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, (1004)
"This is an excellent option to stay in the island, peaceful area, very beautiful property with very good services and daily events for entertainment. Highly recommended."
The price is €196
includes taxes & fees
3 May - 4 May
Hilton Vacation Club Royal Palm St. Maarten

The Hills Residence

3.0 star property
9.4 out of 10, Exceptional, (22)
"I loved staying at The Hills because it was very centric, easy to move around. The property has an amazing view with a pool, beautiful decor comfortable bed. I love it all. I will recommend it. I am staying here again. "
The Hills Residence

Simpson Bay Suites

3.5 star property
6.8 out of 10, (121)
"10 out of 10 "
The price is €138
includes taxes & fees
18 Apr - 19 Apr
Simpson Bay Suites

Tradewinds at Simpson Bay

3.5 star property
9.4 out of 10, Exceptional, (23)
"I was staying for two days of business. But the apartment is very well located on Simpson bay. Close to the beach, shops, bars and restaurants. "
Tradewinds at Simpson Bay

Oceanfront amazing 2 bedrooms Condo

9.8 out of 10, Exceptional, (55)
"Very spacious, great access to beach and close to restaurants and shopping."
Oceanfront amazing 2 bedrooms Condo

Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

9.6 out of 10, Exceptional, (7)
"This property is beautiful. The bed is heavenly. The rooftop pool is fabulous, especially if you love watching the planes take off and land. If this is your first time in SXM, just know that this location on the island is right beside the airport. The jets are loud. Bring earplugs to sleep. If you want absolute peace and quiet, this part of the island probably isn’t the best for that. The kitchen is well appointed. They do provide one beach towel but it’s not very think so if we go back we would...
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

Nice and cozy ocean front studio with private terrace. Short walk to beaches.

9.2 out of 10, Wonderful, (15)
"Property is in a safe quiet part of the island and still walking distance to all the Maho activity and nearby beaches. The balcony is private and has phenomenal views of the sunset. At night you can fall asleep to the sound of the ocean outside. Best sleep I've had in ages.The interior is light, clean and comfortable.Will definitely stay here again!"
Nice and cozy ocean front studio with private terrace. Short walk to beaches.

One Hundred Million Dollar Yacht On Land 5 star Villa with backup Generator

9.8 out of 10, Exceptional, (70)
"Me and my wife enjoyed our honeymoon stay here to relax and enjoy the island. The home is in a perfect area even pay cash for rental via Tami we will be back soon great speaker of you want a vibe at the property with pool and drinks. "
One Hundred Million Dollar Yacht On Land 5 star Villa with backup Generator

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

10.0 out of 10, Exceptional, (96)
"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!!

The Horny Toad Guesthouse

3.0 star property
9.4 out of 10, Exceptional, (52)
"We will continue to come back! Beautiful beach, friendly and accommodating hosts, all the amenities you need, perfect distance to everything . The host was so welcoming and made us feel like a part of the family the second we arrived until we left!! "
The Horny Toad Guesthouse

Turquoise paradise, directly ON beach, gated w underground parking!

9.8 out of 10, Exceptional, (20)
"This is the perfect place to stay location wise and with the beach views! Also there is a/c in each room which is super nice! "
The price is €483
includes taxes & fees
8 May - 9 May
Turquoise paradise, directly ON beach, gated w underground parking!

Stunning Beach Front Villa With Infinity Pool

9.4 out of 10, Exceptional, (12)
"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

Maho Beach House - Spacious 1 Bedroom Suite

10.0 out of 10, Exceptional, (3)
"I recently had the pleasure of staying at a rental in Sint Maarten, and it was an unforgettable experience. The property was stunning, offering breathtaking views and a peaceful atmosphere that made me feel completely at home. The location was ideal—close to beautiful beaches, great restaurants, and all the attractions I wanted to explore on the island.What truly made my trip exceptional, however, was the outstanding help I received from Kaya. As a solo traveler, I really appreciated how...
Maho Beach House - Spacious 1 Bedroom Suite

White Sands Retreat - Beachside at Beacon Hill

9.0 out of 10, Wonderful, (32)
"We enjoyed our stay. We really appreciated the extras like the barbeque, beach chairs, etc. We had an issue with the internet but the owner was right on it. The location and beach were great. "
White Sands Retreat - Beachside at Beacon Hill

BEACHFRONT DESIGN VILLA

9.8 out of 10, Exceptional, (116)
"This house provided a wonderful location for our two families, totaling 7 people (3 older teenagers) to spend Spring Break. The house had beautiful outdoor spaces that provided shaded areas throughout the day. There were nice places for everyone; spots to read, have morning coffee, yoga, relax in the pool. The beach was beautiful to look at and listen to but not a good spot for children or casual swimming. The location was easily walkable to Maho beach for pictures but traffic could be a little...
BEACHFRONT DESIGN VILLA

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

10.0 out of 10, Exceptional, (27)
"Our daughter and her husband joined us to St MAARTAN which for all 4 of us needed to be just very relaxing trip. We have been coming to St MAARTAN for over 28 years and staying at various areas on the island. We found this gem and it owner and we were so delighted with EVERYTHING. Can’t say anything negative about the order or the condo, it was Eve we needed and more. "
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.

OASIS Apartments Simpson Bay

4.0 star property
The price is €393
includes taxes & fees
11 Apr - 12 Apr
OASIS Apartments Simpson Bay

Fourteen at Mullet Bay

3.5 star property
9.4 out of 10, Exceptional, (253)
"Our stay at tower B at Fourteen at Mullet Bay was over the top. All of the staff were knowledgeable and friendly. The place was immaculate! Started everyday with Lattes and Croissants at the pool restaurant. The staff there gave us excellent restaurant and places to go and things to do references. Spent a lot of time at the beach which was walking distance from the property. Our Studio apartment was clean and new and had great views from the balcony. Definitely recommend this property for the...
Fourteen at Mullet Bay

July Apartments

3.0 star property
9.0 out of 10, Wonderful, (120)
"This property is a jewel! They had a very clean room for us, a mini fridge, and a full kitchen for us to use. The stairs are the only downfall but the staff makes up for it! Their prices are a real bonus too!"
The price is €81
includes taxes & fees
16 Apr - 17 Apr
July Apartments

Mullet Bay Suites: Your Luxury Stay Awaits

4.0 star property
9.8 out of 10, Exceptional, (88)
"As former owners at the Towers, we were initially upset with a new property being built, but after our stay, MBS has to be one of the most exceptional properties we have stayed at. The views were spectacular, the balcony and chairs kept us out there most nights. The interior decorating was interesting, but all things were comfortable, clean and well supplied. The pool and restaurant were wonderful with great service! This is definitely on our places to return to."
The price is €290
includes taxes & fees
7 May - 8 May
Mullet Bay Suites: Your Luxury Stay Awaits
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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Other types of properties in Simpson Bay you may be interested in

The Morgan Resort Spa Village

4.0 star property
9.0 out of 10, Wonderful, (1635)
"Everything was wonderful but the house keeping. When asked for service they did a very poor job. They didn’t change the sheets and didn’t replace all of the towels. They also left food service trays in the hallway for two days. The rest of the staff was very nice and the pool and live music was great! Just wish the cleaning staff did a better job."
The price is €406
includes taxes & fees
17 Apr - 18 Apr
The Morgan Resort Spa Village

Simpson Bay Resort, Marina & Spa

4.0 star property
8.8 out of 10, Excellent, (1053)
"Fantastic staff from the front desk to the cleaning staff, the security team and the many bar and restaurant staff! People truly make the difference in a resort experience. "
The price is €161
includes taxes & fees
29 Apr - 30 Apr
Simpson Bay Resort, Marina & Spa

The Villas at Simpson Bay Resort

4.0 star property
9.2 out of 10, Wonderful, (1153)
"Great location!!"
The price is €205
includes taxes & fees
7 May - 8 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.

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 top-notch restaurants and lively bars.

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

Aura: This holiday home rental outside of Simpson Bay offers a private beach, a terrace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of garden in this rental home to help you unwind. Some other homes for rent in Simpson Bay include White Sands Retreat - Beachside at Beacon Hill and Large Pool/ 1 BR/1Bath Apt. in Beautiful St. Martin in Simpson Bay!.

How many holiday rentals are there in Simpson Bay?

With 64 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. In the wider area, you’ll find popular places such as Maho Beach and Orient Bay Beach.

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.