House holiday 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.
Holiday 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 Collectivité de Saint-Martin, St. Martin
4.88 out of 5 average rating, 32 reviewsNew "Salty Beach" 1 bdr beachfront
16–23 Nov
Home in saint-martin, St. Martin
4.96 out of 5 average rating, 49 reviewsSlowlife! Blooming Villa! Your ideal vacation home
13–20 Dec
Home in Lowlands, Sint Maarten
5.0 out of 5 average rating, 7 reviewsVilla d’artiste moderne
22–29 Jun
Home in Cupecoy, Sint Maarten
4.94 out of 5 average rating, 18 reviews"Divine In You Cupecoy" Rainbow Ocean View 2BR
26 Dec – 2 Jan
Home in Simpson Bay, Sint Maarten
4.78 out of 5 average rating, 18 reviewsStunning 7 BR Beachfront Villa w/Pool
23–30 Sep
Home in Koolbaai, Sint Maarten
5.0 out of 5 average rating, 6 reviewsBlue Palm Estate Townhouse w/ Ocean View
5–12 Oct
Home in Les Terres Basses, Guadeloupe
4.96 out of 5 average rating, 47 reviewsLuxurious bungalow with private pool
9–16 Nov
Home in Collectivité de Saint-Martin, St. Martin
5.0 out of 5 average rating, 11 reviewsAmazing Seablue villa with sea view!
12–19 Nov
Weekly house rentals
Home in Grand-Case, St. Martin
4.94 out of 5 average rating, 34 reviewsBeach house, all comfort.
6–13 Apr
Home in Philipsburg, Sint Maarten
4.96 out of 5 average rating, 27 reviews3-Bedroom Home In Philipsburg, Near the Beach
3–10 Nov
Home in Simpson Bay, Sint Maarten
4.8 out of 5 average rating, 10 reviewsSea La’Vie
18–25 Apr
Home in Upper Prince's Quarter, Sint Maarten
5.0 out of 5 average rating, 18 reviewsPeaceful secluded 2BR apt w. sunrise & ocean views
5–12 Sep
Home in Cul-de-Sac, St. Martin
5.0 out of 5 average rating, 3 reviewsVitamin Sea: Sea view, 3 beds, pool pool, sea access
27 Apr – 4 May
Home in Collectivité de Saint-Martin, St. Martin
5.0 out of 5 average rating, 7 reviewsPrestigious Villa with Breathtaking Ocean View
11–18 Oct
Home in Great Bay Beach, Sint Maarten
4.85 out of 5 average rating, 54 reviewsPrivateHome In Greatbay FreeWi-fi &Private Parking
3–10 Aug
Home in Upper Prince's Quarter, Sint Maarten
5.0 out of 5 average rating, 59 reviewsVilla Tamarind | Luxury Oasis | Ocean views | 4BDR
1–8 Sep
Private house rentals
Home in Collectivité de Saint-Martin, St. Martin
5.0 out of 5 average rating, 7 reviewsVilla near the beach
29 Dec – 5 Jan
Home in Cul-de-Sac, St. Martin
4.93 out of 5 average rating, 27 reviewsVilla Zen : confort et luxe vue mer St Martin
24–31 Mar
Home in Upper Prince's Quarter, Sint Maarten
5.0 out of 5 average rating, 3 reviews«La Vue SXM» Paradise "Villa Rosa" 5 bedroom Rate
21–28 Jan
Home in Collectivité de Saint-Martin, St. Martin
4.9 out of 5 average rating, 10 reviewsBlue Horizon villa
18–25 Mar
Home in Cul-de-Sac, St. Martin
4.93 out of 5 average rating, 15 reviewsVilla Azur Pinel Cul de Sac
26 Oct – 2 Nov
Home in Orient Bay, St. Martin
5.0 out of 5 average rating, 9 reviews3 bedrooms walking distance to Orient beach
14–21 Jan
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
25 Nov – 2 Dec
Home in Cul-de-Sac, St. Martin
4.83 out of 5 average rating, 6 reviewsVilla Essentielle, 3 bedrooms and pool!
22–29 Apr
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
$118 NZD before taxes and fees
Destinations to explore
- Orient Bay Holiday rentals
- Grand Case Holiday rentals
- Gustavia Holiday rentals
- Philipsburg Holiday rentals
- Bakers Bay Holiday rentals
- Baie Nettlé Holiday rentals
- Maho Beach Holiday rentals
- Marigot Holiday rentals
- Cul-de-Sac Holiday rentals
- Anse Marcel Holiday rentals
- Mont Vernon Holiday rentals
- San Juan Holiday rentals
- Guesthouse rentals Saint Martin
- House rentals Saint Martin
- Guesthouse rentals Sint Maarten
- House rentals Sint Maarten
- Guesthouse rentals Sint Maarten
- House rentals Sint Maarten
- House rentals Saint Barthélemy
- Serviced apartment rentals Simpson Bay
- Rentals with a patio Simpson Bay
- Pet-friendly rentals Simpson Bay
- Beachfront rentals Simpson Bay
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- Apartment rentals Simpson Bay
- Villa rentals Simpson Bay
- Rentals with beach access Simpson Bay
- Rentals with a washing machine and dryer Simpson Bay
- Rentals with outdoor seating Simpson Bay
- Fitness-friendly rentals Simpson Bay
- Smoking-friendly rentals Simpson Bay
- Beach condo rentals Simpson Bay
- Rentals with a hot tub Simpson Bay
- Monthly Rentals Simpson Bay
- Waterfront rentals Simpson Bay
- Condo rentals Simpson Bay
- Rentals with pools Simpson Bay
- Kid-friendly rentals Simpson Bay
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