50 Best Vacation Rentals in Philipsburg - Holiday Lettings - Cabins

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123 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 $311 / night

$2175 / week

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Responds fast!
avg. 3 hours 39 minutes

from $311 / 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 $192 / night

$1339 / week

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from $192 / 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 $478 / night

$3346 / week

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from $478 / 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
  • 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 $50 / night

$343 - $595 / week

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Responds fast!
avg. 3 hours 32 minutes

from $50 / 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 12 minutes

from $200 / 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

(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 $60 / night

$415 - $525 / week

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Responds fast!
avg. 3 hours 32 minutes

from $60 / 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
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

20

Vacation villa rental

Sint Maarten / Philipsburg

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Beach House Gianna is a lovely waterfront villa overlooking Dawn Beach, one of the island's finest beaches. The home offers exceptional views of the sea and nearby Dawn Beach. Completely renovated, including but not limited to all new Tekalu windows and doors, rolling s …see more

from $450 / night

$3150 - $5775 / week

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from $450 / 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

(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 $858 / night

$6000 / week

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from $858 / night

14

Vacation villa with swimming pool in Philipsburg

Sint Maarten / Philipsburg

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
7th Night Free! - Apr 15 - Dec 15, 2017Saturday to Saturday Bookings Only!Rates may vary depending on # of bedrooms rented. Please see rate table or call for details.Valhalla boasts one of the most expansive ocean views on the island with 270 degree views from Oyster Po …see more

from $486 / night

$3401 - $7500 / week

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from $486 / night

(2) Excellent 

24

Philipsburg Vacation villa rental

Sint Maarten / Philipsburg

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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

$5200 / week

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from $743 / night

17

Philipsburg Vacation apartment rental

Sint Maarten / Philipsburg

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
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

$1675 - $2075 / week

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from $239 / night

(2)  

25

Vacation apartment rental

Sint Maarten / Philipsburg

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Ask about children
Enjoy the privacy and tranquility that sets Cupecoy Beach Club apart from the hustle and bustle of other St. Maarten resorts. Situated on top of the beautiful Cupecoy cliffs, these condos offer spectacular views of Saba and the turquoise Caribbean Sea. Ocean breezes alo …see more

from $199 / night

$1395 - $1696 / week

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from $199 / 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

33

Philipsburg Vacation home rental

Sint Maarten / Philipsburg

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ask about children
Villa Rosa is a located in the Dawn Beach area, which is one of the most beautiful places to stay on the island of St Maarten. The Atlantic Ocean is right out your window, along with a view of St. Barth’s Island. Enjoy the ocean breezes and as you refresh and revitalize …see more

from $407 / night

$2850 - $3551 / week

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from $407 / night

(2) Good 

35

Philipsburg Vacation home rental

Sint Maarten / Philipsburg

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Ask about children
Villa Blanco is a beautiful vacation rental located in the exciting area of Dawn Beach. The master suite has an open shower and bathtub. There is a laundry room with a guest bathroom and if needed, a futon bed for an extra guest. The living room, dining area, full kitch …see more

from $393 / night

$2950 - $3551 / week

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from $393 / 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

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 $373 / night

$2600 - $4750 / week

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from $373 / 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

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 $358 / night

$2500 - $10000 / week

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from $358 / night

24

Home rental in Philipsburg with swimming pool

Sint Maarten / Philipsburg

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
7th Night Free! - Apr 15 - Dec 15, 2017Restrictions Apply! 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 o …see more

from $608 / night

$4255 - $12000 / week

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from $608 / 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

25

Vacation home with swimming pool in Philipsburg

Sint Maarten / Philipsburg

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • 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 rateValid on al …see more

from $286 / night

$2000 - $8500 / week

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from $286 / 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

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 $400 / night

$2800 / week

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from $400 / 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 53 minutes

from $60 / night

16

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
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 rate Embark on …see more

from $635 / night

$4445 - $7175 / week

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from $635 / night

(2) Very Good 

18

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

$4000 / week

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from $572 / night

(1) Excellent 

21

Vacation apartment rental

Sint Maarten / Philipsburg

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Car not necessary
  • Air conditioning
Set into the Sint Maarten country hillsides my home is in walking distance just across the Great Salt Pond and from sweeping ocean sands. I am a 7 minute scenic drive (15 minutes walk) to the quaint streets of Philipsburg, Capital City. And I am also an 8 minute scenic …see more

from $70 / night

$440 / week

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Responds fast!
avg. 3 hours 53 minutes

from $70 / 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

(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

(8) Very Good 

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
Valid on all NEW BOOKINGS ONLY 15% Discount on bookings of 3 - 6 nights - Summer/Fall Season 2017 25% Discount on bookings of 7 nights or more - Summer/Fall Season 2017 El Sueño means "The Dream" in Spanish which is what this villa is all about! This beautiful three bed …see more

from $400 / night

$2800 - $7000 / week

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from $400 / 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 $373 / night

$2600 - $6500 / week

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from $373 / 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 $393 / night

$2750 - $6000 / week

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from $393 / 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 $182 / night

$1275 - $1975 / week

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from $182 / night

23

Vacation villa with swimming 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

(3) Very Good 

31

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. "The Starfish Villa" provides breathtaking ocean views and commands one of the largest living (2400 sqft indoor) and outdoor terrace and pool (1500 sqft terrace and 525 sqft poo …see more

from $550 / night

$3850 - $12145 / week

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from $550 / night

1