Best Vacation Homes in Simpson Bay
Villa
10.0(133 Reviews)
1 Bedroom
1 Bath
2 Guests
900 ft²
Private Pool
Oceanfront
Pool
Ocean View
AU $428/Night
7 Nights - AU $2,999
House
10.0(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
861.11 ft²
- Oceanfront
- Pool
- Ocean View
Balcony/Terrace
AU $354/Night
7 Nights - AU $2,476
Hotel
9.4(237 Reviews)
1 Bath
Spa- Pool
- Ocean View
- Balcony/Terrace
AU $1,365/Night
7 Nights - AU $9,553
Condo
10.0(90 Reviews)
1 Bedroom
2 Baths
4 Guests
753 ft²
- Oceanfront
Fireplace/Heating- Pool
- Ocean View
AU $350/Night
7 Nights - AU $2,452
Villa
10.0(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1184.03 ft²
Private Beach- Oceanfront
- Pool
- Ocean View
AU $455/Night
7 Nights - AU $3,183
Villa
10.0(72 Reviews)
3 Bedrooms
3 Baths
6 Guests
1918 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
AU $641/Night
7 Nights - AU $4,488
House
10.0(57 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Oceanfront
Hot Tub- Fireplace/Heating
AU $1,973/Night
7 Nights - AU $13,814
Villa
10.0(53 Reviews)
5 Bedrooms
5 Baths
12 Guests
7535 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
AU $1,698/Night
7 Nights - AU $11,883
Simpson Bay Luxury Rentals
Villa
7 Bedrooms
7 Baths
14 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Spa
AU $12,859/Night
7 Nights - AU $90,015
Villa
10 Bedrooms
10 Baths
20 Guests
10000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
AU $11,173/Night
7 Nights - AU $78,212
AU $10,873/Night
7 Nights - AU $76,110
Villa
6 Bedrooms
6 Baths
14 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
AU $10,676/Night
7 Nights - AU $74,733
Villa
6 Bedrooms
6 Baths
12 Guests
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
AU $10,557/Night
7 Nights - AU $73,903
Villa
10 Bedrooms
3 Baths
20 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
AU $10,482/Night
7 Nights - AU $73,373
Villa
6 Bedrooms
7 Baths
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
AU $10,301/Night
7 Nights - AU $72,106
Villa
10.0(1 Review)
6 Bedrooms
5 Baths
12 Guests
8000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
AU $10,250/Night
7 Nights - AU $71,753
Simpson Bay Pet Friendly Vacation Rentals
Villa
10.0(50 Reviews)
2 Bedrooms
2 Baths
4 Guests
807 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
AU $267/Night
7 Nights - AU $1,871
Apartment
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
753.47 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
AU $282/Night
7 Nights - AU $1,976
House
10.0(32 Reviews)
7 Bedrooms
5 Baths
13 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
AU $2,301/Night
7 Nights - AU $16,104
Villa
10.0(1 Review)
6 Bedrooms
7 Baths
14 Guests
5381.95 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
AU $2,390/Night
7 Nights - AU $16,730
Apartment
10.0(23 Reviews)
1 Bedroom
1 Bath
4 Guests
463 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
AU $219/Night
7 Nights - AU $1,534
House
10.0(21 Reviews)
3 Bedrooms
1 Bath
4 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
AU $818/Night
7 Nights - AU $5,727
Villa
10.0(18 Reviews)
7 Bedrooms
7 Baths
14 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $4,524/Night
7 Nights - AU $31,666
House
10.0(15 Reviews)
6 Bedrooms
7 Baths
12 Guests
5382 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
AU $3,754/Night
7 Nights - AU $26,276
Simpson Bay Large Vacation Homes
Villa
10.0(47 Reviews)
2 Bedrooms
2 Baths
4 Guests
1507 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
AU $652/Night
7 Nights - AU $4,567
Villa
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
16145.86 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
AU $1,618/Night
7 Nights - AU $11,327
Villa
10.0(28 Reviews)
4 Bedrooms
5 Baths
8 Guests
6500 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
AU $1,164/Night
7 Nights - AU $8,144
Villa
9.8(4 Reviews)
4 Bedrooms
4 Baths
8 Guests
3229.17 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
AU $905/Night
7 Nights - AU $6,336
Villa
10.0(15 Reviews)
3 Bedrooms
3 Baths
6 Guests
1600 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
AU $987/Night
7 Nights - AU $6,906
Villa
10.0(13 Reviews)
4 Bedrooms
4 Baths
8 Guests
3444 ft²
- Private Pool
- Pool
- Balcony/Terrace
Kitchen
AU $1,269/Night
7 Nights - AU $8,881
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Pool
Pet Friendly- Kitchen
AU $794/Night
7 Nights - AU $5,560
Villa
10.0(12 Reviews)
6 Bedrooms
2 Baths
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
AU $7,802/Night
7 Nights - AU $54,614
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.
Best Times to Visit Simpson Bay
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit this destination ensures you enjoy ideal weather and less crowded attractions, making your stay in Simpson Bay, St. Martin, truly memorable and relaxing.
Peak Season Highlights
December to April
During the winter months, this destination experiences peak tourism as travelers seek warm weather and sunshine, making it the ideal time for beach activities and outdoor exploration.
Average Temperature Daytime: around 82°F (28°C) - Nighttime: about 75°F (24°C)
July to August
The summer months see a surge in visitors looking to enjoy lively events and vibrant nightlife, offering the perfect atmosphere for those seeking an energetic vacation on the island.
Average Temperature Daytime: approximately 85°F (29°C) - Nighttime: roughly 78°F (26°C)
Off-Season Highlights
May to June
In the late spring to early summer, fewer crowds gather here, providing a more relaxed experience while still enjoying warm, tropical weather.
Average Temperature Daytime: around 84°F (29°C) - Nighttime: approximately 76°F (24.5°C)
September to November
During the fall, the region sees less tourist activity, often aligning with the quieter shoulder season when rain showers are more common but accommodation rates tend to decrease.
Average Temperature Daytime: about 83°F (28°C) - Nighttime: near 77°F (25°C)
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 cool off and relax in the warm Caribbean sun.
- Take advantage of spacious outdoor terraces or patios perfect for dining al fresco with scenic views.
- Make the most of landscaped gardens and lush greenery that surround your rental, creating a peaceful environment.
- Relish access to outdoor grilling areas or barbecue stations for delicious meals under the stars.
- Benefit from outdoor lounge furniture designed for sunbathing or unwinding after a day of exploring the region.
- Utilize outdoor shower facilities ideal for rinsing off after a day spent at nearby beaches or pools.
- Capitalize on easy proximity to stunning beaches and waterfronts, allowing for effortless outdoor seaside activities.
Top Attractions Around Simpson Bay
What attractions are nearby?
Nearby in this vibrant region, you can enjoy a variety of water sports, explore beautiful beaches, or indulge in local dining experiences that showcase the island’s unique Caribbean charm, making your stay in Simpson Bay truly unforgettable.
Family Activities
- Maho Beach: You can enjoy the famous sunset views and watch planes land just overhead while relaxing on this popular family-friendly spot.
- Simpson Bay Lagoon: Explore the calm waters with a family boat tour or water sports, offering safe and fun aquatic adventures suitable for all ages.
- Local Markets: Discover fresh produce, local crafts, and souvenirs that provide an authentic taste of the region's vibrant culture and are perfect for family outings.
- Snorkeling Adventures: Experience the colorful marine life in nearby shallow reefs, making it an ideal activity for children and beginners here in this lively region.
Adult Activities
- Island Hopping Tours: Explore the surrounding islands with guided boat trips that offer scenic views and opportunities for snorkeling in clear Caribbean waters.
- Sunset Cruises: Experience the mesmerizing sunset over the bay while enjoying a relaxing cruise, perfect for winding down after a day of adventure.
- Water Sports Adventures: Engage in activities like jet skiing, paddleboarding, or parasailing to make the most of the region’s warm, inviting waters.
- Local Dining Experiences: Savor authentic Caribbean cuisine at seaside restaurants where fresh seafood and tropical flavors come together in a vibrant atmosphere.
Other Places to Stay in Simpson Bay
Sint Maarten
Cole Bay
Philipsburg
Simpson Bay Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining options: Take advantage of the area's renowned restaurants to enjoy authentic Caribbean cuisine during your stay.
- Plan water activities wisely: Make the most of the region's beautiful beaches and clear waters by scheduling water sports and boat excursions ahead of time.
- Discover cultural experiences: Engage with the local community by visiting nearby markets or attending events that showcase the island’s vibrant traditions.
- Select the right vacation rental: Choose a well-located property here that offers comfort and easy access to key attractions and scenic spots in the area.
Transportation Options
- Car Rentals: Exploring the area with a rental car provides flexibility and convenience, allowing you to easily visit local beaches and attractions.
- Taxis and Rideshare Services: Accessible taxis and rideshare options offer comfortable and quick transportation around this popular destination.
- Marina Ferries: For scenic crossings or trips to nearby islands, ferries departing from the marina are a reliable way to enjoy the region's maritime beauty.
- Public Buses: Budget-friendly public buses connect key parts of the area, making it easy to navigate without the need for private transportation.
Local Customs Options
- Local Seafood Cuisine: You can savor the region’s fresh seafood as it’s an integral part of the area’s culinary traditions, reflecting its maritime heritage.
- Carnival Celebrations: Participating in or observing colorful carnival festivities offers a vibrant glimpse into local culture and community spirit here.
- Respect for Water Customs: When visiting the area, you’ll notice a cultural respect for the sea, which influences social gatherings and local rituals.
- Greeting Etiquette: Greeting locals with warm smiles and friendly gestures is customary, emphasizing the welcoming atmosphere of this destination.
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:
- Romantic Luxurious Peaceful Getaway For A Couple With 200° Sea And Sunset View
- On the beach ! Villa ELBA A French Touch unit, pools, tennis, sea view
- Stunning View of Ocean & Lagoon from Pool, 3 Min Walk to Baie Rouge, Cottage
- Villa ocean view, near to the beach, absolute calm
- OCEAN VIEW MODERN AND DESIGN VILLA
- Beach villa, pool, exotic garden, private terrace, safety water tank
- Slowlife - Freshly Renovated Villa Blooming
- Appartment on the beach, exceptional sea view, condo BORA BORA
- Villa 180 ° ocean view, 2 swimming pools, absolute calm, near to the beach
- LUXURY 4 BEDROOM VILLA - JARDIN CREOLE TERRES BASSE - JUST TWO MINUTES TO BEACH
2. How many vacation rentals have private pools in Simpson Bay?
There are 862 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 1487 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, St. Martin?
Cancellation policies vary depending on the specific property listing. You should review the rental details and contact the host directly for information on cancellations and any potential fees or refund options.
6. How do I confirm my booking in Simpson Bay's vacation rentals?
You can confirm your reservation after completing the booking process on the platform. It’s recommended to read the listing carefully and reach out to the owner if you have any questions before finalizing your reservation.
7. Are there any additional fees I should be aware of when booking here?
Additional fees, such as cleaning charges or service fees, are typically detailed in the rental listing. Always review the total cost breakdown in the booking details and contact the owner if you need clarification.
8. What amenities are typically included with vacation rentals in this area?
Most properties offer amenities like Wi-Fi, fully equipped kitchens, air conditioning, and private outdoor spaces, but availability can vary. Check each listing for a complete list of included amenities and contact the host if you require specific features.
9. How close are the vacation rentals to local attractions and beaches?
Many rentals are conveniently located near popular beaches and attractions in the region. Precise distances and proximity details are provided in each listing, so it’s best to review these to choose a property that meets your plans.
Simpson Bay Top Rated Vacation Rentals
Condo
10.0(41 Reviews)
1 Bedroom
2 Baths
4 Guests
753 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
AU $288/Night
7 Nights - AU $2,019
Apartment
10.0(26 Reviews)
2 Bedrooms
1 Bath
5 Guests
646 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
AU $297/Night
7 Nights - AU $2,078
Condo
10.0(21 Reviews)
1 Bedroom
1 Bath
4 Guests
753 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
AU $338/Night
7 Nights - AU $2,365
Apartment
10.0(16 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Pool
- Ocean View
View- Kitchen
AU $424/Night
7 Nights - AU $2,964
Apartment
10.0(15 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Pool
- Ocean View
- View
AU $416/Night
7 Nights - AU $2,911
House
10.0(14 Reviews)
2 Bedrooms
2 Baths
6 Guests
861 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
AU $297/Night
7 Nights - AU $2,078
Apartment
10.0(13 Reviews)
1 Bedroom
2 Baths
4 Guests
753 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
AU $286/Night
7 Nights - AU $2,004
Condo
10.0(13 Reviews)
1 Bedroom
2 Baths
4 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
AU $270/Night
7 Nights - AU $1,890
