50 Best Vacation Rentals in Philipsburg - Holiday Lettings - Cabins

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5,114 Vacation rentals

(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

$2,352 / week

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Responds fast!
avg. 3 hours 34 minutes

from $336 / 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 $213 / night

$1,487 / week

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from $213 / 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 $346 / night

$2,416 / week

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from $346 / 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 $444 / night

$3,098 / week

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from $444 / 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 $531 / night

$3,717 / week

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from $531 / 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 $200 / night

$1,400 - $3,500 / week

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from $200 / night

(1) Excellent 

27

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Villa Seascapes is a wonderful 4 bedroom/4 bathroom villa located in the gated community of Dawn Beach 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 space, r …see more

from $515 / night

$3,605 - $6,006 / week

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from $515 / night

13

Vacation villa in Philipsburg

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Paradijs 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. This 3 bedroom, 3 bathroom villa is nestled in the prestigious Oyster Pond hills …see more

from $215 / night

$1,505 - $3,500 / week

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from $215 / night

(25) 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

8

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
Rise to the magnificent scenery of the Caribbean's emerald waters on this tropical estate set in the midst of one of the most prestigious areas in the Caribbean, Oyster Pond. The four bedroom, four and a half bathroom main house of this deluxe estate is tastefully appoi …see more

from $300 / night

$2,100 - $8,806 / week

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from $300 / 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 59 minutes

from $75 / night

(2) Very Good 

25

Vacation villa rental

Sint Maarten / Philipsburg

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This wonderful 5-bedroom, 5-bath villa overlooks beautiful Dawn Beach on the island of St. Maarten. The villa is a short walk to the beach and is located in the gated community of Dawn Beach Estates. Dawn Beach Estates is a ten minute drive from Phillipsburg, the capita …see more

from $372 / night

$2,604 - $9,002 / week

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from $372 / 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 $412 / night

$2,884 - $6,300 / week

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from $412 / 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

(8) Very Good 

20

Vacation villa with swimming pool in Philipsburg

Sint Maarten / Philipsburg

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Additional amenities: Beach Towels, Concierge Service, Full Kitchen, JetSki (Personal Watercraft) …see more

from $1,000 / night

$7,000 / week

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from $1,000 / night

11

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
Villa Bougainvillea, located in Dawn Beach Estates, is a very stylish villa with fabulous views overlooking Dawn Beach & St. Barths. Every attention to detail has been made in this new deluxe villa. The property is surrounded by natural rock walls. The 3 story villa off …see more

from $643 / night

$4,501 - $12,005 / week

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from $643 / night

25

Vacation home with swimming pool in Philipsburg

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Additional amenities: Beach Towels, Concierge Service, Full Kitchen …see more

from $543 / night

$3,800 - $7,500 / week

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from $543 / night

25

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

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
Additional amenities: Beach Towels, Full Kitchen, JetSki (Personal Watercraft) …see more

from $700 / night

$4,900 - $6,500 / week

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from $700 / night

25

Philipsburg Vacation villa accommodation

Sint Maarten / Philipsburg

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
Villa Sky Blue - Luxurious ocean view villa where you will see all the hues of the blue sky and ocean... A wonderful, 5 bedroom/5.5 bathroom villa located in the exclusive gated community of Dawn Beach Estates on St. Maarten. The villa offers extraordinary views of the …see more

from $856 / night

$5,992 - $12,005 / week

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from $856 / 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

23

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
This brand new villa, "Villa Bliss", is a lovely villa located Cliffside with direct waterfront views located in a gated community in Dawn Beach Estates. The villa offers fabulous direct views of the Ocean and the neighboring island of St. Barths. The villa offers moder …see more

from $479 / night

$3,353 - $7,504 / week

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from $479 / 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 $365 / night

$2,555 - $4,956 / week

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from $365 / 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
  • Suitable for children age 5+
  • 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 $372 / night

$2,604 - $6,503 / week

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from $372 / night

29

Vacation villa rental

Sint Maarten / Philipsburg

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • 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

4

Apartment rental in Philipsburg

Sint Maarten / Philipsburg

1 2 6 nights min

  • 1 bedroom
  • Sleeps 2
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Located in Beacon Hill, this apartment is ideal for a travelling tourist, for a students on intern ship, or for an ex pat on a job . Find yourself near the KLM plane take off, and the night life of Simpson-bay bars and restaurant. Not to mention living in a quiet area n …see more

from $69 / night

$477 / week

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from $69 / 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 34 minutes

from $200 / night

(2) Very Good 

25

Vacation villa with shared pool in Philipsburg

Sint Maarten / Philipsburg

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Gianna is a lovely waterfront villa overlooking Dawn Beach, one of the island's finest. The home offers exceptional views of the sea and nearby Dawn Beach. The villa is a split level style and the interiors offer tiled floors and are furnished with rattan and hand made …see more

from $395 / night

$2,765 - $5,950 / week

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from $395 / 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

29

Vacation villa in Philipsburg

Sint Maarten / Philipsburg

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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

(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 $379 / night

$2,653 - $6,006 / week

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from $379 / 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 $372 / night

$2,604 - $6,006 / week

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from $372 / 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

18

Vacation villa in Philipsburg

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
This 3 Bedroom Villa can be rented as a 2 Bedroom Villa at a special rate! El Sueño means "The Dream" in Spanish which is what this villa is all about! This beautiful three bedroom, three bathroom villa is nestled in Little Bay, Philipsburg offering amazing views of th …see more

from $643 / night

$4,501 / week

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from $643 / night

37

Philipsburg Vacation apartment rental

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Additional amenities: Beach Towels, Full Kitchen, JetSki (Personal Watercraft) …see more

from $900 / night

$6,300 / week

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from $900 / night

(2) Excellent 

24

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
Nestled into the hillside of Little Bay in Philipsburg, Villa En’Sea boasts breathtaking views of Great Bay Harbor, Philipsburg, St. Barths, St. Kitts, Nevis and Saba. What was once a family home and a Governor’s Residence, Villa En’Sea has recently been transformed int …see more

from $743 / night

$5,200 / week

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from $743 / 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

(7) Very Good 

30

Vacation villa with swimming pool in Philipsburg

Sint Maarten / Philipsburg

6 12 5 nights min

  • 6 bedrooms
  • Sleeps 12
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This impressive 6 bedroom, 6 bathroom luxurious villa is located in Red Pod Estates and offers hard wood floors throughout and has been furnished with contemporary designer furnishing providing all necessary amenities to please our guests. The main part of the villa off …see more

from $857 / night

$6,000 / week

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from $857 / night

18

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Andrea is a French style home located in an exclusive gated community on St. Maarten. You will enjoy ever present trade winds and view of 5 other islands. Each bedroom has its own bath and AC surrounding the unique pool. Dining and living room are open to the pool …see more

from $457 / night

$3,500 - $6,125 / week

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from $457 / 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 windows and do …see more

from $395 / night

$2,765 - $5,950 / week

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from $395 / night