Holiday Rentals in Simpson Bay

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Holiday Rentals in Simpson Bay

Outdoor pool, an infinity pool
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste
10.0 out of 10, Exceptional, (65)
"We stayed here for a week and the Villa is beautiful and communication with the host was always easy. Great place to stay and relax!!"
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste
Beach
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
10.0 out of 10, Exceptional, (24)
"Our family of 5 (2-10yr old boys, 1-14yr old girl) were very pleased with the condo. The location was prime in Simpson Bay. Within walking distance to a few beach bars and walked over to Maho Beach too a few times. The pool was nice (warm) and had plenty of seating, always a few seats available. There are beach chairs, toys on the porch along with a beach umbrella. The kitchen was well equipped and left us not needing anything. Bath linens could use a refresh but was sufficient. The only...
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
Property grounds
Anchor House - Direct Oceanfront - Luxury & Modern Style
10.0 out of 10, Exceptional, (125)
"This property is simply stunning. Very clean. Safe area. Walkable to restaurants, bars, markets and the beach, however we did rent a car. Property manager Stacey was amazing. The pictures are spot on for this property and we are booking again in the coming months! I was a little worried that sometimes you aren’t sure what you are booking but this was amazingly perfect. Can’t wait to go back!"
Anchor House - Direct Oceanfront - Luxury & Modern Style
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On the beach, beach bar
Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!
10.0 out of 10, Exceptional, (19)
"Beautiful beach front unit. The planes landing and taking off add an option that was unexpected but not bothersome at all. A bit more comfortable seating and dinner/cookware would be nice but 6 of us survived quite nicely. Definitely a place we’ll return to."
Lovely 3 Bedroom Beachfront Condo located at Coco's Beach Club!
Pool
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!
10.0 out of 10, Exceptional, (80)
"As advertised. There is a security guard shack steps from the property which is manned 6 pm - 6am."
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!
Exterior
Maho Beach Escape; Sunset Ocean View
10.0 out of 10, Exceptional, (3)
"Self check in and out was a nice experience "
The price is €193
per night
6 May - 7 May
Maho Beach Escape; Sunset Ocean View
On the beach, sun-loungers, beach towels
Serenity On The Sand, Beachfront Paradise @ Simpson Bay w/ Captivating Oceanview
10.0 out of 10, Exceptional, (5)
"We really enjoyed our stay over Easter weekend. The beach was busy."
Serenity On The Sand, Beachfront Paradise @ Simpson Bay w/ Captivating Oceanview
Terrace/patio
Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
10.0 out of 10, Exceptional, (42)
"This is my 4th straight year in St Marteen , I never stayed at this property and I absolutely will return work I come back next year ( god willing ) The property is beautiful and clean "
The price is €174
per night
6 May - 7 May
Mullet Bay Suites: Your Luxury Stay Awaits
Sun-loungers, beach towels
Villa Little Paradise - BIG DISCOUNT MARCH - APRIL !!
10.0 out of 10, Exceptional, (7)
"Lovely house, everything you need, beautiful island!"
Villa Little Paradise - BIG DISCOUNT MARCH - APRIL !!
Pool
Villa Bahia Blue - Four Bedroom Villa, Sleeps 8
10.0 out of 10, Exceptional, (12)
"2 familes each with 2 kids had a great time. Very close to baie rouge. Pool was nice. Hot tub water seemed bad so we didnt use it. Housekeeper and concierge were really nice. Rented a car and drove all over the small island. Would recommend and would stay again"
Villa Bahia Blue - Four Bedroom Villa, Sleeps 8
Outdoor pool
LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site
10.0 out of 10, Exceptional, (66)
"The view from this property strikes you the minute you walk in the front door. All you can see is your pool, the beach and then St. Barth off in the distance. The property is very well maintained and easy to find. It is well located between the French and Dutch sides of the island. The restaurant Big Fish is a 30 second walk from the front door and was delicious. Overall a great place to stay in St. Maarten."
LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site
Outdoor pool
Luxury Villa w Spectacular Ocean Views, private pool/Hottub, Walk to Beach
10.0 out of 10, Exceptional, (116)
"We stayed at Villa Valhalla with our 3 teenage kids and another family of 4. The house was beautiful, clean, well stocked with stunning views! Plenty of room for us all. It’s located in a safe and quiet neighborhood overlooking Dawn Beach. Everything was as stated from the website, except the kitchen has been updated and looks great. We had excellent communication before and during the trip. We were able to walk to the beach, and had dinner at the new JW Marriott. It was nice to have a close...
Luxury Villa w Spectacular Ocean Views, private pool/Hottub, Walk to Beach
On the beach, sun-loungers, beach umbrellas, beach towels
ON THE BEACH CONDO WITH PANORAMIC VIEW ON GRAND CASE BEACH
10.0 out of 10, Exceptional, (62)
"A great location, clean with a perfect view!"
ON THE BEACH CONDO WITH PANORAMIC VIEW ON GRAND CASE BEACH
Property grounds
Villa Pinel Beach front property , Sea View Villa , heated swimming pool ,beach
10.0 out of 10, Exceptional, (71)
"Very well appointed with everything you could possibly need. View is mesmerizing . Owner is so hospitable and helpful and available to help with anything."
Villa Pinel Beach front property , Sea View Villa , heated swimming pool ,beach
Beach
Beautiful Ocean Front Penthouse/New Furnishings/Stunning View/Private Beach!
10.0 out of 10, Exceptional, (63)
"This is a beautiful place to stay. The apartment and property are well maintained and everyone I interacted with was helpful and friendly. I really appreciated the location, being able to walk to the grocery store or bakery,and being right on the water with an amazing view. Most of all, Susan was very communicative and provided wonderful tips. She was never more than a message away. We were well taken care of."
Beautiful Ocean Front Penthouse/New Furnishings/Stunning View/Private Beach!
Outdoor pool
Oceanfront amazing 2 bedrooms Condo
9.8 out of 10, Exceptional, (48)
"The place was very nice. John was supreme host. Place was very clean and service was wonderful. Wasn’t as quiet as expected. Being so close to the airport had it’s draw backs. But the condo was close to Simpsom Bay, food shopping and a nice beach restaurant. Traveled a few times to Orient Beach, fantastic beach just a little bit of a distance to travel. But overall this place meet our needs. Thank you John for the enjoyment of your Villa."
Oceanfront amazing 2 bedrooms Condo
Outdoor pool
BEACHFRONT DESIGN VILLA
9.8 out of 10, Exceptional, (110)
"Overall we had a great time at Secrets. Listening to the waves crash on the shore was very soothing and relaxing. The location is great - close to Maho beach, Mullet Beach and a small market. The home is clean but a bit worn. The pool wasn’t cleaned before we arrived but management was responsive is having pool cleaners come quickly. The kitchen is very well stocked. The dishwasher rack was broken and was annoying. The beds are quite comfortable but they need to upgrade the linens. Despite those...
BEACHFRONT DESIGN VILLA
Property grounds
Top of the art penthouse on the beach - 4000 sq. ft of luxury
9.8 out of 10, Exceptional, (59)
"Well laid out property, centrally located on the ilsland wirh rhe bonus of being on the Simpson Bay beachfront."
Top of the art penthouse on the beach - 4000 sq. ft of luxury
Property grounds
Beachfront villa with pool in Cul de Sac
9.8 out of 10, Exceptional, (60)
"We lucked out on selecting this place since we've never been. The french side is the place to stay. The airport, the cruise ships and all the tourist shops are on the dutch side ands its packed all the time. On the french side its beautiful, less touristy an A"
Beachfront villa with pool in Cul de Sac
Property grounds
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO
9.6 out of 10, Exceptional, (71)
"Beautiful building, property, and very spacious condo with great views. Highly recommended."
*SPECIALS* SIMPSON BAY _ LUXURY BEACHFRONT CONDO
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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.

Other types of properties in Simpson Bay you may be interested in

Outdoor pool, pool loungers
The Morgan Resort Spa Village
4.0 star property
9.2 out of 10, Wonderful, (1166)
"Stayed at the Morgan Resort for my birthday and it was truly an amazing experience. From the driver Ravi who picked me up at the airport, the young lady who checked me in, the lady who assisted in decorating my room, to the spa staff everyone was very kind and welcoming. I would definitely recommend and stay again, the drinks & food was very tasty. I received a relaxation massage and that was immaculate. 10/10"
The price is €308
per night
20 May - 21 May
The Morgan Resort Spa Village
Outdoor pool, pool loungers
Hilton Vacation Club Flamingo Beach St. Maarten
3.5 star property
9.2 out of 10, Wonderful, (1023)
"I did not like when we cheked IN WAS TOLD FLAMINGO HOTEL DID NOT RECEIVED CONF FROM EXPEDIA WHICH WAS NOT TRUE BECAUSE I SHOWED THE E MAIL CONFIRMATION THEY GAVE US A ROOM FOR 3 DAYS IT WAS A BAD START OF VACATION AFTER WE MOVED TO THE ROOM WE PAID WITH SPECIAL ACCOMODATION WE PAID FOR, "
The price is €120
per night
1 Jun - 2 Jun
Hilton Vacation Club Flamingo Beach St. Maarten
BBQ/picnic Area
The Villas at Simpson Bay Resort
4.0 star property
9.0 out of 10, Wonderful, (1008)
"We really liked Simpson Bay. Our room was beautiful - spacious with a great view! I would definitely stay there again if i was to return to St. Marteen."
The price is €282
per night
16 May - 17 May
The Villas at Simpson Bay 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.

Everything you need to know about Simpson Bay holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Simpson Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Simpson Bay holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simpson Bay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simpson Bay holiday rentals we have selected for you start as low as €174 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Simpson Bay rentals

At Expedia, we put the best Simpson Bay holiday 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 holiday.

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

Can I find a holiday rental in Simpson Bay?

Yes, there are holiday rentals close to the most popular sights in Simpson Bay, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the array of shops and popular beaches in Simpson Bay. While you're here, grab a bite or have a drink at the lively bars and top-notch restaurants.

What are some of the best holiday rentals that Simpson Bay has to offer?

White Sands Retreat - Beachside at Beacon Hill: This highly rated holiday home rental in Simpson Bay is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a selection of games and 1 hot tub. Other favourite homes for rent in Simpson Bay are Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool and Nice & Cosy 3BR Villa with private pool / Ocean View and beach access.

How many holiday rentals are there in Simpson Bay?

With 67 Expedia holiday rentals, you're guaranteed to find just the right place for your Simpson Bay stay.

What’s there to see and do in Simpson Bay?

Kim Sha Beach and Flamingo Beach are a couple of lovely local spots to get outside and enjoy nature. Simpson Bay Beach and Hollywood Casino are other places to visit while you're in town.

What’s a holiday rental in Simpson Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Simpson Bay. Holiday rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.

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