsburg

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Stunning French Creole villa for luxury rental located in the exclusive area of Guana Bay, Dutch Sint Maarten. Situated on an acre of tropical gardens, Villa Mahogany is an elegantly appointed residence providing the ultimate in relaxation. Enjoy ocean views and b …see more

from $715 / night

$5,000 - $6,600 / week

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from $715 / night

32

Vacation villa with swimming pool in Philipsburg

Sint Maarten / Philipsburg

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Please inquire about lower rates offered for less than full occupancy.En’Sea boasts breathtaking views of Great Bay Harbor, Philipsburg, St. Barths, St. Kitts, Nevis and Saba. It is nestled into the hillside of Little Bay in Philipsburg. What was once a family home and …see more

from $929 / night

$6,500 - $10,000 / week

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from $929 / night

30

Villa rental in Philipsburg with swimming pool

Sint Maarten / Philipsburg

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
With Panoramic views of the turquoise sea, which can be enjoyed from all angles, this villa is located in a quiet residential neighborhood within minutes to great beaches, restaurants, supermarkets and the shopping capital of the Island Philipsburg. The infinity pool c …see more

from $412 / night

$2,884 / week

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from $412 / night

38

Philipsburg Vacation apartment rental

Sint Maarten / Philipsburg

2 2 7 nights min

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
This is a Studio 1 bathroom Suite with partial kitchen that sleeps 2. All inclusive is optional and available directly through the resort for $85 per adult per day and $63 per child per day, prices subject to change. Saturday or Sunday check in is required for a minim …see more

from $159 / night

$1,113 / week

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Responds fast!
avg. 1 hour 28 minutes

from $159 / night

20

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Casa Linda, an Italian-designed villa, is located on the Dutch side of the island, close to the French border. Experience these two unique worlds as they blend together, offering the best of both diverse cultures. Wake up to the sunrise overlooking St. Barths, the Atlan …see more

from $429 / night

$3,003 - $6,006 / week

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from $429 / night

25

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Ask about pets
Villa Sea La Vie is located in the gated community of Red Pond Estates on the highly sought after tropical paradise of St Martin. Offering stunning views of the turquoise ocean and the gorgeous island of St Barts in the distance, this villa is the ultimate mixture of co …see more

from $700 / night

$2,800 - $8,500 / week

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from $700 / night

13

Vacation condo in Philipsburg

Sint Maarten / Philipsburg

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
The Dawn Beach Club, in Oyster Pond on the Dutch side of the island, offers a luxurious Caribbean experience with 3 restaurants, a spa, casino, pool with swim up bar, fitness center, and a location right on the white sand beach. Unit sleeps 8, faces the ocean with a bal …see more

from $536 / night

$3,750 / week

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from $536 / night

(1) Very Good 

37

Vacation villa with indoor pool in Philipsburg

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Villa Crystal is a modern villa located on Sint Maarten, in the Caribbean Islands. From the out side terrace of the villa an incredible view of St. Barth Island can be seen. Every room of the villa enters onto the terrace and faces the breath taking view. The morning …see more

from $400 / night

$2,500 - $4,500 / week

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from $400 / night

(2) Very Good 

18

Vacation villa with shared pool in Philipsburg

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Bell'mare is Italian for "beautiful sea" and that will be your view from this wonderful three bedroom, three bath villa. The home sits overlooking Dawn beach, one of the nicest beaches on the island. Bell'mare is the only home in the gated community of Dawn Beach Estate …see more

from $515 / night

$3,605 - $6,300 / week

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from $515 / night

28

Vacation apartment with shared pool in Philipsburg

Sint Maarten / Philipsburg

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
VILLA#9 on the east 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 tranquilllity. On the ground floor: terrace on the beach with wooden floor, a lanai to enj …see more

from $200 / night

$1,400 - $2,450 / week

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from $200 / night