Search Holiday Rentals in Simpson Bay

    price find illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Save instantly and earn perks with One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Top Holiday Rentals in Simpson Bay

Hilton Vacation Club Royal Palm St. Maarten

4.0 star property
9.0 out of 10, Wonderful, (1040)
"Great place to stay"
The price is £156
includes taxes & fees
29 Jun - 30 Jun
Hilton Vacation Club Royal Palm St. Maarten

The Hills Residence

3.0 star property
9.0 out of 10, Wonderful, (34)
"Nice, clean I realy feel home"
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

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

9.8 out of 10, Exceptional, (71)
"We loved this house with the sound of the waves and the ocean front view. Pool was great and was a wonderful place to hang out. The house is Close to many things but still feels very private. House was clean and had everything we needed to cook most our meals. "
One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean

Oceanfront amazing 2 bedrooms Condo

9.8 out of 10, Exceptional, (57)
"Gorgeous property, great pool, and convenient location... walkable to maho beach! Would stay again!"
Oceanfront amazing 2 bedrooms Condo

Simpson Bay Suites

3.5 star property
6.8 out of 10, (123)
"Highly recommended and friendly staff…"
The price is £101
includes taxes & fees
24 Jun - 25 Jun
Simpson Bay Suites

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

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

10.0 out of 10, Exceptional, (100)
"Super great time. Best location for all activities. Would stay again."
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!!

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

10.0 out of 10, Exceptional, (73)
"Amazing property Fantastic location Incredible views Great getaway "
Top of the art penthouse on the beach - 4000 sq. ft of luxury

Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

9.6 out of 10, Exceptional, (10)
"I would stay here again"
Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath

Anchor House - Direct Oceanfront - Luxury & Modern Style

10.0 out of 10, Exceptional, (144)
"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

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

10.0 out of 10, Exceptional, (9)
"Will stay again. "
Large 1BR/1Bath Apt in Beautiful St Martin in Simpson Bay

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

10.0 out of 10, Exceptional, (29)
"Loved the place/ location. Definitely will be back soon! 🐠😊"
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.

Ruby Room · CocoVaa Boutique Hotel - Ruby Suite

10.0 out of 10, Exceptional, (1)
"We were on the beach, next to a wonderful restaurant, and able to walk along the beach nearly all by ourselves. We’ll be back! "
The price is £177
includes taxes & fees
26 Jun - 27 Jun
Ruby Room · CocoVaa Boutique Hotel - Ruby Suite

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.

White Sands Retreat - Beachside at Beacon Hill

9.0 out of 10, Wonderful, (34)
"We had an amazing time! We will definitely be back again. LOVED being about to grill and cone and go easily. Plane watching was so fun at D’s bar "
White Sands Retreat - Beachside at Beacon Hill

Stunning Beach Front Villa With Infinity Pool

9.4 out of 10, Exceptional, (13)
"My group sailed in the 45th Heinekens Regatta and 7 of us stayed in this Villa . We had a great time and will consider coming back . The maid comes every day except Sunday . She keeps this property very clean and it was a pleasure to stay here "
Stunning Beach Front Villa With Infinity Pool

OASIS Apartments Simpson Bay

4.0 star property
OASIS Apartments Simpson Bay

ALMA - DIRECT BEACH ACCESS 4 BR VILLA

10.0 out of 10, Exceptional, (56)
"Beautiful location and interior. Some of the furniture is a bit low making the up and down process a bit of a strain for seniors."
ALMA - DIRECT BEACH ACCESS 4 BR VILLA

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 £225
includes taxes & fees
3 Jul - 4 Jul
Maho Beach House - Spacious 1 Bedroom Suite
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.
Save an average of 15% on thousands of hotels when you're signed in

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.

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

White Sands Retreat - Beachside at Beacon Hill: This highly rated holiday home rental in Simpson Bay is located on the beach, and has a patio, a garden and a BBQ 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 holiday with amenities such as a selection of games. Other favourite homes for rent in Simpson Bay are Dream Beachfront Home : Stunning sea views, private pool and walking distance and Caribbean Sea Studio next to The Morgan Resort.

How many holiday rentals are there in Simpson Bay?

With 67 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. 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.