Vacation rentals in Simpson Bay

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Top-rated vacation rentals in Simpson Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Guesthouse in Simpson Bay, Sint Maarten
White Sands Beach Studio
This is the studio apartment you want. In a prime location in a safe neighborhood, with everything need to enjoy a perfect vacation. You have supermarkets, car rentals, restaurants, and bars within walking distance. A 30-second walk from Simpson Bay beach &6 min to Maho Beach, our world-famous airport beach. Public transportation is also available there. The apartment is recently renovated and equipped with AC, Netflix, a cozy kitchen, a magnificent garden, and a terrace overlooking the airport.
Jul 7 – 14
$94 per night
4.93 out of 5 average rating, 54 reviews
Guest favorite
Condo in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
5 star hotel luxury is yours in this modern beach home! 2 guest rooms with en-suite bathrooms and deck access. Enjoy cooking your own meals and dine inside or on the deck (or beach!). Largest deck on Simpson Bay beach has it all: huge daybed, loungers, living and dining areas for your comfort and pleasure. Unwind in the den and enjoy the big screen there or in either bedroom. Your neighbor is a boutique hotel and will gladly serve you meals and drinks right to your deck! Much more info available
Oct 31 – Nov 7
$658 per night
5.0 out of 5 average rating, 53 reviews
Guest favorite
Guesthouse in Simpson Bay
Simpson Bay Beach Apartment. Topdeck. Ocean View
Modern 1 bedroom luxury apartment detached from the main house. Marble floors throughout. All stainless appliances in a full size kitchen. Granite counter top. Free WIFI inside and on roof deck. Satellite TV. Additional Queen sofa sleeper in living room sleeps 2. Washer/Dryer. 90 steps to the beautiful Simpson Bay Beach. Private roof deck with 360° views. Beach chairs, beach towels umbrella, coolers. Parking right outside your gate. Onsite massage available. Roof deck with grill, fridge and sink
Aug 28 – Sep 4
$136 per night
4.96 out of 5 average rating, 96 reviews

Popular amenities for Simpson Bay vacation rentals

Stay near Simpson Bay's top sights

Simpson Bay Yacht Club6 locals recommend
Mary's Boon Beach Resort & Spa8 locals recommend
Kim Sha Beach10 locals recommend
Casino Royale15 locals recommend
Sunset Bar and Grill29 locals recommend
Sonesta Maho Beach Resort, Casino & Spa6 locals recommend

Other great vacation rentals in Simpson Bay

Guest favorite
Villa in Simpson Bay, Sint Maarten
Waterfront "BONJOUR" Beacon Hill St Maarten
Jun 10 – 17
$787 per night
4.98 out of 5 average rating, 40 reviews
Guest favorite
Apartment in Simpson Bay
Le Petit Paradis - Beachfront 1 Bedroom Apartment
Sep 26 – Oct 3
$193 per night
4.93 out of 5 average rating, 92 reviews
Guest favorite
Apartment in Simpson Bay
HARMONY HAVEN on Simpson Bay Beach Beacon Hill
Jun 12 – 19
$855 per night
5.0 out of 5 average rating, 44 reviews
Guest favorite
Apartment in Simpson Bay
Le Papillon -Modern, beachfront, 550sq. ft terrace
Sep 24 – Oct 1
$375 per night
5.0 out of 5 average rating, 25 reviews
Guest favorite
Apartment in Simpson Bay
Simpson Bay apartment-free parking, great location
May 23 – 30
$128 per night
4.88 out of 5 average rating, 43 reviews
Guest favorite
Condo in Simpson Bay
Beachside Escape
Sep 6 – 13
$350 per night
5.0 out of 5 average rating, 15 reviews
Guest favorite
Condo in Simpson Bay
Five Star Luxury Beachfront Condo Private Hot Tub
Sep 25 – Oct 2
$406 per night
4.96 out of 5 average rating, 71 reviews
Guest favorite
Condo in Simpson Bay, Sint Maarten
OCEAN FRONT Steps From BEACH!
Jul 14 – 21
$297 per night
5.0 out of 5 average rating, 26 reviews
Guest favorite
Apartment in Simpson Bay
Vista Blue-Newly Renovated
Oct 3 – 10
$405 per night
5.0 out of 5 average rating, 11 reviews
Guest favorite
Condo in Lowlands
Sint Maarten La Terrasse Maho
May 18 – 25
$112 per night
4.94 out of 5 average rating, 84 reviews
Guest favorite
Condo in Simpson Bay, Sint Maarten
Hamaka condo, a beachfront retreat on Simpson Bay
Jan 14 – 21
$283 per night
4.97 out of 5 average rating, 33 reviews
Guest favorite
Home in Simpson Bay
Villa Blue View .. stunning views of endless sea!
Aug 18 – 25
$675 per night
5.0 out of 5 average rating, 64 reviews

Quick stats about vacation rentals in Simpson Bay

Total rentals

330 properties

Rentals with a pool

210 properties have a pool

Pet-friendly rentals

50 properties allow pets

Family-friendly rentals

140 properties are a good fit for families

Total number of reviews

7.5K reviews

Nightly prices starting at

$30 before taxes and fees

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Simpson Bay?

    Simpson Bay has more than 140 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Simpson Bay have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Simpson Bay have a bbq area?

    Absolutely! We offer over 10 villa rentals with a bbq area in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Villa Rentals in Simpson Bay?

    Enhance your stay in our Villa Rentals with the most popular amenities: over 30 homes with wifi, over 10 homes with a bbq area, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there pet-friendly vacation rentals in Simpson Bay?

    Four-legged friends are welcome in Simpson Bay. Choose from more than 50 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Simpson Bay?

    Yes! Work meets play with ease at over 150 vacation rentals in Simpson Bay featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Simpson Bay vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 210 vacation homes with pools in Simpson Bay, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in serviced apartment rentals in Simpson Bay?

    Experience the best of Simpson Bay with our serviced apartment rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do villa rentals in Simpson Bay have wifi?

    Absolutely! We offer over 30 villa rentals with wifi in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Simpson Bay have a gym?

    Absolutely! We offer over 30 apartment rentals with a gym in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

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