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Holiday Rentals in Simpson Bay

Find the holiday rentals that appeal to you the most

The best holiday rentals in Simpson Bay

Check out our pick of great holiday rentals in Simpson Bay

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Blue Sail Apartments

Simpson Bay

Boasting pool with a view, garden and views of pool, Blue Sail Apartments is set in Simpson Bay, 700 metres from Kim Sha Beach. A hot tub and a car rental service are available for guests.

R
Raul
From
Estonia
Kay was very understanding and lovely person.
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 804 reviews
Price from
US$68.40
1 night, 2 adults

Villa Cleavage

Simpson Bay

Located in Simpson Bay and only 1.1 km from Kim Sha Beach, Villa Cleavage provides accommodation with mountain views, free WiFi and free private parking.

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 16 reviews
Price from
US$115
1 night, 2 adults

Mullet Bay Suites - Your Luxury Stay Awaits

Cupecoy (Near Simpson Bay)

Set in Cupecoy, Mullet Bay Suites - Your Luxury Stay Awaits offers beachfront accommodation 100 metres from Mullet Bay Beach and provides various facilities, such as pool with a view, a fitness centre...

D
DANIEL
From
Poland
Perfect location for exploring the island. Nice apartment in new building, I think one of the highest on island. Nice view, good parking spot in front of the building. Daniel and Alina
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 174 reviews
Price from
US$217.80
1 night, 2 adults

condostmaarten by the sea -Adults Only-

Koolbaai (Near Simpson Bay)

Condostmaarten by the sea -Adults Only- is situated in Koolbaai and has a pool with a view and sea views. This beachfront property offers access to a balcony, free private parking and free WiFi.

a
aram
From
Afghanistan
Beautiful location. Always great waking up to the sounds of the ocean crashing against the rocks. the large swimming pool overlooking the sea is magical. the panoramic room is an amazing experience. great restaurant nearby. One thing I did learn is that you should definitely rent a car but everything is at 5minutes driving from the condo. Supermarkets, restaurants, beaches
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 129 reviews
Price from
US$403
1 night, 2 adults

Modern 3BR Home with Own Private Pool

Philipsburg (Near Simpson Bay)

Boasting air-conditioned accommodation with a private pool, garden view and a patio, Modern 3BR Home with Own Private Pool is set in Philipsburg.

L
Luana
From
United Kingdom
Great location and the host was super helpful and responsive, suggesting things to do and asking how our first night was. The property was very modern and somewhere we could stay for a long trip.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 32 reviews
Price from
US$344.40
1 night, 2 adults

1 bedroom apt with pool in Simpson Bay

Koolbaai (Near Simpson Bay)

Featuring air-conditioned accommodation with a private pool, 1 bedroom apt with pool in Simpson Bay is set in Koolbaai. This property offers access to a terrace, free private parking and free WiFi.

C
Claudia
From
United Kingdom
I liked the shared pool it was very nice.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 10 reviews
Price from
US$211.31
1 night, 2 adults

Serenity Penthouse

Lowlands (Near Simpson Bay)

Set in Lowlands, Serenity Penthouse offers accommodation with rooftop pool, free WiFi and free private parking for guests who drive.

T
Tahfere
From
United States
The space was very clean , super spacious. Extremely relaxing ! Pool is heated view is amazing !
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 6 reviews
Price from
US$800
1 night, 2 adults

The Castle

Philipsburg (Near Simpson Bay)

A recently renovated property, The Castle is set in Philipsburg near Great Bay Beach, Little Bay Beach.

C
Clif
From
United Kingdom
Everything about the property was top notch, very clean, welcoming and in a prime location. It is safe, providing extra safety access to guests. Amenities are walking distance and the property is equipped with a new kitchen giving the choice to self cater or visit one of the many restaurants nearby. The hosts were exceptionally professional and friendly, Louis went out of his way to ensure comfort, even when I locked myself out and messaged him at three o’clock in the morning, he politely and quickly came to my rescue. lol (more than once) very nice place, I will definitely recommend.
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 118 reviews
Price from
US$120
1 night, 2 adults

The Aquila Villa

Philipsburg (Near Simpson Bay)

Situated in Philipsburg, 300 metres from Great Bay Beach and 2.8 km from Little Bay Beach, The Aquila Villa offers a casino and air conditioning.

m
mason
From
United States
We like the space, the view and privacy of the Villa. All facilities were excellent.
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 90 reviews
Price from
US$91.91
1 night, 2 adults

The Black Palm

Philipsburg (Near Simpson Bay)

The Black Palm is located in Philipsburg and features a private pool and sea views. This beachfront property offers access to a balcony, free private parking and free WiFi.

F
Francois
From
United Arab Emirates
The hosts were exceptional, from booking, to directions, hospitality upon arrival, the pictures don't do the place justice, it really is a special place. Mathilde and Kevin took great care of us and even arranged a private couples massage in our room.
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 72 reviews
Price from
US$368
1 night, 2 adults
All holiday rentals in Simpson Bay

Top picks for Simpson Bay hotels

Explore our most popular hotels in Simpson Bay

Filter by:

Review score

Blue Sail Apartments

Simpson Bay

Boasting pool with a view, garden and views of pool, Blue Sail Apartments is set in Simpson Bay, 700 metres from Kim Sha Beach. A hot tub and a car rental service are available for guests.

R
Raul
From
Estonia
Kay was very understanding and lovely person.
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 804 reviews
Price from
US$68.40
1 night, 2 adults

Villa Cleavage

Simpson Bay

Located in Simpson Bay and only 1.1 km from Kim Sha Beach, Villa Cleavage provides accommodation with mountain views, free WiFi and free private parking.

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 16 reviews
Price from
US$115
1 night, 2 adults

Mullet Bay Suites - Your Luxury Stay Awaits

Cupecoy (Near Simpson Bay)

Set in Cupecoy, Mullet Bay Suites - Your Luxury Stay Awaits offers beachfront accommodation 100 metres from Mullet Bay Beach and provides various facilities, such as pool with a view, a fitness centre...

D
DANIEL
From
Poland
Perfect location for exploring the island. Nice apartment in new building, I think one of the highest on island. Nice view, good parking spot in front of the building. Daniel and Alina
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 174 reviews
Price from
US$217.80
1 night, 2 adults

condostmaarten by the sea -Adults Only-

Koolbaai (Near Simpson Bay)

Condostmaarten by the sea -Adults Only- is situated in Koolbaai and has a pool with a view and sea views. This beachfront property offers access to a balcony, free private parking and free WiFi.

a
aram
From
Afghanistan
Beautiful location. Always great waking up to the sounds of the ocean crashing against the rocks. the large swimming pool overlooking the sea is magical. the panoramic room is an amazing experience. great restaurant nearby. One thing I did learn is that you should definitely rent a car but everything is at 5minutes driving from the condo. Supermarkets, restaurants, beaches
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 129 reviews
Price from
US$403
1 night, 2 adults

Modern 3BR Home with Own Private Pool

Philipsburg (Near Simpson Bay)

Boasting air-conditioned accommodation with a private pool, garden view and a patio, Modern 3BR Home with Own Private Pool is set in Philipsburg.

L
Luana
From
United Kingdom
Great location and the host was super helpful and responsive, suggesting things to do and asking how our first night was. The property was very modern and somewhere we could stay for a long trip.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 32 reviews
Price from
US$344.40
1 night, 2 adults

1 bedroom apt with pool in Simpson Bay

Koolbaai (Near Simpson Bay)

Featuring air-conditioned accommodation with a private pool, 1 bedroom apt with pool in Simpson Bay is set in Koolbaai. This property offers access to a terrace, free private parking and free WiFi.

C
Claudia
From
United Kingdom
I liked the shared pool it was very nice.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 10 reviews
Price from
US$211.31
1 night, 2 adults

Serenity Penthouse

Lowlands (Near Simpson Bay)

Set in Lowlands, Serenity Penthouse offers accommodation with rooftop pool, free WiFi and free private parking for guests who drive.

T
Tahfere
From
United States
The space was very clean , super spacious. Extremely relaxing ! Pool is heated view is amazing !
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 6 reviews
Price from
US$800
1 night, 2 adults

The Castle

Philipsburg (Near Simpson Bay)

A recently renovated property, The Castle is set in Philipsburg near Great Bay Beach, Little Bay Beach.

C
Clif
From
United Kingdom
Everything about the property was top notch, very clean, welcoming and in a prime location. It is safe, providing extra safety access to guests. Amenities are walking distance and the property is equipped with a new kitchen giving the choice to self cater or visit one of the many restaurants nearby. The hosts were exceptionally professional and friendly, Louis went out of his way to ensure comfort, even when I locked myself out and messaged him at three o’clock in the morning, he politely and quickly came to my rescue. lol (more than once) very nice place, I will definitely recommend.
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 118 reviews
Price from
US$120
1 night, 2 adults

The Aquila Villa

Philipsburg (Near Simpson Bay)

Situated in Philipsburg, 300 metres from Great Bay Beach and 2.8 km from Little Bay Beach, The Aquila Villa offers a casino and air conditioning.

m
mason
From
United States
We like the space, the view and privacy of the Villa. All facilities were excellent.
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 90 reviews
Price from
US$91.91
1 night, 2 adults

The Black Palm

Philipsburg (Near Simpson Bay)

The Black Palm is located in Philipsburg and features a private pool and sea views. This beachfront property offers access to a balcony, free private parking and free WiFi.

F
Francois
From
United Arab Emirates
The hosts were exceptional, from booking, to directions, hospitality upon arrival, the pictures don't do the place justice, it really is a special place. Mathilde and Kevin took great care of us and even arranged a private couples massage in our room.
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 72 reviews
Price from
US$368
1 night, 2 adults
All holiday rentals in Simpson Bay

Most booked holiday rentals in Simpson Bay and surroundings in the past month

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Popular with guests booking holiday rentals in Simpson Bay

Popular with guests booking holiday rentals in Simpson Bay

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 6 reviews

Popular with guests booking holiday rentals in Simpson Bay

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 16 reviews

Popular with guests booking holiday rentals in Simpson Bay

Popular with guests booking holiday rentals in Simpson Bay

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 10 reviews

Popular with guests booking holiday rentals in Simpson Bay

Scored out of 10, guest rating 7.7
Good - What previous guests thought, 23 reviews

Popular with guests booking holiday rentals in Simpson Bay

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 10 reviews

Popular with guests booking holiday rentals in Simpson Bay

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 165 reviews

Popular with guests booking holiday rentals in Simpson Bay

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 217 reviews

Popular with guests booking holiday rentals in Simpson Bay

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 804 reviews

These holiday rentals in Simpson Bay and nearby have options with free cancellation

Diamond Gem Residence

Koolbaai
Free cancellation options available
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 112 reviews

Diamond Gem Residence features rooms in Koolbaai. The property features sea and garden views. The guest house offers rooms with air conditioning, free private parking and free WiFi.

From US$156.60 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 107 reviews

Set in Marigot, just less than 1 km from Nettle Bay Beach, Superbe studio Dolce Vita vue mer plage piscine offers beachfront accommodation with a private beach area, an outdoor swimming pool and free...

Divine Rest

Philipsburg
Free cancellation options available
Scored out of 10, guest rating 7.5
Good - What previous guests thought, 35 reviews

Situated in Philipsburg, within 1.9 km of Little Bay Beach, Divine Rest offers accommodation with air conditioning.

The Castle

Philipsburg
Free cancellation options available
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 118 reviews

A recently renovated property, The Castle is set in Philipsburg near Great Bay Beach, Little Bay Beach.

From US$145.80 per night

Over The Hill Residence

Grand Case
Free cancellation options available
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 166 reviews

Boasting an outdoor swimming pool and views of sea, Over The Hill Residence is a recently renovated guest house situated in Grand Case, 1.5 km from Grand Case Beach.

From US$219.93 per night

Villa Branca - Les Terres Basses

Marigot
Free cancellation options available
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 5 reviews

Situated in Marigot, Villa Branca - Les Terres Basses features accommodation with private pool, free WiFi and free private parking for guests who drive. This villa has a garden.

From US$622.35 per night

Sea-Renity

Oyster Pond
Free cancellation options available
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 4 reviews

Sea-Renity has sea views, free WiFi and free private parking, situated in Oyster Pond, 1.2 km from Dawn Beach. With mountain views, this accommodation features a terrace and a swimming pool.

From US$288.33 per night

C'RENITY VILLA

Cul de Sac
Free cancellation options available
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 51 reviews

Located in Cul de Sac and only 1.9 km from Orient Bay Beach, C'RENITY VILLA provides accommodation with mountain views, free WiFi and free private parking.

Highly rated holiday rentals in Simpson Bay and nearby

The Black Palm

Philipsburg
8.0+ review score
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 72 reviews

The Black Palm is located in Philipsburg and features a private pool and sea views. This beachfront property offers access to a balcony, free private parking and free WiFi.

From US$583.20 per night
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 174 reviews

Set in Cupecoy, Mullet Bay Suites - Your Luxury Stay Awaits offers beachfront accommodation 100 metres from Mullet Bay Beach and provides various facilities, such as pool with a view, a fitness centre...

From US$326.51 per night

C'Renity Studio

Cul de Sac
8.0+ review score
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 46 reviews

Boasting accommodation with a patio, C'Renity Studio is set in Cul de Sac.

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 10 reviews

Featuring air-conditioned accommodation with a private pool, 1 bedroom apt with pool in Simpson Bay is set in Koolbaai. This property offers access to a terrace, free private parking and free WiFi.

From US$303.21 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 5 reviews

Boasting air-conditioned accommodation with a private pool, Luxurious 1 bedroom Apt with pool in Simpson Bay is situated in Koolbaai. This property offers access to a terrace and free private parking.

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 21 reviews

Boasting air-conditioned accommodation with a private pool, garden view and a patio, Spacious 3BR Home with Own Private Cozy Pool is situated in Koolbaai.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 32 reviews

Boasting air-conditioned accommodation with a private pool, garden view and a patio, Modern 3BR Home with Own Private Pool is set in Philipsburg.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 11 reviews

Featuring air-conditioned accommodation with a pool with a view, mountain view and a balcony, Aquamarine, private room in Villa Casa Blue pool sea view is set in Koolbaai.

Holiday Rentals with swimming pools in Simpson Bay and nearby

Scored out of 10, guest rating 7.5
Good - What previous guests thought, 2 reviews

Located just 1.1 km from Simpson Bay Beach, Blue Sky 2 bedr apartment with pool in Simpson bay provides accommodation in Koolbaai with access to an outdoor swimming pool, a garden, as well as a lift.

Scored out of 10, guest rating 7.7
Good - What previous guests thought, 23 reviews

Pelican Pearl is set in Simpson Bay and offers an outdoor swimming pool and a garden.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

2.8 km from Little Bay Beach in Koolbaai, Blue Sanctuary provides accommodation with access to a hot tub, spa facilities and fitness centre.

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 2 reviews

Featuring air-conditioned accommodation with a patio, Villa Casa Blue, between sky and ocean, Almond Grove is located in Koolbaai.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 9 reviews

Featuring air-conditioned accommodation with a pool with a view, Moonstone, private room in Villa Casa Blue pool sea view is located in Koolbaai.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 129 reviews

Condostmaarten by the sea -Adults Only- is situated in Koolbaai and has a pool with a view and sea views. This beachfront property offers access to a balcony, free private parking and free WiFi.

From US$610 per night
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 6 reviews

Located in Maho Reef and only 2.4 km from Simpson Bay Beach, Reflection Z 5 Star Villa provides accommodation with sea views, free WiFi and free private parking.

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 10 reviews

Boasting air-conditioned accommodation with a private pool, lake view and a balcony, Refait à neuf, magnifique vue sur le lagon appartement 4 à 5p is situated in Marigot.

Enjoy breakfast in Simpson Bay and nearby

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 3 reviews

Boasting air-conditioned accommodation with a private pool, The luxe 1 bedroom apartment is set in Koolbaai. This property offers access to a terrace and free private parking.

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 1 review

Situated in Koolbaai, Blue Sky 1 bedroom apartment in Simpson Bay features accommodation with private pool, free WiFi and free private parking for guests who drive.

Scored out of 10, guest rating 7.0
Good - What previous guests thought, 1 review

Featuring air-conditioned accommodation with a private pool, Blue Sky apartment with lagoon view is located in Koolbaai. This property offers access to a terrace, free private parking and free WiFi.

Boasting air-conditioned accommodation with a private pool, Villa Zircon in Pelican Key awaits you is situated in Koolbaai.

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 16 reviews

Featuring garden views, SXM Spotters Paradise features accommodation with patio, around 300 metres from Simpson Bay Beach. This property offers access to a terrace and free private parking.

Scored out of 10, guest rating 7.0
Good - What previous guests thought, 7 reviews

Boasting a balcony with garden views, a private beach area and a casino, Maho Beach Ocean View Corner Suite can be found in Maho Reef, close to Maho Beach and less than 1 km from Simpson Bay Beach.

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 36 reviews

Boasting air-conditioned accommodation with a balcony, Maho Beach Bright Studio, Ocean View is situated in Maho Reef.

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 20 reviews

Boasting air-conditioned accommodation with a patio, Maho Beach 1-BR Ocean Suite is situated in Maho Reef. Private parking is available on site.

FAQ about holiday rentals in Simpson Bay

Holiday rentals that guests love in Simpson Bay

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Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 10 reviews
Gorgeous villa with good facilities, beautiful pool and lovely patio.
Guest review by
Sanne
People with friends