Villa holiday rentals in Simpson Bay
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Top-rated villa rentals in Simpson Bay
Guests agree: these villas 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 villa rentals in Simpson Bay
Private villa rentals
Villa in Collectivity of Saint Martin, St. Martin
5.0 out of 5 average rating, 49 reviewsVilla Tibo
1–8 Dec
Villa in Les Terres Basses, St. Martin
4.99 out of 5 average rating, 77 reviews"La Maison de Vacances", Nearby Baie Longue
16–23 Nov
Villa in Koolbaai, Sint Maarten
4.85 out of 5 average rating, 53 reviewsPelican Key "Shoreline" Villa 3BD+Sofa
26 May – 2 Jun
Villa in Cay Bay, Sint Maarten
4.98 out of 5 average rating, 65 reviewsMake your dream come true!
18–25 Jan
Villa in Pelican Key, Sint Maarten
5.0 out of 5 average rating, 16 reviewsVilla Sea Forever @ Pelican Key - Paradise Awaits!
2–9 Nov
Villa in Collectivity of Saint Martin, St. Martin
5.0 out of 5 average rating, 17 reviewsBeach villa, pool, terrace, safety water tank.
14–21 Aug
Villa in Philipsburg, Sint Maarten
5.0 out of 5 average rating, 18 reviewsLuxury 6 BR. Ocean View - Villa Kimon With a Pool.
9–16 Sep
Villa in Collectivity of Saint Martin, St. Martin
4.96 out of 5 average rating, 27 reviewsVilla KALYA - Orient Bay - 3 bedrooms
11–18 Aug
Luxury villa rentals
Villa in Sint Maarten, Sint Maarten
4.93 out of 5 average rating, 15 reviewsVILLA MUMBAI - Beach Access - 3 bedrooms
9–16 Sep
Villa in Collectivity of Saint Martin, St. Martin
5.0 out of 5 average rating, 3 reviewsNouveau! Merveilleux 5 chambres, plage, piscines
19–26 Sep
Villa in Koolbaai, Sint Maarten
4.75 out of 5 average rating, 12 reviewsVilla Livity 6 Bed Luxury Sea view boutique villa
15–22 Jul
Villa in MF, St. Martin
4.96 out of 5 average rating, 51 reviewsPrivate Orient Bay Villa with Spectacular Views
10–17 Jul
Villa in Upper Prince's Quarter, Sint Maarten
4.9 out of 5 average rating, 10 reviewsVilla Seascapes, Stunning 180° Ocean view
4–11 Aug
Villa in Cul-de-Sac, St. Martin
4.95 out of 5 average rating, 41 reviewsAquaZen... 3 bedrooms, pool, private sea access
3–10 Apr
Villa in Cul-de-Sac, St. Martin
4.86 out of 5 average rating, 21 reviewsVilla Chloé SXM - Beachfront & Pinel view 🌴☀️🐬
6–13 Nov
Villa in Upper Prince's Quarter, Sint Maarten
4.78 out of 5 average rating, 40 reviews"Villa Le Point" Design/Heated Pool/ view St Barth
20–27 May
Villa rentals with a pool
Villa in Simpson Bay, Sint Maarten
4.78 out of 5 average rating, 37 reviewsVilla Sunset : very close to two beaches !
9–16 Mar
Villa in Upper Princess Quarter, Sint Maarten
5.0 out of 5 average rating, 10 reviewsLuxury Villa Twin Palms
10–17 Jul
Villa in Collectivity of Saint Martin, St. Martin
5.0 out of 5 average rating, 16 reviewsOOF architect villa sea view facing Pinel Island
16–23 Sep
Villa in Indigo Bay, Sint Maarten
4.95 out of 5 average rating, 55 reviewsVilla Ocean - Indulge Yourself in Paradise
30 Oct – 6 Nov
Villa in Sint Maarten, Sint Maarten
4.88 out of 5 average rating, 8 reviewsLa Casa al Mare: cheerful 2 bedroom villa
17–24 May
Villa in Collectivité de Saint-Martin, St. Martin
4.86 out of 5 average rating, 7 reviewsReine-de-Saba 3BR peaceful home near the beach
16–23 Jun
Villa in Saint Martin, St. Martin
5.0 out of 5 average rating, 11 reviewsVilla Véronica - Orient Bay
1–8 Sep
Villa in Collectivity of Saint Martin, St. Martin
4.93 out of 5 average rating, 15 reviewsVilla Paradis - Unbeatable views of the island.
4–11 May
Quick stats about villa rentals in Simpson Bay
Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with a pool
20 properties have a pool
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
200 reviews
Nightly prices starting at
€ 158 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
- Villa rentals Saint Martin
- Villa rentals Sint Maarten
- Villa rentals Sint Maarten
- Villa rentals Saint Barthélemy
- Apartment rentals Simpson Bay
- Rentals with pools Simpson Bay
- Beachfront rentals Simpson Bay
- House rentals Simpson Bay
- Waterfront rentals Simpson Bay
- Family-friendly rentals Simpson Bay
- Rentals with outdoor seating Simpson Bay
- Pet-friendly rentals Simpson Bay
- Rentals with beach access Simpson Bay
- Rentals with a washing machine and dryer Simpson Bay
- Smoking-friendly rentals Simpson Bay
- Rentals with a patio Simpson Bay
- Flat rentals Simpson Bay
- Fitness-friendly rentals Simpson Bay
- Serviced apartment rentals Simpson Bay
- Beach apartment rentals Simpson Bay
- Family-friendly rentals Simpson Bay
- Monthly Rentals Simpson Bay
- Rentals with a hot tub Simpson Bay
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