50 Best Vacation Rentals in Philipsburg - Holiday Lettings - Cabins

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168 Vacation rentals

(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

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

(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

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 $480 / night

$3363 / week

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from $480 / night

25

Vacation villa in Philipsburg

Sint Maarten / Philipsburg

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • Child friendly
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 design …see more

from $1000 / night

$7000 - $13503 / week

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from $1000 / 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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from $200 / night

23

Vacation villa with shared pool in Philipsburg

Sint Maarten / Philipsburg

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #********. Our Service Guarantee ensures you the best villa experience. This 5 Bedroom Villa can be rented as a 2, 3 or 4 Be …see more

from $600 / night

$4200 / week

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from $600 / night

19

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

3 6 Min stay varies

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

$2954 - $4956 / week

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from $422 / night

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

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 $236 / night

$1652 - $3500 / week

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from $236 / night

24

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
Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #********. Our Service Guarantee ensures you the best villa experience. This 6 Bedroom Villa can be rented as a 3, 4 or 5 Be …see more

from $787 / night

$5503 / week

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from $787 / night

(5) Excellent 

28

Philipsburg Vacation apartment rental

Sint Maarten / Philipsburg

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning
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 $49 / night

$343 - $595 / week

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from $49 / night

(2) Very Good 

31

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 $500 / night

$3500 - $6300 / week

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from $500 / night

8

Vacation villa in Philipsburg

Sint Maarten / Philipsburg

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
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 $643 / night

$4501 - $8806 / week

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from $643 / night

24

Vacation villa with shared pool in Philipsburg

Sint Maarten / Philipsburg

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #********. Our Service Guarantee ensures you the best villa experience. This 6 Bedroom Villa can be rented as a 3, 4 or 5 Be …see more

from $715 / night

$5005 / week

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from $715 / 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
7th Night Free! Apr 15 - Dec 15, 2017 & Jan 7 - Dec 15, 2018Restrictions Apply!Rates may vary depending on # of bedrooms rented. Please see rate table or call for details.Bell'Mare is the only home in the gated community of Dawn Beach Estates that has direct beach acces …see more

from $500 / night

$3500 - $6300 / week

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from $500 / 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 $429 / night

$3003 - $6006 / week

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from $429 / night

(2) Excellent 

13

Vacation apartment in Philipsburg

Sint Maarten / Philipsburg

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
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 $86 / night

$595 / week

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from $86 / night

5

Vacation apartment 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
Facing the ocean at Dawn beach in St-Martin, the unit has a fully-equipped kitchen, first-class furnishings, amenities and housekeeping. As part of the Westin five-star resort site, you'll have access to all the resort amenities - pool, beach, bars and restaurants. …see more

from $429 / night

$3000 / week

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from $429 / night

13

Vacation apartment with shared pool, golf nearby in Philipsburg

Sint Maarten / Philipsburg

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $300 / night

$2100 - $2800 / week

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from $300 / 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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from $89 / night

13

Vacation villa in Philipsburg

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
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 $286 / night

$2002 - $3500 / week

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from $286 / night

25

Vacation villa rental

Sint Maarten / Philipsburg

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #********. Our Service Guarantee ensures you the best villa experience. This 5 Bedroom Villa can be rented as a 3 or 4 Bedro …see more

from $743 / night

$5201 / week

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from $743 / night

(2) Excellent 

18

Vacation apartment with shared pool in Philipsburg

Sint Maarten / Philipsburg

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
DISCOUNTS APPLY TO NEW BOOKINGS ONLY!20% Off excludindg holiday season -5 night mimum Embark on a journey to Coral Beach Club and find yourself home... Relax, Rejuvenate and More at Condo Sea Star #24 located at Coral Beach Club. The property has been designed for peopl …see more

from $240 / night

$1680 - $2800 / week

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from $240 / 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 $558 / night

$3906 - $6503 / week

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from $558 / night

25

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
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.En’Sea boasts breathtaking views of Great Bay Harbor, Philipsburg, St. Barths, St. Kitts, Nevis and Saba. It is nest …see more

from $743 / night

$5200 - $10000 / week

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from $743 / night

23

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Villa Prana, a non-smoking villa, is a deluxe and spacious 4 bedroom villa located in Dawn Beach Estate with a very short walk to Dawn Beach. The villa offers 3 equal size bedrooms on the top level with ensuite bathrooms, which open directly onto the pool deck.The maste …see more

from $572 / night

$4004 - $8505 / week

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from $572 / night

(1) Excellent 

25

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

3 6 Min stay varies

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

$3353 - $6006 / week

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from $479 / night

20

Philipsburg Vacation apartment rental

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
15% Discount! Apr 15 - Dec 15, 2017 For 5 - 6 nights... 25% Discount! Apr 15 - Dec 15, 2017 For 7 nights or more... Escape to your home in Paradise…The Lighthouse is ideal for those looking for luxury, privacy and relaxation and at the same time have access to all the a …see more

from $450 / night

$3150 - $6300 / week

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from $450 / night

28

Villa rental in Philipsburg with swimming pool

Sint Maarten / Philipsburg

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • 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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from $643 / night

25

Philipsburg Vacation home rental

Sint Maarten / Philipsburg

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • 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.Villa Star is a wonderful 3 bedroom/3.5 bathroom villa lo …see more

from $394 / night

$2750 - $6000 / week

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from $394 / night

(1) Very Good 

19

Villa rental in Philipsburg

Sint Maarten / Philipsburg

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
This impressive large villa with 5 bedrooms and 5 1/2 baths sits high atop the hillside overlooking Oyster Pond, Dutch St. Maarten. It is designed in a Mediterranean style elegance that can be matched by few. All 4 bedrooms have a private bathroom and air-conditioning. …see more

from $429 / night

$3003 - $12005 / week

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from $429 / night

(7) Very Good 

30

Vacation villa with swimming pool in Philipsburg

Sint Maarten / Philipsburg

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • 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

$6000 / week

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from $857 / night

39

Vacation home 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
7th Night Free! Travel Apr 15 - Dec 15, 2017You’ll find everything you expect from a relaxed Caribbean vacation in Villa Summer Time. Step into a vacation rental that’s located in the upscale, secluded and gated villa estate of Tamarind Hill. Here you’ll find peace, bea …see more

from $429 / night

$3000 - $10000 / week

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from $429 / 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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from $457 / night

(1) Excellent 

27

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 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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from $515 / 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

$4900 - $8505 / week

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from $700 / 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 $643 / night

$4501 - $9002 / week

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from $643 / night

23

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
Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #********. Our Service Guarantee ensures you the best villa experience. This 5 Bedroom Villa can be rented as a 2, 3 or 4 Be …see more

from $457 / night

$3199 / week

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from $457 / night

12

Vacation villa in Philipsburg

Sint Maarten / Philipsburg

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
This is the Oyster Bay Beach Resort located on the Dutch side (but right at the French border) in Sint Maarten (the smallest land mass shared by two countries). It sits on Dawn Beach and has a spectacular infinity pool. You are minutes away from Downtown Philipsburg, f …see more

from $315 / night

$2200 / week

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from $315 / night

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