
Vacation rentals in Simpson Bay
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Simpson Bay
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

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.

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. Apartment with modern amenities and comforts. A perfect vacation spot ! Back up system installed to insure electricity.

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

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

Cupecoy Garden Side 1
Delightful one bedroom appt. Fully furnished with mid century teak furniture. A spacious 70m2 space with large terrace in a mature tropical garden. A brand new fully equipped kitchen was added in October 2022. Located in trendy and safe Cupecoy. CJ1 is a quiet oasis to relax in the luxurious garden, or head for the the renowned beach of Mullet bay within a 3 minute walk. Supermarkets, gym yoga studio very close by. This is the place to be.

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.

Stunning 2 BD Ocean View - Terraces Lt Bay
Treat yourself to the utmost stylish and modern ocean view apartment located in the exclusive Little Bay Hill . This spacious environment, is designed to be enjoyed as a family, has a terrace with stunning sea views, private pool, one master suites ( Japanese king bed and a walking closet), one bedroom suite with two twin size beds ( could be converted to king size bed ) . Welcome to Terraces Little Bay !

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.

Independent apartment at the bottom of the villa – Indigo Bay
The Villa Stella apartment welcomes you in a unique setting with spectacular views of the Caribbean Sea. Located in a 24-hour secure residence, tranquility awaits. You will be just an 8-minute walk to Indigo Bay Beach and close to shops and restaurants in the Dutch side. Composed of 2 bedrooms and 2 bathrooms, you can relax in the pool/jacuzzi overlooking the bay.

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.

Top of the art penthouse
Le Papillon enjoys one of the best locations on St. Martin, with many wonderful restaurants nearby and a beach that is close to private. If you would like to rent this property for less than what is required minimum please contact us and we will try to accommodate you.
Popular amenities for Simpson Bay vacation rentals
Other great vacation rentals in Simpson Bay

Waterfront "Bonjour" Beacon Hill St Maarten

"Blue Emerald ¤ Studio" swimming pool & fitness in Maho

Ocean Dream Villa

Indigo Bay Villa Poolside - Ocean 14

Beacon Hill Hideaway: Luxury Condo in Simpson Bay

Escape at Seagrape

The Hideaway

The Lost Paradise
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $213 | $229 | $208 | $182 | $166 | $158 | $169 | $151 | $139 | $143 | $158 | $183 |
| Avg. temp | 79°F | 79°F | 79°F | 80°F | 82°F | 84°F | 84°F | 84°F | 84°F | 83°F | 82°F | 80°F |
Frequently Asked Questions
Are there family-friendly vacation rentals in Simpson Bay?
Simpson Bay has more than 150 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.
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 20 homes with a kitchen, over 30 homes with air conditioning, over 20 homes with free parking, 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 70 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 220 vacation homes with pools in Simpson Bay, available on Airbnb. Make a splash and soak up the sun in style!
Do serviced apartment rentals in Simpson Bay have a kitchen?
Absolutely! We offer over 10 serviced apartment rentals with a kitchen in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.
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 condo rentals in Simpson Bay have free parking?
Absolutely! We offer over 60 condo rentals with free parking in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Simpson Bay have wifi?
Absolutely! We offer over 150 apartment rentals with wifi in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Simpson Bay

Total vacation rentals
Explore 360 vacation rentals in Simpson Bay

Nightly prices starting at
Simpson Bay vacation rentals start at $30 per night before taxes and fees

Verified guest reviews
Over 10,970 verified reviews to help you choose

Family-friendly vacation rentals
150 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Vacation rentals with a pool
220 properties feature pools

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wi-Fi availability
350 of Simpson Bay vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Simpson Bay rentals

4.8 Average rating
Simpson Bay stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- San Juan Vacation rentals
- Carolina Vacation rentals
- Sainte-Anne Vacation rentals
- Culebra Vacation rentals
- Saint Thomas Vacation rentals
- St. Croix Vacation rentals
- Fort-de-France Vacation rentals
- Basse-Terre Island Vacation rentals
- Tortola Vacation rentals
- Le Gosier Vacation rentals
- Aguadilla Vacation rentals
- Rincón Vacation rentals
- Family-friendly rentals Simpson Bay
- Apartment rentals Simpson Bay
- Rentals with pools Simpson Bay
- Fitness-friendly rentals Simpson Bay
- Smoking-friendly rentals Simpson Bay
- Beach condo rentals Simpson Bay
- Rentals with beach access Simpson Bay
- Rentals with a hot tub Simpson Bay
- Rentals with a washer and dryer Simpson Bay
- Pet-friendly rentals Simpson Bay
- Rentals with breakfast Simpson Bay
- Condo rentals Simpson Bay
- Villa rentals Simpson Bay
- Serviced apartment rentals Simpson Bay
- Rentals with outdoor seating Simpson Bay
- House rentals Simpson Bay
- Rentals with a patio Simpson Bay
- Waterfront rentals Simpson Bay
- Beachfront rentals Simpson Bay
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes




