Simpson Bay 2-bedroom Villas, Vacation Rentals & More - 96 Rentals Available.
96 Vacation rentals
Filters applied: 2+ Bedrooms
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
Coco Beach Duplex
Simpson Bay Villa
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 4 4
- Min stay varies
- Child friendly
$229
from $229 / 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
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
Simpson Bay Yacht Club Condo - Unit 6
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 3 nights min
- Swimming pool
- Ask about children
$157
from $157 / night
Villa Hardman
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
$142
from $142 / 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
- Child friendly
- Air conditioning
$358
from $358 / night
SAPPHIRE... a casual hillside 3 BR villa, St Maarten villa with ocean views in
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$358
from $358 / 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 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
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
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
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
BELLA VITA... a gorgeous, 7BR super deluxe... views galore
Simpson Bay Villa
- 7 bedrooms 7
- 8 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1200
from $1200 / 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
- Child friendly
- Air conditioning
$858
from $858 / 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
- Child friendly
- Air conditioning
$336
from $336 / night
Witenblauw Estate at Pelican Key, Saint Maarten - Directly On The Beach
Simpson Bay Villa
- 6 bedrooms 6
- 7 bathrooms
- Sleeps 22 22
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1800
from $1800 / night
CASA DE BELLA (formally known as CASELLA)...beautifully furnished, lots of
Simpson Bay House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$179
from $179 / 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
- Suitable for children age 5+
- Air conditioning
$415
from $415 / night
Daffodil at Pelican Key, Saint Maarten - Beachfront, Gated Community, Pool
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1071
from $1071 / 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
BEACHSIDE CONDO... you can't get much closer to the beach than this!!
Simpson Bay Apartment
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$279
from $279 / night
El Sueño - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Child friendly
- Air conditioning
$643
from $643 / night
Villa Amaryllis 2 Bedroom (In A Stunning Waterfront Location On The Simpson Bay
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643
from $643 / night
Coco Beach #5 ON THE BEACH
Simpson Bay Apartment
- 2 bedrooms 2
- 5 bathrooms
- Sleeps 6 6
- 1 night min
- Beach/lakeside relaxation
- Swimming pool
- Air conditioning
$372
from $372 / 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
$1230
from $1230 / 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
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
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
Belle Amour - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Child friendly
- Air conditioning
$543
from $543 / night
Villa Sapphire - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Child friendly
- Air conditioning
$358
from $358 / 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
- Child friendly
- Air conditioning
$643
from $643 / 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
- Suitable for children age 5+
- Air conditioning
$340
from $340 / 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
- Child friendly
- Air conditioning
$1500
from $1500 / 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
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
SEA BEACH TREASURE...Gorgeous 2BR Penthouse on Simpson Bay Beach, St Maarten
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$265
from $265 / 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
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
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