Apartment
10.0(92 Reviews)
3 Bedrooms
8 Guests
Oceanfront
Hot Tub
Parking
Ocean View
CA $952/Night
7 Nights - CA $6,664
Simpson Bay Villa Rentals
We compare villas and rental homes from owners across Booking.com, Vrbo and Expedia.
- Up-front pricing
- No markup
- Trusted partners
Compare Villas, Resorts, & Rentals in Simpson Bay
10.0
Apartment
1 Bedroom
3 Guests
Pool
Balcony/Terrace
Kitchen
Air Conditioner
CA $556/Night
7 Nights - CA $3,893
Condo
10.0(82 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $897/Night
7 Nights - CA $6,283
CA $1,128/Night
7 Nights - CA $7,894
Condo
10.0(63 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $955/Night
7 Nights - CA $6,688
Condo
10.0(60 Reviews)
2 Bedrooms
4 Guests
Private Pool- Oceanfront
- Hot Tub
- Parking
CA $722/Night
7 Nights - CA $5,056
Villa
10.0(53 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $418/Night
7 Nights - CA $2,924
Condo
10.0(37 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $1,256/Night
7 Nights - CA $8,795
Luxury Places to Stay in Simpson Bay
Over 683+ Luxury Places to Stay in or Near Simpson Bay
CA $4,916/Night
7 Nights - CA $34,411
House
4 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $3,871/Night
7 Nights - CA $27,095
Villa
4 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $2,961/Night
7 Nights - CA $20,730
Villa
10.0(5 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
Breakfast- Parking
CA $2,837/Night
7 Nights - CA $19,860
CA $2,825/Night
7 Nights - CA $19,778
CA $2,823/Night
7 Nights - CA $19,764
CA $2,756/Night
7 Nights - CA $19,293
Villa
10.0(15 Reviews)
6 Bedrooms
12 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $2,608/Night
7 Nights - CA $18,259
Top-Rated Villas with a Pool in Simpson Bay
Over 441+ Top-Rated Private Villas with a Pool in or Near Simpson Bay
Resort
10.0(94 Reviews)
5 Guests
- Breakfast
- Parking
- Pool
- Balcony/Terrace
CA $752/Night
7 Nights - CA $5,265
Condo
10.0(36 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $613/Night
7 Nights - CA $4,292
Condo
10.0(28 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $610/Night
7 Nights - CA $4,271
Condo
10.0(23 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $600/Night
7 Nights - CA $4,203
Villa
10.0(21 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
CA $1,350/Night
7 Nights - CA $9,446
Apartment
10.0(21 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $226/Night
7 Nights - CA $1,584
New
Villa
10.0(19 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $1,376/Night
7 Nights - CA $9,632
Condo
10.0(19 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
CA $837/Night
7 Nights - CA $5,857
Condo
10.0(17 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $488/Night
7 Nights - CA $3,417
Pet-Friendly Villas in Simpson Bay
Over 55+ Pet-Friendly Private Villas in or Near Simpson Bay
CA $1,120/Night
7 Nights - CA $7,842
Apartment
9.8(4 Reviews)
2 Bedrooms
6 Guests
Private Beach- Oceanfront
- Parking
- Pool
CA $697/Night
7 Nights - CA $4,879
Villa
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
CA $1,015/Night
7 Nights - CA $7,108
Apartment
9.0(13 Reviews)
1 Bedroom
2 Guests
- Parking
View- Air Conditioner
Internet
CA $161/Night
7 Nights - CA $1,128
Condo
10.0(2 Reviews)
1 Bedroom
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $376/Night
7 Nights - CA $2,634
Condo
10.0(2 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $300/Night
7 Nights - CA $2,099
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $582/Night
7 Nights - CA $4,075
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $184/Night
7 Nights - CA $1,287
Villa
9.8(31 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Breakfast
- Parking
- Pool
CA $1,630/Night
7 Nights - CA $11,410
Large Private Villas in Simpson Bay
Over 124+ Large Villas in or Near Simpson Bay for Groups and Families
Villa
10.0(14 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $433/Night
7 Nights - CA $3,029
Villa
10.0(1 Review)
1 Bedroom
8 Guests
- Parking
- Pool
- Balcony/Terrace
- View
CA $801/Night
7 Nights - CA $5,605
CA $1,805/Night
7 Nights - CA $12,635
House
10.0(7 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $1,700/Night
7 Nights - CA $11,901
Apartment
9.2(170 Reviews)
12 Bedrooms
30 Guests
- Pool
- Balcony/Terrace
- View
- Air Conditioner
CA $353/Night
7 Nights - CA $2,471
Apartment
10.0(4 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
CA $1,503/Night
7 Nights - CA $10,522
Villa
10.0(3 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $539/Night
7 Nights - CA $3,770
New
Villa
10.0(3 Reviews)
1 Bedroom
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $277/Night
7 Nights - CA $1,942
Villa
10.0(2 Reviews)
6 Bedrooms
12 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $2,571/Night
7 Nights - CA $17,996
Wheelchair Accessible Holiday Homes in Simpson Bay
Over 170+ Wheelchair Accessible Villas and Holiday Homes in or Near Simpson Bay
Condo
10.0(26 Reviews)
1 Bedroom
3 Guests
- Kitchen
- Air Conditioner
- Internet
Child Friendly
CA $526/Night
7 Nights - CA $3,686
Resort
8.9(242 Reviews)
18 Guests
- Private Beach
- Hot Tub
- Parking
- Pool
CA $429/Night
7 Nights - CA $3,005
Resort
9.2(1787 Reviews)
- Breakfast
- Parking
- Pool
- Balcony/Terrace
CA $218/Night
7 Nights - CA $1,524
Condo
10.0(18 Reviews)
1 Bedroom
3 Guests
- Oceanfront
- Ocean View
- View
- Kitchen
CA $470/Night
7 Nights - CA $3,291
Resort
8.5(786 Reviews)
32 Guests
- Private Beach
- Oceanfront
- Hot Tub
- Parking
CA $213/Night
7 Nights - CA $1,488
Condo
10.0(12 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $546/Night
7 Nights - CA $3,824
Condo
10.0(9 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $553/Night
7 Nights - CA $3,871
Apartment
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $860/Night
7 Nights - CA $6,018
Condo
10.0(4 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $513/Night
7 Nights - CA $3,593
Simpson Bay Villas, Airbnb and Holiday Homes Under $200
Over 107+ Simpson Bay Private Villas, Airbnb and Holiday Homes Under $200
Condo
10.0(13 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
CA $233/Night
7 Nights - CA $1,631
Apartment
9.6(5 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
- View
CA $203/Night
7 Nights - CA $1,422
CA $171/Night
7 Nights - CA $1,196
Apartment
10.0(11 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
CA $258/Night
7 Nights - CA $1,804
Apartment
8.9(12 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
- View
CA $258/Night
7 Nights - CA $1,807
Apartment
10.0(11 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $152/Night
7 Nights - CA $1,066
New
Apartment
10.0(9 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- View
- Kitchen
CA $238/Night
7 Nights - CA $1,664
Apartment
10.0(3 Reviews)
1 Bedroom
4 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $279/Night
7 Nights - CA $1,951
Apartment
10.0(2 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $277/Night
7 Nights - CA $1,942
Instantly Bookable Villa Rentals in Simpson Bay
Over 371+ Instantly Bookable Private Villas in or Near Simpson Bay
Condo
10.0(10 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $712/Night
7 Nights - CA $4,983
Condo
2 Bedrooms
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $649/Night
7 Nights - CA $4,542
Condo
10.0(8 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $622/Night
7 Nights - CA $4,351
Condo
10.0(5 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $933/Night
7 Nights - CA $6,534
Condo
10.0(5 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $300/Night
7 Nights - CA $2,097
Condo
10.0(4 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $443/Night
7 Nights - CA $3,104
Condo
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Pool
- Kitchen
- Child Friendly
CA $1,431/Night
7 Nights - CA $10,018
Condo
10.0(3 Reviews)
3 Bedrooms
7 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,133/Night
7 Nights - CA $7,933
Condo
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Child Friendly
Security/Safety
CA $730/Night
7 Nights - CA $5,110
Book a Last Minute Place to Stay in Simpson Bay
About Simpson Bay Vacation Rentals
There are more than 692 incredible getaway rentals that are available in Simpson Bay. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Simpson Bay.
BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Simpson Bay, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Simpson Bay. Places to stay near Simpson Bay are 880.24 ft² on average, with prices averaging CA $745 a night.
BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Simpson Bay. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods Simpson Bay, SX
There are 56 hotels in Simpson Bay 32 resorts, and 447 rentals
- Prices for a holiday home in Simpson Bay start at CA $149
- Top rated vacation home in Simpson Bay is Royal Dream Beachfront Condo- Walk Out to Palm Tree Lined Beach & Pool
- Most popular short term in Simpson Bay is The Morgan Resort Spa Village
- Cheapest place to stay in Simpson Bay is Blue Sail Rooms
- Most expensive holiday rental in Simpson Bay is La Villa Salee
Recently Booked Hotels, Resorts, or Rentals in Simpson Bay
Frequently Asked Questions About Simpson Bay?
What are the top hotels or resorts in Simpson Bay?
We provide an array of great vacation destinations in Simpson Bay. If you are looking to stay in or around the Simpson Bay area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Simpson Bay:
- Royal Dream Beachfront Condo- Walk Out to Palm Tree Lined Beach & Pool
- Top of the art penthouse on the beach - 4000 sq. ft of luxury
- LUXURIOUS BEACH FRONT UNIT - SPECTACULAR OCEAN VIEWS.
- The Penthouse at LaSiesta Stunning views in luxurious surroundings!
- Popular Beachfront Condo directly on Simpson Bay beach in St. Maarten
- Oceanfront villa with breathtaking views–2BR/2BA in Pelican Key, Simpson Bay
- OCEAN FRONT 3 BEDROOM PENTHOUSE UNIT. STAY IN LUXURY.
- Perfect beach front condo in Simpson Bay Beach 2 bedroom+ Loft, 2.5 Baths.
- Beach Front Modern Condo on the beach
- UNBRIDLED Le Papillon: Beachfront Elegance with Backup Generator
How many vacation rentals have private pools in Simpson Bay?
We have 101 luxury villas and vacation rentals featuriung a private pool in and near Simpson Bay. Some of the best destinations to stay that feature or have access to a swimming pool are:
Which hotel or resort in Simpson Bay is best for families?
Searching for a family-friendly getaway in Simpson Bay? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
How many hotels, resorts, or rentals are available in Simpson Bay?
BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 692 in the Simpson Bay area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Simpson Bay.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Maho Rental Villas and Private Getaways in Simpson Bay | 416 |
| Pelican Key Rental Villas and Private Getaways in Simpson Bay | 93 |
