Simpson Bay Vacation Rentals

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Vacation Rentals in Simpson Bay

Hilton Vacation Club Royal Palm St. Maarten

4.0 star property
9.0 out of 10, Wonderful, (1012)
"Great place to vacation with family "
The price is CA $190
CA $235 total
includes taxes & fees
May 10 - May 11
Hilton Vacation Club Royal Palm St. Maarten

The Hills Residence

3.0 star property
9.2 out of 10, Wonderful, (25)
"Great place to stay! "
The Hills Residence

Tradewinds at Simpson Bay

3.5 star property
9.4 out of 10, Exceptional, (27)
"Was an amazing stay definitely recommend this place ! "
Tradewinds at Simpson Bay

Simpson Bay Suites

3.5 star property
6.8 out of 10, (122)
"Highly recommended and friendly staff…"
The price is CA $186
CA $208 total
includes taxes & fees
May 3 - May 4
Simpson Bay Suites

Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

9.6 out of 10, Exceptional, (8)
"Was very clean and close to the beach and D's Beach Bar."
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

Oceanfront amazing 2 bedrooms Condo

9.8 out of 10, Exceptional, (55)
"beautiful view....great property"
Oceanfront amazing 2 bedrooms Condo

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

10.0 out of 10, Exceptional, (97)
"Excellent communication with owner before and during our stay. Great location with a small private beach."
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

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

9.4 out of 10, Exceptional, (17)
"The view from the terrace was amazing. Short walk to Maho. Host was very nice. Would stay here again."
Nice and cozy ocean front studio with private terrace. Short walk to beaches.

Gorgeous Beachfront Ground Floor 2 Bedroom 2 Bath Condo

10.0 out of 10, Exceptional, (9)
"Amazing location just steps to the beach. The condo is as you see in pics. Everything is well stocked. I would definitely recommend and would love the opportunity to stay here again!"
Gorgeous Beachfront Ground Floor 2 Bedroom 2 Bath Condo

Stunning Beach Front Villa With Infinity Pool

9.4 out of 10, Exceptional, (12)
"This home was beautiful and the perfect place to stay! The home is professionally managed and very nicely appointed. The view and pool are breathtaking. It’s also so rare to find a place where each guest can have their own bedroom and bathroom. I would absolutely stay here again!"
Stunning Beach Front Villa With Infinity Pool

BEACHFRONT DESIGN VILLA

9.8 out of 10, Exceptional, (118)
"The house was comfortable and plenty of space for 7 adults. The outside seating areas were perfect for playing games and lounging. The small issues we encountered were consist hot water in the showers. The water was more tepid than hot in all showers but the red bathroom. We had some remotes and safes needing new batteries. It would be helpful to have manuals for the kitchen appliances and a/c remotes. Overall, the stay was pleasant and would recommend to friends."
BEACHFRONT DESIGN VILLA

OASIS Apartments Simpson Bay

4.0 star property
OASIS Apartments Simpson Bay

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

10.0 out of 10, Exceptional, (28)
"Loved the place/ location. Definitely will be back soon! 🐠😊"
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.

Charming 2-bedroom villa with AC, WiFi, stunning ocean views

10.0 out of 10, Exceptional, (3)
"Great quiet location. Absolutely beautiful views and sunsets on the pool deck. Definitely a nice hidden gem. "
Charming 2-bedroom villa with AC, WiFi, stunning ocean views

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...
The price is CA $154
CA $263 total
includes taxes & fees
May 4 - May 5
Maho Beach House - Spacious 1 Bedroom Suite

Villa Sunshine: Beachfront! 10 min. walk to the famous Maho Beach!

9.6 out of 10, Exceptional, (29)
"Rikki was waiting at the rental car company for us. He was warm & so helpful. The villa was absolutely spotless & in the best location. The 10 of us girls had an absolutely wonderful time. Can't wait to return to wonderful St Martin."
Villa Sunshine: Beachfront! 10 min. walk to the famous Maho Beach!

Fourteen at Mullet Bay

3.5 star property
9.2 out of 10, Wonderful, (260)
"This property has a great view, clean and great staff."
Fourteen at Mullet Bay

July Apartments

3.0 star property
9.0 out of 10, Wonderful, (123)
"very chill spot"
The price is CA $117
CA $123 total
includes taxes & fees
May 2 - May 3
July Apartments

Mullet Bay Suites: Your Luxury Stay Awaits

4.0 star property
9.8 out of 10, Exceptional, (90)
"Nice property, staff was terrific, and a 3-minute walk to a great beach."
The price is CA $304
CA $422 total
includes taxes & fees
May 11 - May 12
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

Simpson Bay Resort, Marina & Spa

4.0 star property
8.8 out of 10, Excellent, (1062)
"Great Place to stay "
The price is CA $165
CA $198 total
includes taxes & fees
May 15 - May 16
Simpson Bay Resort, Marina & Spa

The Morgan Resort Spa Village

4.0 star property
9.0 out of 10, Wonderful, (1652)
"Great location, food and entertainment."
The price is CA $410
CA $521 total
includes taxes & fees
May 20 - May 21
The Morgan Resort Spa Village

Hilton Vacation Club Flamingo Beach St. Maarten

4.0 star property
9.0 out of 10, Wonderful, (1004)
"Everything was great, location and beach were awesome. Would stay again "
The price is CA $145
CA $189 total
includes taxes & fees
May 11 - May 12
Hilton Vacation Club Flamingo Beach St. Maarten
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 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?

White Sands Retreat - Beachside at Beacon Hill: Visitors like this Simpson Bay vacation home rental. It is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games. Other favorite homes for rent in Simpson Bay are Large Pool/ 1 BR/1Bath Apt. in Beautiful St. Martin in Simpson Bay! and Caribbean Sea Studio next to The Morgan Resort.

How many vacation rentals are there in Simpson Bay?

With 65 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. In the larger area, you’ll find popular places like Maho Beach and Orient Bay Beach.

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.