701+ Private Villas and Holiday Rentals in Simpson Bay |
Simpson Bay Holiday Rentals
10.0
Exceptional
(154 Reviews)
- Simpson Bay
- Beacon Hill
- 0.20 mi to center
4500 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Private Pool
- Oceanfront
- Pool
R12,045/Night
For 7 Nights R84,318
10.0
Exceptional
(2 Reviews)
- Sint Maarten
- Simpson Bay
- 0.14 mi to center
1700.7 ft²
8 Guests
4 Bedrooms
6 Bathrooms
Free Cancellation
Apartment
- Oceanfront
- Pool
- Ocean View
R14,060/Night
For 7 Nights R98,418
9.4
Exceptional
(54 Reviews)
- Sint Maarten
- Simpson Bay
- 0.35 mi to center
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Ocean View
- Balcony/Terrace
- View
R6,010/Night
For 7 Nights R42,067
10.0
Exceptional
(112 Reviews)
- Simpson Bay
- Beacon Hill
- 0.08 mi to center
1200 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R4,375/Night
For 7 Nights R30,634
10.0
Exceptional
(1 Review)
- Simpson Bay
- Pelican Key
- 0.29 mi to center
13993.08 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Free Cancellation
House
- Oceanfront
- Pool
- Ocean View
R13,417/Night
For 7 Nights R93,918
10.0
Exceptional
(86 Reviews)
- Sint Maarten
- Simpson Bay
- 0.30 mi to center
4000 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Apartment
- Hot Tub
- Ocean View
- Balcony/Terrace
R10,812/Night
For 7 Nights R75,684
10.0
Exceptional
(80 Reviews)
- Sint Maarten
- Simpson Bay
- 0.36 mi to center
3067 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
R9,537/Night
For 7 Nights R66,751
10.0
Exceptional
(74 Reviews)
- Simpson Bay
- Pelican Key
- 0.31 mi to center
3000 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R11,141/Night
For 7 Nights R77,984
10.0
Exceptional
(60 Reviews)
- Simpson Bay
- Beacon Hill
- 0.21 mi to center
4306 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R18,149/Night
For 7 Nights R127,035
Luxury Holiday Rentals in Simpson Bay
Over 692+ Luxury Holiday Rentals in or Near Simpson Bay
New
- Simpson Bay
- Beacon Hill
- 0.05 mi to center
12917 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Ocean View
- Balcony/Terrace
- View
R96,812/Night
For 7 Nights R677,691
New
- Simpson Bay
- Pelican Key
- 0.21 mi to center
14 Guests
7 Bedrooms
8 Bathrooms
Group Friendly
Villa
- Fireplace/Heating
- Air Conditioner
- Internet
R96,668/Night
For 7 Nights R676,674
10.0
Exceptional
(1 Review)
- Simpson Bay
- Pelican Key
- 0.27 mi to center
6000 ft²
14 Guests
6 Bedrooms
7 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Kitchen
- Parking
R83,649/Night
For 7 Nights R585,540
New
- Simpson Bay
- Pelican Key
- 0.27 mi to center
5995.5 ft²
16 Guests
8 Bedrooms
9 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
R58,486/Night
For 7 Nights R409,405
New
- Sint Maarten
- Simpson Bay
- 0.48 mi to center
12 Guests
6 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R55,076/Night
For 7 Nights R385,538
New
- Simpson Bay
- Beacon Hill
- 0.18 mi to center
12 Guests
6 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R37,490/Night
For 7 Nights R262,436
10.0
Exceptional
(5 Reviews)
- Sint Maarten
- Simpson Bay
- 0.38 mi to center
10 Guests
5 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Fireplace/Heating
R36,733/Night
For 7 Nights R257,136
New
- Simpson Bay
- Beacon Hill
- 0.05 mi to center
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R35,572/Night
For 7 Nights R249,003
10.0
Exceptional
(14 Reviews)
- Simpson Bay
- Beacon Hill
- 0.22 mi to center
2150 ft²
12 Guests
6 Bedrooms
6 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R32,633/Night
For 7 Nights R228,436
Top-Rated Holiday Rentals with a Pool in Simpson Bay
Over 456+ The Best Private Villas and Holiday Rentals in Simpson Bay with a Pool
10.0
Exceptional
(59 Reviews)
- Sint Maarten
- Simpson Bay
- 0.08 mi to center
2280 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
R10,206/Night
For 7 Nights R71,434
10.0
Exceptional
(58 Reviews)
- Sint Maarten
- Simpson Bay
- 0.14 mi to center
1680 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Private Pool
- Hot Tub
- Fireplace/Heating
R7,954/Night
For 7 Nights R55,684
10.0
Exceptional
(52 Reviews)
- Simpson Bay
- Pelican Key
- 0.19 mi to center
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Pool
- Ocean View
- Balcony/Terrace
R4,932/Night
For 7 Nights R34,517
10.0
Exceptional
(44 Reviews)
- Simpson Bay
- Pelican Key
- 0.15 mi to center
2153 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R12,603/Night
For 7 Nights R88,218
10.0
Exceptional
(36 Reviews)
- Sint Maarten
- Simpson Bay
- 0.45 mi to center
1500 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Pool
- Ocean View
- Balcony/Terrace
R8,286/Night
For 7 Nights R58,001
10.0
Exceptional
(35 Reviews)
- Simpson Bay
- Beacon Hill
- 0.19 mi to center
2800 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
R13,045/Night
For 7 Nights R91,318
10.0
Exceptional
(31 Reviews)
- Sint Maarten
- Simpson Bay
- 0.17 mi to center
1000 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
R4,996/Night
For 7 Nights R34,967
10.0
Exceptional
(29 Reviews)
- Sint Maarten
- Simpson Bay
- 0.55 mi to center
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Pool
- Ocean View
- Balcony/Terrace
R9,533/Night
For 7 Nights R66,734
10.0
Exceptional
(29 Reviews)
- Simpson Bay
- Pelican Key
- 0.24 mi to center
800 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Pool
- Ocean View
- Balcony/Terrace
R3,679/Night
For 7 Nights R25,750
Pet-Friendly Holiday Rentals in Simpson Bay
Over 61+ Pet-Friendly Holiday Rentals in or Near Simpson Bay
10.0
Exceptional
(17 Reviews)
- Simpson Bay
- Beacon Hill
- 0.12 mi to center
2691 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R14,833/Night
For 7 Nights R103,834
10.0
Exceptional
(1 Review)
- Simpson Bay
- Beacon Hill
- 0.25 mi to center
1700.7 ft²
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Apartment
- Pet Friendly
- Parking
- Air Conditioner
R7,951/Night
For 7 Nights R55,667
10.0
Exceptional
(11 Reviews)
- Simpson Bay
- Beacon Hill
- 0.14 mi to center
2200 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R12,483/Night
For 7 Nights R87,384
9.8
Exceptional
(4 Reviews)
- Simpson Bay
- Beacon Hill
- 0.28 mi to center
1603.82 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Private Beach
- Oceanfront
- Spa
R9,042/Night
For 7 Nights R63,301
10.0
Exceptional
(6 Reviews)
- Simpson Bay
- Pelican Key
- 0.18 mi to center
6 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Pool
- Balcony/Terrace
- Pet Friendly
R10,833/Night
For 7 Nights R75,834
10.0
Exceptional
(4 Reviews)
- Simpson Bay
- Beacon Hill
- 0.25 mi to center
500 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Ocean View
- Balcony/Terrace
R6,383/Night
For 7 Nights R44,684
10.0
Exceptional
(2 Reviews)
- Simpson Bay
- Pelican Key
- 0.18 mi to center
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R14,522/Night
For 7 Nights R101,651
10.0
Exceptional
(2 Reviews)
- Simpson Bay
- Beacon Hill
- 0.06 mi to center
500 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Ocean View
- Balcony/Terrace
R6,319/Night
For 7 Nights R44,234
10.0
Exceptional
(2 Reviews)
- Simpson Bay
- Beacon Hill
- 0.12 mi to center
1250 ft²
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Ocean View
- Balcony/Terrace
R4,610/Night
For 7 Nights R32,267
Large Holiday Rentals and Private Villas in Simpson Bay
Over 128+ Large Holiday Rentals and Private Villas in or Near Simpson Bay
10.0
Exceptional
(27 Reviews)
- Simpson Bay
- Pelican Key
- 0.10 mi to center
5597 ft²
18 Guests
8 Bedrooms
7 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
R15,472/Night
For 7 Nights R108,301
10.0
Exceptional
(1 Review)
- Simpson Bay
- Pelican Key
- 0.28 mi to center
1700.7 ft²
8 Guests
1 Bedroom
3 Bathrooms
Free Cancellation
Villa
- Pool
- Balcony/Terrace
- View
R9,526/Night
For 7 Nights R66,684
New
- Simpson Bay
- Pelican Key
- 0.30 mi to center
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Pool
- Balcony/Terrace
- Kitchen
R21,475/Night
For 7 Nights R150,318
10.0
Exceptional
(13 Reviews)
- Simpson Bay
- Pelican Key
- 0.15 mi to center
2200 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
R6,284/Night
For 7 Nights R43,984
9.3
Exceptional
(168 Reviews)
- Sint Maarten
- Simpson Bay
- 0.04 mi to center
613.54 ft²
30 Guests
12 Bedrooms
10 Bathrooms
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
R2,813/Night
For 7 Nights R19,684
10.0
Exceptional
(5 Reviews)
- Simpson Bay
- Pelican Key
- 0.26 mi to center
13993 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
R20,202/Night
For 7 Nights R141,418
10.0
Exceptional
(5 Reviews)
- Simpson Bay
- Beacon Hill
- 0.20 mi to center
3229 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
R19,242/Night
For 7 Nights R134,701
10.0
Exceptional
(3 Reviews)
- Simpson Bay
- Pelican Key
- 0.20 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Pool
- Balcony/Terrace
- Air Conditioner
R2,662/Night
For 7 Nights R18,634
10.0
Exceptional
(2 Reviews)
- Sint Maarten
- Simpson Bay
- 0.81 mi to center
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Kitchen
R10,833/Night
For 7 Nights R75,834
Wheelchair Accessible Holiday Homes in Simpson Bay
Over 169+ Wheelchair Accessible Holiday Homes in or Near Simpson Bay
10.0
Exceptional
(41 Reviews)
- Sint Maarten
- Simpson Bay
- 0.30 mi to center
2151 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Ocean View
- Balcony/Terrace
- View
R7,036/Night
For 7 Nights R49,251
8.9
Fabulous
(329 Reviews)
- Sint Maarten
- Simpson Bay
- 0.23 mi to center
1115.86 ft²
18 Guests
1 Bathroom
Free Cancellation
Resort
- Private Beach
- Oceanfront
- Hot Tub
R9,042/Night
For 7 Nights R63,301
9.2
Exceptional
(1494 Reviews)
- Simpson Bay
- Pelican Key
- 0.23 mi to center
1 Bathroom
Family Friendly
Resort
- Pool
- Balcony/Terrace
- Breakfast
R3,189/Night
For 7 Nights R22,317
10.0
Exceptional
(25 Reviews)
- Sint Maarten
- Simpson Bay
- 0.38 mi to center
2000 ft²
6 Guests
3 Bedrooms
4 Bathrooms
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
R7,643/Night
For 7 Nights R53,501
8.5
Fabulous
(908 Reviews)
- Simpson Bay
- Pelican Key
- 0.07 mi to center
656.6 ft²
32 Guests
1 Bathroom
Free Cancellation
Resort
- Private Beach
- Oceanfront
- Hot Tub
R4,146/Night
For 7 Nights R29,017
10.0
Exceptional
(24 Reviews)
- Sint Maarten
- Simpson Bay
- 0.24 mi to center
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Kitchen
- Air Conditioner
- Internet
R5,680/Night
For 7 Nights R39,767
10.0
Exceptional
(19 Reviews)
- Sint Maarten
- Simpson Bay
- 0.07 mi to center
2400 ft²
5 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
R5,829/Night
For 7 Nights R40,800
10.0
Exceptional
(17 Reviews)
- Sint Maarten
- Simpson Bay
- 0.12 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
R9,917/Night
For 7 Nights R69,417
10.0
Exceptional
(17 Reviews)
- Sint Maarten
- Simpson Bay
- 0.59 mi to center
1100 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
R5,317/Night
For 7 Nights R37,217
Simpson Bay Private Villas and Holiday Homes Under $200
Over 119+ Simpson Bay Private Villas and Holiday Homes Under $200
10.0
Exceptional
(56 Reviews)
- Sint Maarten
- Simpson Bay
- 0.38 mi to center
500 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Ocean View
- Balcony/Terrace
R2,676/Night
For 7 Nights R18,734
9.6
Exceptional
(10 Reviews)
- Simpson Bay
- Beacon Hill
- 0.08 mi to center
645.83 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- View
- Pet Friendly
- Parking
R1,917/Night
For 7 Nights R13,417
9.4
Exceptional
(373 Reviews)
- Sint Maarten
- Simpson Bay
- 0.31 mi to center
1 Bathroom
Ocean View
Hotel
- Spa
- Ocean View
- Balcony/Terrace
R3,008/Night
For 7 Nights R21,050
10.0
Exceptional
(19 Reviews)
- Simpson Bay
- Pelican Key
- 0.10 mi to center
700 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Private Pool
- Pool
- Ocean View
R2,656/Night
For 7 Nights R18,584
9.5
Exceptional
(4 Reviews)
- Simpson Bay
- Pelican Key
- 0.15 mi to center
376.74 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Oceanfront
- Pool
- Ocean View
R2,417/Night
For 7 Nights R16,917
10.0
Exceptional
(11 Reviews)
- Simpson Bay
- Beacon Hill
- 0.18 mi to center
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Pool
- Kitchen
- Parking
R3,325/Night
For 7 Nights R23,284
10.0
Exceptional
(9 Reviews)
- Sint Maarten
- Simpson Bay
- 0.25 mi to center
430 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Ocean View
R2,366/Night
For 7 Nights R16,567
10.0
Exceptional
(4 Reviews)
- Sint Maarten
- Simpson Bay
- 0.49 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Pool
- Balcony/Terrace
R2,336/Night
For 7 Nights R16,350
10.0
Exceptional
(2 Reviews)
- Sint Maarten
- Simpson Bay
- 0.86 mi to center
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Private Pool
- Pool
- Ocean View
R2,793/Night
For 7 Nights R19,550
Instantly Bookable Holiday Homes in Simpson Bay
Over 385+ Instantly Bookable Holiday Homes in or Near Simpson Bay
10.0
Exceptional
(13 Reviews)
- Sint Maarten
- Simpson Bay
- 0.07 mi to center
1750 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Pool
- Ocean View
- Balcony/Terrace
R5,333/Night
For 7 Nights R37,334
New
- Simpson Bay
- Pelican Key
- 0.05 mi to center
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Condo
- Oceanfront
- Ocean View
- Balcony/Terrace
R7,719/Night
For 7 Nights R54,034
10.0
Exceptional
(8 Reviews)
- Sint Maarten
- Simpson Bay
- 0.53 mi to center
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
R4,761/Night
For 7 Nights R33,334
10.0
Exceptional
(7 Reviews)
- Sint Maarten
- Simpson Bay
- 0.30 mi to center
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Pool
- Ocean View
- Balcony/Terrace
R7,322/Night
For 7 Nights R51,251
10.0
Exceptional
(7 Reviews)
- Simpson Bay
- Pelican Key
- 0.16 mi to center
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
R6,574/Night
For 7 Nights R46,017
10.0
Exceptional
(7 Reviews)
- Sint Maarten
- Simpson Bay
- 0.08 mi to center
1032 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
R4,614/Night
For 7 Nights R32,300
10.0
Exceptional
(5 Reviews)
- Sint Maarten
- Simpson Bay
- 0.40 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Pool
- Ocean View
- Balcony/Terrace
R12,724/Night
For 7 Nights R89,068
10.0
Exceptional
(3 Reviews)
- Simpson Bay
- Beacon Hill
- 0.16 mi to center
7 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Pool
- Ocean View
- Balcony/Terrace
R11,979/Night
For 7 Nights R83,851
10.0
Exceptional
(3 Reviews)
- Sint Maarten
- Simpson Bay
- 0.14 mi to center
1938 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Pool
- Ocean View
- Balcony/Terrace
R8,038/Night
For 7 Nights R56,267
Book a Last Minute Place to Stay in Simpson Bay
About Casai's Private Villas and Holiday Rentals in Simpson Bay
Discover more than 701 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 947.16 ft², with nightly prices averaging R8,919.
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.
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Top Accommodation Types in Simpson Bay
| Type | Count |
|---|---|
| Holiday Apartments | 265 |
| Villas | 121 |
| Vacation Homes | 68 |
| Cottages | 1 |
Use these Quick Filters to Find a Holiday Rental in Simpson Bay
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Simpson Bay.
Weather in Simpson Bay, SX
View the weather forecast for Simpson Bay before booking your Simpson Bay Vacation Rentals to confirm your best time to go.
December - February
High 85°F Low 69°F
March - May
High 87°F Low 72°F
June - August
High 89°F Low 76°F
September - November
High 88°F Low 73°F
Top Attractions Around Simpson Bay, SX
Casai offers a large selection of top attractions around Simpson Bay . Research things to do on your vacation before you visit Simpson Bay.
Other Places to Stay in Simpson Bay, SX
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:
- Anchor House - Direct Oceanfront - Luxury & Modern Style
- 3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! nRates start at 250/nt!
- Top of the art penthouse on the beach - 4000 sq. ft of luxury
- LUXURIOUS BEACH FRONT UNIT - SPECTACULAR OCEAN VIEWS.
- WOW! WOW! WOW!, NEW VILLA LIBRE` STUNNING INSIDE AND OUT!
- ALMA - DIRECT BEACH ACCESS 4 BR VILLA
- The Penthouse at LaSiesta nnStunning views in luxurious surroundings!
- Popular Beachfront Condo directly on Simpson Bay beach in St. Maarten
- Simpson Bay Beach Modern Apartment. Roof deck Ocean Views WIFI Satellite TV.
- Oceanfront villa with breathtaking views–2BR/2BA in Pelican Key, Simpson Bay
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.
- Paradise in the West Indies
- ☀️ Infinity by IRE Vacations - Luxury Oceanfront Penthouse with Rooftop Pool
- Oceanview Oasis - Villa Del Sol W/Generator
- NEWLY BUILT VILLA FRANGIPANI 2nd Row Beachfront
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.co.za holiday rentals are available in Simpson Bay?
As of 2026, Casai boasts over 701 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 | 433 |
| Pelican Key Vacation Rentals in Simpson Bay | 95 |
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Finding the best prices in Simpson Bay
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