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Vacation Rentals in Simpson Bay

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The best vacation rentals in Simpson Bay

Check out our selection of great vacation rentals in Simpson Bay

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The Hills Residence

Simpson Bay

The Hills Residence offers a hot tub and free private parking, and is within a 7-minute walk of Kim Sha Beach.

A
Alexia
From
Saint Vincent & Grenadines
The location was very convenient to all the hot spots near by. The room was very comfortable and fully equipped with everything that we could need. We really did enjoy our stay and would highly recommend.
Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 344 reviews
Price from
$304.45
1 night, 2 adults

Blue Sail Apartments

Simpson Bay

Blue Sail Apartments in Simpson Bay provides accommodations with a garden and barbecue facilities. A solarium and a car rental service are available for guests.

M
Micheline
From
Saint Martin
Blue dream is a picturesque beautiful comfortable place to stay. It's clean ,quiet ,and conveniently located near many restaurants and bars . It's walking distance from the most gorgeous blue beaches. My family absolutely loved the pools and the hot tub there. Ms Kay the manager will accommodate you with the most heartwhelming smile and she will do her best to make your stay wonderful. The other staff were also very friendly and discreet. Got any problems and Emmanuel will solve it lol. And the ocean view is breathtaking. Just an absolutely excellent place to stay.
Scored out of 10, guest rating 7.9
Good - What previous guests thought, 962 reviews
Price from
$89.25
1 night, 2 adults

Villa Cleavage

Simpson Bay

Featuring a garden, Villa Cleavage provides accommodations in Simpson Bay.

Scored out of 10, guest rating 7.8
Good - What previous guests thought, 18 reviews
Price from
$115
1 night, 2 adults

condostmaarten by the sea -Adults Only-

Koolbaai (Near Simpson Bay)

Condostmaarten by the sea -Adults Only- features air-conditioned accommodations in Koolbaai. This beachfront property offers access to a balcony, free private parking, and free Wifi.

M
Martin
From
St. Maarten
The location was awesome. The views are amazing. The host was very informative on what ever we needed. To sum it up this will one of our get away for the year . I have spoken to my friends and they are coming.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 134 reviews
Price from
$550
1 night, 2 adults

Modern 3BR Home with Own Private Pool

Philipsburg (Near Simpson Bay)

This property offers access to a balcony, free private parking, and free Wifi.

r
richards
From
Saint Martin
The home was beautiful the irea was very quiet
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 35 reviews
Price from
$359.10
1 night, 2 adults

Fun under the sun!

Cupecoy (Near Simpson Bay)

Just a 5-minute walk from Cupecoy Beach and 0.6 miles from Mullet Bay Beach, Fun under the sun! features accommodations in Cupecoy with a garden.

v
van Putten
From
Curaçao
Very clean and quiet place and everyone was so helpfull
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 7 reviews
Price from
$116
1 night, 2 adults

Sky Blue Residence

Lower Princeʼs Quarter (Near Simpson Bay)

Providing mountain views, Sky Blue Residence in Lower Princeʼs Quarter offers accommodations and a garden. This guest house provides free private parking, luggage storage space, and free Wifi.

S
Steven
From
Canada
The family was hospitable and the accommodation and facilities suited our needs. The bed was comfortable, the room has a large smart TV with good wifi and access to Netflix, etc., air conditioning, a fridge/freezer, and a kettle. The bathroom is just outside the room but it was allocated to us during our stay. This room is part of a larger family home and the hosts Claudia, Jean Paul, and Dawn are kind and helpful. They offer airport pick-ups and drop-offs (for a reasonable fee) as well. There are a few small grocery stores within a 5-10 minute walk and a bigger one at about 20-25 minutes (or 5 minutes by car). Philipsburg is about a 50 minute walk or just under 10-minutes by car. The family can also help arrange for (3rd party) transportation to get around the island although we had a rental car during our stay.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 34 reviews
Price from
$66
1 night, 2 adults

Mullet Bay Suites - Your Luxury Stay Awaits

Cupecoy (Near Simpson Bay)

Mullet Bay Suites - Your Luxury Stay Awaits in Cupecoy provides adults-only accommodations with a fitness center, massage services, and a garden.

A
Akira
From
Anguilla
The Location,The View & Amazing service.
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 247 reviews
Price from
$326.65
1 night, 2 adults

The Castle

Philipsburg (Near Simpson Bay)

The Castle is a recently renovated apartment in Philipsburg near Great Bay Beach.

B
Bernis
From
Anguilla
It was in the ideal location, clean and comfortable.
Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 174 reviews
Price from
$120
1 night, 2 adults

Convenient Studio Apt Near Airport, Beaches & Food

Cupecoy (Near Simpson Bay)

Convenient Studio Apt Near Airport, Beaches & Food offers accommodations in Cupecoy, a 6-minute walk from Mullet Bay Beach. This apartment offers air-conditioned accommodations with a balcony.

G
Genesis
From
Anguilla
2nd time staying here. Place was excellent, very clean, very near to shops, and restaurants.
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 36 reviews
Price from
$128.50
1 night, 2 adults
All vacation rentals in Simpson Bay

Most booked vacation rentals in Simpson Bay and surrounding area in the past month

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Popular with guests booking vacation rentals in Simpson Bay

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 962 reviews

Popular with guests booking vacation rentals in Simpson Bay

Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 344 reviews

Popular with guests booking vacation rentals in Simpson Bay

Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 72 reviews

Popular with guests booking vacation rentals in Simpson Bay

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 169 reviews

Popular with guests booking vacation rentals in Simpson Bay

Scored out of 10, guest rating 7.8
Good - What previous guests thought, 18 reviews

Popular with guests booking vacation rentals in Simpson Bay

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 13 reviews

Popular with guests booking vacation rentals in Simpson Bay

Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 13 reviews

Popular with guests booking vacation rentals in Simpson Bay

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 21 reviews

Popular with guests booking vacation rentals in Cupecoy

Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 256 reviews

Vacation Rentals with swimming pools in Simpson Bay and nearby

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Scored out of 10, guest rating 7.9
Good - What previous guests thought, 962 reviews

Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 344 reviews

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 169 reviews

Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 13 reviews

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 21 reviews

Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 7 reviews

Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 2 reviews

Enjoy breakfast in Simpson Bay and nearby

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Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 42 reviews

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 17 reviews

Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 247 reviews

Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 22 reviews

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 4 reviews

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

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Studio Sleeps 2 with Free Parking

05 BEACHCOMBER ROAD
Free cancellation options available
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 13 reviews

Diamond Gem Residence

Peter John Road
Free cancellation options available
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 96 reviews

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

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 2 reviews
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 10 reviews
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 134 reviews

The Black Palm

Island View Lane The Black Palm
Free cancellation options available
Scored out of 10, guest rating 8.4
Very Good - What previous guests thought, 67 reviews

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 17 reviews

Highly rated vacation rentals in Simpson Bay and nearby

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Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 72 reviews
Scored out of 10, guest rating 7.8
Good - What previous guests thought, 18 reviews
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 12 reviews

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 25 reviews

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

Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 21 reviews

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 11 reviews

Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 37 reviews

FAQ about vacation rentals in Simpson Bay

Vacation Rentals That Guests Love in Simpson Bay

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Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 13 reviews
Gorgeous villa with good facilities, beautiful pool and lovely patio.
Guest review bySanne
Travelers with friends