Simpson Bay Villas & Vacation Rentals with Swimming Pool - 84 Rentals Available.
84 Vacation rentals
Filters applied: Swimming pool
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
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
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
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 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
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
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
Provence - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$572
from $572 / 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
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 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
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
$543
from $543 / 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
Villa Amaryllis 3 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$700
from $700 / night
A LA PLAGE..1BR condo located on one of St Maarten's finest beaches, Simpson
Simpson Bay Apartment
- 1 bedroom 1
- 2 bathrooms
- Sleeps 2 2
- 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
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
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
Faja Lobie - 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
$543
from $543 / 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
Villa Amaryllis 2 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643
from $643 / 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
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
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
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
$400
from $400 / 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
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 Amaryllis 3 Bedroom SPECIAL OFFER
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 Speranza 3 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$629
from $629 / 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
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
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
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
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
Villa Amaryllis 2 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643
from $643 / 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
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
Classy 5 Bedroom Villa in Pelican Bay
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- 4 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$1430
from $1430 / 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
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
$1800
from $1800 / night
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