Simpson Bay Villas & Vacation Rentals - 103 Rentals Available
103 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
MARISOL...light and airy townhouse at Point Blue in Pelican Key Estate
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$258
from $258 / 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
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
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
$279
from $279 / 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
Villa Amaryllis 4 + 1 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$787
from $787 / night
IL PUNTO BLU...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
$265
from $265 / night
Witenblauw Estate at Pelican Key, Saint Maarten - Directly On The Beach
Simpson Bay Villa
- 6 bedrooms 6
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1801
from $1801 / 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
La Perla Estate at Terres Basses, Saint Maarten - Oceanfront, Luxury, Private
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
Inquire for Rates
Pricing unknown
Coco unit 16 - Luxury ocean front condo
Simpson Bay House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 4 nights min
- Ask about children
$343
from $343 / 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
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
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 Yacht Club Condo - Unit 6
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 3 nights min
- Ask about children
$157
from $157 / 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
DAFFODIL... on the beach at Pelican Key, this luxurious, unique villa promises
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$787
from $787 / 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
$857
from $857 / 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
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
UNFORGETTABLE... indeed! Wonderful beachfront contemporary complex on fabulous
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$398
from $398 / 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
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
$750
from $750 / 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
Villa Tara at Beacon Hill, Saint Maarten - Oceanfront & Pool
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$657
from $657 / night
Beachfront, Ideal for Couples & Families, Rooftop Hot Tub, Stunning Views
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 1 night 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
$414
from $414 / night
RIVIERA... 3 BR hillside villa in Pelican Key, St Maarten
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$415
from $415 / night
ROYAL PALM BEACH #101 ...affordable 3 BR beachfront resort! Close to
Simpson Bay Apartment
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$343
from $343 / 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
$414
from $414 / night
ST TROPEZ... amazing views of Heineken Regatta from this beautiful villa in
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$500
from $500 / night
Unforgettable at Las Arenas - 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
$398
from $398 / night
Villa Hardman
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
$850
from $850 / 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
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
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
$383
from $383 / 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
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
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