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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Top Holiday Rentals in Simpson Bay

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

Hilton Vacation Club Royal Palm St. Maarten

4.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (1154)
"Beautiful vacation "
Canada
alonzo
The price is ฿4,402
฿5,473 total
includes taxes & fees
17 Dec - 18 Dec
Hilton Vacation Club Royal Palm St. Maarten
Amazing Top Floor Apartment | Balcony
The Hills Residence

The Hills Residence

3.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (49)
"This apartment was nice, clean, modern, walking distance to restaurants and shops. "
United States
Lionel
The Hills Residence
Exterior
Tradewinds at Simpson Bay

Tradewinds at Simpson Bay

3.5 star property
Simpson Bay
9.4 out of 10, Exceptional, (30)
"This place is amazing. Great price. Super helpful and flexible owner and staff. They truly did everything to help and make my stay perfect. The room was clean. The bed was very comfortable. There's beautiful sunset view from this property. Great seafood restaurant next door. I'll definitely be back. 10 out of 10"
United States
hanan
Tradewinds at Simpson Bay
Beach nearby, white sand, sun-loungers, beach umbrellas
Simpson Bay Suites

Simpson Bay Suites

3.5 star property
Simpson Bay
6.8 out of 10, (125)
"No issues. Staff were very welcoming and accommodating. Was a pleasant stay. "
United States
Sharmain
The price is ฿3,937
฿4,410 total
includes taxes & fees
23 Nov - 24 Nov
Simpson Bay Suites
Orchid | View from room
The Horny Toad Guesthouse

The Horny Toad Guesthouse

3.0 star property
Simpson Bay
9.4 out of 10, Exceptional, (53)
"We like it being beachfront, wide verandas, spacious unit, host and staff were excellent!"
United States
Melanie Pacoli
The Horny Toad Guesthouse
Outdoor pool
Cliff House

Cliff House

3.5 star property
Simpson Bay
8.8 out of 10, Excellent, (3)
"Amazing location. Views of the bay and the ocean on each side. Walkable to Maho restaurants and grocery. Would stay again"
United States
Cami
Cliff House
Deluxe Condo, 1 Bedroom, Balcony, Beach View | Terrace/patio
Fourteen at Mullet Bay

Fourteen at Mullet Bay

3.5 star property
Maho
9.2 out of 10, Wonderful, (382)
"Great stay"
United States
Sherlon
Fourteen at Mullet Bay
Front of property
July Apartments

July Apartments

3.0 star property
Madame's Estate
9.2 out of 10, Wonderful, (154)
"Amazing place. "
United States
Cristina
July Apartments
Terrace/patio
Mullet Bay Suites: Your Luxury Stay Awaits

Mullet Bay Suites: Your Luxury Stay Awaits

4.0 star property
Maho
9.8 out of 10, Exceptional, (106)
"I was warmly welcomed by a great staff who helped me get settled in. The room was fantastic. I very much felt at home. I hope to come back again. "
United States
Jordon
The price is ฿7,595
฿10,388 total
includes taxes & fees
25 Nov - 26 Nov
Mullet Bay Suites: Your Luxury Stay Awaits
Sun deck
Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten

4.0 star property
Oyster Pond
8.8 out of 10, Excellent, (21)
"Wonderful vacation spot in st maarten"
United States
Debasis
Dawn Beach Club Resort Sint Maarten
Room, 2 Bedrooms | Balcony view
Sea Palace

Sea Palace

3.0 star property
Downtown Philipsburg
8.6 out of 10, Excellent, (108)
"Will stay here again for sure.💕"
United States
Gina
The price is ฿4,381
฿4,600 total
includes taxes & fees
23 Nov - 24 Nov
Sea Palace
Exterior
The Forest

The Forest

4.0 star property
Anse Marcel
10.0 out of 10, Exceptional, (15)
"Great boutique hotel in anse Marcel. Owners are hands on and very pleasant. Look forward to going again. "
Canada
Nadalina
The price is ฿16,501
฿17,161 total
includes taxes & fees
8 Dec - 9 Dec
The Forest
On the beach, sun-loungers, beach towels
Residence Alamanda

Residence Alamanda

Orient Bay
9.0 out of 10, Wonderful, (21)
"Everything was great, but would make a suggestion Add a couple more towels to the bathroom The hot water never worked in the shower the whole time we were there kind of annoying Other than that, we had a great time"
United States
KURT Martin
Residence Alamanda
Restaurant
Karibuni Boutique Hotel - Adults Only

Karibuni Boutique Hotel - Adults Only

Cul de Sac
9.8 out of 10, Exceptional, (32)
"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!!"
United States
Rebecca
Karibuni Boutique Hotel - Adults Only
Exterior
Aura Anse-Marcel

Aura Anse-Marcel

Anse Marcel
9.4 out of 10, Exceptional, (12)
"The view and space inside the property is amazing and Consierge service is very good"
United States
Jacques
Aura Anse-Marcel
On the beach, white sand
Cupecoy Beach Club

Cupecoy Beach Club

3.0 star property
Maho
9.0 out of 10, Wonderful, (2)
"Great location, spacious accomodations"
Canada
Alvin
Cupecoy Beach Club
Panoramic Apartment, Ocean View | Beach | On the beach, white sand
condostmaarten by the sea -Adults Only-

condostmaarten by the sea -Adults Only-

4.0 star property
Indigo Bay
9.6 out of 10, Exceptional, (23)
"Good location easy access to a private beach "
United States
All About
The price is ฿8,749
฿13,221 total
includes taxes & fees
24 Nov - 25 Nov
condostmaarten by the sea -Adults Only-
On the beach, white sand
Anse Marcel Cove Suites St. Martin

Anse Marcel Cove Suites St. Martin

Anse Marcel
Anse Marcel Cove Suites St. Martin
Standard Apartment, 2 Bedrooms | Balcony
Cozy one-bedroom & mezzanine apartment

Cozy one-bedroom & mezzanine apartment

3.0 star property
Point Blanche
9.2 out of 10, Wonderful, (20)
"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. "
United States
Kevin
Cozy one-bedroom & mezzanine apartment
Villa | Living area
Avenue du lagon

Avenue du lagon

Oyster Pond
The price is ฿46,987
฿63,449 total
includes taxes & fees
23 Nov - 24 Nov
Avenue du lagon
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
"Large comfortable room. Amazing beach!"
Andrea 5-night trip
Posted 2 days ago
The Villas at Simpson Bay Resort

Find out more about Simpson Bay

Search for holiday rentals in Simpson Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Simpson Bay using one of the methods below:

  • View our selection of featured holiday rentals in Simpson Bay
  • Use the map to find apartments and other holiday homes in the Simpson Bay neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Simpson Bay while they last

Look no further and take a look at our great range of rental properties in Simpson Bay!

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 37 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. 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.