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  • Vittoria in Simpson Bay by Personal Villas - Elegant, Stunning Ocean Views
    From $1507 per night (USD)

    VRBO

    Vittoria in Simpson Bay by Personal Villas - Elegant, Stunning Ocean Views

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    12

    Summary: VITTORIA, Simpson Bay, St. Maarten In a prime location on the southern coastline of Dutch Sint Maarten, beau ...

    From $1507 per night (USD)

    VRBO

    Details
  • Maho Studio with Runway and Ocean Views - Free Wi-Fi!
    From $93 per night (USD)

    Expedia

    Maho Studio with Runway and Ocean Views - Free Wi-Fi!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to "Flight Deck", a cozy and unique studio apartment overlooking the Princess Juliana International Airport & ru ...

    From $93 per night (USD)

    Expedia

    Details
  • Emerald Pearl Studio in Maho - Full Amenities
    Click For Pricing

    VRBO

    Emerald Pearl Studio in Maho - Full Amenities

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Kick back and relax in this calm, stylish and comfortable studio. Centrally located in the Maho district of St. Maarten. ...

    Click For Pricing

    VRBO

    Details
  • Blue Dove Luxury apartment
    Click For Pricing

    Expedia

    Blue Dove Luxury apartment

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Blue Dove is a lovely three-bedroom condominium located within the exclusive gated beachfront community of Shore Point i ...

    Click For Pricing

    Expedia

    Details
  • Beautiful Allegra Luxury villa
    From $1266 per night (USD)

    VRBO

    Beautiful Allegra Luxury villa

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Villa Allegra is luxury living at its finest, this exquisite 5-bedroom villa situated on the serene shores of the pictur ...

    From $1266 per night (USD)

    VRBO

    Details
  • Farniente (2/4 Rooms)
    From $1210 per night (USD)

    Expedia

    Farniente (2/4 Rooms)

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    *** Only 2 out of 4 bedrooms and 3 bathrooms will be available for your use at this rate. The remaining bedrooms will be ...

    From $1210 per night (USD)

    Expedia

    Details
  • Beautiful Mumbai Luxury villa
    From $972 per night (USD)

    VRBO

    Beautiful Mumbai Luxury villa

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Mumbai's exotic name reflects its exotic location, the private village of Cupecoy's Shore Pointe right on the French/Dut ...

    From $972 per night (USD)

    VRBO

    Details
  • Farniente Luxury villa
    From $1560 per night (USD)

    Expedia

    Farniente Luxury villa

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Villa Farniente on St. Martin is a gorgeous and exceptionally popular villa located at the beautiful Shore Pointe on the ...

    From $1560 per night (USD)

    Expedia

    Details
  • Farniente (3/4 Rooms)
    From $1372 per night (USD)

    VRBO

    Farniente (3/4 Rooms)

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    *** Only 3 out of 4 bedrooms and 4 bathrooms will be available for your use at this rate. The remaining bedrooms will be ...

    From $1372 per night (USD)

    VRBO

    Details
  • Mumbai (2/3 Rooms) Luxury villa
    From $858 per night (USD)

    Expedia

    Mumbai (2/3 Rooms) Luxury villa

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    *** Only 2 out of 3 bedrooms and 2 bathrooms will be available for your use at this rate. The remaining bedrooms will be ...

    From $858 per night (USD)

    Expedia

    Details
  • Sea Esta Luxury apartment
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    VRBO

    Sea Esta Luxury apartment

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    Located within the residential beachfront enclave of Shore Pointe at Cupecoy on Sint Maarten's beautiful Gold Coast, thi ...

    Click For Pricing

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    Details
  • The Great Escape
    From $681 per night (USD)

    Expedia

    The Great Escape

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to The Great Escape, this is a perfect place to come to fully relax and hear the ocean sounds while enjoying the ...

    From $681 per night (USD)

    Expedia

    Details
  • Aqua (3/4 Rooms) Luxury villa
    From $1008 per night (USD)

    VRBO

    Aqua (3/4 Rooms) Luxury villa

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    *** Only 3 out of 4 bedrooms and 4 bathrooms will be available for your use at this rate. The remaining bedrooms will be ...

    From $1008 per night (USD)

    VRBO

    Details
  • Beautiful Aqua Luxury villa
    From $1205 per night (USD)

    Expedia

    Beautiful Aqua Luxury villa

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Construction is taking place nearby and may create some noise issues. Contact a Rental Escapes villa specialist for more ...

    From $1205 per night (USD)

    Expedia

    Details
  • Vittoria Luxury villa
    From $1544 per night (USD)

    VRBO

    Vittoria Luxury villa

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    12

    In a prime location on the southern coastline of Dutch Sint Maarten, beautiful Villa Vittoria sits on the popular white ...

    From $1544 per night (USD)

    VRBO

    Details
  • Off the beaten path on Dawn Beach
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    Expedia

    Off the beaten path on Dawn Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Beautifully decorated condo that is situated right on the French/Dutch border. Fabulous pool with swim up bar. You can ...

    Click For Pricing

    Expedia

    Details
  • Villa Rendezvous, Las Arenas by Fantasia Villas
    From $579 per night (USD)

    VRBO

    Villa Rendezvous, Las Arenas by Fantasia Villas

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    From the moment you set foot inside the luxurious, gated courtyard of Las Arenas in Sint Maarten, you know that this is ...

    From $579 per night (USD)

    VRBO

    Details
  • Villa Tropical Waves by Fantasia Villas
    From $487 per night (USD)

    Expedia

    Villa Tropical Waves by Fantasia Villas

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    A brand new, luxury, hip 2 bedroom, 2.5 bath residence in Porto Cupecoy - just steps to the BEACH! The location within ...

    From $487 per night (USD)

    Expedia

    Details
  • Villa Crystal by Fantasia Villas
    From $717 per night (USD)

    VRBO

    Villa Crystal by Fantasia Villas

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Villa Crystal is a very chic and modern 3 bedroom, 3 1/2 bath private villa located in Red Pond Estates, close to Dawn B ...

    From $717 per night (USD)

    VRBO

    Details
  • Villa Bell'Mare by Fantasia Villas
    From $678 per night (USD)

    Expedia

    Villa Bell'Mare by Fantasia Villas

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Bell'mare is Italian for "beautiful sea" and that will be your view from this wonderful three bedroom, three bath beachf ...

    From $678 per night (USD)

    Expedia

    Details
  • Villa Esperanza by Fantasia Villas
    From $471 per night (USD)

    VRBO

    Villa Esperanza by Fantasia Villas

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Drop your anchor here at the Villa Esperanza atop a beautiful St. Maarten mountain giving you and yours the dramatic and ...

    From $471 per night (USD)

    VRBO

    Details
  • Chef included by Fantasia Villas: Villa Aqua
    From $1256 per night (USD)

    Expedia

    Chef included by Fantasia Villas: Villa Aqua

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    To enhance your stay and help make it a magical one, your private VIP chef is included (excluding menu/ingredients) with ...

    From $1256 per night (USD)

    Expedia

    Details
  • Sea Breeze - Views of Porto Cupecoy - Tennis Court, Pool, Gym
    From $600 per night (USD)

    VRBO

    Sea Breeze - Views of Porto Cupecoy - Tennis Court, Pool, Gym

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Sea Breeze at Porto Cupecoy, Sint Maarten Escape to luxury at Sea Breeze, a stunning 2,750 square foot condo ...

    From $600 per night (USD)

    VRBO

    Details
  • Royal Islander La Plage in St. Maarten, available Jan 29 - Feb 5 for $1500
    Click For Pricing

    Expedia

    Royal Islander La Plage in St. Maarten, available Jan 29 - Feb 5 for $1500

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    La Plage: Overlooking the Caribbean Sea and St. Maarten’s tropical foliage, La Plage is a private resort with fully furn ...

    Click For Pricing

    Expedia

    Details
  • The Great Escape Luxury condo
    From $750 per night (USD)

    VRBO

    The Great Escape Luxury condo

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    The Great Escape, where the name says it all! This spacious unit is in a prime location - directly on the beach! Whate ...

    From $750 per night (USD)

    VRBO

    Details
  • The Great Escape (2/3 Rooms)
    From $589 per night (USD)

    Expedia

    The Great Escape (2/3 Rooms)

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    *** Only 2 out of 3 bedrooms and 2 bathrooms will be available for your use at this rate. The remaining bedrooms will be ...

    From $589 per night (USD)

    Expedia

    Details
  • Moonrise Condo near beaches, concierge service
    From $315 per night (USD)

    VRBO

    Moonrise Condo near beaches, concierge service

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Moonrise, a stunning 2-bedroom condo nestled in the heart of Cupecoy, Sint Maarten, within the prestigious Bl ...

    From $315 per night (USD)

    VRBO

    Details
  • Beautiful 2 bedroom 2.5 bath Beachfront Condo
    From $375 per night (USD)

    Expedia

    Beautiful 2 bedroom 2.5 bath Beachfront Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This is a gorgeous 2 bedroom- 2.5 bath beachfront condo located at The Cliff with beautiful Caribbean Ocean views in St. ...

    From $375 per night (USD)

    Expedia

    Details
  • Beautiful St Maarten Ocean front 3 BR with secluded beach
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    VRBO

    Beautiful St Maarten Ocean front 3 BR with secluded beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Dawn Beach club is a secluded resort on the French boarder. Pool on the beach with swim up bar. MBR & LR include balconi ...

    Click For Pricing

    VRBO

    Details
  • Villa Myles: Beachfront
    From $825 per night (USD)

    Expedia

    Villa Myles: Beachfront

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Villa Myles is a coastal-inspired, modern 3 bedroom, 3.5 bath villa with a gorgeous view of the sunset and Burgeaux Bay ...

    From $825 per night (USD)

    Expedia

    Details
  • Dawn Beach Club 2 Bed…2Bath Villa, With Beach Access & Resort Bar
    From $285 per night (USD)

    VRBO

    Dawn Beach Club 2 Bed…2Bath Villa, With Beach Access & Resort Bar

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Dawn Beach Club 2 Bedroom Villa with Beach Access in a Gated Community with 24/7h Security offers accommodation with a ...

    From $285 per night (USD)

    VRBO

    Details
  • Stay on the Beach in Saint Maarten!
    From $532 per night (USD)

    Expedia

    Stay on the Beach in Saint Maarten!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    The Pristine Dawn Beach Club offers affordable 5 star luxury accommodations in a 3 bedroom (8 person) suite for a total ...

    From $532 per night (USD)

    Expedia

    Details
  • Sea Esta - Lovely Oasis within beachfront Shore Pointe
    From $742 per night (USD)

    VRBO

    Sea Esta - Lovely Oasis within beachfront Shore Pointe

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Booking this property includes airport pickup, concierge service, and housekeeping. Located within the resident ...

    From $742 per night (USD)

    VRBO

    Details
  • Farniente - Exceptional villa located in Shore Pointe
    From $1462 per night (USD)

    Expedia

    Farniente - Exceptional villa located in Shore Pointe

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Keep it simple Villa Farniente on St. Martin is a gorgeous and exceptionally popular villa located at the beaut ...

    From $1462 per night (USD)

    Expedia

    Details
  • Blue Dove - Lovely Modern Villa with Private Pool
    From $628 per night (USD)

    VRBO

    Blue Dove - Lovely Modern Villa with Private Pool

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Blue Dove is a lovely 3 bedroom condominium located within the exclusive gated beachfront community of Shore Po ...

    From $628 per night (USD)

    VRBO

    Details
  • Condo in Porto Cupecoy, close to beach, free concierge & housekeeping
    From $440 per night (USD)

    Expedia

    Condo in Porto Cupecoy, close to beach, free concierge & housekeeping

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Marina 360 is in one of the prime locations at the new Porto Cupecoy Marina Resort, sitting at the entrance to the Marin ...

    From $440 per night (USD)

    Expedia

    Details
  • OASIS deluxe 1 bedroom apartment with Pool & Generator
    From $182 per night (USD)

    VRBO

    OASIS deluxe 1 bedroom apartment with Pool & Generator

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    3

    This gorgeous apartment is located in the best spot of the island. You have everything right at your doorstep. Of cours ...

    From $182 per night (USD)

    VRBO

    Details
  • Oasis Simpson Bay 1 Bedroom -1.5 Bath apartment - GENERATOR
    From $176 per night (USD)

    Expedia

    Oasis Simpson Bay 1 Bedroom -1.5 Bath apartment - GENERATOR

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    3

    This large apartment is located in the best spot of the island! Being in the middle of Simpson Bay, you have everything ...

    From $176 per night (USD)

    Expedia

    Details
  • Steps to beautiful Simpson Bay Beach! Oceanfront newly furnished 2-bedroom condo
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    VRBO

    Steps to beautiful Simpson Bay Beach! Oceanfront newly furnished 2-bedroom condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy our beautiful ocean front condo that is only steps to the lovely Simpson Bay Beach. Relax on the private terrace o ...

    Click For Pricing

    VRBO

    Details
  • La terrasse de Maho Saint Martin
    From $251 per night (USD)

    Expedia

    La terrasse de Maho Saint Martin

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located in the heart of the liveliest district of the island day and night, the apartment offers very large living space ...

    From $251 per night (USD)

    Expedia

    Details
  • Ocean view with concierge, housekeeping, and airport pickup
    From $1113 per night (USD)

    VRBO

    Ocean view with concierge, housekeeping, and airport pickup

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Each booking includes an assigned concierge, housekeeping, & airport pickup. Pure architectural lines and pristine whit ...

    From $1113 per night (USD)

    VRBO

    Details
  • Nice  ocean view  , direct beach access , and beautiful near by beaches and golf
    From $181 per night (USD)

    Expedia

    Nice ocean view , direct beach access , and beautiful near by beaches and golf

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Nice spacious studio, 68 m2 with terrace , beautiful garden and ocean view , located at SBC , Cupecoy discrete . Swimmin ...

    From $181 per night (USD)

    Expedia

    Details
  • Ocean Pearl Luxury villa
    From $852 per night (USD)

    VRBO

    Ocean Pearl Luxury villa

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    14

    Location, location, location: You’ll never get tired of the ocean views, all the way to St. Barths and Anguilla, or on l ...

    From $852 per night (USD)

    VRBO

    Details
  • Ocean Pearl (4\/6 Rooms)
    From $641 per night (USD)

    VRBO

    Ocean Pearl (4\/6 Rooms)

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    *** Only 4 out of 6 bedrooms and 4 bathrooms will be available for your use at this rate. The remaining bedrooms will be ...

    From $641 per night (USD)

    VRBO

    Details
  • Ocean Pearl (5\/6 Rooms)
    From $722 per night (USD)

    VRBO

    Ocean Pearl (5\/6 Rooms)

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    *** Only 5 out of 6 bedrooms and 4 bathrooms will be available for your use at this rate. The remaining bedrooms will be ...

    From $722 per night (USD)

    VRBO

    Details
  • Newly Renovated 3 bedroom 3.5 bath on Simpson Bay Beach 🏝
    From $398 per night (USD)

    Expedia

    Newly Renovated 3 bedroom 3.5 bath on Simpson Bay Beach 🏝

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Spacious 3 bedroom 3.5 bath condo located on Simpson Bay Beach. Newly renovated with beautiful ocean views from all 3 ou ...

    From $398 per night (USD)

    Expedia

    Details
  • Bella Mare at La Siesta
    From $384 per night (USD)

    VRBO

    Bella Mare at La Siesta

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Bella Mare @ La Siesta is a new, luxurious ground floor 2-bedroom/2 bath villa offering direct beach access to the sand ...

    From $384 per night (USD)

    VRBO

    Details
  • Ocean Front Top Floor
    From $400 per night (USD)

    Expedia

    Ocean Front Top Floor

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Top Floor with a private balcony overlooking spectacular view of the Atlantic Ocean and the island of St. Barths. Enjoy ...

    From $400 per night (USD)

    Expedia

    Details
  • Standard Double Room
    From $63 per night (USD)

    VRBO

    Standard Double Room

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Blue Sky Residence is located in Middle Region with just 6-minute drive to Oyster Pond beach, 6 minutes to the capital P ...

    From $63 per night (USD)

    VRBO

    Details
  • Spacious Simpsonbay Yachtclub apartment with pool
    From $196 per night (USD)

    Expedia

    Spacious Simpsonbay Yachtclub apartment with pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Imagine having breakfast on this balcony overlooking the 25meter pool surrounded by swaying palm trees! This apartment i ...

    From $196 per night (USD)

    Expedia

    Details
  • Dawn Beach Club Villa. With Beach access.
    From $305 per night (USD)

    VRBO

    Dawn Beach Club Villa. With Beach access.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Dawn Beach Club 2 Bedroom Villa with Beach Access in a Gated Community with 24/7h Security offers accommodation with a l ...

    From $305 per night (USD)

    VRBO

    Details
  • Amalia in Guana Bay by Personal Villas - Stunning Oceanfront with Heated Pool
    From $3419 per night (USD)

    Expedia

    Amalia in Guana Bay by Personal Villas - Stunning Oceanfront with Heated Pool

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    12

    Summary: VILLA AMALIA 6BR, Guana Bay, St Maarten Villa Amalia is an ideal vacation spot for people looking for privac ...

    From $3419 per night (USD)

    Expedia

    Details
  • Sublime Stay - Royal Retreats at Maho Beach
    From $130 per night (USD)

    VRBO

    Sublime Stay - Royal Retreats at Maho Beach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Stunning Maho Beach 1 bedroom condo located within Royal Islander's La Terrasse building that sleeps 4. Enjoy s ...

    From $130 per night (USD)

    VRBO

    Details
  • Optimum Oasis - Royal Retreats at Maho Beach Studio
    From $111 per night (USD)

    Expedia

    Optimum Oasis - Royal Retreats at Maho Beach Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Stunning Maho Beach studio condo located within Royal Islander's La Terrasse building that sleeps 2. Enjoy stun ...

    From $111 per night (USD)

    Expedia

    Details
  • Heavenly Haven - Royal Retreats at Maho Beach
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    Expedia

    Heavenly Haven - Royal Retreats at Maho Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Stunning Maho Beach 1 bedroom condo located within Royal Islander's La Terrasse building that sleeps 4. Enjoy s ...

    Click For Pricing

    Expedia

    Details
  • DREAM 5-Star Premier BEACHFRONT 3 Bedroom Villa + Private Pool
    From $867 per night (USD)

    Expedia

    DREAM 5-Star Premier BEACHFRONT 3 Bedroom Villa + Private Pool

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    Beautiful sunrise and gorgeous sunsets while you enjoy your drinks and hear the ocean sounds. Beautifully appointed and ...

    From $867 per night (USD)

    Expedia

    Details
  • Beach Secrets 4BR in Beacon Hill by Personal Villas - Modern Oceanfront Villa
    From $1315 per night (USD)

    VRBO

    Beach Secrets 4BR in Beacon Hill by Personal Villas - Modern Oceanfront Villa

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Summary: VILLA BEACH SECRETS 4BR, Beacon Hill, St. Maarten Villa Beach Secrets is a modern 4-bedroom house located in ...

    From $1315 per night (USD)

    VRBO

    Details
  • Beautiful 3 BR Condo w/ oceanfront view, pool bar and beach
    From $553 per night (USD)

    Expedia

    Beautiful 3 BR Condo w/ oceanfront view, pool bar and beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Saturday-to-Saturday rental. Dates of stay must be requested 14 days prior to see if unit is available before booking Sl ...

    From $553 per night (USD)

    Expedia

    Details
  • Beautiful walk out condo to pools and beaches,, 10% discount to 1st customer
    From $294 per night (USD)

    VRBO

    Beautiful walk out condo to pools and beaches,, 10% discount to 1st customer

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Phenomenal ocean views, sunsets,convenient walking distance to restaurants, beaches,stores,nite life.this magnificent co ...

    From $294 per night (USD)

    VRBO

    Details
  • Villa Caribbean Pearl by Fantasia Villas
    From $408 per night (USD)

    Expedia

    Villa Caribbean Pearl by Fantasia Villas

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    CARIBBEAN PEARL - named for the gem that it is - is in a perfect location within the exciting Porto Cupecoy Marina Resor ...

    From $408 per night (USD)

    Expedia

    Details
  • Villa Beach House Younes by Fantasia Villas
    From $573 per night (USD)

    VRBO

    Villa Beach House Younes by Fantasia Villas

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    The Beach House Younes is truly one of a kind. A very special place. Its location is perfect being directly on the ocea ...

    From $573 per night (USD)

    VRBO

    Details
  • Agua Azul by Fantasia Villas
    From $417 per night (USD)

    Expedia

    Agua Azul by Fantasia Villas

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Agua Azul is a luxurious 2 bedroom, 2.5 bathroom condo with breathtaking views of the Caribbean Sea, Simpson Bay and Por ...

    From $417 per night (USD)

    Expedia

    Details
  • Oceanfront Villa Tara
    From $717 per night (USD)

    VRBO

    Oceanfront Villa Tara

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Built on a cliff, directly above the tropical blue sea. The rental Villa Tara offers vacationers a ‘one of a kind’ exper ...

    From $717 per night (USD)

    VRBO

    Details
  • Oceanfront Caribbean Blue
    From $919 per night (USD)

    Expedia

    Oceanfront Caribbean Blue

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Caribbean Blue is a beach front villa in Pelican Key. With five bedrooms and five and an half bathrooms, it is a perfect ...

    From $919 per night (USD)

    Expedia

    Details
  • Beachfront villa with concierge service, housekeeping, airport pickup, pool
    From $895 per night (USD)

    VRBO

    Beachfront villa with concierge service, housekeeping, airport pickup, pool

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Mumbai's exotic name reflects its exotic location, the private village of Cupecoy's Shore Pointe right on the French/Dut ...

    From $895 per night (USD)

    VRBO

    Details
  • NEWLY BUILT VILLA FRANGIPANI 2nd Row Beachfront
    From $1796 per night (USD)

    Expedia

    NEWLY BUILT VILLA FRANGIPANI 2nd Row Beachfront

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Gated Villa Fangy in Pelican Key Estate is definitely a special home, surrounded by a mature tropical garden of flowers ...

    From $1796 per night (USD)

    Expedia

    Details
  • Westin Dawn Beach Club_Luxury Apartment_Outstanding Service_Amazing Place_Enjoy!
    From $369 per night (USD)

    VRBO

    Westin Dawn Beach Club_Luxury Apartment_Outstanding Service_Amazing Place_Enjoy!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Dawn Beach Club stretches along the shore of Dawn Beach on the island's Dutch side. Guests will enjoy accommodations wit ...

    From $369 per night (USD)

    VRBO

    Details
  • Beachfront Villa w/ pool, concierge service and airport transfers by SXMSIR
    From $1447 per night (USD)

    Expedia

    Beachfront Villa w/ pool, concierge service and airport transfers by SXMSIR

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    12

    In a prime location on the southern coastline of Dutch Sint Maarten, beautiful Villa Vittoria sits on the popular white ...

    From $1447 per night (USD)

    Expedia

    Details
  • FLASH SALE June-Oct. 2025!! Tropical Gem! Ocean+Beach+Garden Views + MANY PERKS!
    Click For Pricing

    VRBO

    FLASH SALE June-Oct. 2025!! Tropical Gem! Ocean+Beach+Garden Views + MANY PERKS!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    WEEKLY AND MONTHLY DISCOUNTS OFFERED, DEPENDING ON IF A DISCOUNT SALE IS CURRENTLY ALREADY BEING OFFERED, OR NOT. IF YOU ...

    Click For Pricing

    VRBO

    Details
  • Ocean Front Studio Week 3 & 4 Annually
    From $396 per night (USD)

    Expedia

    Ocean Front Studio Week 3 & 4 Annually

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Deluxe Ocean front studio facing Simpson Bay; just a few steps from the beach. The Flamingo Beach Resort is ALL NEW in 2 ...

    From $396 per night (USD)

    Expedia

    Details
  • Villa Zircon in Pelican Key awaits you - GENERATOR
    From $685 per night (USD)

    VRBO

    Villa Zircon in Pelican Key awaits you - GENERATOR

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Newly remodeled 4 bedroom - 4 bath villa in the heart of Pelican. This luxurious villa has a beautiful private pool with ...

    From $685 per night (USD)

    VRBO

    Details
  • Villa Domila-Luxury 3Bed & 3Bath with private pool-Free airport transfer-Central
    From $373 per night (USD)

    Expedia

    Villa Domila-Luxury 3Bed & 3Bath with private pool-Free airport transfer-Central

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    7

    Villa Domila is gorgeous and spacious with a modern Caribbean look. She is perfectly located in the private community of ...

    From $373 per night (USD)

    Expedia

    Details
  • 6 bedroom villa in a relaxed and very pleasant setting
    From $1212 per night (USD)

    VRBO

    6 bedroom villa in a relaxed and very pleasant setting

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    The Space: Enjoy your vacation with style in this comfortable villa in a relaxed and very pleasant settings. This family ...

    From $1212 per night (USD)

    VRBO

    Details
  • Beautiful 5 Bedroom Villa with Panoramic Views!
    Click For Pricing

    Expedia

    Beautiful 5 Bedroom Villa with Panoramic Views!

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    PLEASE NOTE THAT ALL RATES ARE BASED ON 2 GUESTS PER BEDROOM. VILLA MARY RENTS AS A 3, 5 OR 5 BEDROOM VILLA. IF YOU WOUL ...

    Click For Pricing

    Expedia

    Details
  • The Cliff Luxury Condo, Oceanfront, infinity pool 3 Shades of blue!
    From $314 per night (USD)

    VRBO

    The Cliff Luxury Condo, Oceanfront, infinity pool 3 Shades of blue!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Eden. Luxury surrounds you with an Infinity pool just outside your living room. The best of everything inside ...

    From $314 per night (USD)

    VRBO

    Details
  • Chic, Tranquil, Modern Apartment
    Click For Pricing

    Expedia

    Chic, Tranquil, Modern Apartment

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    3

    You won’t want to go back home after staying in this beautiful 2BR apartment. Sea-Renity is designed to cater to long-st ...

    Click For Pricing

    Expedia

    Details
  • A Caribbean Dream Vacation w/ Breathtaking Views\n
    From $215 per night (USD)

    VRBO

    A Caribbean Dream Vacation w/ Breathtaking Views\n

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    A relaxing spot with amazing views from every direction. It's also close to night life and wonderful restaurants. Bet ...

    From $215 per night (USD)

    VRBO

    Details
  • Cross the street and you at the beach! Spacious 3 bedroom/ 2bath vacation spot..
    From $266 per night (USD)

    Expedia

    Cross the street and you at the beach! Spacious 3 bedroom/ 2bath vacation spot..

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This is a 3 bed, 2 bath, living room, dining room, entertainment room. This property is located in the capital of the Du ...

    From $266 per night (USD)

    Expedia

    Details
  • St. Maarten, Pelican Key Near The Beach, 2 Bedrooms, Roomy And Comfortable.
    Click For Pricing

    VRBO

    St. Maarten, Pelican Key Near The Beach, 2 Bedrooms, Roomy And Comfortable.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    1300 sq foot, pleasant and comfortable. The unit has central A/C as well as individual AC units for each bedroom. Fully ...

    Click For Pricing

    VRBO

    Details
  • Villa Sea Joli-captivating panoramic island views
    From $304 per night (USD)

    Expedia

    Villa Sea Joli-captivating panoramic island views

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    A piece of Paradise Overlooking the other Caribbean Island, St. Barth, Saba and St. Kitts. Forget your worries and troub ...

    From $304 per night (USD)

    Expedia

    Details
  • Beautiful 6 bedroom Villa on the popular white sandy beach of Simpson bay
    From $1589 per night (USD)

    VRBO

    Beautiful 6 bedroom Villa on the popular white sandy beach of Simpson bay

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    12

    Summary: This elegant 2 level villa offers 6 bedrooms and beautiful Italianate architectural features. Wrought iron gate ...

    From $1589 per night (USD)

    VRBO

    Details
  • Villa Mila: The Pearl of Sint Maarten - #1 Rated villa in Oyster Bay
    From $1095 per night (USD)

    Expedia

    Villa Mila: The Pearl of Sint Maarten - #1 Rated villa in Oyster Bay

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    12

    Experience refined luxury at the newly transformed Villa Mila Estate – an avant-garde masterpiece with 5 lavish beds and ...

    From $1095 per night (USD)

    Expedia

    Details
  • The CLIFF - Luxury Beachfront Resort - Full Amenities --> Spa - Restaurant - etc
    From $259 per night (USD)

    VRBO

    The CLIFF - Luxury Beachfront Resort - Full Amenities --> Spa - Restaurant - etc

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    The Cliff is proud to present its great pools: The infinity pool Overlooking the Ocean perfect for a sunset moment, the ...

    From $259 per night (USD)

    VRBO

    Details
  • Walking distance to everything on Simpson bay area Restaurants, Beach, Nite Life
    From $309 per night (USD)

    Expedia

    Walking distance to everything on Simpson bay area Restaurants, Beach, Nite Life

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Spacious 2 Bedroom Apt on first floor, beautifully appointed, gated community 24/7 security, community pool right outsid ...

    From $309 per night (USD)

    Expedia

    Details
  • Villa Bonjour water front villa next to Maho
    From $865 per night (USD)

    VRBO

    Villa Bonjour water front villa next to Maho

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    <p>A short distance from sailing, scuba diving, and more, this beach villa lets you experience it all. Burgeaux Bay Beac ...

    From $865 per night (USD)

    VRBO

    Details
  • Exclusive 5 Star Luxury Villa at Westin Hotel Dawn Beach Club Resort & Spa
    Click For Pricing

    Expedia

    Exclusive 5 Star Luxury Villa at Westin Hotel Dawn Beach Club Resort & Spa

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Set on a white sand beach, this upscale resort dotted with palm trees is 9 km from the historic Fort Amsterdam and 14 km ...

    Click For Pricing

    Expedia

    Details
  • Luxurious villa ON THE BEACH in Guana Bay
    Click For Pricing

    VRBO

    Luxurious villa ON THE BEACH in Guana Bay

    Bedrooms:
    9
    Bathrooms:
    10
    Sleeps:
    4

    Super villa, spacious, fully furnished and in excellent condition (20 people max). This villa has a huge beachfront, 2 b ...

    Click For Pricing

    VRBO

    Details
  • Modern cozy studio apartment
    Click For Pricing

    Expedia

    Modern cozy studio apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    You have access to the entire apartment along with your private balcony. The unit is an open-concept studio consisting o ...

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    Expedia

    Details
  • The Westin Dawn Beach Resort & Spa, St. Maarten
    Click For Pricing

    VRBO

    The Westin Dawn Beach Resort & Spa, St. Maarten

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The Westin Dawn Beach Resort & & Spa, St. Maarten sits on the edge of a private beach and offers spacious rooms and suit ...

    Click For Pricing

    VRBO

    Details
  • Luxurious apartment with amazing sea view
    From $684 per night (USD)

    Expedia

    Luxurious apartment with amazing sea view

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    2

    This is a spacious 2 bedroom apartment which includes a master suite with a breathtaking sea view, hotel quality king si ...

    From $684 per night (USD)

    Expedia

    Details
  • LUXURY apartment with breathtaking sea view
    From $684 per night (USD)

    VRBO

    LUXURY apartment with breathtaking sea view

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    3

    <p>Located in Lowlands, this 2-bedroom, 2-bathroom apartment lets you experience it all. Fans of nature and the outdoors ...

    From $684 per night (USD)

    VRBO

    Details
  • Deluxe private studio
    Click For Pricing

    Expedia

    Deluxe private studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    A nice deluxe private studio at Cupecoy touristic district . Nice garden and ocean view. Direct access to a beautiful sa ...

    Click For Pricing

    Expedia

    Details
  • Great view of Sunset
    Click For Pricing

    VRBO

    Great view of Sunset

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Spacious one bedroom overlooking Simpson Bay sleeps six with two Murphy beds. Full kitchen with dishwasher and balcony ...

    Click For Pricing

    VRBO

    Details
  • Beautiful location, steps away from St. Maarten's Dawn Beach
    Click For Pricing

    Expedia

    Beautiful location, steps away from St. Maarten's Dawn Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Each three-bedroom residence is appointed for luxury and comfort. Amenities include flat-screen TVs, spacious dining are ...

    Click For Pricing

    Expedia

    Details
  • Porto Cupecoy, 66 Rhine Rd, 25-3A, Sin
    Click For Pricing

    VRBO

    Porto Cupecoy, 66 Rhine Rd, 25-3A, Sin

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Sunrise, sunset. Enjoy unsurpassed views of both from the three large, covered terraces of your luxury Penthouse on the ...

    Click For Pricing

    VRBO

    Details
  • DISCOUNTED Royal Islander Club 2 Bdrm Suite, Sleeps 6, Wifi, Pool, - MAHO BEACH!
    From $201 per night (USD)

    Expedia

    DISCOUNTED Royal Islander Club 2 Bdrm Suite, Sleeps 6, Wifi, Pool, - MAHO BEACH!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to your Home away from Home! Staying at this beautifully decorated 2 bedroom suite is guaranteed to enhance yo ...

    From $201 per night (USD)

    Expedia

    Details
  • Luxury Luxury Luxury Villa living right on the beach ...
    From $1291 per night (USD)

    VRBO

    Luxury Luxury Luxury Villa living right on the beach ...

    Bedrooms:
    1
    Bathrooms:
    5
    Sleeps:
    8

    A completely new 2500 sq. ft. Villa with 2 levels, 3 bedrooms, 3 baths, and 2 common rooms for rent 7-day rental to incl ...

    From $1291 per night (USD)

    VRBO

    Details
  • Prestige Studio - Pool & Gym
    From $124 per night (USD)

    Expedia

    Prestige Studio - Pool & Gym

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    <p>Close to the sea, a golf course, and more, this smoke-free apartment brings it all within reach. There's convenient o ...

    From $124 per night (USD)

    Expedia

    Details
  • Rare Gem: 3-Bedroom with Direct Pool Access & Peloton Bike!
    From $494 per night (USD)

    VRBO

    Rare Gem: 3-Bedroom with Direct Pool Access & Peloton Bike!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Escape to Rainbow Beach Club resort on Sint Maarten Island for an idyllic island getaway. Enjoy a private beach, two poo ...

    From $494 per night (USD)

    VRBO

    Details
  • Picturesque 1 bedroom apartment
    From $178 per night (USD)

    Expedia

    Picturesque 1 bedroom apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Picturesque brand new one bedroom apartment , that is centrally located to Philipsburg and Simpsonbay, with magnificen ...

    From $178 per night (USD)

    Expedia

    Details