House vacation rentals in Simpson Bay
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Top-rated house rentals in Simpson Bay
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Simpson Bay house rentals
House rentals with a pool
Home in Sint Maarten, Sint Maarten
4.76 out of 5 average rating, 89 reviewsStunning 5 bedroom villa with 180° ocean view !
Dec 27 – Jan 3
Home in saint-martin, St. Martin
4.96 out of 5 average rating, 49 reviewsSlowlife! Blooming Villa! Your ideal vacation home
Jan 8 – 15
Home in Collectivity of Saint Martin, St. Martin
4.97 out of 5 average rating, 39 reviewsNew! On La Plage Villa 2ch sea view pool
Apr 16 – 23
Home in Cole Bay, Sint Maarten
4.79 out of 5 average rating, 39 reviewsSaint-Tropez With Ocean View - Boat Charter
Sep 19 – 26
Home in Cupecoy, Sint Maarten
4.94 out of 5 average rating, 18 reviews"Divine In You Cupecoy" Rainbow Ocean View 2BR
Dec 9 – 16
Home in Pelican, Sint Maarten
5.0 out of 5 average rating, 3 reviewsVilla Ladida-Luxurious villa with magnificent view
May 15 – 22
Home in Lowlands, Sint Maarten
5.0 out of 5 average rating, 7 reviewsModern artist villa
Jul 17 – 24
Home in Simpson Bay, Sint Maarten
4.78 out of 5 average rating, 18 reviewsStunning 7 BR Beachfront Villa w/Pool
Oct 28 – Nov 4
Weekly house rentals
Home in Philipsburg, Sint Maarten
4.96 out of 5 average rating, 27 reviews3-Bedroom Home In Philipsburg, Near the Beach
Jun 28 – Jul 5
Home in Simpson Bay, Sint Maarten
4.8 out of 5 average rating, 10 reviewsSea La’Vie
Jul 15 – 22
Home in Upper Prince's Quarter, Sint Maarten
5.0 out of 5 average rating, 19 reviewsPeaceful secluded 2BR apt w. sunrise & ocean views
Oct 15 – 22
Home in Koolbaai, Sint Maarten
5.0 out of 5 average rating, 6 reviewsBlue Palm Estate Townhouse w/ Ocean View
Nov 17 – 24
Home in Upper Prince's Quarter, Sint Maarten
5.0 out of 5 average rating, 60 reviewsVilla Tamarind | Luxury Oasis | Ocean views | 4BDR
Oct 3 – 10
Home in Upper Prince's Quarter, Sint Maarten
5.0 out of 5 average rating, 4 reviews«La Vue SXM» Paradise "Villa Rosa" 5 bedroom Rate
Aug 5 – 12
Home in Sint Maarten lowlands Maho , Sint Maarten
4.76 out of 5 average rating, 54 reviewsVilla Blue Lagoon SXM
Oct 8 – 15
Home in Collectivité de Saint-Martin, St. Martin
5.0 out of 5 average rating, 7 reviewsPrestigious Villa with Breathtaking Ocean View
Jun 15 – 22
Private house rentals
Home in Great Bay Beach, Sint Maarten
4.85 out of 5 average rating, 54 reviewsPrivateHome In Greatbay FreeWi-fi &Private Parking
Feb 15 – 22
Home in Cul-de-Sac, St. Martin
4.93 out of 5 average rating, 28 reviewsVilla Zen : confort et luxe vue mer St Martin
Mar 15 – 22
Home in Upper Prince's Quarter, Sint Maarten
5.0 out of 5 average rating, 7 reviewsTropical Oasis/Million $ Views!
Apr 2 – 9
Home in Caribbean, Sint Maarten
4.88 out of 5 average rating, 50 reviewsPelican Paradise
Jan 10 – 17
Home in Grandes Cayes, St. Martin
4.94 out of 5 average rating, 16 reviewsVilla Red Rock: 3 bedrooms & private pool
Mar 21 – 28
Home in Collectivité de Saint-Martin, St. Martin
4.89 out of 5 average rating, 9 reviewsNEW House 2 bathrooms, 3 terraces and ocean view
Mar 2 – 9
Home in Collectivité de Saint-Martin, St. Martin
4.91 out of 5 average rating, 11 reviewsVilla Louisiana
Aug 8 – 15
Home in Orient Bay, St. Martin
5.0 out of 5 average rating, 9 reviews3 bedrooms walking distance to Orient beach
Sep 19 – 26
Quick stats about house rentals in Simpson Bay
Total rentals
20 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
460 reviews
Nightly prices starting at
$70 before taxes and fees
Destinations to explore
- Orient Bay Vacation rentals
- Grand Case Vacation rentals
- Gustavia Vacation rentals
- Philipsburg Vacation rentals
- Bakers Bay Vacation rentals
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- Maho Beach Vacation rentals
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- Cul-de-Sac Vacation rentals
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- House rentals Sint Maarten
- Guesthouse rentals Sint Maarten
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- Rentals with beach access Simpson Bay
- Pet-friendly rentals Simpson Bay
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- Rentals with outdoor seating Simpson Bay
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- Rentals with a hot tub Simpson Bay
- Rentals with a patio Simpson Bay
- Rentals with pools Simpson Bay
- Villa rentals Simpson Bay
- Rentals with a washer and dryer Simpson Bay
- Apartment rentals Simpson Bay
- Fitness-friendly rentals Simpson Bay
- Monthly Rentals Simpson Bay
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