Simpson Bay Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

Vacation Rentals in Simpson Bay

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

Hilton Vacation Club Royal Palm St. Maarten

4.0 star property
9.0 out of 10, Wonderful, (1120)
"Clean area, usually book here "
The price is P5,761
P7,575 total
includes taxes & fees
Sep 29 - Sep 30
Hilton Vacation Club Royal Palm St. Maarten
The Hills Residence
Balcony

The Hills Residence

3.0 star property
9.0 out of 10, Wonderful, (45)
"Love the view first of all. Property was in a great location. "
The Hills Residence
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
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 P6,280
P7,034 total
includes taxes & fees
Sep 29 - Sep 30
Simpson Bay Suites
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, (352)
"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, (149)
"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 P12,676
P17,597 total
includes taxes & fees
Oct 2 - Oct 3
Mullet Bay Suites: Your Luxury Stay Awaits
Dawn Beach Club Resort Sint Maarten
Sundeck

Dawn Beach Club Resort Sint Maarten

4.0 star property
8.8 out of 10, Excellent, (21)
"Wonderful vacation spot in st maarten"
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 P12,509
P13,010 total
includes taxes & fees
Sep 29 - Sep 30
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 P7,862
P8,255 total
includes taxes & fees
Oct 2 - Oct 3
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 P15,700
P23,724 total
includes taxes & fees
Sep 29 - Sep 30
condostmaarten by the sea -Adults Only-
Residence Alamanda
On the beach, sun loungers, beach towels

Residence Alamanda

9.0 out of 10, Wonderful, (20)
"We absolutely loved Alamana! Ocean front suite with beautiful sunrises and sunsets. Chelsea was so helpful with any questions and setting up transportation for us.and setting up transpo"
Residence Alamanda
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

Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

10/10 Excellent
"The rooms were super comfy and clean. The Spanish bartender at Pelican was awesome with customer service. The food at Pelican was outstanding The beach and Jacuzzi added to relaxation Not having access to front desk via our room telephone "
Lola 5-night trip
Posted 5 days ago
Hilton Vacation Club Flamingo Beach St. Maarten

Find out more about Simpson Bay

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:

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

Frequently asked questions

Can I find a vacation rental in Simpson Bay?

Yes, we give you a choice of vacation rentals near top attractions in Simpson Bay, or you can choose a secluded option if you'd like a relaxing place to 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 vacation rentals are there in Simpson Bay?

With 39 Expedia vacation rentals, you're sure 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 vacation rental in Simpson Bay like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Simpson Bay. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for families.