Skip to main content

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

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.

M
Marcio
From
Brazil
We were very well received! The facilities are great and clean! Beds are very comfortable and the pool is wonderful! Very calm and peaceful place! Perfect for a stay with family or friends!
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 781 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...

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 9.3
Superb - What previous guests thought, 168 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.

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 9.5
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$349.65
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
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

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.

D
Dahlia
From
United States
The Black Palm is an exceptional property. The room was so well appointed and designed. Liz was AMAZING! She was so helpful, checking on us when we arrived from the airport and were delayed in traffic, and also when we traveled to other nearby islands, to make sure we were okay. She shared tons of local recommendations and made sure we had everything we needed. The view from the room was so beautiful and great to watch the sunset each night. The area is safe and had a security gate to enter. There is a lively restaurant and beach nearby. The area of Indigo Bay is very peaceful and quiet amidst the hustle and bustle of Saint Martin. I can’t say enough good things about this hotel and how beautiful the room was!
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 74 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 7.3
Good - What previous guests thought, 33 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

See all

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 9.7
Exceptional - What previous guests thought, 93 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 9.2
Superb - What previous guests thought, 6 reviews

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

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, 205 reviews

Popular with guests booking holiday rentals in Simpson Bay

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 781 reviews

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

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.

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 28 reviews

Duplex JUNGLE BLEUE Terrasse vue mer incroyable is a recently renovated apartment in Marigot, where guests can makes the most of its pool with a view, private beach area and garden.

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

Over The Hill Residence

Grand Case
Free cancellation options available
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 168 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$145.25 per night

Akunamatata Guest House Grand Case

Grand Case
Free cancellation options available
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 138 reviews

Boasting a shared lounge, Akunamatata Guest House Grand Case is situated in Grand Case, 200 metres from Grand Case Beach.

C'Renity Studio

Cul de Sac
Free cancellation options available
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 44 reviews

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

From US$209.25 per night
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.

From US$410.94 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.

Enjoy breakfast in Simpson Bay and nearby

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 168 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$483.92 per night
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.

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

Villa Cleavage

Simpson Bay
Breakfast options
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.

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.

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.

From US$218.46 per night
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.

The Black Palm

Philipsburg
8.0+ review score
Scored out of 10, guest rating 8.8
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.

From US$676.35 per night
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 6 reviews

Located in Oyster Pond, 600 metres from Coralita Beach, The View, Pool, Sea View, Oyster Pond Balconies provides air-conditioned accommodation with a balcony and free WiFi.

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 8.6
Fabulous - What previous guests thought, 117 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
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.

Holiday Rentals with swimming pools in Simpson Bay and nearby

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.

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 9.1
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.

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 19 reviews

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

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 34 reviews

Set in Maho Reef, 90 metres from Maho Beach and less than 1 km from Simpson Bay Beach, Maho Beach House - Spacious 1 Bedroom Suite offers spacious air-conditioned accommodation with a terrace and free...

FAQ about holiday rentals in Simpson Bay

Holiday rentals that guests love in Simpson Bay

See all
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
gogless