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Simpson Bay Vacation Rentals
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Vacation Rentals in Simpson Bay
2 Vlaun Drive, Simpson Bay
The price is $149 per night from Oct 2 to Oct 3
$149
per night
Oct 2 - Oct 3
Stay at this 3-star beach apartment in Simpson Bay. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Kim Sha Beach and Simpson Bay Beach ...
9.4/10 Exceptional! (48 reviews)
"The view from this property is amazing. Debbie and Doug are amazing hosts and want this to feel like home for you. One of the best experiences with a room I have had. The pictures do not do this place justice. It is so much better than it shows. I WILL BE BACK!!!!"
Reviewed on Jan 5, 2023
Beacon Hill
Stay at this beach villa in Simpson Bay. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Dunes Casino and Simpson Bay Beach are located ...
9.8/10 Exceptional! (39 reviews)
Perfect for our family of 4
"Everything was as it was described. Bob was very hospitable. We enjoyed our stay in this house that had a convenient location, just a few minutes from a market for groceries. Our two kids (2 & 4) loved swimming in the pool, playing in the sand, and throwing stones and shells in the ocean. Overall ..."
Reviewed on Jun 14, 2023
Beacon Hill
Stay at this family-friendly condo in Simpson Bay. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Simpson Bay Beach and Dunes Casino ...
9.4/10 Exceptional! (18 reviews)
Amazing property!
"What a stunning place overlooking Simpson Bay. Check in was a breeze, any questions I had John and Stacey were quick to respond. It's exactly as described, so much space!! We'd definitely come back!!"
Reviewed on Mar 12, 2023
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Simpson Bay
Stay at this beach condo in Simpson Bay. Enjoy a beach locale, WiFi, and onsite parking. Popular attractions Kim Sha Beach and Flamingo Beach are located nearby. ...
9.4/10 Exceptional! (38 reviews)
Peaceful beauty
"Could use some updated furniture for living area but a great value for the view and location. Great restaurants within walking distance. Our 3rd time renting this property. 10+ year St Martin visitor"
Reviewed on Jun 24, 2023
Cupecoy
Stay at this condo in Simpson Bay. Enjoy free WiFi, private pools, and breakfast. Popular attractions Dunes Casino and Maho Bay are located nearby. Discover ...
9.8/10 Exceptional! (64 reviews)
Great location!
"This condo was in an excellent location! The home was very secure/safe. The communication was always outstanding from booking through check out. The home is spacious and well appointed. The pool is awesome and hearing the sound of the waves crashing is amazing. Would definitely return and stay here ..."
Reviewed on Jul 17, 2023
11 The Corner Road, Simpson Bay, Sint Maarten
Stay at this 4-star apartment in Simpson Bay. Enjoy free WiFi, a balcony, and Netflix. Popular attractions Dunes Casino and Simpson Bay Beach are located nearby. ...
Beacon Hill
Stay at this beach villa in Simpson Bay. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Dunes Casino and Maho Bay are located nearby. ...
9.8/10 Exceptional! (56 reviews)
Nice place
"Overall, we were fairly happy with our stay here. The outside area was beautiful, the ACs units were cold, comfortable furniture and beds, well equipped kitchen. We loved the snorkeling/kids gear too! Being within 10 minutes of walking distance to the airplane beach was nice. The reviews mentioned ..."
Reviewed on Aug 7, 2023
Simpson Bay
Stay at this 3-star apartment in Simpson Bay. Enjoy free WiFi, free parking, and a garden. Popular attractions Dunes Casino and Simpson Bay Beach are located ...
Beacon Hill
Stay at this beach villa in Simpson Bay. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Dunes Casino and Simpson Bay Beach are located ...
9.2/10 Wonderful! (40 reviews)
Amazed
"Really nice property; owner responsive. Great stay ; I would go back"
Reviewed on Aug 18, 2023
2 University Drive, Cupecoy, Lowlands
The price is $228 per night from Oct 5 to Oct 6
$228
per night
Oct 5 - Oct 6
Stay at this 3.5-star beach aparthotel in Lowlands. Enjoy free WiFi, free parking, and a casino. Popular attractions Mullet Bay Beach and Mullet Bay are located ...
9.8/10 Exceptional! (29 reviews)
"This place was amazing, it was a last minute find so reasonably priced and made out stay exceed our expectations. The condo was gorgeous and had the most amazing views. The amenities were amazing. This place alone made us not want to leave Sint Maarten. Just absolutely beautiful"
Reviewed on Sep 24, 2023
A.T. Illidge Road 117, Philipsburg
Fully refundableReserve now, pay when you stay
The price is $75 per night from Oct 2 to Oct 3
$75
per night
Oct 2 - Oct 3
Stay at this 4.5-star luxury aparthotel in Philipsburg. Enjoy free WiFi, free parking, and a terrace. Popular attractions Sint Maarten Park and Yoda Guy Movie ...
9.2/10 Wonderful! (8 reviews)
"nice place"
Reviewed on Aug 15, 2023
SAINT MARTIN
Stay at this beach villa in Cul de Sac. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Cul-de-Sac Bay and Mont Vernon are located nearby. ...
10/10 Exceptional! (13 reviews)
An absolute gem
"We loved our stay at Villa Hortense! Maly was always just a text away. The villa was beautiful, and we also loved the location overlooking Isle Pinel / the bay!"
Reviewed on Jul 7, 2023
144 Oyster Pond Rd, Oyster Pond, Sint Maarten
Fully refundableReserve now, pay when you stay
The price is $464 per night from Oct 3 to Oct 4
$464
per night
Oct 3 - Oct 4
Stay at this 4-star beach condo in Oyster Pond. Enjoy free parking, 2 restaurants, and a beach locale. Popular attractions Dawn Beach and Oyster Bay Marina are ...
9.8/10 Exceptional! (7 reviews)
"Dawn Beach Club was an amazing place to stay. From the food, drinks, staff and overall warm welcoming energy I enjoyed my stay and will for sure be back again. Thank you DBC you truly made my birthday the best so far!"
Reviewed on May 3, 2023
Lot 29, les terrasses, Cul de Sac, Saint Martin
Stay at this aparthotel in Cul de Sac. Enjoy free breakfast, free parking, and concierge services. Popular attractions Mont Vernon and Cul-de-Sac Bay are located ...
10/10 Exceptional! (13 reviews)
"The place is beautiful , the Pinel island is amazing but I will recommend a car rental because there is nothing around the hotel for dinner or entertainment"
Reviewed on May 10, 2023
32 Goldfinch Road, Pointe Blanche, Sint Maarten, Philipsburg
The price is $162 per night from Oct 2 to Oct 3
$162
per night
Oct 2 - Oct 3
Stay at this 3.5-star apartment in Philipsburg. Enjoy free WiFi, private pools, and a terrace. Popular attractions Museum of Sint Maarten and Cyrus Wathey Square ...
10/10 Exceptional! (1 review)
"Excelente location, view and hosts. Also very clean."
Reviewed on May 15, 2023
Rhine Rd. 9, Lowlands
The price is $90 per night from Oct 7 to Oct 8
$90
per night
Oct 7 - Oct 8
Stay at this 3.5-star golf aparthotel in Lowlands. Enjoy free WiFi, free parking, and a golf course. Popular attractions Cupecoy Beach and Mullet Bay Beach are ...
7/10 Good! (11 reviews)
First trip to St. Maarten, awful hotels.com suppor
"Firstly the name was confusing. The property is known as Saphire not Caribbean vacation rental. I called hotels.com representative for guidance. Checking in was prolonged since the reception wasn’t informed about my booking and then after she received the email and could check me in. At the time ..."
Reviewed on Sep 11, 2023
Front Street 147, Philipsburg
Stay at this 3-star beach aparthotel in Philipsburg. Enjoy free WiFi, a beach locale, and onsite parking. Popular attractions Yoda Guy Movie Exhibit and Philipsburg ...
8.2/10 Very Good! (76 reviews)
"I love the staff"
Reviewed on Aug 21, 2023
Cupecoy
Stay at this beach condo in Lowlands. Enjoy free WiFi, a beach locale, and onsite parking. Popular attractions Mullet Bay Beach and Mullet Bay are located nearby. ...
9.8/10 Exceptional! (48 reviews)
EXCEEDED EXPECTATIONS
"Beautiful, quiet, and peaceful place. Just what we were looking for. Magnificent views! Condo very clean and property well-maintained."
Reviewed on Sep 1, 2023
Sandy Ground
Stay at this beach villa in Nettle Bay. Enjoy free WiFi, a beach locale, and onsite parking. Popular attractions Mercure Beach and St. Martin Beaches are located ...
9.6/10 Exceptional! (17 reviews)
"There were three of us on this trip and we all absolutely loved this place! Betty and Pascal are amazing hosts and went above and beyond of for us on our six night stay. We forgot to bring a few essentials and they made sure to get it for us when they didn't have to do that. You can tell they really ..."
Reviewed on Apr 22, 2023
Cupecoy
Stay at this beach condo in Lowlands. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Mullet Bay Beach and Mullet Bay are located nearby. ...
9.6/10 Exceptional! (40 reviews)
The Cliff is a breathtaking place!
"I belong to the group of individuals who claim that life is too brief to revisit the same location repeatedly. However, I've now defied this rule for the seventh time. I can confidently declare that St. Maarten has become a home away from home for us. This exquisite and opulent property is ideally ..."
Reviewed on Sep 6, 2023
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.
Simpson Bay Vacation Rental Travel Info
Number of vacation rentals | 167 |
|---|---|
Popular accommodation | Simpson Bay villas |
Known landmarks | Maho Beach, Mullet Bay Beach and Simpson Bay Beach |
International airport | Philipsburg (SXM-Princess Juliana Intl.) |
Other types of properties in Simpson Bay you may be interested in
The Morgan Resort Spa Village
2 Beacon Hill Road, Simpson Bay
Fully refundableReserve now, pay when you stay
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37, Simpson Bay
Fully refundableReserve now, pay when you stay
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.
Everything you need to know about Simpson Bay vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simpson Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simpson Bay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Simpson Bay vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Simpson Bay. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Simpson Bay in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
How to find incredible deals on Simpson Bay rentals
At Expedia, we put the best Simpson Bay vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Simpson Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simpson Bay vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simpson Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
Frequently asked questions
Recent reviews of Simpson Bay propertiesExpedia verified reviews
Sonesta Ocean Point All Inclusive, Adults Only Resort
5/5 Excellent
"Had an amazing time here had no complaints only thing is the bed isn’t the most comfortable but everything else was amazing food was delicious everywhere on the resort including the buffet . I’ll definitely be returning without a doubt ."
A verified traveler stayed at Sonesta Ocean Point All Inclusive, Adults Only Resort
Posted 2 days ago
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