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 Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts 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 Holiday Rentals in Simpson Bay
Over 678+ Luxury Holiday Rentals 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 Holiday Rentals with a Pool in Simpson Bay
Over 442+ The Best Private Villas and Holiday Rentals in Simpson Bay with a Pool
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 Holiday Rentals in Simpson Bay
Over 57+ Pet-Friendly Holiday Rentals 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 Holiday Rentals and Private Villas in Simpson Bay
Over 122+ Large Holiday Rentals and Private Villas in or Near Simpson Bay
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 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 Private Villas and Holiday Homes Under $200
Over 114+ Simpson Bay Private Villas 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 Holiday Homes in Simpson Bay
Over 366+ Instantly Bookable Holiday Homes 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 Casai's Private Villas and Holiday Rentals in Simpson Bay
Discover more than 687 vacation rentals available in Simpson Bay. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Simpson Bay.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Simpson Bay, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Simpson Bay. On average, places to stay near Simpson Bay offer 882 ft², with nightly prices averaging US $524.
With Casai, finding and comparing holiday rentals in Simpson Bay is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Simpson Bay, SX
There are 687 Simpson Bay, SX Holiday 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 Holiday Rentals in Simpson Bay
Frequently Asked Questions About Simpson Bay?
What are the top holiday rentals in Simpson Bay?
With numerous options available in Simpson Bay, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday 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 holiday rentals have private pools in Simpson Bay?
Discover a selection of holiday rentals with private pools near Simpson Bay with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Simpson Bay are best for families?
If you're searching for a family-friendly holiday home in Simpson Bay, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Simpson Bay:
How many Casai.nz holiday rentals are available in Simpson Bay?
As of 2026, Casai boasts over 687 properties listed in the Simpson Bay area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Simpson Bay.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Maho Vacation Rentals in Simpson Bay | 419 |
| Pelican Key Vacation Rentals in Simpson Bay | 94 |
