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Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
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Sep 12 - Sep 14
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Oct 10 - Oct 12

Condo Rentals in Simpson Bay

1-bedroom condo in amazing Simpson Bay Pool Steps from the beach, with WiFi, AC
On the beach, sun loungers, beach towels

1-bedroom condo in amazing Simpson Bay Pool Steps from the beach, with WiFi, AC

1-bedroom condo in amazing Simpson Bay Pool Steps from the beach, with WiFi, AC
Oceanfront amazing 2 bedrooms Condo
Property grounds

Oceanfront amazing 2 bedrooms Condo

9.6 out of 10, Exceptional, (58)
"Gorgeous property, great pool, and convenient location... walkable to maho beach! Would stay again!"
Oceanfront amazing 2 bedrooms Condo
Tradewinds at Simpson Bay
Exterior

Tradewinds at Simpson Bay

3.5 star property
9.4 out of 10, Exceptional, (28)
"We enjoyed the stay to the fullest"
Tradewinds at Simpson Bay
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath
On the beach

Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

9.6 out of 10, Exceptional, (13)
"I would stay here again"
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath
Luxury Penthouse with Private Rooftop Directly on Beach, Best Location, pool!
Terrace/patio

Luxury Penthouse with Private Rooftop Directly on Beach, Best Location, pool!

10.0 out of 10, Exceptional, (2)
"The entire complex was nice and well kept. Very close to the airport with stellar views! The unit was very clean and was overall a great experience. I would stay there again. "
Luxury Penthouse with Private Rooftop Directly on Beach, Best Location, pool!
Maho Beach House - Spacious 1 Bedroom Suite
Property grounds

Maho Beach House - Spacious 1 Bedroom Suite

10.0 out of 10, Exceptional, (3)
"I booked this very last minute for a short (2 night) stay. They were very quick to reply and confirm. It was a big place for a one bedroom on a island. It was very clean, well decorated and with a nice view of the ocean and planes coming in to land. The air-conditioning worked well and I was happy to find the bedroom had a ceiling fan. The location worked well for me, there was a charge for parking, but it is gated and guarded. When I had an issue logging onto the wifi I sent a msg via the VRBO...
Maho Beach House - Spacious 1 Bedroom Suite
2 BR 2 BA, beachfront condo, amazing oceanview, private beach access
On the beach, sun loungers, beach towels

2 BR 2 BA, beachfront condo, amazing oceanview, private beach access

9.4 out of 10, Exceptional, (15)
"The island is beautiful with the condo situated in a perfect location. Short walk to restaurants/bars, shopping, and grocery stores. The sounds of Simpson Bay's rolling surf and the soft sands of Simpson Bay Beach right out your front door. What is not to love!"
2 BR 2 BA, beachfront condo, amazing oceanview, private beach access
Popular Beachfront Condo directly on Simpson Bay beach in St. Maarten
On the beach, sun loungers, beach towels

Popular Beachfront Condo directly on Simpson Bay beach in St. Maarten

10.0 out of 10, Exceptional, (57)
"This property has a wonderful beachfront location with great view of the bay Silvia & Kapi were great hosts - great with communication and provide everything so you can just relax & unwind. Thank you for a memorable vacation ! "
Popular Beachfront Condo directly on Simpson Bay beach in St. Maarten
Sun-kissed Beachfront Condo with Pool & Gorgeous Sunsets at Encanto- La Siesta
Outdoor pool

Sun-kissed Beachfront Condo with Pool & Gorgeous Sunsets at Encanto- La Siesta

10.0 out of 10, Exceptional, (10)
"Had a great time in Simpson Bay. The condo has all the necessities, the view is amazing. Perfect place for a beach vacation. "
Sun-kissed Beachfront Condo with Pool & Gorgeous Sunsets at Encanto- La Siesta
GORGEOUS Direct Beach Access 2 King Bedrooms Ground Floor
On the beach, sun loungers, beach towels

GORGEOUS Direct Beach Access 2 King Bedrooms Ground Floor

10.0 out of 10, Exceptional, (1)
GORGEOUS Direct Beach Access 2 King Bedrooms Ground Floor
Spacious Studio Overlooking Simpson Bay Beach
Property grounds

Spacious Studio Overlooking Simpson Bay Beach

10.0 out of 10, Exceptional, (4)
"It has everything for a single person or couple. loved the property & location. I will be back"
Spacious Studio Overlooking Simpson Bay Beach
Sunny Outlook - Beautiful 1 bedroom in beachfront complex!
On the beach

Sunny Outlook - Beautiful 1 bedroom in beachfront complex!

9.2 out of 10, Wonderful, (5)
"Had a wonderful time at this condo unit. "
Sunny Outlook - Beautiful 1 bedroom in beachfront complex!
SIMPSON BAY YACHT CLUB NEW VERY LARGE STUDIO CONDO 872 SQFT IN THE HEART OF SXM!
Pool

SIMPSON BAY YACHT CLUB NEW VERY LARGE STUDIO CONDO 872 SQFT IN THE HEART OF SXM!

8.4 out of 10, Very Good, (6)
"Host was very informative, accommodating and very responsive. Went out of her way to have property manager get me a hairdryer. Location is in a wonderful area with lots of things to do near by. Only thing needed was a firm pillow. "
SIMPSON BAY YACHT CLUB NEW VERY LARGE STUDIO CONDO 872 SQFT IN THE HEART OF SXM!
The Penthouse at LaSiesta Stunning views in luxurious surroundings!
Outdoor pool

The Penthouse at LaSiesta Stunning views in luxurious surroundings!

10.0 out of 10, Exceptional, (56)
"We had an amazing time, we were able to walk to plenty of restaurants and bars."
The Penthouse at LaSiesta Stunning views in luxurious surroundings!
Cozy condo in Blue Pelican - 5 min from the beach!
Pool

Cozy condo in Blue Pelican - 5 min from the beach!

Cozy condo in Blue Pelican - 5 min from the beach!
Gorgeous 2 Bedroom Beachfront Privately Owned Condo 4th Floor
Beach towels

Gorgeous 2 Bedroom Beachfront Privately Owned Condo 4th Floor

Gorgeous 2 Bedroom Beachfront Privately Owned Condo 4th Floor
Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay
Outdoor dining

Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay

10.0 out of 10, Exceptional, (10)
"Will stay again. "
Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay
Anchor House - Direct Oceanfront - Luxury & Modern Style
Terrace/patio

Anchor House - Direct Oceanfront - Luxury & Modern Style

10.0 out of 10, Exceptional, (145)
"The property itself was beautiful and the view was or if this world! Access to nightlife, beaches, restaurants was perfect. So quiet and peaceful. We were so sad to leave!"
Anchor House - Direct Oceanfront - Luxury & Modern Style
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
On the beach, sun loungers, beach towels

Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.

10.0 out of 10, Exceptional, (31)
"Lovely decks and pool area. Walking distance to town for restaurants, casino, stores, etc. Close to the beach to jump in the waves. Lovely beach bar & restaurant close by. Host always reachable. "
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
Pirates Booty - Beach Bar Studio next to The Morgan Resort
Beach

Pirates Booty - Beach Bar Studio next to The Morgan Resort

8.6 out of 10, Excellent, (4)
"Welcoming love the area we will be coming back thank you so much "
$230 nightly
The price is $230
Aug 13 - Aug 14
Total includes taxes and fees
Pirates Booty - Beach Bar Studio next to The Morgan Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Simpson Bay Hotel Reviews

Baker's Suites

Baker's Suites

10/10 Excellent
"The property is great. It's close to a number of restaurants and bars that are in walking distance. The staff is really nice. Latoya at the front desk has excellent customer service. She made us feel welcomed and her food recommendations were the best. Housekeeping (can't remember her name) was also great. We would stay at Baker Suites again. "
Reisa 3-night trip
Posted 15 hours ago
Baker's Suites