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.

M
Marcimone
From
Italy
Super place. Relax and the hostess are very nice and great welcoming:)
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.

A
Alexandre
From
Saint Barthelemy
We had an excellent stay in this tastefully decorated apartment close to all Simpson Bay attractions. The private garden and outdoor kitchen allowed us to concoct a delicious dinner with a view of the Simpson Bay lagoon. We will definitely come back to this apartment!
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, 725 reviews
Price from
US$121.50
1 night, 2 adults
Check availability

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...

E
Esther Cheri Henriquez
From
Netherlands
We had communicated our arrival time and were greeted by Emmanuel immediately after our arrival at reception. He led us directly to our large brand new luxury suite, fully equipped with modern electrical equipment (such as washing machine and dryer), with beautiful views from the rooms that differ depending on the room you are in. You can enjoy a sunrise or sunset, a beautiful golf course and a view of the French part of St. Marten, depending on the room you are in. There are several suites available and they differ from each other in terms of views, furnishings, but all suites also differ in theme in terms of decor and color. It is therefore important that you contact the manager after you have booked and indicate your specific wishes if you have certain expectations. We were able to enjoy the sunrise and sunset every day. There is a spacious gym and very large pool with facilities. The beautiful beach is a 5-minute walk away and has various food and drink posibilities as well as water sports activities. The photos speak for themselves. In short, an excellent stay, perfect location and highly recommended!!!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 159 reviews
Price from
US$229.50
1 night, 2 adults
Check availability

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
Check availability

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
Check availability

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
Check availability

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
careem
From
Saint Kitts and Nevis
It's right in the heart of town. Literally as you step outside your right in the middle of everything. Can do all your shopping and dining and not take 10 steps.
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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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

  • Diamond Gem Residence

    Koolbaai
    Free cancellation options available
    Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 123 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

  • Modern 3BR Home with Own Private Pool

    Philipsburg
    Free cancellation options available
    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 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$205.57 per night
  • Scored out of 10, guest rating 9.0
    Superb - 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...

    From US$134.11 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$121.61 per night

  • 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$170.65 per night

  • Fun under the sun!

    Cupecoy
    Free cancellation options available
    Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 12 reviews

    Located only 1.8 km from Baie Longue Beach in Cupecoy, Fun under the sun! features accommodation fitted with a patio, garden and year-round outdoor pool.

  • 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

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 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 8.6
    Fabulous - What previous guests thought, 26 reviews

    Set in Philipsburg with Dawn Beach nearby, Cozy Studio Apartment in Quiet Neighborhood! provides accommodation with free private parking. The property has garden views.

    From US$86.40 per night
  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 7 reviews

    Providing a garden, Waterfront 2 Bedroom MobilHome provides accommodation in Quartier dʼOrléans. The property has lake and garden views, and is 1.4 km from Coralita Beach.

    From US$126.07 per night
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 36 reviews

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

  • C'RENITY VILLA

    Cul de Sac
    8.0+ review score
    Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 54 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.

    From US$295.33 per night

  • C'Renity Studio

    Cul de Sac
    8.0+ review score
    Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 47 reviews

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

    From US$173.72 per night

Holiday rentals that guests love in Simpson Bay

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