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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
Rogers
From
Anguilla
The location was great, quiet, PERFECT!!!!!!
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 790 reviews
Price from
US$69.30
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...

C
Connor
From
South Africa
Was an absolute amazing suite with great views and awesome facilities. The staff where super helpful and very accommodating with me and definitely will be staying again
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 170 reviews
Price from
US$218.70
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.

C
Charlene
From
United Kingdom
I loved the deco of apartments, they are also very clean and modern. It's a spacious apartment, with everything you may need provided. The owner is alao very accommodating
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$352.80
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$995
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, 112 reviews
Price from
US$120
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.

B
Beatrix
From
Hungary
Great apartment, clean, comfortable and well equipped. The hosts are very nice and helpfull. The swimming pool was great and the view for the sea is georgeous.
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 73 reviews
Price from
US$368
1 night, 2 adults

Divine Rest

Philipsburg (Near Simpson Bay)

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

C
Colin P
From
United Kingdom
Great host, clean place, secure, easy walking distance to bars, cafes, shops & beach.
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 34 reviews
Price from
US$76.50
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, 23 reviews

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 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, 163 reviews

Popular with guests booking holiday rentals in Simpson Bay

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 208 reviews

Popular with guests booking holiday rentals in Simpson Bay

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 790 reviews

Holiday Rentals with swimming pools in Simpson Bay and nearby

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$1,030 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 73 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.

Ti Koala

Baie Nettle
Swimming pool
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 105 reviews

Set 60 metres from Nettle Bay Beach, Ti Koala offers a private beach area, pool with a view and air-conditioned accommodation with a balcony and free WiFi.

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 170 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$633.41 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 167 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$232.95 per night

Spacious villa with sea view in Saint Martin + private pool. Is located in Les Terres Basses and offers an outdoor swimming pool and a garden.

From US$13,840.87 per night
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.

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.

Highly rated holiday rentals in Simpson Bay and nearby

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.

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 115 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$124.20 per night

The Castle

Philipsburg
8.0+ review score
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 112 reviews

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

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 32 reviews

Boasting a garden, Vacances entre mer et colline is set in Oyster Pond, within 2.3 km of Dawn Beach.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 15 reviews

Résidence Adam et Eve in Orient Bay provides adults-only accommodation with an outdoor swimming pool, a garden and a bar.

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 26 reviews

Featuring air-conditioned accommodation with a pool with a view, Charm and sea, large studio designed by architect is located in Cul de Sac.

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.

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

Divine Rest

Philipsburg
Free cancellation options available
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 34 reviews

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

The luxe 1 bedroom apartment

Koolbaai
Free cancellation options available
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 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.

Blue Sky 1 bedroom apartment in Simpson Bay

Koolbaai
Free cancellation options available
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.

Blue Sky apartment with lagoon view

Koolbaai
Free cancellation options available
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.

Villa Zircon in Pelican Key awaits you

Koolbaai
Free cancellation options available

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

Villa Cleavage

Simpson Bay
Free cancellation options available
Scored out of 10, guest rating 7.9
Good - What previous guests thought, 16 reviews

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.

Modern 3BR Home with Own Private Pool

Philipsburg
Free cancellation options available
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.

Enjoy breakfast in Simpson Bay and nearby

Blue Sanctuary

Koolbaai
Breakfast options
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 9.2
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.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 8 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 8.5
Very good - 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 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.

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 House - Luxe 1 Bedroom - Ocean Hideaway can be found in Maho Reef, close to Maho Beach and less than 1 km from...

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 35 reviews

Boasting air-conditioned accommodation with a balcony, Maho Beach House - Luxe Studio - Ocean Escape is situated in Maho Reef.

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