The 10 best holiday rentals in Simpson Bay, Sint Maarten | Booking.com
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Holiday Rentals in Simpson Bay

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The best holiday rentals in Simpson Bay

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Tradewinds Apartments Simpson Bay

Simpson Bay

Tradewinds Apartments Simpson Bay is set in Simpson Bay and features a pool with a view and sea views. There is a private entrance at the apartment for the convenience of those who stay.

A
Alexandra
From
Netherlands
Amazing place and fantastic hosts!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 168 reviews
Price from
US$300
1 night, 2 adults
Check availability

The Hills Residence

Simpson Bay

Set in Simpson Bay, 600 metres from Kim Sha Beach, The Hills Residence offers accommodation with a rooftop pool, free private parking, a casino and a terrace.

L
Leif
From
Germany
It’s very modern and luxurious furnished with great views over Simpson Bay. The location is very central with supermarkets, restaurants, beach and bars in walking distance
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 195 reviews
Price from
US$164.59
1 night, 2 adults
Check availability

Blue Dream Apartments

Simpson Bay

Boasting pool with a view, garden and views of pool, Blue Dream 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 8.3
Very good - What previous guests thought, 724 reviews
Price from
US$144.90
1 night, 2 adults
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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 8.0
Very good - What previous guests thought, 16 reviews
Price from
US$115
1 night, 2 adults
Check availability

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...

G
Gia
From
Canada
Rooms exactly as in picture.excellent views from the room Bed supper comfy. Unit provided all your housing needs. Safe and extremely secure. I travelled alone and felt safe. Daily cleaner. 5 min walk to beach. Pool and restaurant on site.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 159 reviews
Price from
US$226.80
1 night, 2 adults
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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.

L
Leeana
From
Trinidad and Tobago
Lovely and well maintained property! Location is a bit further out but with a large fully equipped kitchen and a lovely restaurant within walking distance didn’t miss anything at all. Highlight was staying in bed and just enjoying the view of the beautiful water. Lovely getaway that I would love to return to! Hosts communicated well and were very helpful. Definitely recommend!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 126 reviews
Price from
US$403
1 night, 2 adults
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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 9.7
Exceptional - What previous guests thought, 31 reviews
Price from
US$414.75
1 night, 2 adults
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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 9.0
Superb - What previous guests thought, 9 reviews
Price from
US$211.31
1 night, 2 adults
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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
Check availability

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 8.5
Very good - What previous guests thought, 109 reviews
Price from
US$120
1 night, 2 adults
Check availability
All holiday rentals in Simpson Bay

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

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Highly rated holiday rentals in Simpson Bay and nearby

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 9 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$205.41 per night
  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 122 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$97.20 per night
  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 31 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.

    From US$408.24 per night
  • Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 126 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$430 per night

  • The Black Palm

    Philipsburg
    8.0+ review score
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 74 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.

  • Scored out of 10, guest rating 8.2
    Very good - What previous guests thought, 5 reviews

    Boasting air-conditioned accommodation with a patio, Patmay Greenery. Fresh air, vacation get away. Is set in Saint-James. This property offers access to a balcony, free private parking and free WiFi.

    From US$205.54 per night

  • Perle Des Sables

    Marigot
    8.0+ review score
    Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 42 reviews

    Situated in Marigot, just 600 metres from Nettle Bay Beach, Perle Des Sables features beachfront accommodation with a private beach area, an outdoor swimming pool and free WiFi.

    From US$168.78 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 53 reviews

    Located in Marigot, just less than 1 km from Nettle Bay Beach, Appartement PIEDS DANS L'EAU VUE MER ACCES PLAGE ET PISCINE provides beachfront accommodation with a private beach area, pool with a view...

    From US$121.59 per night

Enjoy breakfast in Simpson Bay and nearby

  • Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 159 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$279.83 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 8.3
    Very good - What previous guests thought, 3 reviews

    Boasting air-conditioned accommodation with a private pool, OASIS deluxe 1 bedroom apartment with Pool is situated in Koolbaai. The property has lake views and is 400 metres from Kim Sha Beach.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Boasting air-conditioned accommodation with a balcony, OASIS Penthouse with private garden & shared pool is situated in Koolbaai.

  • 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.

  • 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.

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

  • Lagoon Terrace grand studio

    Baie Nettle
    Free cancellation options available
    Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 87 reviews

    Featuring air-conditioned accommodation with a private pool, Lagoon Terrace grand studio is located in Baie Nettle. This beachfront property offers access to free WiFi and free private parking.

  • Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 11 reviews

    Joli appartement entier sur jardin avec salle d'eau et chambre indépendantes et cuisine équipée is situated in Marigot.

  • Fraicheur Des Caraibes

    Marigot
    Free cancellation options available
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 30 reviews

    Boasting sea views, Fraicheur Des Caraibes is situated in Marigot, around 300 metres from Baie de la Potence Beach. This beachfront property offers access to free WiFi and free private parking.

    From US$170.63 per night

  • The Castle

    Philipsburg
    Free cancellation options available
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 109 reviews

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

    From US$129.60 per night

  • The Aquila Villa

    Philipsburg
    Free cancellation options available
    Scored out of 10, guest rating 8.1
    Very good - What previous guests thought, 89 reviews

    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.

    From US$99.26 per night

  • Cozy apartment with garden in La Savane 75 m² mountain view is situated in Happy Bay and offers barbecue facilities.

    From US$324.24 per night

  • Charming Apartment in La Savane - 65 m² - Terrace with View is situated in Happy Bay.

    From US$312.66 per night
  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 1 review

    Situated in Happy Bay and only 1.5 km from Grand Case Beach, Charming Apartment in La Savane, 65 sqm with Terrace features accommodation with garden views, free WiFi and free private parking.

Holiday rentals that guests love in Simpson Bay

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Hotels in Simpson Bay

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Apartments in Simpson Bay

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