Simpson Bay Holiday Rentals

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Check prices for these dates

In two weeks
26 Sept - 28 Sept
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec

Holiday Rentals in Simpson Bay

Our top choices for Simpson Bay holiday rentals

Hilton Vacation Club Royal Palm St. Maarten
Outdoor pool, pool loungers

Hilton Vacation Club Royal Palm St. Maarten

4.0 star property
9.0 out of 10, Wonderful, (1115)
"Most convenient hotel to stay, due to an array of shopping and dinning options near the property."
The price is S$217
includes taxes & fees
21 Sept - 22 Sept
Hilton Vacation Club Royal Palm St. Maarten
The Hills Residence
Balcony

The Hills Residence

3.0 star property
9.0 out of 10, Wonderful, (44)
"Love the view first of all. Property was in a great location. "
The Hills Residence
Simpson Bay Suites
Beach nearby, white sand, sun-loungers, beach umbrellas

Simpson Bay Suites

3.5 star property
6.8 out of 10, (123)
"Highly recommended and friendly staff…"
The price is S$155
includes taxes & fees
16 Sept - 17 Sept
Simpson Bay Suites
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
The Horny Toad Guesthouse
View from room

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
Cliff House
Outdoor pool

Cliff House

3.5 star property
8.8 out of 10, Excellent, (3)
"Great stay at the Cliff house. Very private accommodations and plenty of room for a couple or a family experience. Easy parking, but only a short 7 minute walk into town. "
Cliff House
Fourteen at Mullet Bay
Terrace/patio

Fourteen at Mullet Bay

3.5 star property
9.2 out of 10, Wonderful, (348)
"Amazing view and apartment. Condos are centrally located near shops and restaurants. Will definitely stay again. "
Fourteen at Mullet Bay
July Apartments
Front of property

July Apartments

3.0 star property
9.2 out of 10, Wonderful, (147)
"Nice hotel"
July Apartments
Mullet Bay Suites: Your Luxury Stay Awaits
Terrace/patio

Mullet Bay Suites: Your Luxury Stay Awaits

4.0 star property
9.8 out of 10, Exceptional, (103)
"Building is very secure. Walking distance to beach and backpack chairs are provided. "
The price is S$388
includes taxes & fees
23 Sept - 24 Sept
Mullet Bay Suites: Your Luxury Stay Awaits
Dawn Beach Club Resort Sint Maarten
Sun deck

Dawn Beach Club Resort Sint Maarten

4.0 star property
8.8 out of 10, Excellent, (21)
"Wonderful vacation spot in st maarten"
The price is S$1,077
includes taxes & fees
25 Sept - 26 Sept
Dawn Beach Club Resort Sint Maarten
The Forest
Exterior

The Forest

4.0 star property
10.0 out of 10, Exceptional, (14)
"Great boutique hotel in anse Marcel. Owners are hands on and very pleasant. Look forward to going again. "
The price is S$266
includes taxes & fees
16 Sept - 17 Sept
The Forest
Aura Anse-Marcel
Exterior

Aura Anse-Marcel

9.4 out of 10, Exceptional, (12)
"The view and space inside the property is amazing and Consierge service is very good"
Aura Anse-Marcel
Sea Palace
Balcony view

Sea Palace

3.0 star property
8.4 out of 10, Very good, (106)
"Will stay here again for sure.💕"
The price is S$161
includes taxes & fees
19 Sept - 20 Sept
Sea Palace
Cupecoy Beach Club
On the beach, white sand

Cupecoy Beach Club

3.0 star property
9.0 out of 10, Wonderful, (2)
"Parking is random and limited "
Cupecoy Beach Club
Karibuni Boutique Hotel - Adults Only
Restaurant

Karibuni Boutique Hotel - Adults Only

9.8 out of 10, Exceptional, (30)
"This hotel was fantastic! It’s even better than the pictures, the staff was super friendly and knowledgeable, the exclusive early access to Pinel Island was amazing, oh, and the breakfast was superb!!"
Karibuni Boutique Hotel - Adults Only
The Cliff
Private beach, white sand, beach umbrellas, beach towels

The Cliff

3.0 star property
8.4 out of 10, Very good, (8)
"Wonderful apartment with all the space you could ever need. Beautiful surroundings and very attentive staff. Good location especially If you rent a car to get you the few miles to Maho village or indeed anywhere on the island. Only drawback were catching a few cockroaches. "
The Cliff
Cozy one-bedroom & mezzanine apartment
Balcony

Cozy one-bedroom & mezzanine apartment

3.0 star property
9.4 out of 10, Exceptional, (19)
"The host was incredibly communicative throughout our entire stay, from pre-arrival to departure. The location was perfect, with supermarkets and shopping centers nearby, and just a 12-minute walk to the town center. The apartment was beautifully presented, featuring a lovely shared pool and equipped with everything we needed. We'll definitely be staying here again on our next visit. "
Cozy one-bedroom & mezzanine apartment
condostmaarten by the sea -Adults Only-
Beach

condostmaarten by the sea -Adults Only-

4.0 star property
9.6 out of 10, Exceptional, (22)
"Good location easy access to a private beach "
The price is S$454
includes taxes & fees
22 Sept - 23 Sept
condostmaarten by the sea -Adults Only-
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

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

10/10 Excellent
"Nice place to stay, very clean and good service also affordable "
Hylenne 3-night trip
Posted 5 days ago
The Villas at Simpson Bay Resort

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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 top-notch restaurants and lively bars.

How many holiday rentals are there in Simpson Bay?

With 40 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. Kim Sha 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.