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 house rentals in Simpson Bay
House rentals with a pool
Home in Cul de Sac, St. Martin
5.0 out of 5 average rating, 48 reviewsvilla koala saint martin un petit coin de paradis
11–18 Oct
Home in Cole Bay, Sint Maarten
4.89 out of 5 average rating, 38 reviewsSaint-Tropez With Ocean View - Boat Charter
5–12 Sep
Home in Cupecoy, Sint Maarten
4.94 out of 5 average rating, 18 reviews"Divine In You Cupecoy" Rainbow Ocean View 2BR
6–13 Dec
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 reviewsModern artist villa
17–24 Jul
Home in Les Terres Basses, Guadeloupe
4.96 out of 5 average rating, 48 reviewsLuxurious bungalow with private pool
14–21 May
Home in Collectivité de Saint-Martin, St. Martin
5.0 out of 5 average rating, 11 reviewsAmazing Seablue villa with sea view!
9–16 Apr
Home in Simpson Bay, Sint Maarten
4.78 out of 5 average rating, 18 reviewsStunning 7 BR Beachfront Villa w/Pool
23–30 Sep
Weekly house rentals
Home in Simpson Bay, Sint Maarten
5.0 out of 5 average rating, 10 reviewsBeach cottage in Simpson bay
9–16 Dec
Home in Grand-Case, St. Martin
4.94 out of 5 average rating, 35 reviewsBeach house, all comfort.
16–23 Mar
Home in Simpson Bay, Sint Maarten
4.8 out of 5 average rating, 10 reviewsSea La’Vie
23–30 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
29 Aug – 5 Sep
Home in Collectivité de Saint-Martin, St. Martin
5.0 out of 5 average rating, 7 reviewsPrestigious Villa with Breathtaking Ocean View
12–19 Jun
Home in Upper Prince's Quarter, Sint Maarten
5.0 out of 5 average rating, 59 reviewsVilla Tamarind | Luxury Oasis | Ocean views | 4BDR
5–12 Sep
Home in Collectivité de Saint-Martin, St. Martin
5.0 out of 5 average rating, 7 reviewsVilla near the beach
5–12 Mar
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
6–13 Aug
Private house rentals
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 Sep – 2 Oct
Home in Upper Prince's Quarter, Sint Maarten
5.0 out of 5 average rating, 7 reviewsTropical Oasis/Million $ Views!
7–14 Apr
Home in Caribbean, Sint Maarten
4.88 out of 5 average rating, 50 reviewsPelican Paradise
7–14 Jan
Home in Cul-de-Sac, St. Martin
4.93 out of 5 average rating, 28 reviewsVilla Zen : confort et luxe vue mer St Martin
15–22 Feb
Home in Orient Bay, St. Martin
5.0 out of 5 average rating, 9 reviews3 bedrooms walking distance to Orient beach
22–29 Apr
Home in Grandes Cayes, St. Martin
4.94 out of 5 average rating, 16 reviewsVilla Red Rock: 3 bedrooms & private pool
28 Nov – 5 Dec
Home in Orient Bay, St. Martin
5.0 out of 5 average rating, 12 reviewsAquamarine, lovely 2 bedroom house with private pool!
10–17 May
Home in Cul-de-Sac, St. Martin
4.93 out of 5 average rating, 15 reviewsVilla Azur Pinel Cul de Sac
16–23 Jul
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
€ 65 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
- Mont Vernon Holiday rentals
- Anse Marcel Holiday rentals
- San Juan Holiday rentals
- Guest house rentals Saint Martin
- House rentals Saint Martin
- Guest house rentals Sint Maarten
- House rentals Sint Maarten
- Guest house rentals Sint Maarten
- House rentals Sint Maarten
- House rentals Saint Barthélemy
- Apartment rentals Simpson Bay
- Rentals with pools Simpson Bay
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- Family-friendly rentals Simpson Bay
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- Pet-friendly rentals Simpson Bay
- Rentals with beach access Simpson Bay
- Rentals with a washing machine and dryer Simpson Bay
- Villa rentals Simpson Bay
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- Monthly Rentals Simpson Bay
- Rentals with a hot tub Simpson Bay
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