Simpson Bay Villas & Vacation Rentals - 69 Rentals Available
69 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
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
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$787
from $787 / night
Coco Beach Duplex
Simpson Bay Villa
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 4 4
- Min stay varies
- Child friendly
$230
from $230 / 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
$459
from $459 / 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
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
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
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
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
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
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
Caribbean Blue at Pelican Key, Saint Maarten - Beachfront, Amazing Sunset View
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$843
from $843 / 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
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
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
Villa Hardman
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
$142
from $142 / 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
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
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
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
Villa La Di Da 5 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Child friendly
$750
from $750 / night
Villa Amaryllis 3 Bedroom
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$700
from $700 / 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 2 Bedroom
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643
from $643 / 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
WITENBLAUW... Magical Beach Front Estate on Pelican Key
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1800
from $1800 / night
Villa La Di Da 4 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Child friendly
$643
from $643 / 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
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 Amaryllis 3 Bedroom
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$700
from $700 / night
Villa Amaryllis 2 Bedroom
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643
from $643 / 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
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
$358
from $358 / 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 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
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
Villa Hope
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$629
from $629 / night
SUNSHINE VILLA... Huge, affordable beachfront villa, full AC, walk to
Simpson Bay House
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Child friendly
- Air conditioning
$429
from $429 / night
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