A wooden pier extending into calm waters with sailboats anchored nearby.

Search Condos Rentals in Simpson Bay from CA $174

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Simpson Bay condo rentals

A white building with a pool, surrounded by a garden with pink flowers and a view of the sea.

1. Blue Sail Apartments - Double room

Blue Sail Apartments - Double room
Pelican Key
2.0 out of 10, (1 review)
The price is CA $145
CA $174 total
includes taxes & fees
Oct 2 - Oct 3
Blue Sail Apartments - Double room
A wooden deck leading to a beach with clear turquoise water and a rocky shoreline.

2. Maho Beach House: Studio Getaway, Oceanfront Vibe

Maho Beach House: Studio Getaway, Oceanfront Vibe
Maho, Sint Maarten
10.0 out of 10, Exceptional, (2 reviews)
"Nothing fancy just a nice clean place to stay. Great location. Lots of restaurants nearby. Dwayne was a great communicator and very accommodating."
United States
Colleen M.
The price is CA $230
CA $343 total
includes taxes & fees
Oct 20 - Oct 21
Maho Beach House: Studio Getaway, Oceanfront Vibe
A coastal scene with two large yachts on the water, palm trees, and a building with a balcony.

3. Utopia A3 | Beachside Stay @ The Drake Residences

Utopia A3 | Beachside Stay @ The Drake Residences
Simpson Bay
The price is CA $347
CA $1,095 total
includes taxes & fees
Oct 6 - Oct 7
Utopia A3 | Beachside Stay @ The Drake Residences
A coastal scene with two yachts on the water, palm trees, and a building with a white facade.

4. Nirvana A4 | Beachside @ The Drake Residences

Nirvana A4 | Beachside @ The Drake Residences
Simpson Bay
The price is CA $359
CA $1,137 total
includes taxes & fees
Oct 17 - Oct 18
Nirvana A4 | Beachside @ The Drake Residences
A poolside area with a wooden table, lounge chairs, and a view of the ocean.

5. Blue Sail Apartments - Two bedroom apartments

Blue Sail Apartments - Two bedroom apartments
Pelican Key
6.0 out of 10, (3 reviews)
"Check in was seamless accommodations were exactly as expected and the staff were very friendly. We noticed many things were brand new and we were informed that there was a new owner- appears that they are working hard!"
United States
Heidi
The price is CA $174
CA $203 total
includes taxes & fees
Oct 2 - Oct 3
Blue Sail Apartments - Two bedroom apartments
A poolside area with a wooden table, lounge chairs, and a view of the ocean.

6. Blue Sail Apartments - 1 bedroom apartments

Blue Sail Apartments - 1 bedroom apartments
Pelican Key
The price is CA $246
CA $277 total
includes taxes & fees
Oct 2 - Oct 3
Blue Sail Apartments - 1 bedroom apartments
A wooden deck leading to a beach with clear turquoise water and a rocky shoreline.

7. Maho Beach House - Petit Studio Océanique - Charmante Vue

Maho Beach House - Petit Studio Océanique - Charmante Vue
Maho, Sint Maarten
9.4 out of 10, Exceptional, (3 reviews)
"Very close to the sunset bar and interesting views of approaching aircraft. Excellent sunset views from the Sunset bar or the Morgan resort on the other side of the unit. Morgan resort also had excellent dining area and bar facilities open to the public."
United States
Roy N.
Maho Beach House - Petit Studio Océanique - Charmante Vue
A beach with a KLM airplane flying overhead, a sandy beach, and buildings in the background.

8. 2BR Maho Oasis | Walk to Beaches & Nightlife!

2BR Maho Oasis | Walk to Beaches & Nightlife!
Simpson Bay
2BR Maho Oasis | Walk to Beaches & Nightlife!
A balcony with white railings, a bench, and two chairs.

9. Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central

Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central
South Reward
10.0 out of 10, Exceptional, (3 reviews)
"Home away from home "
United States
Trevayne
The price is CA $160
CA $326 total
includes taxes & fees
Oct 6 - Oct 7
Hillside Penthouse spacious 2-bed/bath condo - ideal getaway but still central
Terrace/patio

10. Starfruit Condo with ocean view in Kombawa Domaine

Starfruit Condo with ocean view in Kombawa Domaine
Les Terres Basses
The price is CA $563
CA $809 total
includes taxes & fees
Oct 2 - Oct 3
Starfruit Condo with ocean view in Kombawa Domaine
A beach with a KLM airplane flying overhead, a sandy beach, and buildings in the background.

11. Stylish Maho Condo w/ Pool | Walk to Everything!

Stylish Maho Condo w/ Pool | Walk to Everything!
Simpson Bay
2.0 out of 10, (1 review)
"At the very last minute after getting off the airplane, we received a notice that our reservation had been changed and received poor instructions to find the place. Our taxi could not locate, so we were forced to find last minute accomodation costing of course more money. We are not happy about this experience at all. Countless messages back and forth with the host, who was claiming not to be receiving our messages, yet acknowledge some and not others. We are requesting a full refund. We are...
Canada
Elizabeth S.
Stylish Maho Condo w/ Pool | Walk to Everything!
A living room with a sofa, coffee table, and chairs, a dining table with chairs, large windows, and artwork on the walls.

12. Sovereign Suites Maho | 2BR w/ Pool, Beach Gear

Sovereign Suites Maho | 2BR w/ Pool, Beach Gear
Simpson Bay
8.0 out of 10, Very good, (1 review)
"We were a bit disappointed in our initial assessment of this property. It was a bit hard to find as there is no actual address. With the help of some very kind neighbours we did locate the suite. We found the suite could use some updating. The ad mentions beach extras like beach towels and blanket etc. Those things were not in the suite. At least we never found them. One thing the ad does not mention is that the condo is second floor but 3 flights of stairs on a spiral staircase. Anyone with...
Canada
Tracy W.
Sovereign Suites Maho | 2BR w/ Pool, Beach Gear
A white building with a gated entrance, surrounded by lush green foliage.

13. SXM Hillside Retreat large 3-bed/bath condo, tucked in the hills but central

SXM Hillside Retreat large 3-bed/bath condo, tucked in the hills but central
South Reward
The price is CA $221
CA $409 total
includes taxes & fees
Oct 14 - Oct 15
SXM Hillside Retreat large 3-bed/bath condo, tucked in the hills but central
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Simpson Bay Hotel Reviews

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

10/10 Excellent
"The only problem was American visitors who were not following the rules at the pool. They were aggressive, rude and used very foul language with me when I politely asked them to turn off their boom box, stop throwing things around and respect other people at the pool. I got absolutely no support from the bartender when Americans wouldn’t stop what they were doing. She was condescending and joined the Americans in shouting abuse at me. When I called security I got a very annoyed guard who was impatient and obviously sided with the Americans. I have complained to the resort requesting a response but have heard absolutely nothing. For the rest of my time there I kept running into the Americans which kind of ruined my holiday."
Shauna 14-night trip
Posted 12 hours ago
Simpson Bay Resort, Marina & Spa

Find out more about Simpson Bay

Simpson Bay Condo Rentals information

Number of reviews
10
Accommodation
69 Condo Rentals
Lowest Price
CA $174
Highest Price
CA $1,137

Frequently asked questions

How much do condos in Simpson Bay cost?
Condos in Simpson Bay range from CA $174 to CA $1,137 per night. These properties offer lots of room for the entire family at a price that's friendly on the pocket. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best condos in Simpson Bay?
You can pick from multiple condos in Simpson Bay with a total average guest review rating of 7.2. Light House 3c By Redawning comes highly rated if you're travelling with the family or you simply want to spread out. This 3-star stay also has a swimming pool and an oven. Ocean's Luxury 2 Bedroom Suites is another top option. It has a 3.5-star rating and conveniences such as an ocean view and clothes washing facilities.
How many condos are there in Simpson Bay?
You'll find 69 condos in Simpson Bay. Whether you're taking a trip with the kids or planning a weekend escape with your pals, Expedia will help you find the right space for your squad.
What are the best cheap condos in Simpson Bay?
Condos start from only CA $174 per night, so your Simpson Bay vacation doesn't have to stretch your finances! Aazure 1bedroom 1. 5ba Is A Beautifully Condo Overlooking The Gardens And Pool Of Porto Cupecoy is a top wallet-friendly pick that offers lots of amenities, including a swimming pool and WiFi. Acadia Lovely Oceanfront, 1 To 3 Bedroom Condo Is Located On The Cliffs Of Cupecoy is another of our favourite condos. Use conveniences such as a swimming pool and WiFi. Seeing free attractions in Simpson Bay makes your travel budget stretch even further. Maho Beach and Orient Bay Beach are visitor favourites. With the dollars you save, you can explore some more! This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly condos in Simpson Bay?
Get comfortable at Light House 3c By Redawning, a 3-star option just a quick drive from downtown. Amenities here include a swimming pool and clothes washing facilities. Another family-friendly condo is Ocean's Luxury 2 Bedroom Suites. An ocean view and a nearby boardwalk help make this 3.5-star escape a guest favourite. After checking in and chilling out together in your new digs, it's time to hit the road and visit some of the local sights. Maho Beach and Orient Bay Beach are fun family-friendly attractions in Simpson Bay.
Are there any 5-star condos in Simpson Bay?
Condo Corfu is a popular 5-star condo in Simpson Bay. Around 5 kilometres from downtown, concierge services and massage services are among its many conveniences. Condo Figueira is another upscale stay around 5 kilometres from the centre. Also rated 5 stars, it features concierge services and a swimming pool.
Why book your condo in Simpson Bay with Expedia?
Use Expedia to find your ideal condo in Simpson Bay. Looking for a luxury stay? Find your way to the filters to search for properties that have a 5-star rating. If you have a budget, choose how much you'd like to spend and then browse our amazing deals. We'll help you find the perfect stay whatever your vacation looks like.
How can I find cheap condos in Simpson Bay?
A good way to uncover cheap condos in Simpson Bay is with Expedia's convenient filter tool. Tailor your search results by star rating, amenities and budget to grab unbeatable prices with only a few clicks.
What is there to do in Simpson Bay near my condo?
There are loads of fantastic things to put on your itinerary in Simpson Bay. Make tracks to well-known attractions like Simpson Bay Beach, Flamingo Beach and Kim Sha Beach. Hollywood Casino, Dunes Casino and Lay Bay Beach also appeal to many visitors.