50 Best Vacation Rentals in Philipsburg - Holiday Lettings - Cabins

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164 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

$2352 / week

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from $336 / 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 $327 / night

$2287 / week

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Responds fast!
avg. 3 hours 39 minutes

from $327 / 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 $202 / night

$1408 / week

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from $202 / night

26

Philipsburg Vacation apartment rental

Sint Maarten / Philipsburg

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
The Westin Dawn Beach Resort & Spa is located 25 minutes from the international airport Princes Juliana and just 10 minutes by air from St Barthelemy, Anguilla and Saba. Nestled among the lush hills, the Westin Dawn Beach Resort & Spa overlooks kilometers of white sandy …see more

from $106 / night

$845 / week

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from $106 / 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 $502 / night

$3519 / week

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from $502 / night

24

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 $420 / night

$2932 / week

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from $420 / 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

$1400 - $2450 / week

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Responds fast!
avg. 2 hours 28 minutes

from $200 / night

(9) Excellent 

20

Vacation home with shared pool in Philipsburg

Sint Maarten / Philipsburg

10 20 5 nights min

  • 10 bedrooms
  • Sleeps 20
  • 5 nights min
  • Swimming pool
  • Ask about children
Villa Casa Sunshine is a spectacular ocean front luxury estate for rent in Guana Bay. Escape from the ordinary on your next trip to St. Maarten! Treat yourself and get away from it all at a true world class property! You will be rewarded by a wonderful relaxing, peacefu …see more

from $1192 / night

$8350 - $9850 / week

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from $1192 / night

(1) Excellent 

21

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Suitable for children age 5+
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

$2604 - $6503 / week

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from $372 / 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

$3605 - $6006 / week

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Responds fast!
avg. 3 hours 15 minutes

from $515 / night

(25) Excellent 

23

Vacation apartment in Philipsburg

Sint Maarten / Philipsburg

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • 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 $225 / night

$1575 / week

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from $225 / night

23

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
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

$2604 - $6006 / week

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from $372 / night

(2) Excellent 

28

Vacation apartment in Philipsburg

Sint Maarten / Philipsburg

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 $59 / night

$415 - $525 / week

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Responds fast!
avg. 3 hours 32 minutes

from $59 / 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
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 $183 / night

$1275 - $1975 / week

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from $183 / 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
7th Night Free! Apr 15 - Dec 15, 2017Restrictions Apply!Rates may vary depending on # of bedrooms rented. Please see rate table or call for details.This property may accept holiday stays of less than 14 nights.Caribella is located on the Dutch side of the island, close …see more

from $372 / night

$2600 - $6501 / week

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from $372 / 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 $350 / night

$2450 / week

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from $350 / night

(5) Excellent 

50

Condo rental in Philipsburg with shared pool

Sint Maarten / Philipsburg

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • 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 - $973 / week

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Responds fast!
avg. 3 hours 32 minutes

from $89 / night

(1) Very Good 

18

Vacation villa in Philipsburg

Sint Maarten / Philipsburg

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
A beautiful Caribbean villa located in a tranquil community of Geo Villas in Guana Bay on the Dutch side of St. Maarten. Meters from the Caribbean sea with a beautiful, quiet beach and a view on the island of St. Barth. Only 10 minutes drive from Philipsburg, the capita …see more

from $130 / night

$950 - $1995 / week

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from $130 / 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

$3000 / week

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from $429 / night

(2) Very Good 

25

Vacation villa rental

Sint Maarten / Philipsburg

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
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

$2604 - $9002 / week

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from $372 / 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

$2500 - $6501 / week

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from $400 / night

(5) Very Good 

27

Villa rental in Philipsburg with swimming pool

Sint Maarten / Philipsburg

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This property may accept holiday stays of less than 14 nights. Rates may vary depending on # of bedrooms rented. Please see rate table or call for details.Beach House Gianna is a lovely waterfront villa overlooking Dawn Beach, one of the island's finest beaches. The hom …see more

from $383 / night

$2675 - $5950 / week

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from $383 / night

16

Vacation apartment rental

Sint Maarten / Philipsburg

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
One full week duration rental of a Luxury suite of 1650 sqmt with 3 BR 2 BA. Confort occupancy 6 persons Maximum 8 pers. Main parental BR with ensuite BA & dressing. Additional sofa bed in living. All equiped american kitchen. Dining room. 4 Sat TV. WiFi access. Washin …see more

from $286 / night

$2000 - $6501 / week

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Responds fast!
avg. 3 hours 5 minutes

from $286 / night

19

Vacation villa in Philipsburg

Sint Maarten / Philipsburg

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
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

$1400 - $3500 / week

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from $200 / 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

$3500 - $6125 / week

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Responds fast!
avg. 55 minutes

from $457 / night

(3) Excellent 

22

Philipsburg Vacation home rental

Sint Maarten / Philipsburg

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Ask about children
This exquisite location, Villa Dolfijn, provides the ultimate St. Maarten Island experience. With the ocean breezes, sunshine and the spectacular views, you are set for the vacation of a lifetime. This villa itself has a luxurious feel throughout. Truly one of the most …see more

from $314 / night

$2200 - $3150 / week

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from $314 / night

11

Vacation villa in Philipsburg

Sint Maarten / Philipsburg

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
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

$4501 - $12005 / week

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from $643 / night

28

Villa rental in Philipsburg

Sint Maarten / Philipsburg

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
This wonderful 6-bedroom, 6-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 $643 / night

$4501 - $9002 / week

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Responds fast!
avg. 3 hours 15 minutes

from $643 / night

(2) Very Good 

38

Vacation villa in Philipsburg

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
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 $400 / night

$2800 - $6300 / week

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from $400 / 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

$5992 - $12005 / week

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Responds fast!
avg. 3 hours 15 minutes

from $856 / night

21

Villa rental in Philipsburg

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

$2800 - $6300 / week

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Responds fast!
avg. 3 hours 15 minutes

from $400 / night

25

Vacation villa rental

Sint Maarten / Philipsburg

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Villa Sky Blue - Luxurious ocean view villa where you will see all the hues of the blue sky and ocean... A wonderful, 4 bedroom/4.5 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 $1036 / night

$7250 / week

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from $1036 / night

42

Philipsburg Vacation condo rental

Sint Maarten / Philipsburg

1 6 7 nights min

  • 1 bedroom
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Sint Maarten Sea Palace: 1-Br with Full Kitchen and 2 Bathrooms, Sleeps 6. Fixed week rental, check in / changeover: Saturdays only. Studio (Sleeps 2) & 2-Bedrooms (Sleeps 8) units are or may be also available - please inquire about rates and availability. Sleeping A …see more

from $143 / night

$995 - $1275 / week

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Responds fast!
avg. 2 hours 48 minutes

from $143 / night

23

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
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

$3353 - $7504 / week

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from $479 / night

20

Vacation villa 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
Rates may vary depending on # of bedrooms rented. Please see rate table or call for details.On the cliffs of Dawn Beach Estates, Sea Watch views St. Barths and the clear, remarkable turquoise Atlantic Ocean. The views of the sea and sounds of its surf are unsurpassed he …see more

from $372 / night

$2600 - $4750 / week

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from $372 / 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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Responds fast!
avg. 3 hours 12 minutes

from $60 / 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

$5000 - $6600 / week

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Responds fast!
avg. 3 hours 15 minutes

from $715 / night

41

Philipsburg Vacation home rental

Sint Maarten / Philipsburg

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Gorgeous 2 bedroom, 2.5 baths luxurious townhouse located in Coral Beach Club, Dutch St Maarten. Are you looking for the perfect, private accommodations while you explore and enjoy the island of St. Maarten/St. Martin? Want to be steps from a beautiful beach? Love …see more

from $495 / night

$3465 - $5775 / week

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Responds fast!
avg. 3 hours 15 minutes

from $495 / night

(2) Very Good 

22

Vacation villa 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
Caribbean Summer Promotion!Booking window Aug 1 till Aug 31 2017Travel Window Aug 1 till Dec 14 2017 (Thanksgiving week excluded)5-6 nights stay additional 10% discount on the best available rate7 nights stay additional 15% discount on the best available rate7th Night F …see more

from $400 / night

$2800 - $6300 / week

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from $400 / night

(1) Excellent 

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
2017 Promotional DiscountsTravel Apr 17 – Dec 16... 3 or 4 nights... 20% offTravel Apr 17 – Dec 16... 5 + nights... 20% offTravel Sept 1 – Oct 31... 5 + nights... 30% off Travel Nov 1 – Dec 16... 5 or 6 nights... 20% offTravel Nov 1 – Dec 16... 7 + nights... 25% off Wel …see more

from $845 / night

$5915 - $9765 / week

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from $845 / night