Holiday Rentals in Simpson Bay

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Holiday Rentals in Simpson Bay

Hilton Vacation Club Royal Palm St. Maarten

4.0 star property
9.0 out of 10, Wonderful, (1049)
"Great place to stay"
The price is €252
includes taxes & fees
15 Jul - 16 Jul
Hilton Vacation Club Royal Palm St. Maarten

The Hills Residence

3.0 star property
9.0 out of 10, Wonderful, (34)
"Nice, clean I realy feel home"
The Hills Residence

Tradewinds at Simpson Bay

3.5 star property
9.4 out of 10, Exceptional, (27)
"Was an amazing stay definitely recommend this place ! "
Tradewinds at Simpson Bay

Simpson Bay Suites

3.5 star property
6.8 out of 10, (123)
"Highly recommended and friendly staff…"
The price is €103
includes taxes & fees
13 Jul - 14 Jul
Simpson Bay Suites

One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean

9.8 out of 10, Exceptional, (71)
"We loved this house with the sound of the waves and the ocean front view. Pool was great and was a wonderful place to hang out. The house is Close to many things but still feels very private. House was clean and had everything we needed to cook most our meals. "
One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean

Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

9.8 out of 10, Exceptional, (11)
"I would stay here again"
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

The Horny Toad Guesthouse

3.0 star property
9.4 out of 10, Exceptional, (53)
"We like it being beachfront, wide verandas, spacious unit, host and staff were excellent!"
The Horny Toad Guesthouse

Anchor House - Direct Oceanfront - Luxury & Modern Style

10.0 out of 10, Exceptional, (144)
"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

Oceanfront amazing 2 bedrooms Condo

9.8 out of 10, Exceptional, (57)
"Gorgeous property, great pool, and convenient location... walkable to maho beach! Would stay again!"
Oceanfront amazing 2 bedrooms Condo

Stunning Beach Front Villa With Infinity Pool

9.4 out of 10, Exceptional, (13)
"Loved the property. Location was fantastic. Views from the house and description of property really didn’t do it justice. Would definitely recommend to anyone visiting the island. "
Stunning Beach Front Villa With Infinity Pool

3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!

10.0 out of 10, Exceptional, (101)
"Super great time. Best location for all activities. Would stay again."
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!

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

10.0 out of 10, Exceptional, (9)
"Will stay again. "
Large 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay

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 BR Villa - 2 min from the beach

9.4 out of 10, Exceptional, (95)
"Good stay nice place property is comfortable, quiet, private, easily accessible, amenities worked well, kitchen very well equipment. Enjoyed my stay so did my group."
Oceanfront amazing 2 BR Villa - 2 min from the beach

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

10.0 out of 10, Exceptional, (3)
"This was an excellent place to bring our family to ! The beautiful house was spacious with multiple bedrooms and a large living area. The outside space was also great with a really nice pool for adults and kids and lots of outdoor seating . There is also access to the beach! We really enjoyed our stay and the view was spectacular !! Eli was always available to answer questions and help to make our stay memorable !"
Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool

A curated two bedroom suite near Maho beach.

10.0 out of 10, Exceptional, (2)
"Great place. Nice and quite with beaches close "
A curated two bedroom suite near Maho beach.

Top of the art penthouse on the beach - 4000 sq. ft of luxury

10.0 out of 10, Exceptional, (74)
"Amazing property Fantastic location Incredible views Great getaway "
Top of the art penthouse on the beach - 4000 sq. ft of luxury

Ruby Room · CocoVaa Boutique Hotel - Ruby Suite

10.0 out of 10, Exceptional, (1)
"We were on the beach, next to a wonderful restaurant, and able to walk along the beach nearly all by ourselves. We’ll be back! "
The price is €181
includes taxes & fees
22 Jul - 23 Jul
Ruby Room · CocoVaa Boutique Hotel - Ruby Suite

ALMA - DIRECT BEACH ACCESS 4 BR VILLA

10.0 out of 10, Exceptional, (56)
"We loved our stay here. The views are gorgeous and the house was clean and exactly as described. Plenty of room for parking if you have a rental and easy enough to walk to the beach bars by Maho if you don’t feel like driving. Communication with the owner was easy and reliable. Only recommendation I’d have would be to replace/upgrade the pillows as they were all flat and not the most comfortable. Everything else was great! "
ALMA - DIRECT BEACH ACCESS 4 BR VILLA

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

10.0 out of 10, Exceptional, (30)
"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.
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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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 and your friends and family can relax into your holiday with amenities such as a selection of games. Other favourite homes for rent in Simpson Bay are Dream Beachfront Home : Stunning sea views, private pool and walking distance and Ruby Room · CocoVaa Boutique Hotel - Ruby Suite.

How many holiday rentals are there in Simpson Bay?

With 73 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?

Flamingo Beach and Simpson Bay Beach are a couple of lovely local spots to get outside and enjoy nature. Hollywood Casino and Kim Sha Beach 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.