Apartment
10.0(92 Reviews)
3 Bedrooms
8 Guests
Hot Tub
Parking
Ocean View
Balcony/Terrace
US $771/Night
7 Nights - US $5,397
Simpson Bay Villa Rentals
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Compare Villas, Resorts, & Rentals in Simpson Bay
10.0
US $805/Night
7 Nights - US $5,635
Condo
9.6(49 Reviews)
1 Bedroom
2 Guests
Oceanfront
Pool- Ocean View
- Balcony/Terrace
US $220/Night
7 Nights - US $1,540
Condo
10.0(63 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $682/Night
7 Nights - US $4,771
Condo
10.0(60 Reviews)
2 Bedrooms
4 Guests
Private Pool- Hot Tub
- Parking
- Pool
US $452/Night
7 Nights - US $3,163
Villa
10.0(53 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $292/Night
7 Nights - US $2,044
Condo
10.0(37 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $912/Night
7 Nights - US $6,383
Condo
10.0(36 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $413/Night
7 Nights - US $2,889
Luxury Places to Stay in Simpson Bay
Over 678+ Luxury Places to Stay in or Near Simpson Bay
Villa
7 Bedrooms
14 Guests
Air Conditioner
Internet
Child Friendly
Laundry
US $5,652/Night
7 Nights - US $39,564
US $3,509/Night
7 Nights - US $24,564
House
4 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $2,699/Night
7 Nights - US $18,896
US $2,002/Night
7 Nights - US $14,015
Villa
10.0(5 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
Breakfast- Parking
US $1,982/Night
7 Nights - US $13,874
Villa
10.0(15 Reviews)
6 Bedrooms
12 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,915/Night
7 Nights - US $13,402
Villa
10.0(2 Reviews)
6 Bedrooms
12 Guests
- Ocean View
- Balcony/Terrace
View
Kitchen
US $1,861/Night
7 Nights - US $13,024
Villa
10.0(1 Review)
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,849/Night
7 Nights - US $12,945
Top-Rated Villas with a Pool in Simpson Bay
Over 442+ Top-Rated Private Villas with a Pool in or Near Simpson Bay
Resort
10.0(94 Reviews)
5 Guests
- Breakfast
- Parking
- Pool
- Ocean View
US $423/Night
7 Nights - US $2,958
Condo
10.0(28 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $436/Night
7 Nights - US $3,049
Condo
10.0(23 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $449/Night
7 Nights - US $3,141
Villa
10.0(21 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $956/Night
7 Nights - US $6,694
Apartment
10.0(21 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $168/Night
7 Nights - US $1,179
Condo
10.0(19 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $597/Night
7 Nights - US $4,181
New
Villa
10.0(18 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $856/Night
7 Nights - US $5,990
Condo
10.0(17 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $415/Night
7 Nights - US $2,903
Condo
10.0(16 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $536/Night
7 Nights - US $3,751
Pet-Friendly Villas in Simpson Bay
Over 57+ Pet-Friendly Private Villas in or Near Simpson Bay
US $800/Night
7 Nights - US $5,598
Apartment
9.8(4 Reviews)
2 Bedrooms
6 Guests
Private Beach- Oceanfront
- Parking
- Pool
US $516/Night
7 Nights - US $3,614
Villa
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $745/Night
7 Nights - US $5,212
Apartment
9.0(13 Reviews)
1 Bedroom
2 Guests
- Parking
- View
- Air Conditioner
- Internet
US $115/Night
7 Nights - US $805
Condo
10.0(2 Reviews)
1 Bedroom
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $302/Night
7 Nights - US $2,111
Condo
10.0(2 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $242/Night
7 Nights - US $1,694
US $829/Night
7 Nights - US $5,803
US $430/Night
7 Nights - US $3,011
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $115/Night
7 Nights - US $807
Large Private Villas in Simpson Bay
Over 122+ Large Villas in or Near Simpson Bay for Groups and Families
Villa
10.0(14 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $309/Night
7 Nights - US $2,162
Villa
10.0(1 Review)
1 Bedroom
8 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $572/Night
7 Nights - US $4,001
US $1,288/Night
7 Nights - US $9,019
House
10.0(6 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,212/Night
7 Nights - US $8,486
Apartment
9.2(170 Reviews)
12 Bedrooms
30 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $225/Night
7 Nights - US $1,575
Apartment
10.0(4 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $919/Night
7 Nights - US $6,433
Villa
10.0(3 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $393/Night
7 Nights - US $2,748
Villa
10.0(3 Reviews)
1 Bedroom
2 Guests
- Pool
- Balcony/Terrace
- Air Conditioner
- Internet
US $199/Night
7 Nights - US $1,393
Villa
10.0(2 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $1,061/Night
7 Nights - US $7,426
Wheelchair Accessible Holiday Homes in Simpson Bay
Over 167+ 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
US $390/Night
7 Nights - US $2,732
Resort
8.9(256 Reviews)
18 Guests
- Private Beach
- Oceanfront
- Hot Tub
- Parking
US $306/Night
7 Nights - US $2,145
Resort
9.2(1756 Reviews)
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $154/Night
7 Nights - US $1,081
Condo
10.0(17 Reviews)
1 Bedroom
3 Guests
- Ocean View
- View
- Air Conditioner
- Internet
US $346/Night
7 Nights - US $2,419
Resort
8.5(795 Reviews)
32 Guests
- Private Beach
- Oceanfront
- Hot Tub
- Parking
US $152/Night
7 Nights - US $1,062
Condo
10.0(12 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $385/Night
7 Nights - US $2,693
Condo
10.0(9 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $303/Night
7 Nights - US $2,124
Apartment
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $805/Night
7 Nights - US $5,637
Condo
10.0(4 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $383/Night
7 Nights - US $2,683
Simpson Bay Villas, Airbnb and Holiday Homes Under $200
Over 114+ Simpson Bay Private Villas, Airbnb and Holiday Homes Under $200
Condo
10.0(13 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $158/Night
7 Nights - US $1,108
Apartment
9.6(5 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Breakfast
- Parking
- Pool
US $145/Night
7 Nights - US $1,015
US $121/Night
7 Nights - US $844
Apartment
10.0(11 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $184/Night
7 Nights - US $1,288
Apartment
8.9(12 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $184/Night
7 Nights - US $1,290
Apartment
10.0(11 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $118/Night
7 Nights - US $824
New
Apartment
10.0(9 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- View
US $154/Night
7 Nights - US $1,078
Condo
10.0(5 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $185/Night
7 Nights - US $1,297
Apartment
10.0(3 Reviews)
1 Bedroom
4 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $189/Night
7 Nights - US $1,324
Instantly Bookable Villa Rentals in Simpson Bay
Over 366+ Instantly Bookable Private Villas in or Near Simpson Bay
Condo
10.0(10 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $451/Night
7 Nights - US $3,158
Condo
2 Bedrooms
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $463/Night
7 Nights - US $3,242
House
10.0(9 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $481/Night
7 Nights - US $3,364
Condo
10.0(8 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $404/Night
7 Nights - US $2,827
Condo
10.0(5 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $666/Night
7 Nights - US $4,664
Condo
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Pool
- Kitchen
- Child Friendly
US $1,008/Night
7 Nights - US $7,059
Condo
10.0(3 Reviews)
3 Bedrooms
7 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $723/Night
7 Nights - US $5,063
Condo
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Child Friendly
Security/Safety
US $531/Night
7 Nights - US $3,716
Condo
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Child Friendly
- Security/Safety
US $498/Night
7 Nights - US $3,485
Book a Last Minute Place to Stay in Simpson Bay
About Simpson Bay Vacation Rentals
There are more than 687 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 882 ft² on average, with prices averaging US $524 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 31 resorts, and 443 rentals
- Prices for a holiday home in Simpson Bay start at US $90
- Top rated vacation home in Simpson Bay is Amazing Beachfront Condo in Simpson Bay -Walk Out 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 The Ultimate Private Experience. 7 Bedroom Villa in Dutch Sint Maarten
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:
- Amazing Beachfront Condo in Simpson Bay -Walk Out Beach/Pool
- Top of the art penthouse on the beach - 4000 sq. ft of luxury
- 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
- Gorgeous Beachfront Ground Floor 2 Bedroom 2 Bath Condo
How many vacation rentals have private pools in Simpson Bay?
We have 104 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 687 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 | 419 |
| Pelican Key Rental Villas and Private Getaways in Simpson Bay | 94 |
