Best Vacation Homes in Simpson Bay
Condo
10.0(158 Reviews)
3 Bedrooms
3 Baths
6 Guests
4500 ft²
Private Pool
Oceanfront
Pool
Ocean View
R11,909/Night
7 Nights - R83,371
Apartment
10.0(2 Reviews)
4 Bedrooms
6 Baths
8 Guests
1700.7 ft²
- Oceanfront
- Pool
- Ocean View
Balcony/Terrace
R13,902/Night
7 Nights - R97,313
Condo
9.6(47 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R3,626/Night
7 Nights - R25,379
Villa
10.0(112 Reviews)
3 Bedrooms
3 Baths
6 Guests
1200 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R4,759/Night
7 Nights - R33,306
House
10.0(1 Review)
5 Bedrooms
5 Baths
10 Guests
13993.08 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R13,266/Night
7 Nights - R92,863
Apartment
10.0(88 Reviews)
3 Bedrooms
3 Baths
8 Guests
4000 ft²
Hot Tub- Ocean View
- Balcony/Terrace
View
R10,559/Night
7 Nights - R73,912
Condo
10.0(80 Reviews)
2 Bedrooms
2 Baths
4 Guests
3067 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
R9,341/Night
7 Nights - R65,392
Villa
10.0(75 Reviews)
3 Bedrooms
3 Baths
6 Guests
3000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R10,645/Night
7 Nights - R74,505
Simpson Bay Luxury Rentals
Villa
4 Bedrooms
4 Baths
8 Guests
12917 ft²
- Ocean View
- Balcony/Terrace
- View
Kitchen
R95,726/Night
7 Nights - R670,084
Villa
7 Bedrooms
8 Baths
14 Guests
Fireplace/Heating
Air Conditioner
Internet
Child Friendly
R95,583/Night
7 Nights - R669,079
House
10.0(1 Review)
6 Bedrooms
7 Baths
14 Guests
6000 ft²
- Balcony/Terrace
- Kitchen
Parking- Air Conditioner
R82,710/Night
7 Nights - R578,967
Villa
8 Bedrooms
9 Baths
16 Guests
5995.5 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R57,829/Night
7 Nights - R404,809
R54,458/Night
7 Nights - R381,210
Villa
6 Bedrooms
5 Baths
12 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
R37,069/Night
7 Nights - R259,490
Villa
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
R35,172/Night
7 Nights - R246,208
Villa
10.0(5 Reviews)
5 Bedrooms
5 Baths
10 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R32,860/Night
7 Nights - R230,025
Simpson Bay Pet Friendly Vacation Rentals
Villa
10.0(44 Reviews)
3 Bedrooms
2 Baths
6 Guests
2153 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R12,426/Night
7 Nights - R86,980
Apartment
10.0(1 Review)
1 Bedroom
2 Baths
6 Guests
1700.7 ft²
Pet Friendly- Parking
- Air Conditioner
- Internet
R7,862/Night
7 Nights - R55,042
Villa
10.0(19 Reviews)
4 Bedrooms
4 Baths
8 Guests
2691 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R14,337/Night
7 Nights - R100,362
Apartment
9.8(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
1603.82 ft²
Private Beach- Oceanfront
Spa- Pool
R8,940/Night
7 Nights - R62,590
Villa
10.0(13 Reviews)
3 Bedrooms
3 Baths
6 Guests
2200 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R12,343/Night
7 Nights - R86,403
House
10.0(6 Reviews)
4 Bedrooms
4 Baths
6 Guests
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
R10,712/Night
7 Nights - R74,983
Condo
10.0(4 Reviews)
1 Bedroom
1 Bath
3 Guests
500 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R3,057/Night
7 Nights - R21,407
Villa
10.0(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R14,359/Night
7 Nights - R100,510
Simpson Bay Large Vacation Homes
Villa
10.0(61 Reviews)
4 Bedrooms
3 Baths
8 Guests
4306 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R30,867/Night
7 Nights - R216,066
Villa
10.0(1 Review)
1 Bedroom
3 Baths
8 Guests
1700.7 ft²
- Pool
- Balcony/Terrace
- View
- Parking
R9,419/Night
7 Nights - R65,936
R21,234/Night
7 Nights - R148,631
Villa
10.0(52 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
R4,876/Night
7 Nights - R34,130
Apartment
9.3(168 Reviews)
12 Bedrooms
10 Baths
30 Guests
613.54 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R2,781/Night
7 Nights - R19,463
Villa
10.0(27 Reviews)
8 Bedrooms
7 Baths
18 Guests
5597 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R14,749/Night
7 Nights - R103,246
Villa
10.0(14 Reviews)
6 Bedrooms
6 Baths
12 Guests
2150 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R32,267/Night
7 Nights - R225,872
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
5 Guests
2200 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R5,718/Night
7 Nights - R40,029
Why Choose Rent By Owner for your Simpson Bay Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Simpson Bay Vacation Rentals
Where are the best neighborhoods to stay in Simpson Bay?
When choosing where to stay in Simpson Bay, Sint Maarten, you'll discover a vibrant neighborhood that offers a perfect blend of lively atmosphere and relaxed comfort. This area is renowned for its picturesque waterfront views and easy access to local dining, shopping, and entertainment options. Whether you're seeking a lively hub or a peaceful retreat, the neighborhoods here provide a range of options for your ideal vacation rental experience. Each area delivers the convenience and charm that make Simpson Bay a sought-after destination for travelers looking to explore Sint Maarten's unique Caribbean appeal.
Pelican Key
Enjoy a tranquil retreat in Pelican Key, where your choice of vacation rentals offers easy access to the scenic beauty and peaceful ambiance of this part of the region. Here, you can relax in comfort while being close to local amenities and stunning waterfront views.
View 97+ Rentals in Pelican KeyMaho
Experience vibrant energy and convenience when staying near Maho, known for its lively atmosphere and proximity to popular attractions. This destination provides an ideal base for exploring the area's renowned nightlife and breathtaking coastal scenery.
View 431+ Rentals in MahoBest Times to Visit Simpson Bay
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you can fully enjoy the region’s vibrant atmosphere and ideal weather conditions, making your vacation in Simpson Bay, Sint Maarten, an unforgettable experience.
Peak Season Highlights
December to April
During these months, you can enjoy ideal weather conditions with warm temperatures and low humidity, making it perfect for outdoor activities and beach lounging in this Caribbean destination.
Average Temperature Daytime: 28°C (82°F) - Nighttime: 22°C (72°F)
June to August
This period marks the peak of summer, where the region experiences lively events and vibrant local culture, attracting visitors seeking sun-soaked days in this tropical paradise.
Average Temperature Daytime: 30°C (86°F) - Nighttime: 24°C (75°F)
Off-Season Highlights
May and November
These shoulder months offer fewer crowds and more affordable rates while still providing pleasant weather for exploring and relaxing in this popular Caribbean area.
Average Temperature Daytime: 27°C (81°F) - Nighttime: 21°C (70°F)
September to October
Typically the off-peak period due to higher chances of rain and the tail end of the hurricane season, making it a quieter time to enjoy peace and tranquility here.
Average Temperature Daytime: 29°C (84°F) - Nighttime: 23°C (73°F)
Weekly Weather Forecast for Simpson Bay
How to Book Your Simpson Bay Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Simpson Bay
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor pool to relax and unwind in the warm Caribbean sun.
- Take advantage of spacious patios or decks for outdoor dining and entertaining.
- Make the most of lush gardens or landscaped yards surrounding your rental property.
- Benefit from direct access to scenic beaches or waterfront areas nearby.
- Utilize outdoor grilling facilities to prepare delicious meals with local flavors.
- Relax in shaded lounge areas or cabanas designed for comfort and privacy.
- Explore outdoor recreational options like tennis courts or hiking trails within close proximity.
Top Attractions Around Simpson Bay
What attractions are nearby?
In this vibrant area, you can enjoy a variety of activities from relaxing on beautiful beaches to exploring local dining and lively nightlife, all within easy reach when staying at your chosen vacation rentals in Simpson Bay, Sint Maarten.
Family Activities
- Beach Days at Simpson Bay Beach: Enjoy building sandcastles, swimming, and relaxing on the soft sands right along this popular stretch here in the region.
- Snorkeling Adventures: Explore the vibrant marine life just off the coast, making it a fun and educational activity suitable for all ages.
- Boat Tours and Water Sports: Experience family-friendly boat excursions or try water sports like paddleboarding and kayaking for an exciting day on the water.
- Visit the Local Marina and Dining Spots: Discover charming waterfront restaurants and watch boats come and go, offering a delightful way to end your day together.
Adult Activities
- Sailing and Water Sports: You can enjoy the vibrant sailing scene here, with opportunities for paddleboarding, jet skiing, and snorkeling right off the coast of this lively destination.
- Relaxing on the Beach: Spend your days unwinding on the pristine beaches nearby, soaking up the sun and taking in the stunning sea views that make this area a perfect escape.
- Dining at Local Restaurants: Experience the region’s rich culinary scene through its diverse restaurants, offering delicious local flavors and international cuisine just steps from your vacation rental.
- Exploring Marine Parks and Nature Reserves: Discover the area's natural beauty by visiting marine parks and protected reserves ideal for kayaking, bird watching, and enjoying scenic coastal walks.
Other Places to Stay in Simpson Bay
Kim Sha Beach
Flamingo Beach
Simpson Bay Beach
Hollywood Casino
Lay Bay Beach
Dunes Casino
Pelican Key
Beacon Hill
Simpson Bay Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Experiences: Take advantage of the area’s vibrant culinary scene to enjoy authentic Caribbean flavors that perfectly complement your stay in Simpson Bay.
- Plan Water-Based Activities: Make the most of the region's stunning beaches and calm waters by scheduling snorkeling, sailing, or paddleboarding excursions during your visit.
- Choose the Right Accommodation: Select a well-reviewed vacation rental in Simpson Bay that offers convenient access to popular spots and comfort for a relaxing stay.
- Visit During Off-Peak Seasons: Consider traveling during less busy times to enjoy quieter beaches and better rates, enhancing your overall experience here.
Transportation Options
- Rental Cars: You can rent a car to explore the area at your own pace, with several local agencies offering convenient options for travelers staying in Simpson Bay.
- Taxis and Ride-Sharing Services: Taxis and ride-sharing options like Uber provide reliable transportation around this destination, making it easy to get to popular spots and back to your rental seamlessly.
- Public Buses: The regional public bus system offers an affordable way to navigate the region, connecting you to key areas and attractions near Simpson Bay.
- Boat Transfers and Ferries: Water-based transportation such as boat transfers are available for scenic trips across the region's waters, enriching your experience here with beautiful maritime views.
Local Customs Options
- Local Greetings and Politeness: Embrace the warm and friendly way residents of this Caribbean destination greet each other with handshakes and bright smiles, reflecting the welcoming spirit of the area.
- Celebration of Carnival and Festivals: Participate in vibrant local celebrations that showcase colorful costumes, lively music, and traditional dances unique to this region's cultural heritage.
- Respect for Marine Etiquette: When enjoying the area's stunning beaches and waters, observe customary marine practices such as snorkeling and boating etiquette to preserve the natural beauty.
- Use of Local Language and Phrases: While English is widely spoken here, learning simple Creole phrases can enrich your interactions and demonstrate appreciation for the local culture.
Frequently Asked Questions About Simpson Bay?
1. What are the top vacation rentals in Simpson Bay?
There are a lot of options in Simpson Bay. If you plan on staying in the Simpson Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Simpson Bay:
- Anchor House - Direct Oceanfront - Luxury & Modern Style
- 3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! nRates start at 250/nt!
- Top of the art penthouse on the beach - 4000 sq. ft of luxury
- LUXURIOUS BEACH FRONT UNIT - SPECTACULAR OCEAN VIEWS.
- WOW! WOW! WOW!, NEW VILLA LIBRE` STUNNING INSIDE AND OUT!
- ALMA - DIRECT BEACH ACCESS 4 BR VILLA
- The Penthouse at LaSiesta nnStunning views in luxurious surroundings!
- Popular Beachfront Condo directly on Simpson Bay beach in St. Maarten
- Simpson Bay Beach Modern Apartment. Roof deck Ocean Views WIFI Satellite TV.
- Oceanfront villa with breathtaking views–2BR/2BA in Pelican Key, Simpson Bay
2. How many vacation rentals have private pools in Simpson Bay?
There are 117 vacation rentals with private pools near Simpson Bay. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Simpson Bay are best for families?
If you are looking for a family-friendly vacation home in Simpson Bay, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Simpson Bay:
4. How many Rentbyowner vacation rentals are available in Simpson Bay?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 702 in the Simpson Bay area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Simpson Bay.
5. What is the cancellation policy for vacation rentals in Simpson Bay?
The cancellation policy varies by listing, so it’s important to review the specific terms outlined in the rental agreement or contact the property owner directly for detailed information.
6. Are there any house rules I should be aware of when booking a vacation rental in this area?
Yes, each property may have unique house rules related to check-in times, smoking, pets, and other guidelines. These details are typically provided in the listing and should be reviewed before confirming your reservation.
7. How do I secure my reservation in Simpson Bay without any issues?
Reservations can be secured through the host’s booking process, which often includes a deposit or full payment. It’s recommended to communicate with the property owner if you have any questions or special requests prior to booking.
8. What amenities can I expect from vacation rentals in this destination?
Most listings offer essential amenities such as Wi-Fi, air conditioning, and kitchen facilities, but it’s best to check each property’s description for specific features and additional comforts included.
9. Is there a recommended time to book a vacation rental to ensure availability in the region?
Booking well in advance during peak travel seasons is advisable to secure your preferred property. The availability can vary, so early planning helps to find the best options here.
Simpson Bay Top Rated Vacation Rentals
Condo
10.0(60 Reviews)
3 Bedrooms
3 Baths
6 Guests
2280 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R10,091/Night
7 Nights - R70,632
Condo
10.0(59 Reviews)
2 Bedrooms
2 Baths
4 Guests
1680 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R8,263/Night
7 Nights - R57,844
Condo
10.0(36 Reviews)
3 Bedrooms
3 Baths
6 Guests
2800 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
R11,776/Night
7 Nights - R82,432
Condo
10.0(36 Reviews)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
R8,242/Night
7 Nights - R57,696
Condo
10.0(31 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R5,389/Night
7 Nights - R37,722
Condo
10.0(29 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
R9,426/Night
7 Nights - R65,985
Condo
10.0(29 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
R3,637/Night
7 Nights - R25,461
Condo
10.0(26 Reviews)
3 Bedrooms
4 Baths
6 Guests
2000 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R7,654/Night
7 Nights - R53,576
