Simpson Bay Villas & Vacation Rentals - 102 Rentals Available
102 Vacation rentals
Paradise Found at Las Arenas - Beachfront Luxury!
Simpson Bay Apartment
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$358
from $358 / night
SIMPSON BAY BEACH CONDO #3...right on the beach at Simpson Bay
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$258
from $258 / night
Villa La-Di-Da at Pelican Key, Saint Maarten - Spectacular Ocean View, Infinity
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$858
from $858 / night
The Reef at Simpson Bay, Saint Maarten - Private Pool, Ocean Views, Modern
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$1143
from $1143 / night
Beachfront, Ideal for Couples & Families, Rooftop Hot Tub, Stunning Views
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Suitable for children age 5+
$536
from $536 / night
Il Punto Blu - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Apartment
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$336
from $336 / night
IL PUNTO BLUE...located right on the beach in prestigious Pelican Key
Simpson Bay Apartment
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$215
from $215 / night
La Casita - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$358
from $358 / night
CARISMA on the BEACH... Totally charming beachfront 2BR in great location!
Simpson Bay House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Suitable for children age 5+
- Air conditioning
$258
from $258 / night
Charming Apartment with View on the Pool and Simpson Bay Lagoon
Simpson Bay Apartment
- 1 bedroom 1
- 1 bathroom
- Sleeps 2 2
- Min stay varies
- Suitable for children age 5+
$158
from $158 / night
Coco Beach Duplex
Simpson Bay Villa
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 4 4
- Min stay varies
- Child friendly
$229
from $229 / night
Exclusive location, Serene Surroundings
Simpson Bay Villa
- 1 bedroom 1
- 2 bathrooms
- Sleeps 2 2
- Min stay varies
- Suitable for children age 5+
$200
from $200 / night
Sunshine at Beacon Hill, St. Maarten - Beachfront, Pool
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
$1500
from $1500 / night
Villa La-Di-Da - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$858
from $858 / night
Bella Vita - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 7 bedrooms 7
- 9 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1500
from $1500 / night
PROVENCE... affordable 6BR villa w/ gorgeous views, close to lots of dining
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$572
from $572 / night
Unforgettable at Las Arenas - Ideal for Couples and Families, Beautiful Pool
Simpson Bay Apartment
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Suitable for children age 5+
- Air conditioning
$340
from $340 / night
Sur Mer at Simpson Bay, Saint Maarten - Beachfront Gated Community, Pool
Simpson Bay Apartment
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$415
from $415 / night
$458
from $458 / night
Villa Amaryllis 4 + 1 Bedroom (The Villa Is Located In A Gated Residence Just
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$786
from $786 / night
Colony Manor
Simpson Bay House
- 1 bedroom 1
- 2 bathrooms
- Sleeps 2 2
- Min stay varies
- Ask about children
- Air conditioning
- Ask about pets
$200
from $200 / night
AQUALINA 102...Face the gorgeous Caribbean Sea along one of St. Maartens
Simpson Bay Apartment
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$315
from $315 / night
COLONY MANOR GUEST COTTAGE... romantic hideaway right on Simpson Bay Beach!
Simpson Bay Studio
- Studio -1
- 1 bathroom
- Sleeps 2 2
- Min stay varies
- Child friendly
- Air conditioning
$200
from $200 / night
Beautiful 5 bedroom contemporary villa
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1219
from $1219 / night
Tropical Paradise Villa at Coral Shores in Pelican
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 5 nights min
$234
from $234 / night
SUR MER * Coco's Beach Club... gorgeous beach front condo on beautiful Simpson
Simpson Bay Apartment
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$343
from $343 / night
RENDEZVOUS... at Las Arenas.., a fabulous 2 BR contemporary 2 BR condo unit on
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$340
from $340 / night
Provence at Pelican Key, Saint Maarten - Ocean View, Pool, Lovely Outdoor
Simpson Bay Villa
- 6 bedrooms 6
- 5 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$643
from $643 / night
Caribbean Blue - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 2 2
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643
from $643 / night
COCO BEACH CLUB 6...walk right out onto the beach at Simpson Bay
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$272
from $272 / night
ATLANTIS...* COCO BEACH CLUB...Located right on the beach at Simpson Bay!
Simpson Bay Apartment
- 1 bedroom 1
- 1 bathroom
- Sleeps 2 2
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$229
from $229 / night
Riviera - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$415
from $415 / night
LA DI DA...St Maarten villa high atop a mountain at the mouth of Pelican Key
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$500
from $500 / night
Summer Hill in Pelican Key, Saint Maarten - Gated, private pool
Simpson Bay Villa
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$614
from $614 / night
Faja Lobie at Beacon Hill, Saint Maarten - Beachfront & Pool
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$412
from $412 / night
Aqualina 102
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Child friendly
- Ask about pets
$314
from $314 / night
Aqualina 102 - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Apartment
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Suitable for children age 5+
- Air conditioning
$415
from $415 / night
SIMPSON BAY BEACH CONDO #2...located right on the beach at beautiful Simpson Bay
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$258
from $258 / night
SMART VILLA...nestled beachfront at Pelican Key
Simpson Bay Villa
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 6 6
- Min stay varies
- Child friendly
- Air conditioning
$258
from $258 / night
Villa Amaryllis 3 Bedroom (Built On 3 Levels Offering Dazzling White Interiors
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$700
from $700 / night
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.