Simpson Bay Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

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, (1119)
"Most convenient hotel to stay, due to an array of shopping and dinning options near the property."
The price is ￥16,817
￥21,565 total
includes taxes & fees
Sep 29 - Sep 30
Hilton Vacation Club Royal Palm St. Maarten
The Hills Residence
Amazing Top Floor Apartment | 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 ￥15,942
￥17,855 total
includes taxes & fees
Sep 29 - Sep 30
Simpson Bay Suites
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath
On the beach

Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

9.6 out of 10, Exceptional, (14)
"I would stay here again"
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath
The Horny Toad Guesthouse
Orchid | 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
One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean
On the beach, beach towels

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

9.8 out of 10, Exceptional, (77)
"We chose the property based on proximity to family in the neighborhood and we could not have been happier with our selection. The private pool and access to beach was wonderful. The facility was beautiful and clean and suited our needs perfectly as the en suite bathroom for each bedroom was great."
One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean
Maho Beach House - Spacious 1 Bedroom Suite
Property grounds

Maho Beach House - Spacious 1 Bedroom Suite

10.0 out of 10, Exceptional, (3)
"I booked this very last minute for a short (2 night) stay. They were very quick to reply and confirm. It was a big place for a one bedroom on a island. It was very clean, well decorated and with a nice view of the ocean and planes coming in to land. The air-conditioning worked well and I was happy to find the bedroom had a ceiling fan. The location worked well for me, there was a charge for parking, but it is gated and guarded. When I had an issue logging onto the wifi I sent a msg via the VRBO...
Maho Beach House - Spacious 1 Bedroom Suite
Turquoise paradise, directly ON beach, gated w underground parking!
Property grounds

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 ￥58,306
￥76,610 total
includes taxes & fees
Sep 26 - Sep 27
Turquoise paradise, directly ON beach, gated w underground parking!
A curated two bedroom suite near Maho beach.
Fridge, microwave, oven, stovetop

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.
Oceanfront amazing 2 bedrooms Condo
Property grounds

Oceanfront amazing 2 bedrooms Condo

9.6 out of 10, Exceptional, (59)
"Gorgeous property, great pool, and convenient location... walkable to maho beach! Would stay again!"
Oceanfront amazing 2 bedrooms Condo
Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay
Outdoor dining

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

10.0 out of 10, Exceptional, (11)
"Will stay again. "
Large WATERFRONT 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay
Caribbean Sea Studio next to The Morgan Resort
Property grounds

Caribbean Sea Studio next to The Morgan Resort

8.0 out of 10, Very Good, (1)
Caribbean Sea Studio next to The Morgan Resort
Sunny Days at Simpson Bay Yacht Club
Pool

Sunny Days at Simpson Bay Yacht Club

10.0 out of 10, Exceptional, (2)
"This is a great location to come to: comfortable central location lots to do around restaurant everything you would need in a getaway I will definitely here again"
The price is ￥37,493
￥72,229 total
includes taxes & fees
Sep 29 - Sep 30
Sunny Days at Simpson Bay Yacht Club
Anchor House - Direct Oceanfront - Luxury & Modern Style
Terrace/patio

Anchor House - Direct Oceanfront - Luxury & Modern Style

10.0 out of 10, Exceptional, (146)
"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
Top of the art penthouse on the beach - 4000 sq. ft of luxury
On the beach, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (76)
"Amazing property Fantastic location Incredible views Great getaway "
Top of the art penthouse on the beach - 4000 sq. ft of luxury
Oceanfront amazing 2 BR Villa - 2 min from the beach
Outdoor pool

Oceanfront amazing 2 BR Villa - 2 min from the beach

9.4 out of 10, Exceptional, (96)
"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
4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea
Outdoor pool

4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea

9.6 out of 10, Exceptional, (48)
"The house and view are as amazing as the pictures show. Kitchen is well equipped. Plenty of bath towels and beach towels. Supplies are well equipped as well (detergent, paper towels, toilet paper, etc.). Peaches and Michael are both very quick to respond. Would stay here again and recommend to friends. Great location, close to many great restaurants and activities. One of the nicest personal rentals we have ever stayed at."
4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea
1 bedroom with pool in Simpson Bay - GENERATOR
Pool

1 bedroom with pool in Simpson Bay - GENERATOR

10.0 out of 10, Exceptional, (1)
"Communication with the host was very easy. The location is outstanding and the facility has every amenity. You can imagine. I highly recommend this property and can’t wait to visit again."
The price is ￥16,975
￥32,880 total
includes taxes & fees
Oct 5 - Oct 6
1 bedroom with pool in Simpson Bay - GENERATOR
Pirates Booty - Beach Bar Studio next to The Morgan Resort
Beach

Pirates Booty - Beach Bar Studio next to The Morgan Resort

8.6 out of 10, Excellent, (4)
"Welcoming love the area we will be coming back thank you so much "
Pirates Booty - Beach Bar Studio next to The Morgan 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.
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Top Simpson Bay Hotel Reviews

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

10/10 Excellent
"Amazing location. Friendly staff. Clean environment. Great restaurants. Spacious rooms. I highly recommend. I can’t wait not visit again "
Terrence 5-night trip
Posted 3 days ago
The Villas at Simpson Bay Resort

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:

  • 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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.

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

Amazing 7 Bedroom 5 Bath Villa Beachfront Private Pool : Visitors like this Simpson Bay vacation home rental. It is located on the beach and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Other favorite homes for rent in Simpson Bay are Caribbean Sea Studio next to The Morgan Resort and Charming 3BR Villa w Private Pool in Pelican Key.

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.