Search Your Destination Now!

Flamingo beach Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Update Results Reset Dates
Filter

Results: 296 Rentals

  • Villa Livity 6 Bed Luxury Sea View boutique villa
    From $1290 per night (USD)

    VRBO

    Villa Livity 6 Bed Luxury Sea View boutique villa

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    12

    Come relax and enjoy a serene retreat on the beautiful island of Sint Maarten in a stunningly renovated villa, featuring ...

    From $1290 per night (USD)

    VRBO

    Details
  • Villa Sea Forever @ Pelican Key - Paradise Awaits!
    From $282 per night (USD)

    Expedia

    Villa Sea Forever @ Pelican Key - Paradise Awaits!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Experience a piece of paradise at "Villa Sea Forever" in Pelican Key, Simpson Bay, Sint Maarten! This 2-bedroom, 2.5-bat ...

    From $282 per night (USD)

    Expedia

    Details
  • Cozy studio warm, welcoming and close to many restaurants and beaches.
    From $107 per night (USD)

    VRBO

    Cozy studio warm, welcoming and close to many restaurants and beaches.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Cozi pelican is a very warm and welcoming apartment in one of the best residential areas on the Dutch side of the island ...

    From $107 per night (USD)

    VRBO

    Details
  • Caribbean View Villa-beach-sunset
    From $704 per night (USD)

    VRBO

    Caribbean View Villa-beach-sunset

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    <p>Located in Simpson Bay, this welcoming vacation home lets you experience it all. Flamingo Beach is an easy 6-minute w ...

    From $704 per night (USD)

    VRBO

    Details
  • A116 - Immersive Simpson Bay Lagoon View
    From $198 per night (USD)

    VRBO

    A116 - Immersive Simpson Bay Lagoon View

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Apartment 116 at The Hills Residence in Simpson Bay, Sint Maarten - your luxury first floor hideaway awaits! ...

    From $198 per night (USD)

    VRBO

    Details
  • B254 - Cozy Apartment in the Heart of Simpson Bay
    From $236 per night (USD)

    Expedia

    B254 - Cozy Apartment in the Heart of Simpson Bay

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    3

    Welcome to this stunning one-bedroom apartment with a balcony at The Hills Residence in Simpson Bay, Sint-Maarten! Nestl ...

    From $236 per night (USD)

    Expedia

    Details
  • Gorgeous 2 Bedroom Beachfront  Privately Owned Condo 4th Floor
    From $358 per night (USD)

    VRBO

    Gorgeous 2 Bedroom Beachfront Privately Owned Condo 4th Floor

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located in beautiful Simpson Bay, directly on Kim Sha Beach. Privately owned, Gorgeous Fourth floor 2 Bedroom 2 Bath Con ...

    From $358 per night (USD)

    VRBO

    Details
  • Beautiful White Sand, Sparkling Blue Waters, Sunny Skies-Relax and Enjoy!
    From $119 per night (USD)

    Expedia

    Beautiful White Sand, Sparkling Blue Waters, Sunny Skies-Relax and Enjoy!

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    4

    Flamingo Beach, a Hilton Vacation Club provides everything you’ll need for a relaxing Caribbean getaway. Located on the ...

    From $119 per night (USD)

    Expedia

    Details
  • Beautiful White Sand, Sparkling Blue Waters, Sunny Skies-Relax and Enjoy!
    From $145 per night (USD)

    VRBO

    Beautiful White Sand, Sparkling Blue Waters, Sunny Skies-Relax and Enjoy!

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    4

    Flamingo Beach, a Hilton Vacation Club provides everything you’ll need for a relaxing Caribbean getaway. Located on the ...

    From $145 per night (USD)

    VRBO

    Details
  • Magnifique Penthouse de 400 m2 à Las Brisas Residence
    From $764 per night (USD)

    Expedia

    Magnifique Penthouse de 400 m2 à Las Brisas Residence

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    <p>Located in Cole Bay, this 3-bedroom, 3-bathroom apartment lets you experience it all. Fans of nature and the outdoors ...

    From $764 per night (USD)

    Expedia

    Details
  • Luxurious Villa \ Sea La Vie\ in Pelican Key
    From $625 per night (USD)

    VRBO

    Luxurious Villa \" Sea La Vie\" in Pelican Key

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to the luxurious Villa Sea La Vie located in the prestigious residential area of Pelican Key. It's all about lo ...

    From $625 per night (USD)

    VRBO

    Details
  • Il Punto Blu in Pelican Key by Personal Villas - Spacious and Amazing Views
    From $630 per night (USD)

    VRBO

    Il Punto Blu in Pelican Key by Personal Villas - Spacious and Amazing Views

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    Summary: PROMO! - Valid on all NEW BOOKINGS ONLY : * 7th Night is free traveling from April 15th to December 14th. * 1 ...

    From $630 per night (USD)

    VRBO

    Details
  • Centrally located contemporary apartment in Simpsonbay.
    From $358 per night (USD)

    VRBO

    Centrally located contemporary apartment in Simpsonbay.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Discover The Pineapple Suite, a chic 2-bedroom retreat accommodating up to 4 guests, nestled within the secure confines ...

    From $358 per night (USD)

    VRBO

    Details
  • A111 - Condo with amazing view
    From $273 per night (USD)

    Expedia

    A111 - Condo with amazing view

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    3

    Welcome to this beautiful, one bedroom apartment at The Hills Residence in Simpson Bay, Sint-Maarten! Nestled on the 1st ...

    From $273 per night (USD)

    Expedia

    Details
  • Stunning Beach Front Villa With Infinity Pool
    From $788 per night (USD)

    VRBO

    Stunning Beach Front Villa With Infinity Pool

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    Stunning beach front villa located in Pelican Key, a neighborhood in Simpson Bay. Sit and relax by the infinity pool an ...

    From $788 per night (USD)

    VRBO

    Details
  • A122 - Wonderful Lagoon View with Balcony
    From $275 per night (USD)

    Expedia

    A122 - Wonderful Lagoon View with Balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Apartment A-122 at The Hills Residence Vacation Rentals! Indulge in the epitome of luxury with our stunning s ...

    From $275 per night (USD)

    Expedia

    Details
  • A102 - Cozy Apartment with Garden
    From $288 per night (USD)

    VRBO

    A102 - Cozy Apartment with Garden

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    3

    Welcome to Appt A-102 at The Hills Residence in Simpson Bay, Sint Maarten! This beautiful 1-bedroom apartment offers a c ...

    From $288 per night (USD)

    VRBO

    Details
  • A131 - Exceptional Lagoon View
    From $221 per night (USD)

    Expedia

    A131 - Exceptional Lagoon View

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Introducing Apartment A-131 with its exceptional Lagoon Viewat The Hills Residence Vacation Rentals! Prepare to be capti ...

    From $221 per night (USD)

    Expedia

    Details
  • A136 - Amazing Spacious Apartment Lagoon View with Balcony
    From $211 per night (USD)

    VRBO

    A136 - Amazing Spacious Apartment Lagoon View with Balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Apartment A-136 at The Hills Residence Vacation Rentals! Step into a world of luxury and elegance with our ...

    From $211 per night (USD)

    VRBO

    Details
  • A135 - Sensational Lagoon View
    From $219 per night (USD)

    Expedia

    A135 - Sensational Lagoon View

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Apartment A-135 at The Hills Residence Vacation Rentals with a sensational view on the Lagoon ! Escape to a w ...

    From $219 per night (USD)

    Expedia

    Details
  • A137 - Bright 2 Bedrooms Apartment With Blue Lagoon View
    From $348 per night (USD)

    VRBO

    A137 - Bright 2 Bedrooms Apartment With Blue Lagoon View

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Apartment A-137 at The Hills Residence Vacation Rentals! Escape into a world of luxury and elegance with our ...

    From $348 per night (USD)

    VRBO

    Details
  • A112 - Extraordinary Lagoon View with Balcony
    From $239 per night (USD)

    Expedia

    A112 - Extraordinary Lagoon View with Balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Looking for the perfect getaway in Simpson Bay, Sint Maarten? Look no further! Introducing A112, our stunning one-bedroo ...

    From $239 per night (USD)

    Expedia

    Details
  • Great Escape in Simpson Bay by Personal Villas - Breathtaking Scenery
    From $854 per night (USD)

    VRBO

    Great Escape in Simpson Bay by Personal Villas - Breathtaking Scenery

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Summary: PROMO! - Low season (April 15 - Dec 15) - 7th night free for bookings of 7 nights or more - High season (Dec 15 ...

    From $854 per night (USD)

    VRBO

    Details
  • Peaceful Paradise
    Click For Pricing

    Expedia

    Peaceful Paradise

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    This 3 bed, 3 bath villa has views that can be seen from the master bedroom, master deck, master shower and large deck o ...

    Click For Pricing

    Expedia

    Details
  • Villa Incognito on the Beach
    From $660 per night (USD)

    VRBO

    Villa Incognito on the Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Villa Incognito Managed Sunshine Properties with Olive cleaning you'll Indulge in the epitome of coastal luxury with our ...

    From $660 per night (USD)

    VRBO

    Details
  • Sunset Place Villa - View - SEA - Location #1
    From $760 per night (USD)

    VRBO

    Sunset Place Villa - View - SEA - Location #1

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    <p>Located in Simpson Bay, this welcoming villa lets you experience it all. Flamingo Beach is within an easy 12-minute w ...

    From $760 per night (USD)

    VRBO

    Details
  • Luxury Condo in Simpson Bay
    From $329 per night (USD)

    VRBO

    Luxury Condo in Simpson Bay

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    About this space Welcome to the heart of paradise! Nestled in the vibrant island of Sint Martin, our stunning 2-bedroom ...

    From $329 per night (USD)

    VRBO

    Details
  • Great Escape in Simpson Bay by Personal Villas - Breathtaking Scenery
    From $703 per night (USD)

    VRBO

    Great Escape in Simpson Bay by Personal Villas - Breathtaking Scenery

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Summary: PROMO! - Low season (April 15 - Dec 15) - 7th night free for bookings of 7 nights or more - High season (Dec 15 ...

    From $703 per night (USD)

    VRBO

    Details
  • Elegant 2-bedroom directly on Simpson Bay Beach!!
    From $335 per night (USD)

    VRBO

    Elegant 2-bedroom directly on Simpson Bay Beach!!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Sint Maarten Exclusive Ocean Front Duplex Condo. This beautiful ocean front paradise awaits you on one the Caribbean's ...

    From $335 per night (USD)

    VRBO

    Details
  • Delightful centrally located Simpson Bay Yacht Club condo.
    From $101 per night (USD)

    Expedia

    Delightful centrally located Simpson Bay Yacht Club condo.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Located in the Simpson Bay Yacht Club, the residence is gated and secured 24/7. Available amenities include 2 pools, an ...

    From $101 per night (USD)

    Expedia

    Details
  • La Villa Salée in Pelican by Personal Villas - Casual Elegance and Relaxation
    From $2894 per night (USD)

    VRBO

    La Villa Salée in Pelican by Personal Villas - Casual Elegance and Relaxation

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Summary: LA VILLA SALEE 4BR, Pelican Peninsula, St Maarten Stay in style and luxury at our eight bedroom villa on the D ...

    From $2894 per night (USD)

    VRBO

    Details
  • La Villa Salée in Pelican by Personal Villas - Casual Elegance and Relaxation
    From $3134 per night (USD)

    VRBO

    La Villa Salée in Pelican by Personal Villas - Casual Elegance and Relaxation

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    12

    Summary: LA VILLA SALEE 6BR, Pelican Peninsula, St Maarten Stay in style and luxury at our eight bedroom villa on the D ...

    From $3134 per night (USD)

    VRBO

    Details
  • Bella Vita in Pelican Key by Personal Villas - Spacious and Sophisticated Villa
    From $3805 per night (USD)

    VRBO

    Bella Vita in Pelican Key by Personal Villas - Spacious and Sophisticated Villa

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    12

    Summary: BELLA VITA 6BR, Pelican Key, St Maarten Life is good at Villa Bella Vita, a sumptuous 7 bedroom contemporary ...

    From $3805 per night (USD)

    VRBO

    Details
  • Bella Vita in Pelican Key by Personal Villas - Spacious and Sophisticated Villa
    From $2493 per night (USD)

    VRBO

    Bella Vita in Pelican Key by Personal Villas - Spacious and Sophisticated Villa

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    Summary: BELLA VITA 4BR, Pelican Key, St Maarten Life is good at Villa Bella Vita, a sumptuous 7 bedroom contemporary ...

    From $2493 per night (USD)

    VRBO

    Details
  • Amazing Beachfront Condo in Simpson Bay -Walk Out Beach\/Pool
    From $459 per night (USD)

    VRBO

    Amazing Beachfront Condo in Simpson Bay -Walk Out Beach\/Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to St Maarten the Friendly Island where the sunshine, Caribbean beaches and sunsets will keep you coming back fo ...

    From $459 per night (USD)

    VRBO

    Details
  • Beautiful spacious Studio with spectacular view
    From $150 per night (USD)

    Expedia

    Beautiful spacious Studio with spectacular view

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    we are pleased to welcome you to our beautiful apartment with the most spectacular view of the Island, you can sit on yo ...

    From $150 per night (USD)

    Expedia

    Details
  • SIMPSON BAY YACHT CLUB NEW VERY LARGE 1 BED CONDO 872 SQFT IN THE HEART OF SXM!
    From $190 per night (USD)

    VRBO

    SIMPSON BAY YACHT CLUB NEW VERY LARGE 1 BED CONDO 872 SQFT IN THE HEART OF SXM!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Having owned a much larger villa on the island for 23 years which I rented to a lovely and respectful group of guests, I ...

    From $190 per night (USD)

    VRBO

    Details
  • 2-Bedroom Condo With Marina Views In Simpson Bay
    From $403 per night (USD)

    Expedia

    2-Bedroom Condo With Marina Views In Simpson Bay

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to your ultimate St. Maarten getaway! This newly listed 2-bedroom, 2-bathroom condo, located just off Airport Ro ...

    From $403 per night (USD)

    Expedia

    Details
  • 2 Bedroom 2.5 Bath Penthouse on Simpson Bay Beach
    From $586 per night (USD)

    VRBO

    2 Bedroom 2.5 Bath Penthouse on Simpson Bay Beach

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    The Penthouse at Las Arenas is a 2 bedroom 2.5 bathroom penthouse located on St. Maarten’s longest beach – the Simpson B ...

    From $586 per night (USD)

    VRBO

    Details
  • Ocean Breeze at Le Papillon; Modern with steps to the Beach! Backup Generator!
    From $396 per night (USD)

    VRBO

    Ocean Breeze at Le Papillon; Modern with steps to the Beach! Backup Generator!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    3

    Direct walk out access to the sand and sea is provided from OCEAN BREEZE located in the Le Papillon Complex, Simpson Bea ...

    From $396 per night (USD)

    VRBO

    Details
  • Coco's Beach House Su
    From $495 per night (USD)

    VRBO

    Coco's Beach House Su

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Brand New - Coco's Beach House is a stunning newly renovated property just steps away from the beach. Our Beach ...

    From $495 per night (USD)

    VRBO

    Details
  • A103 - Incredible Apartment with Garden
    From $252 per night (USD)

    Expedia

    A103 - Incredible Apartment with Garden

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    3

    Welcome to Appt A-103 at The Hills Residence in Simpson Bay, Sint Maarten! This beautiful 1-bedroom apartment offers an ...

    From $252 per night (USD)

    Expedia

    Details
  • B256 - Amazing Top Floor Apartment With Balcony
    From $240 per night (USD)

    VRBO

    B256 - Amazing Top Floor Apartment With Balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Apartment B-256 at The Hills Residence Vacation Rentals! Step into a world of luxury and elegance with our ...

    From $240 per night (USD)

    VRBO

    Details
  • B251 - Beautiful 2 Bedroom - 2 Bathroom
    From $362 per night (USD)

    Expedia

    B251 - Beautiful 2 Bedroom - 2 Bathroom

    Bedrooms:
    4
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Apartment A-251 at The Hills Residence in Simpson Bay, Sint Maarten - your luxury lagoon retreat awaits! We ...

    From $362 per night (USD)

    Expedia

    Details
  • A106 - Beautiful Lagoon View with Garden
    From $289 per night (USD)

    VRBO

    A106 - Beautiful Lagoon View with Garden

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    3

    Welcome to Appt A-106 at The Hills Residence in Simpson Bay, Sint Maarten! This beautiful 1-bedroom apartment offers an ...

    From $289 per night (USD)

    VRBO

    Details
  • A107 - Beautiful 2 Bedroom with Garden
    From $382 per night (USD)

    Expedia

    A107 - Beautiful 2 Bedroom with Garden

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to Apartment A-107 at The Hills Residence in Simpson Bay, Sint Maarten - your luxury lagoon retreat awaits! We a ...

    From $382 per night (USD)

    Expedia

    Details
  • A105 - Breathtaking Apartment with Garden
    From $218 per night (USD)

    VRBO

    A105 - Breathtaking Apartment with Garden

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    WWelcome to Appt A-105 at The Hills Residence in Simpson Bay, Sint Maarten! This beautiful 1-bedroom apartment offers a ...

    From $218 per night (USD)

    VRBO

    Details
  • A133 - Top Floor Lagoon View
    From $224 per night (USD)

    Expedia

    A133 - Top Floor Lagoon View

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Introducing Apartment A-133 with its exceptional Lagoon View at The Hills Residence Vacation Rentals! Prepare to be cap ...

    From $224 per night (USD)

    Expedia

    Details
  • B246 - Breathtaking Lagoon View with Balcony
    From $213 per night (USD)

    VRBO

    B246 - Breathtaking Lagoon View with Balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Welcome to Apartment B-246 at The Hills Residence Vacation Rentals! Step into a world of luxury and elegance with our ...

    From $213 per night (USD)

    VRBO

    Details
  • A132 - Glorious Lagoon View Apartment with Balcony
    From $227 per night (USD)

    Expedia

    A132 - Glorious Lagoon View Apartment with Balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Apartment A-132 at The Hills Residence Vacation Rentals! Step into a world of luxury and elegance with our ...

    From $227 per night (USD)

    Expedia

    Details
  • Flamingo Beach by Hilton: Oceanfront Resort, Pools & Spacious Studios To Relax!
    From $102 per night (USD)

    VRBO

    Flamingo Beach by Hilton: Oceanfront Resort, Pools & Spacious Studios To Relax!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Flamingo Beach, a Hilton Vacation Club, where luxury, adventure, and relaxation combine to create the ultimat ...

    From $102 per night (USD)

    VRBO

    Details
  • A breath of fresh air right on the sea - relax and enjoy!
    From $1152 per night (USD)

    Expedia

    A breath of fresh air right on the sea - relax and enjoy!

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    10

    WELCOME TO PUERTA AL MAR! As you step inside, you’ll be greeted by a beautifully remodeled interior with local artwork ...

    From $1152 per night (USD)

    Expedia

    Details
  • Sophisticated 1-bedroom + 1 sofa bed condo in tranquil Simpson Bay Yacht Club
    From $215 per night (USD)

    VRBO

    Sophisticated 1-bedroom + 1 sofa bed condo in tranquil Simpson Bay Yacht Club

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Gated community. Townhouse directly on the Lagoon. One flight of stairs up to the front door. Walking distance to caf ...

    From $215 per night (USD)

    VRBO

    Details
  • Sunny Outlook - Beautiful 1 bedroom in beachfront complex!
    From $221 per night (USD)

    Expedia

    Sunny Outlook - Beautiful 1 bedroom in beachfront complex!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    This amazing completely renovated 1 bedroom 1.5 bathroom unit is located at Palm Beach Condo’s, directly on Simpson Bay ...

    From $221 per night (USD)

    Expedia

    Details
  • Beach Front Condo in Simpson Bay
    From $431 per night (USD)

    VRBO

    Beach Front Condo in Simpson Bay

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Comfortable and beautiful spacious, newly refurbish 2 bedroom, 2 bathroom apartment conveniently located in the heart of ...

    From $431 per night (USD)

    VRBO

    Details
  • Gorgeous 1 bed- 1,5 bath apt in Simpson Bay - GENERATOR
    From $178 per night (USD)

    Expedia

    Gorgeous 1 bed- 1,5 bath apt in Simpson Bay - GENERATOR

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

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

    From $178 per night (USD)

    Expedia

    Details
  • 1 bedroom with pool in Simpson Bay - GENERATOR
    From $203 per night (USD)

    VRBO

    1 bedroom with pool in Simpson Bay - GENERATOR

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $203 per night (USD)

    VRBO

    Details
  • Simpson bay 3bdr \/ 3,5 bath with pools - GENERATOR
    From $561 per night (USD)

    Expedia

    Simpson bay 3bdr \/ 3,5 bath with pools - GENERATOR

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    This beautiful 3 bed - 3,5 bath luxurious corner unit in Simpson Bay Yacht club (SBYC) is located in the best spot of th ...

    From $561 per night (USD)

    Expedia

    Details
  • Blue Sky apartment with lagoon view - GENERATOR
    From $286 per night (USD)

    VRBO

    Blue Sky apartment with lagoon view - GENERATOR

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    A modern 1 bedroom - 2 bath apt with gorgeous views over the lagoon. Wether you are visiting for a vacation or for work ...

    From $286 per night (USD)

    VRBO

    Details
  • The Luxe 1 bedroom apartment with pool - GENERATOR
    From $199 per night (USD)

    Expedia

    The Luxe 1 bedroom apartment with pool - GENERATOR

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $199 per night (USD)

    Expedia

    Details
  • Blue Sky 1 bedroom apartment in Simpson Bay - GENERATOR
    From $202 per night (USD)

    VRBO

    Blue Sky 1 bedroom apartment in Simpson Bay - GENERATOR

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $202 per night (USD)

    VRBO

    Details
  • Pelican Pearl
    From $146 per night (USD)

    Expedia

    Pelican Pearl

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This studio is the perfect place to book when you are looking for an affordable place to stay that is close to the beach ...

    From $146 per night (USD)

    Expedia

    Details
  • Garden view Simpson Bay apartment with pool - GENERATOR
    From $288 per night (USD)

    VRBO

    Garden view Simpson Bay apartment with pool - GENERATOR

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    This renovated 1 bdr apt is located in the best spot of the island.It has a gorgeous (shared) pool. It's at 5 min walkin ...

    From $288 per night (USD)

    VRBO

    Details
  • Pelican Pearl Villa - GENERATOR
    From $613 per night (USD)

    Expedia

    Pelican Pearl Villa - GENERATOR

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    Brilliant 3 bedroom villa with pool and gorgeous ocean views. Pelican is a quiet neighborhood just around the corner of ...

    From $613 per night (USD)

    Expedia

    Details
  • Flamingo Beach by Hilton: Oceanfront Resort, Pools & Spacious Studios To Relax!
    From $209 per night (USD)

    VRBO

    Flamingo Beach by Hilton: Oceanfront Resort, Pools & Spacious Studios To Relax!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Flamingo Beach, a Hilton Vacation Club, where luxury, adventure, and relaxation combine to create the ultimat ...

    From $209 per night (USD)

    VRBO

    Details
  • *New*SeaViews 4Bedroom Penthouse with Private Pool\n\n
    From $1162 per night (USD)

    Expedia

    *New*SeaViews 4Bedroom Penthouse with Private Pool\n\n

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Experience luxury and comfort in our stunning 4-bedroom penthouse, perched elegantly above the pristine Kim Sha Beach. T ...

    From $1162 per night (USD)

    Expedia

    Details
  • *NEW*SeaShores Beach front Apt With Generator\n\n
    From $299 per night (USD)

    VRBO

    *NEW*SeaShores Beach front Apt With Generator\n\n

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to your perfect getaway in Simpson Bay, Sint Maarten! This brand-new, modern 1-bedroom apartment offers an unpar ...

    From $299 per night (USD)

    VRBO

    Details
  • *NEW* SeaHeaven 3BR Beachfront Apt with Generator\n\n
    From $647 per night (USD)

    Expedia

    *NEW* SeaHeaven 3BR Beachfront Apt with Generator\n\n

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Experience the ultimate Caribbean getaway in this luxurious 3-bedroom beachfront apartment, perfectly situated on the pr ...

    From $647 per night (USD)

    Expedia

    Details
  • Ocean Edge Blue Water Beach condo
    From $301 per night (USD)

    VRBO

    Ocean Edge Blue Water Beach condo

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Absolutely gorgeous condo with a spacious bedroom and bathroom on the 2nd floor of a luxury building in the heart of Sim ...

    From $301 per night (USD)

    VRBO

    Details
  • Garden view 1bedr - pool in Simpson bay-generator
    From $222 per night (USD)

    Expedia

    Garden view 1bedr - pool in Simpson bay-generator

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    This recently refurbished apartment is centrally located in the heart of Simpson Bay. You have everything right at your ...

    From $222 per night (USD)

    Expedia

    Details
  • Pelican 2 bedr ocean view apt - shared pool
    From $318 per night (USD)

    VRBO

    Pelican 2 bedr ocean view apt - shared pool

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    This 2 story condo is gorgeously located in the residential Pelican neighborhood with stunning ocean views . This beauti ...

    From $318 per night (USD)

    VRBO

    Details
  • *NEW* SeaShells 2BR Beachfront Apartment Generator
    From $626 per night (USD)

    Expedia

    *NEW* SeaShells 2BR Beachfront Apartment Generator

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Indulge in a luxurious beachfront escape at this modern 2-bedroom apartment, ideally located in the picturesque Simpson ...

    From $626 per night (USD)

    Expedia

    Details
  • *NEW* SeaWaves Beachfront 1 Brm Apt with Generator\n\n
    From $281 per night (USD)

    VRBO

    *NEW* SeaWaves Beachfront 1 Brm Apt with Generator\n\n

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Escape to paradise in this charming 1-bedroom beachfront apartment located in the heart of Simpson Bay, Sint Maarten. Wa ...

    From $281 per night (USD)

    VRBO

    Details
  • Chic 1-bedroom with AC and WiFi in superb Colebay apartment
    From $324 per night (USD)

    Expedia

    Chic 1-bedroom with AC and WiFi in superb Colebay apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Spacious 1-bedroom apartment with rooftop access, equipped kitchen, – perfect for a small family. Located in a quiet, c ...

    From $324 per night (USD)

    Expedia

    Details
  • Unique Luxury Beachfront Penthouse - Simpson Bay
    From $654 per night (USD)

    VRBO

    Unique Luxury Beachfront Penthouse - Simpson Bay

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    Experience unparalleled luxury at Aqualina, a modern beachfront condo on stunning Simpson Bay Beach. Enjoy breathtaking ...

    From $654 per night (USD)

    VRBO

    Details
  • Tiki Top - Beachfront 3 Bedroom in Pelican Key!
    From $628 per night (USD)

    Expedia

    Tiki Top - Beachfront 3 Bedroom in Pelican Key!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    This newly refurbished modern 3 bedrooms 3-bathroom property, located in the well known Pelican Key area, offers a spaci ...

    From $628 per night (USD)

    Expedia

    Details
  • Bikini Bottom - Beach Front 1 bedroom
    From $255 per night (USD)

    VRBO

    Bikini Bottom - Beach Front 1 bedroom

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This amazing completely renovated 1 bedroom 1 bathroom unit is located in Pelican Keys, directly on the beach. This full ...

    From $255 per night (USD)

    VRBO

    Details
  • 2 Bedroom Condo with Marina Views in Simpson Bay
    From $339 per night (USD)

    Expedia

    2 Bedroom Condo with Marina Views in Simpson Bay

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    1

    About this space Experience the ultimate beachside getaway in this spacious 125 m² apartment perfect for those looking t ...

    From $339 per night (USD)

    Expedia

    Details
  • Amazing Ocean views for this Beachfront Condo in Paradise!
    From $381 per night (USD)

    VRBO

    Amazing Ocean views for this Beachfront Condo in Paradise!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Experience Cole Bay like a local in this 2-bedroom beach front condo with an unobstructed view of the ocean. The space b ...

    From $381 per night (USD)

    VRBO

    Details
  • Spacious 3-bedroom home & rooftop access Colebay
    Click For Pricing

    Expedia

    Spacious 3-bedroom home & rooftop access Colebay

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    About this space Charming Stay in a Vibrant Area! Welcome to our cozy haven, nestled in the heart of a bustling, quite n ...

    Click For Pricing

    Expedia

    Details
  • Il Punto Blu in Pelican Key by Personal Villas - Spacious and Amazing Views
    From $511 per night (USD)

    VRBO

    Il Punto Blu in Pelican Key by Personal Villas - Spacious and Amazing Views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Summary: PROMO! - Valid on all NEW BOOKINGS ONLY : * 7th Night is free traveling from April 15th to December 14th. * 1 ...

    From $511 per night (USD)

    VRBO

    Details
  • Welcome to Peace of Mind - Spacious 3 bedroom apartment in Las Brisas, Cole Bay.
    From $508 per night (USD)

    Expedia

    Welcome to Peace of Mind - Spacious 3 bedroom apartment in Las Brisas, Cole Bay.

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    COME STAY IN OUR PEACEFUL HAVEN Magnificent 3-master-bedroom apartment located near Juliana International Airport. A on ...

    From $508 per night (USD)

    Expedia

    Details
  • Beach Casa at Le Papillon; Modern Ground floor!! Generator Backup!!
    From $364 per night (USD)

    VRBO

    Beach Casa at Le Papillon; Modern Ground floor!! Generator Backup!!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Imagine rolling out of bed and finding yourself on one of the most beautiful beaches in the Caribbean! Fifty footsteps ...

    From $364 per night (USD)

    VRBO

    Details
  • COCO'S 15 Beautiful beach front 3BR condo in Simpson Bay Beach.
    From $634 per night (USD)

    Expedia

    COCO'S 15 Beautiful beach front 3BR condo in Simpson Bay Beach.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Step into your dream vacation at this stunning 3-bedroom, 2.5-bathroom beachfront Condo located in Simpson Bay Beach. ...

    From $634 per night (USD)

    Expedia

    Details
  • Palm Sea Views at La Siesta on Simpson Bay beach
    From $505 per night (USD)

    VRBO

    Palm Sea Views at La Siesta on Simpson Bay beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This amazingly remarkable apartment has tranquil Palm and Sea views from sunrise to sunset. It’s an astonishing space fo ...

    From $505 per night (USD)

    VRBO

    Details
  • Le Coeur in the heart of SimpsonBay
    From $171 per night (USD)

    Expedia

    Le Coeur in the heart of SimpsonBay

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Le Cœur De Simpson Bay offers accommodations in Simpson Bay, a 3-minute walk from Kim Sha Beach and 0.6 miles from Simps ...

    From $171 per night (USD)

    Expedia

    Details
  • Beachfront 1 Bedroom - Feet in the sand!
    From $328 per night (USD)

    VRBO

    Beachfront 1 Bedroom - Feet in the sand!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Your Caribbean vacation begins on one of the prettiest unspoiled beaches on all of St. Maarten / St. Martin. Quiet, cal ...

    From $328 per night (USD)

    VRBO

    Details
  • B221 - Beautiful 2 Bedroom - 2 Bathroom
    Click For Pricing

    Expedia

    B221 - Beautiful 2 Bedroom - 2 Bathroom

    Bedrooms:
    4
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Apartment B221 at The Hills Residence in Simpson Bay, Sint Maarten - your luxury lagoon retreat awaits! We a ...

    Click For Pricing

    Expedia

    Details
  • A124 - Wonderfull 3 bedrooms with amazing view
    Click For Pricing

    VRBO

    A124 - Wonderfull 3 bedrooms with amazing view

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to The Hills Residence, Simpson Bay, Sint Maarten! Ideally located, discover this stunning 3-bedroom apartment o ...

    Click For Pricing

    VRBO

    Details
  • B244 - Magnificent Lagoon-View Apartment with Balcony
    Click For Pricing

    Expedia

    B244 - Magnificent Lagoon-View Apartment with Balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to The Hills Residence Vacation Rentals' Apartment B244! Step into a realm of luxury and elegance with our stun ...

    Click For Pricing

    Expedia

    Details
  • B242 - Glorious Lagoon View Apartment with Balcony
    Click For Pricing

    VRBO

    B242 - Glorious Lagoon View Apartment with Balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Apartment B242 at The Hills Residence Vacation Rentals! Enter a realm of luxury and elegance with our stunnin ...

    Click For Pricing

    VRBO

    Details
  • B201 - Wonderfull Apartment with terrasse
    Click For Pricing

    Expedia

    B201 - Wonderfull Apartment with terrasse

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Apartment B201 at The Hills Residence in Simpson Bay, Sint Maarten! This beautiful two-bedroom apartment offe ...

    Click For Pricing

    Expedia

    Details
  • A123 - 1 bedroom with paradise view
    Click For Pricing

    VRBO

    A123 - 1 bedroom with paradise view

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Apartment A123 at The Hills Residence Perched in the heart of the charming and picturesque Simpson Bay in Si ...

    Click For Pricing

    VRBO

    Details
  • B236 - Homely Apartment with Balcony
    Click For Pricing

    Expedia

    B236 - Homely Apartment with Balcony

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Apartment B236 at The Hills Residence in Simpson Bay, Sint Maarten, is a true gem for travelers seeking comfort and luxu ...

    Click For Pricing

    Expedia

    Details
  • B245 - Condo with amazing view
    Click For Pricing

    VRBO

    B245 - Condo with amazing view

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    3

    Welcome to this beautiful, one bedroom apartment at The Hills Residence in Simpson Bay, Sint-Maarten! Nestled on the 4th ...

    Click For Pricing

    VRBO

    Details
  • UNBRIDLED Le Papillon: Beachfront Elegance with Backup Generator
    From $336 per night (USD)

    VRBO

    UNBRIDLED Le Papillon: Beachfront Elegance with Backup Generator

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    3

    Elegance at it's best. With easy access to the sand and sea, Unbridled, located in the new Le Papillon Complex, offers c ...

    From $336 per night (USD)

    VRBO

    Details