Vacation rentals in Simpson Bay

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Top-rated vacation rentals in Simpson Bay

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Superhost

Guesthouse in Simpson Bay, Sint Maarten

4.93 out of 5 average rating, 57 reviews

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.

Aug 27 – Sep 3

$94 per night

Guest favorite

Apartment in Simpson Bay

4.85 out of 5 average rating, 20 reviews

NEW Double S Suite

In the heart of Simpsonbay, close to bars, restaurants, and the beach, you'll find this stylish and newly constructed apartment. Only 4 min from the airport and have double-paned windows to keep out the noise. The apartment has a queen-size bed, free Wi-Fi, and 2 flat-screen TVs; it's also only 2 minutes from Simpson bay beach, known for its clear water. This chic grey and white studio comes with all the amenities necessary for a restful and romantic beach getaway in the middle of St. Maarten.

Mar 10 – 17

$111 per night

Superhost

Apartment in Simpson Bay

4.87 out of 5 average rating, 177 reviews

Apartment on the beach

Let this tranquil, centrally located, 1 bedroom apartment become your home away from home. This beachfront property is located on the BEST and WIDEST stretch of Simpson Bay beach with gentle waves and no rocks, which makes it a perfect spot for swimming. Although this property is tucked away, and there are never many people on this part of the beach, it is in a heart of Simposn Bay. Simpson Bay beach offers one of the longest stretches of uninterrupted sandy, white coastline on Sint Maarten.

Sep 30 – Oct 7

$138 per night

Guest favorite

Apartment in Simpson Bay

5.0 out of 5 average rating, 170 reviews

The Beach House Apartment

A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more

Oct 3 – 10

$271 per night

Guest favorite

Condo in Maho

4.88 out of 5 average rating, 168 reviews

2 Min to Beach/Exclusive Rooftop Jacuzzi, Pool+Bar

This charming, cozy, and tranquil tropical nest is located where all the action is! The golf course, iconic bars, the unprecedented landing strip, the popular Maho and Mullet bay beaches, Maho market with daily fresh take away breakfast/lunch buffets and a divine selection of exotic restaurants are all in walking distance! If you wish to just lounge and relax by the pool, jacuzzi, and private gazebo bar or enjoy the nightlife; it’s all readily available, at your fingertips!

May 14 – 21

$112 per night

Superhost

Apartment in Simpson Bay

4.93 out of 5 average rating, 98 reviews

Le Petit Paradis - Beachfront 1 Bedroom Apartment

"Petit Paradis" (Little Paradise), a genuine Caribbean getaway. A spacious one-bedroom Beachfront apartment right on beautiful Simpson Bay Beach and in the center of all the happenings. Relaxing terrace, five stairs away from the Beach, and within walking distance from great Restaurants, Nightlife, Activities, and Watersports. This modern, fully furnished, and equipped apartment has everything you need for a dream vacation, Hope to invite you soon in our Paradise, Elodie

Aug 30 – Sep 6

$187 per night

Guest favorite

Apartment in Simpson Bay

4.97 out of 5 average rating, 154 reviews

Lilly's Beach

This is a very SPECIAL SMAll RESIDENCE known as Ocean Edge . Beach Front located directly on beautiful Simpson Bay Beach! Enjoys one of the best locations on the island . Panoramic sea views with your toes in the sand and balmy Caribbean breezes. A clear turquoise sea dazzles in tropical sun, powdery white sands stretching along one of St. Maarten's longest beaches. New totally refurbished modern apartment with modern amenities and comforts. A perfect vacation spot !

Jan 29 – Feb 5

$280 per night

Guest favorite

Apartment in Simpson Bay

4.98 out of 5 average rating, 64 reviews

SECOND HOME Beach Apartment

Our SECOND HOME beach apartment is truly designed as a second home. A place to where we can escape from the world and reconnect with ourselves. It has all the amenities one needs, like a comfortable living room, high quality mattress and linens, cozy sitting on the terrace to watch the sunset, fully equipped kitchen, and airconditioning in each room. It is located just two houses away from the beautiful white sand beach of Simpson Bay.

Jul 28 – Aug 4

$104 per night

Guest favorite

Apartment in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 105 reviews

Simpson bay beach, spacious, beautiful views!

Amazing spacious 3 bedroom, 2 bathroom apartment with awesome location in the heart of Simpson Bay. location, location, location in the middle of it all. Right across the 2.5 mile beautiful Simpson Bay Beach. All the beach necessities are there to enjoy, beachchairs, snorkeling gear, fishing rod and even 2 kayaks. You can walk to many nearby restaurants, grocery stores and other shops. Public transportation is also steps away.

May 28 – Jun 4

$210 per night

Superhost

Guest suite in Simpson Bay

4.82 out of 5 average rating, 184 reviews

MYRIEL — Perfect Location/Nightlife/Beach

This Duplex 1 Bed apt is all about LOCATION. Nicest/Safest area of St.Maarten. Few steps from Simpson beach, Maho Beach nightlife/restaurants. 5-10mn walk on the beach to Karakter Beach bar and Sunset Beach Café. Very clean. Perfect for single or couple. Sleep up to 3 with sofa bed.. Private entrance, full kitchen, Stove, Microwave, A/C, WIFI, Linens and towels.

Jul 22 – 29

$68 per night

Guest favorite

Apartment in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 27 reviews

Ocean's Edge

Pure white sand and turquoise waters are steps from this beautiful Ocean's Edge apartment with extraordinary views of the Caribbean sea. Located on Simpson Bay beach - one of the longest and most private beaches on the island, your seaside oasis has been refurbished throughout to provide comfort and privacy for the ultimate vacation experience.

Mar 29 – Apr 5

$170 per night

Guest favorite

Villa in Philipsburg

4.99 out of 5 average rating, 221 reviews

Villa Dream View Belair Sint Maarten SXM

Embrace the tranquility in a friendly tropical caribbean modern designed private villa with spacious rooms that are sure to keep you comfortable and feeling at home. Enjoy the sunny day with infinity pool overlooking caribbean sea or enjoy the sea view while watching the sailing huge cruise ships.

Oct 18 – 25

$399 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Simpson Bay vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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

Apartment in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 24 reviews

The luxe 1 bedroom apt with pool

Sep 3 – 10

$137 per night

Guest favorite

Apartment in Simpson Bay

5.0 out of 5 average rating, 44 reviews

HARMONY HAVEN on Simpson Bay Beach Beacon Hill

Oct 14 – 21

$679 per night

Guest favorite

Home in Simpson Bay

5.0 out of 5 average rating, 67 reviews

Villa Blue View .. stunning views of endless sea!

Jun 25 – Jul 2

$675 per night

Guest favorite

Apartment in Lowlands, Sint Maarten

4.83 out of 5 average rating, 18 reviews

The Emerald at Maho

Aug 27 – Sep 3

$79 per night

Guest favorite

Guesthouse in Simpson Bay

4.96 out of 5 average rating, 96 reviews

Simpson Bay Beach Apartment. Topdeck. Ocean View

May 14 – 21

$122 per night

Superhost

Apartment in Lowlands

5.0 out of 5 average rating, 8 reviews

Emerald Apt at Maho Beach

Jun 1 – 8

$90 per night

Superhost

Apartment in Lowlands, Sint Maarten

4.93 out of 5 average rating, 15 reviews

A Maho Studio

Sep 18 – 25

$72 per night

Guest favorite

Apartment in Simpson Bay, Sint Maarten

4.96 out of 5 average rating, 93 reviews

Top of the art penthouse

Oct 7 – 14

$542 per night

Show all

Quick stats about vacation rentals in Simpson Bay

Total rentals	320 properties
Rentals with a pool	200 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	8.2K 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 Apartment Rentals in Simpson Bay?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a bbq area, over 30 homes with a gym, over 100 homes with air conditioning, over 100 homes with wifi, 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 140 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 200 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 house rentals in Simpson Bay?
Experience the best of Simpson Bay with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Simpson Bay have wifi?
Absolutely! We offer over 100 apartment rentals with wifi in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Simpson Bay have a gym?
Absolutely! We offer over 50 condo rentals with a gym in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Simpson Bay

Top-rated vacation rentals in Simpson Bay

Vacation rentals for every style

Apartments

Villas

Houses

Popular amenities for Simpson Bay vacation rentals

Stay near Simpson Bay's top sights

Other great vacation rentals in Simpson Bay

Apartment in Simpson Bay, Sint Maarten

Apartment in Simpson Bay

Home in Simpson Bay

Apartment in Lowlands, Sint Maarten

Guesthouse in Simpson Bay

Apartment in Lowlands

Apartment in Lowlands, Sint Maarten

Apartment in Simpson Bay, Sint Maarten

Quick stats about vacation rentals in Simpson Bay

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there family-friendly vacation rentals in Simpson Bay?

Do house rentals in Simpson Bay have air conditioning?

Do villa rentals in Simpson Bay have a bbq area?

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

Are there pet-friendly vacation rentals in Simpson Bay?

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

Are there Simpson Bay vacation rentals on Airbnb with pools?

How much does it cost to stay in house rentals in Simpson Bay?

Do apartment rentals in Simpson Bay have wifi?

Do condo rentals in Simpson Bay have a gym?

Destinations to explore