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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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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.

L
Leeana
From
Trinidad and Tobago
Lovely property that’s near everything! Room was comfortable and we thoroughly enjoyed our short stay
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 167 reviews
Price from
US$300
1 night, 2 adults

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.

D
Dorota
From
Poland
We had wonderful time on the island and Blue Dream Appartments were a huge part of it! The appartment we got was spacious, with a terrace, where we had our delicious breakfasts :) The kitchen was fully equipped, with cattle, coffee maker, microwave, oven, gas cooker and fridge. All was nice and clean. 2 swimming pools added up to it all :) There is a small supermarket/deli nearby (walking distance). We didn't use the car. Beach, bars and restaurants are 10-15 minutes away (walking). Overall one of the best vacation - the vibe of the island is great and the host Miss Key is a wonderful person!!
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 731 reviews
Price from
US$95.40
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 8.0
Very 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 9.4
Superb - What previous guests thought, 159 reviews
Price from
US$230.40
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.

j
jhon
From
United States
Very cozy and clean flat. Very silent and comfortable. The view from the bed is amazing. All what you need are here. Beautiful and safe neighborhood. It is ideal place for enjoying the sea, the beach. Highly recommend for relax
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 127 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 9.7
Exceptional - What previous guests thought, 31 reviews
Price from
US$414.75
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, 9 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

Cozy Studio Apartment in Quiet Neighborhood!

Philipsburg (Near Simpson Bay)

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

I
Isabelle
From
Netherlands
Clean, comfortable and very well maintained. Lovely host.
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 26 reviews
Price from
US$80
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

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 9 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

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 9.6
Exceptional - What previous guests thought, 10 reviews

Popular with guests booking holiday rentals in Simpson Bay

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 99 reviews

Popular with guests booking holiday rentals in Simpson Bay

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 166 reviews

Popular with guests booking holiday rentals in Simpson Bay

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 196 reviews

Popular with guests booking holiday rentals in Simpson Bay

Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 732 reviews

Highly rated holiday rentals in Simpson Bay and nearby

Scored out of 10, guest rating 9.1
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 8.7
Fabulous - What previous guests thought, 119 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$102.60 per night
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 127 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 8.8
Fabulous - What previous guests thought, 75 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$436 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$206.36 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 54 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$127.89 per night
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 88 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, 10 reviews

Set in Marigot, 1.2 km from Baie de la Potence Beach and 2.6 km from Nettle Bay Beach, Appartement entier: chambre, cuisine + terrasse au calme sur jardin.

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$304.58 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 8.0
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.

Morea SXM

Simpson Bay
Breakfast options

Featuring air-conditioned accommodation with a private pool, sea view and a terrace, Morea SXM is located in Simpson Bay. Featuring lake and garden views, this apartment also offers free WiFi.

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

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$171.31 per night

Divine Rest

Philipsburg
Free cancellation options available
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 32 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 8.5
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 7.9
Good - What previous guests thought, 171 reviews

Boasting a garden and barbecue facilities, Over The Hill Residence is situated in Grand Case. The property features sea and mountain views, and is 1.5 km from Grand Case Beach.

From US$131.84 per night

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

From US$325.53 per night

Charming Apartment in La Savane - 65 m² - Terrace with View is situated in Happy Bay and offers a garden.

From US$313.90 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.

From US$325.53 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$7,558.06 per night

Holiday Rentals with swimming pools in Simpson Bay and nearby

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 9.1
Superb - What previous guests thought, 52 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$296.46 per night
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$174.39 per night
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 16 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 9.4
Superb - What previous guests thought, 5 reviews

Featuring air-conditioned accommodation with a private pool, pool view and a patio, Appartement Orient Bay-Ti Paradise is located in Orient Bay.

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 9.7
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.

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.

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 8.5
Very good - What previous guests thought, 9 reviews
Gorgeous villa with good facilities, beautiful pool and lovely patio.
Guest review by
Sanne
People with friends