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  • Breathtaking view of Saint Barth - 8 people
    From $1162 per night (USD)

    VRBO

    Breathtaking view of Saint Barth - 8 people

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    <p>Located in Oyster Pond, this welcoming villa brings it all within your reach. With the property's convenient onsite p ...

    From $1162 per night (USD)

    VRBO

    Details
  • Welcome to the Dutch side of St. Maarten. 3 bedroom unforgettable ocean view.
    From $660 per night (USD)

    Expedia

    Welcome to the Dutch side of St. Maarten. 3 bedroom unforgettable ocean view.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to the epitome of luxury living in the heart of Pelican Key, St. Maarten. This exceptional 2900 square feet cond ...

    From $660 per night (USD)

    Expedia

    Details
  • Pelican Pearl 1 bedr - 2bath apt
    From $175 per night (USD)

    VRBO

    Pelican Pearl 1 bedr - 2bath apt

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    3

    This apartment is located in an excellent spot. Being in a residential neighborhood while being at walking distance from ...

    From $175 per night (USD)

    VRBO

    Details
  • Luxurious Hidden Pearl - Private Pool
    From $255 per night (USD)

    Expedia

    Luxurious Hidden Pearl - Private Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This luxurious studio has been remodeled in 2025 and is ready for guests seeking a stylish studio with pool. The room ha ...

    From $255 per night (USD)

    Expedia

    Details
  •  Simpson Bay 3-bedroom condo in Gated community. Waterfront views
    From $606 per night (USD)

    VRBO

    Simpson Bay 3-bedroom condo in Gated community. Waterfront views

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Nestled in Simpson Bay, this delightful condo boasts 3 gorgeous bedrooms with king beds and 4 tranquil bathrooms equippe ...

    From $606 per night (USD)

    VRBO

    Details
  • NEW LISTING: Hidden Pearl Luxurious Villa - Ocean View
    From $2740 per night (USD)

    Expedia

    NEW LISTING: Hidden Pearl Luxurious Villa - Ocean View

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Located in the quiet Pelican area, Hidden Pearl Villa is a lovely home bursting with amenities to make your stay in Sint ...

    From $2740 per night (USD)

    Expedia

    Details
  • Panoramic Ocean View Flat: St Maarten
    From $266 per night (USD)

    VRBO

    Panoramic Ocean View Flat: St Maarten

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Bring the whole family to this great place with lots of room for fun. Indulge in a romantic escape at our 2-bedroom pent ...

    From $266 per night (USD)

    VRBO

    Details
  • Hilton Flamingo Beach St. Maarten Cozy suite in lovely Simpson Bay with WiFi,
    From $573 per night (USD)

    Expedia

    Hilton Flamingo Beach St. Maarten Cozy suite in lovely Simpson Bay with WiFi,

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Get ready to relax in this 1-bedroom hotel suite in Simpson Bay. This charming property features a cozy king bed and a c ...

    From $573 per night (USD)

    Expedia

    Details
  • Beautiful 3 bedroom condo with private pool in St Maarten
    From $904 per night (USD)

    VRBO

    Beautiful 3 bedroom condo with private pool in St Maarten

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This 3 bedroom condo will give you the perfect holiday. It has a private swimming in front of the boats. The view is ama ...

    From $904 per night (USD)

    VRBO

    Details
  • B204 - Amazing 1 Bedroom with terrace
    From $291 per night (USD)

    Expedia

    B204 - Amazing 1 Bedroom with terrace

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    <p>Welcome to Appt B-204 at The Hills Residence in Simpson Bay, Sint Maarten! This charming 1-bedroom apartment provides ...

    From $291 per night (USD)

    Expedia

    Details
  • B231 - Serene Chic 2 Bedroom
    From $364 per night (USD)

    VRBO

    B231 - Serene Chic 2 Bedroom

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    <p><strong>Welcome to Apartment B231 - Serene Chic 2 Bedroom at The Hills Residence in Simpson Bay, Sint Maarten!</stron ...

    From $364 per night (USD)

    VRBO

    Details
  • 2-bedroom apartment, sea view terrace in marvelous Point Blanche, 2 BA, AC, WIFI
    From $290 per night (USD)

    Expedia

    2-bedroom apartment, sea view terrace in marvelous Point Blanche, 2 BA, AC, WIFI

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Get ready to relax in this 2-bedroom apartment terrace facing the Ocean and offering wonderful sunrise and views facing ...

    From $290 per night (USD)

    Expedia

    Details
  • Outstanding apartment at Dawn Beach Club, JW Marriott Resort, Beach and Spa
    From $468 per night (USD)

    VRBO

    Outstanding apartment at Dawn Beach Club, JW Marriott Resort, Beach and Spa

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Hi and welcome! Enjoy an unforgettable stay at our apartment in the stunning Dawn Beach Club, now part of the newly ope ...

    From $468 per night (USD)

    VRBO

    Details
  • Villa Solandra – 3BR Oceanfront Sunset w/ Pool
    From $885 per night (USD)

    Expedia

    Villa Solandra – 3BR Oceanfront Sunset w/ Pool

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Welcome to Villa Solandra, a western facing ocean front luxury 3BR/3BA home with a private pool in Indigo Bay. ...

    From $885 per night (USD)

    Expedia

    Details
  • Cozy 1-BR Balcony apartment in brilliant Maho Beach AC, pool and fitness club.
    From $296 per night (USD)

    VRBO

    Cozy 1-BR Balcony apartment in brilliant Maho Beach AC, pool and fitness club.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Discover the beauty of Maho Beach from this charming 1-bedroom apartment. The soothing king bed in the bedroom and the m ...

    From $296 per night (USD)

    VRBO

    Details
  •  Pelican Key Studio-pool, near the beach. The best area on Dutch side!
    From $155 per night (USD)

    Expedia

    Pelican Key Studio-pool, near the beach. The best area on Dutch side!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Pelican Key is the most desirable areas on the island and a close walk to all of the island amenities on the “Strip “. A ...

    From $155 per night (USD)

    Expedia

    Details
  • Escape to Tranquility 2-bedroom modern home at waterfront with fast Internet.
    From $205 per night (USD)

    VRBO

    Escape to Tranquility 2-bedroom modern home at waterfront with fast Internet.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This cozy and modern home is ideally located just a stone's throw away from the cruise ship harbor, also perfectly sit ...

    From $205 per night (USD)

    VRBO

    Details
  • 3 Sea Vistas, Palm Beach Condos, Simpson Bay Beach
    From $394 per night (USD)

    VRBO

    3 Sea Vistas, Palm Beach Condos, Simpson Bay Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    The condo, located in Palm Beach Apartment complex is a beautiful 2-level, 2-bedroom and 2.5 bathroom condo right on gor ...

    From $394 per night (USD)

    VRBO

    Details
  • Paradise by the Sea
    From $359 per night (USD)

    VRBO

    Paradise by the Sea

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to your Paradise by the Sea. This stunning two-level beachfront apartment blends laid-back island charm with ups ...

    From $359 per night (USD)

    VRBO

    Details
  • The Pearl of Cupecoy
    From $579 per night (USD)

    VRBO

    The Pearl of Cupecoy

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Located in the private community of Cupecoy Beach Club, this 2 story oceanfront, 3 bedrooms, 3.5 bathrooms condominium o ...

    From $579 per night (USD)

    VRBO

    Details
  • C304 – 1 bedroom apartment with terrace
    From $291 per night (USD)

    VRBO

    C304 – 1 bedroom apartment with terrace

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    <p><strong>Charming one-bedroom apartment with terrace in Simpson Bay</strong></p> <p> Welcome to Unit <strong>C-304</s ...

    From $291 per night (USD)

    VRBO

    Details
  • C316 - Lagoon view with balcony
    From $290 per night (USD)

    Expedia

    C316 - Lagoon view with balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    <p><strong>Welcome to Apartment C-316 at The Hills Residence Vacation Rentals!</strong></p> <p>Located on the <strong>f ...

    From $290 per night (USD)

    Expedia

    Details
  • C326 - Beautiful Apartment With Balcony
    From $291 per night (USD)

    VRBO

    C326 - Beautiful Apartment With Balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    <p><strong>Welcome to Apartment C-326 at The Hills Residence Vacation Rentals!</strong></p> <p>Located on the <strong>s ...

    From $291 per night (USD)

    VRBO

    Details
  • C355 - Top Floor with Lagoon View
    From $254 per night (USD)

    Expedia

    C355 - Top Floor with Lagoon View

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Welcome to Apartment C-355 at The Hills Residence in Simpson Bay! Step into this stunning top-floor apartment, featurin ...

    From $254 per night (USD)

    Expedia

    Details
  • C347 – Stylish 2 Bedroom
    From $436 per night (USD)

    VRBO

    C347 – Stylish 2 Bedroom

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    <p><strong></strong>Welcome to <strong>C-347</strong>, a beautifully designed <strong>2-bedroom, 2-bathroom</strong> apa ...

    From $436 per night (USD)

    VRBO

    Details
  • C323 – Elegant apartment with glass wall
    From $276 per night (USD)

    Expedia

    C323 – Elegant apartment with glass wall

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Apartment C-323 at The Hills Residence in Simpson Bay, Sint Maarten! This stylish and modern one-bedroom ap ...

    From $276 per night (USD)

    Expedia

    Details
  • C354 - Top view with balcony
    From $356 per night (USD)

    VRBO

    C354 - Top view with balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    <p><strong>Welcome to Apartment C-354 at The Hills Residence Vacation Rentals!</strong></p> <p>Perched on the <strong>t ...

    From $356 per night (USD)

    VRBO

    Details
  • C351 – Elegance with Stunning Lagon Views
    From $254 per night (USD)

    Expedia

    C351 – Elegance with Stunning Lagon Views

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    <p>Top Floor with Stunning View</p> <p>Perched on the top floor of a modern building, this exclusive condo offers panor ...

    From $254 per night (USD)

    Expedia

    Details
  • Luxury Ocean View Beach Condo on the Beautiful Island of Sint Maarten
    From $857 per night (USD)

    VRBO

    Luxury Ocean View Beach Condo on the Beautiful Island of Sint Maarten

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Located on the same property as the fabulous and brand new 5-star JW Marriott Hotel. Stay comfortably in Oyster Pond a ...

    From $857 per night (USD)

    VRBO

    Details
  • Beautiful 3-bedroom condo with WiFi, AC in fabulous Sint Maarten
    From $971 per night (USD)

    Expedia

    Beautiful 3-bedroom condo with WiFi, AC in fabulous Sint Maarten

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Unwind in SINT MAARTEEN at this lovely Caribbean condo. With 3 brilliant king beds, 2 beautiful bathrooms featuring show ...

    From $971 per night (USD)

    Expedia

    Details
  • Beachside Hideaway in Beacon Hill, St. Maarten
    From $156 per night (USD)

    VRBO

    Beachside Hideaway in Beacon Hill, St. Maarten

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Discover a tranquil Caribbean gem nestled on a quiet peninsula. This property boasts two of the prettiest views you’ll f ...

    From $156 per night (USD)

    VRBO

    Details
  • The Lost Paradise Condo, charming 2-room condo with private pool.
    From $252 per night (USD)

    Expedia

    The Lost Paradise Condo, charming 2-room condo with private pool.

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    <p>Located in Lowlands, this welcoming apartment brings it all within your reach. You'll easily make the quick 19-minute ...

    From $252 per night (USD)

    Expedia

    Details
  • Luxe 3BR Villa: Pool & Sweeping Ocean Views
    From $825 per night (USD)

    VRBO

    Luxe 3BR Villa: Pool & Sweeping Ocean Views

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Discover Villa Kyash, an architectural gem where your private infinity pool dissolves into the endless horizon ...

    From $825 per night (USD)

    VRBO

    Details
  • Relaxing Caribbean Vacation, Twin Palms, Dawn Beach Estates, Pool, AC, and WiFi
    From $585 per night (USD)

    VRBO

    Relaxing Caribbean Vacation, Twin Palms, Dawn Beach Estates, Pool, AC, and WiFi

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Unwind in Dawn Beach Estates at this enchanting villa. With 3 amazing bedrooms featuring king beds, 2 are located in the ...

    From $585 per night (USD)

    VRBO

    Details
  • Homerez - Elegant Apartment in Lowlands 101 m² + Pool
    From $414 per night (USD)

    VRBO

    Homerez - Elegant Apartment in Lowlands 101 m² + Pool

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Discover the ideal getaway in this spacious 101 m² apartment, accommodating up to 6 guests. - Dive into the shared po ...

    From $414 per night (USD)

    VRBO

    Details
  • Homerez - Elegant Studio with Pool in Lowlands - 55 sqm
    From $112 per night (USD)

    VRBO

    Homerez - Elegant Studio with Pool in Lowlands - 55 sqm

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Discover the ideal vacation retreat in Lowlands, where comfort meets practicality. This spacious studio apartment is per ...

    From $112 per night (USD)

    VRBO

    Details
  • Homerez - Apartment in Lowlands, sea view
    From $488 per night (USD)

    VRBO

    Homerez - Apartment in Lowlands, sea view

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Discover a fantastic holiday in this spacious 245 m² apartment accommodating up to 6 guests. Enjoy the private pool, ope ...

    From $488 per night (USD)

    VRBO

    Details
  • Alma Beach Villa
    From $1798 per night (USD)

    VRBO

    Alma Beach Villa

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    <p>ALMA is a stylish, fully rebuilt villa beside Beach Secrets, offering the option to rent both for larger groups. Over ...

    From $1798 per night (USD)

    VRBO

    Details
  • Beach Secrets Villa with Private Pool and Stunning Ocean View
    From $1132 per night (USD)

    VRBO

    Beach Secrets Villa with Private Pool and Stunning Ocean View

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    10

    Enjoy your own private pool with panoramic ocean views, large terraces for sunbathing, and comfortable outdoor lounges w ...

    From $1132 per night (USD)

    VRBO

    Details
  • Cozy 2-bedroom condo with AC, fitness room in lovely Dawn Beach
    From $328 per night (USD)

    Expedia

    Cozy 2-bedroom condo with AC, fitness room in lovely Dawn Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Escape to a charming condo in Dawn Beach for a relaxing getaway. This welcoming 2-bedroom retreat features 2 queen beds, ...

    From $328 per night (USD)

    Expedia

    Details
  • Luxurious Beachfront 3 Bedrooms Presidential Suite with a Spectacular Ocean View
    From $1129 per night (USD)

    VRBO

    Luxurious Beachfront 3 Bedrooms Presidential Suite with a Spectacular Ocean View

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Escape to this fantastic resort in picturesque Oyster Pond. With 3 bedrooms and 2 bathrooms equipped with showers and ha ...

    From $1129 per night (USD)

    VRBO

    Details
  •  Beachfront Penthouse Best View Best location.  Walk to best beaches and dining.
    From $162 per night (USD)

    Expedia

    Beachfront Penthouse Best View Best location. Walk to best beaches and dining.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Overlooking Cupecoy Beach. Top floor Penthouse at Sapphire Beach Club.. Best view in entire full service resort. Comfy ...

    From $162 per night (USD)

    Expedia

    Details
  • Simpson Bay Luxury Loft Stunning Ocean Views
    From $376 per night (USD)

    VRBO

    Simpson Bay Luxury Loft Stunning Ocean Views

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Enjoy your vacation to the fullest in this luxurious duplex loft residence located in Beacon Hill Estates, on the pristi ...

    From $376 per night (USD)

    VRBO

    Details
  • 2-bedroom apartment in charming Sint Maarten with WiFi, AC
    From $137 per night (USD)

    Expedia

    2-bedroom apartment in charming Sint Maarten with WiFi, AC

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    30

    Consider this guest apartment your home away from home while you visit Sint Maarten. This lovely rental features 2 queen ...

    From $137 per night (USD)

    Expedia

    Details
  • Maazoon ~ Modern 3BD Family Home + 2 Parking, Little Bay Dutch side St.Maarten
    From $398 per night (USD)

    VRBO

    Maazoon ~ Modern 3BD Family Home + 2 Parking, Little Bay Dutch side St.Maarten

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Your Home Away From Home in Sunny Sint Maarten! (Minimum stay: 2 nights) Looking for the perfect Caribbean escape while ...

    From $398 per night (USD)

    VRBO

    Details
  • A-503 Stunning one bedroom apartment
    From $363 per night (USD)

    Expedia

    A-503 Stunning one bedroom apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    **Notice: Pool closed for renovations September 7–27, 2026. Beautiful Mullet Bay Beach is steps away, and all other amen ...

    From $363 per night (USD)

    Expedia

    Details
  • C352 - Top view with balcony
    From $290 per night (USD)

    VRBO

    C352 - Top view with balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    <p><strong>Welcome to Apartment C-352 at The Hills Residence Vacation Rentals!</strong></p> <p>Step into a world of <st ...

    From $290 per night (USD)

    VRBO

    Details
  • C342 - Glorious Lagoon View Apartment with Balcony
    From $291 per night (USD)

    Expedia

    C342 - Glorious Lagoon View Apartment with Balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    <p><strong>Welcome to Apartment C-342 at The Hills Residence Vacation Rentals!</strong></p> <p>Located on the <strong>f ...

    From $291 per night (USD)

    Expedia

    Details
  • C324 - Amazing view with balcony
    From $291 per night (USD)

    VRBO

    C324 - Amazing view with balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    <p><strong>Welcome to Apartment C-324 at The Hills Residence Vacation Rentals!</strong></p> <p>Situated on the <strong> ...

    From $291 per night (USD)

    VRBO

    Details
  • Cozy 2-bedroom apartment in enjoyable Oyster Pond with Ocean View
    From $203 per night (USD)

    VRBO

    Cozy 2-bedroom apartment in enjoyable Oyster Pond with Ocean View

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Escape to Paradise in Sint Maarten! Your Dream Vacation Rental Awaits! Relax and unwind in our beautiful, fully equip ...

    From $203 per night (USD)

    VRBO

    Details
  • Tropical 4-bedroom house with AC in Beacon Hill area
    From $508 per night (USD)

    VRBO

    Tropical 4-bedroom house with AC in Beacon Hill area

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    This 4-bedroom house in Simpson Bay is perfect for your escape to paradise. With 2 queen beds and 2 twin beds, this supe ...

    From $508 per night (USD)

    VRBO

    Details
  • Villa Turquoise Heaven
    From $928 per night (USD)

    Expedia

    Villa Turquoise Heaven

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to this marvelous villa in Sint Maarten. This welcoming property boasts 3 bedrooms, including 2 king beds and 1 ...

    From $928 per night (USD)

    Expedia

    Details
  • Beachfront Escape/Rainbow 2BR
    From $379 per night (USD)

    VRBO

    Beachfront Escape/Rainbow 2BR

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Unwind in this spacious, stylish 2BR Caribbean-inspired condo by turquoise waters. Located in Rainbow Beach Club, it off ...

    From $379 per night (USD)

    VRBO

    Details
  • Luxury Beachfront Condo (201)
    From $633 per night (USD)

    Expedia

    Luxury Beachfront Condo (201)

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Luxury 2 bedroom unit at the prestigious Aqualina Beach Club directly on Simpson Bay beach. Unit 201 is ideal for one o ...

    From $633 per night (USD)

    Expedia

    Details
  • Heart of SXM! Mingle with the Locals!
    From $236 per night (USD)

    VRBO

    Heart of SXM! Mingle with the Locals!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    31

    Discover this charming 1-bedroom gem in Cole Bay. This pleasant townhome features a cozy bedroom with a queen bed, perfe ...

    From $236 per night (USD)

    VRBO

    Details
  • Gorgeous Oceanview Apartment W/Generator
    From $251 per night (USD)

    VRBO

    Gorgeous Oceanview Apartment W/Generator

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Escape to a stunning 1-bedroom, 1-bathroom oceanview apartment in Pelican Key, Sint Maarten. This charming retreat featu ...

    From $251 per night (USD)

    VRBO

    Details
  • Oceanview Oasis - Villa Del Sol W/Generator
    From $547 per night (USD)

    VRBO

    Oceanview Oasis - Villa Del Sol W/Generator

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    Escape to this luxurious 3-bedroom, 4-bathroom villa in Pelican Key, Simpson Bay. Enjoy a spacious, air-conditioned retr ...

    From $547 per night (USD)

    VRBO

    Details
  • Oceanview Paradise - Villa Del Sol w/ Generator
    From $826 per night (USD)

    VRBO

    Oceanview Paradise - Villa Del Sol w/ Generator

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    Escape to this luxurious 4-bedroom, 5-bathroom villa in Pelican Key, Simpson Bay. Enjoy a spacious, air-conditioned retr ...

    From $826 per night (USD)

    VRBO

    Details
  • Villa SOLANA - Upscale Indigo Bay with Private Pool
    From $628 per night (USD)

    VRBO

    Villa SOLANA - Upscale Indigo Bay with Private Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Indigo Bay Ocean and Mountain views Villa with private pool in upscale Indigo Bay, Sint Maarten. Villa Solana ...

    From $628 per night (USD)

    VRBO

    Details
  • LARGE LUXURY APARTMENT HILTON VACATION BEACHFRONT CARAIBES
    From $422 per night (USD)

    Expedia

    LARGE LUXURY APARTMENT HILTON VACATION BEACHFRONT CARAIBES

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    <p>Located in Philipsburg, this welcoming condo brings it all within your reach. Rainforest Adventures St. Maarten is ju ...

    From $422 per night (USD)

    Expedia

    Details
  • Chic 1-bedroom apartment with fitness room and AC in welcoming Sint Maarten
    From $358 per night (USD)

    VRBO

    Chic 1-bedroom apartment with fitness room and AC in welcoming Sint Maarten

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Escape to this perfect apartment in picturesque Sint Maarten. This cozy retreat features 1 bedroom with a comfortable ki ...

    From $358 per night (USD)

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  • Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!
    From $506 per night (USD)

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    Beach Front 2 Bed Condon D1.1 with Sea View and Private Pool !!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Kim Sha Beach Front apartment where amazing memories are made! Location is our shining spot! Just mins walk ...

    From $506 per night (USD)

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  • Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!
    From $422 per night (USD)

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    Beach Front 2 Bed Condon C1.1 with Sea View and Private Pool !!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This 2 bedroom, 2 bathroom apartment features a large living room with a fully equipped open kitchen and a queen size so ...

    From $422 per night (USD)

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  • Beach Front 4 Bed Condon C2.1 with Sea View and Private Pool !!
    From $970 per night (USD)

    Expedia

    Beach Front 4 Bed Condon C2.1 with Sea View and Private Pool !!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to Kim Sha Beach Front apartment where amazing memories are made! Location is our shining spot! Just mins walk ...

    From $970 per night (USD)

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  • 2BR Sunset Condo at Blue Mall – Near Maho
    From $570 per night (USD)

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    2BR Sunset Condo at Blue Mall – Near Maho

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Set on the 6th floor of Blue Mall in Cupecoy, Blue 614 is a bright, modern 2-bedroom retreat with open-plan li ...

    From $570 per night (USD)

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  • 2BR Maho Oasis | Walk to Beaches & Nightlife!
    From $387 per night (USD)

    Expedia

    2BR Maho Oasis | Walk to Beaches & Nightlife!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Summary: The perfect St. Maarten getaway for friends and couples! This stylish 2BR/1BA condo is your oasis in the heart ...

    From $387 per night (USD)

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  • Sovereign Suites Maho | 2BR w/ Pool, Beach Gear
    From $376 per night (USD)

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    Sovereign Suites Maho | 2BR w/ Pool, Beach Gear

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Welcome to The Sovereign Suites, your front-row seat to the famous Maho Beach plane-landing show! This refined ...

    From $376 per night (USD)

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  • Stylish Maho Condo w/ Pool | Walk to Everything!
    From $226 per night (USD)

    Expedia

    Stylish Maho Condo w/ Pool | Walk to Everything!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Live at the center of the action! This stylish 1BR condo is your perfect St. Maarten home base, putting Maho B ...

    From $226 per night (USD)

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  • Beachfront Condo in Simpson Bay,2BR/2BA. Ocean View, Pools, SPA, Walk to Dining.
    From $277 per night (USD)

    VRBO

    Beachfront Condo in Simpson Bay,2BR/2BA. Ocean View, Pools, SPA, Walk to Dining.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wake up to breathtaking ocean views in this spacious 2-bedroom, 2-bathroom beachfront condo in the heart of Simpson Bay, ...

    From $277 per night (USD)

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  • Timeless Tides with Ocean Views 3-bdrm 3 bath, Pool, Full AC, Wifi, Dawn Beach.
    From $635 per night (USD)

    Expedia

    Timeless Tides with Ocean Views 3-bdrm 3 bath, Pool, Full AC, Wifi, Dawn Beach.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    This Dawn Beach Estates villa boasts 3 inviting bedrooms, including 1 king bed and 2 queen beds. With amenities like AC, ...

    From $635 per night (USD)

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  • AZUR -  NEW SEA SIDE DR, 4 BR, 4.5 BA -  WALK TO  INDIGO BEACH
    From $770 per night (USD)

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    AZUR - NEW SEA SIDE DR, 4 BR, 4.5 BA - WALK TO INDIGO BEACH

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    AZUR NOW FULLY COMPLETED AND AVAILABLE FOR ADVANCED RESERVATIONS; ELEGANT ISLAND LIVING ON INDIGO BAY, ST. MAARTEN. Wel ...

    From $770 per night (USD)

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  • New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove
    From $475 per night (USD)

    Expedia

    New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to your personal oasis, a charming 3-bedroom, 3-bathroom villa nestled within the exclusive, gated community of ...

    From $475 per night (USD)

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  • Beach Front 1 Bedroom Flat D3
    From $189 per night (USD)

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    Beach Front 1 Bedroom Flat D3

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Kim Sha Beach Front apartment where amazing memories are made! Location is our shining spot! Just mins walk ...

    From $189 per night (USD)

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  • Luxury Ocean View Escape
    From $571 per night (USD)

    VRBO

    Luxury Ocean View Escape

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Your Sint Maarten adventure begins at this marvelous 3-bedroom condo. Each bedroom features a comfortable king bed, ensu ...

    From $571 per night (USD)

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  • Beach Front Studio C3
    From $159 per night (USD)

    VRBO

    Beach Front Studio C3

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Kim Sha Beach Front studio where amazing memories are made! Location is our shining spot! Just mins walking ...

    From $159 per night (USD)

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  • DEEP BLUE SEA at LaSiesta Ground Floor Oceanfront 1-bedroom condo in Simpson Bay
    From $303 per night (USD)

    Expedia

    DEEP BLUE SEA at LaSiesta Ground Floor Oceanfront 1-bedroom condo in Simpson Bay

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This stunning beach front / poolside ground floor 1 bedroom condo was completely renovated August 2025! Deep Blue Sea i ...

    From $303 per night (USD)

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  • Luxury Beach Front Escape
    From $904 per night (USD)

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    Luxury Beach Front Escape

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Your Sint Maarten adventure begins at this marvelous 3-bedroom condo. Each bedroom features a comfortable king bed, ensu ...

    From $904 per night (USD)

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  • Spacious apartment ideal for a family vacation, 5 minutes from the beach.
    From $1770 per night (USD)

    VRBO

    Spacious apartment ideal for a family vacation, 5 minutes from the beach.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    <p>Located in Lower Prince's Quarter, this 3-bedroom, 3-bathroom apartment lets you experience it all. Fans of nature an ...

    From $1770 per night (USD)

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  • Fantastic 2-bedroom condo with unforgettable views of the ocean!
    From $561 per night (USD)

    VRBO

    Fantastic 2-bedroom condo with unforgettable views of the ocean!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located in Pelican, enjoy what this 2-bedroom condo has to offer. With 2 king beds and 2.5 bathrooms equipped with showe ...

    From $561 per night (USD)

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  • Beachside Paradise Resort Apartment  with Spectacular Sea Views & Pool
    From $278 per night (USD)

    VRBO

    Beachside Paradise Resort Apartment with Spectacular Sea Views & Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Located Steps to the beach by the Caribbean Sea, this modern beachfront apartment offers panoramic ocean views, modern c ...

    From $278 per night (USD)

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  • The Lighthouse, Unit 5B, A Stunning Ocean Front Condo in Oyster Bay, St. Maarten
    From $622 per night (USD)

    VRBO

    The Lighthouse, Unit 5B, A Stunning Ocean Front Condo in Oyster Bay, St. Maarten

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to a place of peace! This condo is truly the best of both worlds, complete peace or access to amazing night life ...

    From $622 per night (USD)

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  • Vibra Lux Island Escape Cozy 1BR Near Beaches & Philipsburg
    From $92 per night (USD)

    Expedia

    Vibra Lux Island Escape Cozy 1BR Near Beaches & Philipsburg

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Vibra Lux Cozy Island Escape is a charming one-bedroom apartment nestled in the heart of Belair, Sint Maarten, offering ...

    From $92 per night (USD)

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  • Ocean-View Studio at Flamingo Beach – Beachfront St. Maarten Escape
    From $212 per night (USD)

    VRBO

    Ocean-View Studio at Flamingo Beach – Beachfront St. Maarten Escape

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy an easygoing Caribbean escape in this ocean-view studio at Hilton Vacation Club Flamingo Beach St. Maarten, set di ...

    From $212 per night (USD)

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  • Sophisticated Maho Studio with Resort-Style Amenities in a Gated Community.
    From $178 per night (USD)

    Expedia

    Sophisticated Maho Studio with Resort-Style Amenities in a Gated Community.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Stylish, centrally located studio in the heart of Maho, where island vibes, adventure, and relaxation come together. Jus ...

    From $178 per night (USD)

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    Details
  • Cozy Maho Studio w/ Pool & Gym + Beach Nearby
    From $133 per night (USD)

    VRBO

    Cozy Maho Studio w/ Pool & Gym + Beach Nearby

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Space Welcome to your perfect Maho Beach getaway! This cozy, 24 m² (260 ft²) modern studio is ideal for solo travel ...

    From $133 per night (USD)

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  • A-1101
    From $492 per night (USD)

    Expedia

    A-1101

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    **Notice: Pool closed for renovations September 7–27, 2026. Beautiful Mullet Bay Beach is steps away, and all other amen ...

    From $492 per night (USD)

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  • Charming studio home away from home in serene Cul de Sac St. Peters with AC.
    From $75 per night (USD)

    VRBO

    Charming studio home away from home in serene Cul de Sac St. Peters with AC.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Stay in one of Sint Maarten’s most friendliest neighborhoods; St. Peters and fit right in. In a clean , quiet, comfortab ...

    From $75 per night (USD)

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  • #1 Unique luxury villa, pool & stunning sea views
    From $1192 per night (USD)

    Expedia

    #1 Unique luxury villa, pool & stunning sea views

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Luxury Modern Retreat with Resort-Style Pool | 4BR • 4.5BA • Sleeps 10 Experience elevated living in this stunning 4,00 ...

    From $1192 per night (USD)

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  • Villa Stella By The Sea
    From $1422 per night (USD)

    VRBO

    Villa Stella By The Sea

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    10

    Summary: Experience elevated Caribbean living at Villa Stella, a stunning contemporary villa overlooking the crystal-cl ...

    From $1422 per night (USD)

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  • Villa Serenidade Waterfront Haven
    From $680 per night (USD)

    VRBO

    Villa Serenidade Waterfront Haven

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Escape to Villa Serenidade, a stylish waterfront retreat nestled along the tranquil shores of the Lagoon in Cu ...

    From $680 per night (USD)

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  •  2-bedroom condo in superb Simpson Bay with AC comfort
    From $434 per night (USD)

    VRBO

    2-bedroom condo in superb Simpson Bay with AC comfort

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Hey! Welcome to SXM, and you are lucky to be in the heart of Simpson Bay! Benefits? Below are all within 5 mins of walk: ...

    From $434 per night (USD)

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  • Homerez - Villa in Koolbaai
    From $525 per night (USD)

    VRBO

    Homerez - Villa in Koolbaai

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to this charming villa, perfect for a romantic getaway or relaxation. Enjoy your private pool, lush garden, and ...

    From $525 per night (USD)

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  • Homerez - Apartment in Lowlands
    From $243 per night (USD)

    VRBO

    Homerez - Apartment in Lowlands

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to this spacious 87 m² apartment, perfect for family vacations or with friends. Enjoy a modern and comfortable s ...

    From $243 per night (USD)

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  • Homerez - Apartment in Upper Prince's Quarter
    From $1013 per night (USD)

    VRBO

    Homerez - Apartment in Upper Prince's Quarter

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Experience an unforgettable stay in this spacious apartment located at the JW Marriott St. Maarten Beach Resort & Spa. ...

    From $1013 per night (USD)

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  • 2 Bdrm/2 Bath Beach Front Condo-Pelican Key 11/24/26-11/30/26
    From $215 per night (USD)

    VRBO

    2 Bdrm/2 Bath Beach Front Condo-Pelican Key 11/24/26-11/30/26

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    La Vista Beach Resort is located on the Dutch side of St. Maarten in the Pelican Key Estates area of Simpson Bay. It i ...

    From $215 per night (USD)

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  • Cozy Seascape Condo in Cupecoy
    From $368 per night (USD)

    Expedia

    Cozy Seascape Condo in Cupecoy

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to our 2-bedroom, 2-bathroom condo at Rainbow Beach Club — a resort-style retreat with private beach access and ...

    From $368 per night (USD)

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  • SXM Hillside Retreat large 3-bed/bath condo, tucked in the hills but central
    From $299 per night (USD)

    VRBO

    SXM Hillside Retreat large 3-bed/bath condo, tucked in the hills but central

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Centrally located amid lush, green hills, SXM Hillside Retreat is a sanctuary among mango trees, far from traffic but 10 ...

    From $299 per night (USD)

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  • Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central
    From $234 per night (USD)

    Expedia

    Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Nestled in green hills with superb views, this 2-king-bed, 2-bath penthouse condo is an oasis among mango trees, far fro ...

    From $234 per night (USD)

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  • St. Maarten's Little Bay Villa En'Sea
    From $1847 per night (USD)

    VRBO

    St. Maarten's Little Bay Villa En'Sea

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Villa En sea – Your Luxurious Caribbean Escape Welcome to Villa Ensea, where luxury meets tranquility in a stunning hil ...

    From $1847 per night (USD)

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  • Romantic Caribbean Cottage • Pool & Ocean Views
    From $478 per night (USD)

    VRBO

    Romantic Caribbean Cottage • Pool & Ocean Views

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Where Privacy, Romance and Caribbean Beauty Meet Welcome to Hope Cottage, a romantic one-bedroom hilltop retreat with a ...

    From $478 per night (USD)

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    Details