Simpson Bay Villas & Vacation Rentals with Swimming Pool - 523 Rentals Available.
523 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
Responds fast! Avg. 2 hours 57 minutes
$409.00
from $409.00 / night
TARA... Affordable oceanfront villa, walk to beach
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$657.00
from $657.00 / night
COCO BEACH CLUB #5.... Located on the soft white powdery sand of Simpson Bay be
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$272.00
from $272.00 / night
CARIBBEAN BLUE... 5BR beachfront home in Pelican Key
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$914.00
from $914.00 / night
WITENBLAUW... Magical Beach Front Estate on Pelican Key
Simpson Bay Villa
- 6 bedrooms 6
- 7 bathrooms
- sleeps 12 12
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$2,072.00
from $2,072.00 / night
BISOU DU SOLEIL... beautiful, immaculate, affordable villa in Pelican Key
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Air conditioning
$672.00
from $672.00 / night
SOL Y MAR... fabulous beachfront penthouse on Kimsha Beach! Private pool, Walk t
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$557.00
from $557.00 / 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
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$329.00
from $329.00 / night
IL PUNTO BLUE...Located right on the beach in prestigious Pelican Key
Simpson Bay Apartment
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$336.00
from $336.00 / night
RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit on a great beach!
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$643.00
from $643.00 / night
CASA DE BELLA... Great location at a great price!!
Simpson Bay House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$401.00
from $401.00 / night
PROVENCE... Affordable villa, gorgeous views, close to dining, shopping, casinos
Simpson Bay Villa
- 6 bedrooms 6
- 5 bathrooms
- sleeps 12 12
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$643.00
from $643.00 / night
COCO BEACH CLUB 6...walk out onto the sand of Simpson Bay Beach
Simpson Bay Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$229.00
from $229.00 / 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
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$350.00
from $350.00 / night
ST TROPEZ... amazing views of the Caribbean Sea from this lovely villa in Pelica
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$557.00
from $557.00 / night
Villa Speranza | Near Ocean - Located in Fabulous Simpson Bay with Private Poo
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$660.00
from $660.00 / night
UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$482.00
from $482.00 / night
LA PLAGE PENTHOUSE....3BR suite in Royal Islander Resort...walk to restaurants,
Simpson Bay Apartment
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$572.00
from $572.00 / night
ATLANTIS... Beachfront on Simpson Bay - totally redone after Irma!
Simpson Bay Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$272.00
from $272.00 / night
SUNSHINE VILLA... Huge, affordable beachfront villa, full AC, walk to restaurant
Simpson Bay House
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$850.00
from $850.00 / night
ROYAL PALM BEACH #101 ... 3 BR beachfront resort! Close to restaurants & shoppi
Simpson Bay Condo
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$343.00
from $343.00 / night
SUR MER... Rare 3BR beachfront condo at Coco's Beach Club on Simpson Bay!
Simpson Bay Apartment
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$471.00
from $471.00 / night
LOGAN'S RUN... sweet 2 bedroom duplex located almost on Pelican Key beach and cl
Simpson Bay House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$572.00
from $572.00 / night
SURFSONG... 6BR fall in love again! Breathtaking sunsets, directly on ocean!
Simpson Bay Villa
- 5 bedrooms 5
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,498.00
from $1,498.00 / night
BEACH SECRET...contemporary 4 BR beauty on Burgeaux Bay, walk to Maho!
Simpson Bay Villa
- 4 bedrooms 4
- 5 bathrooms
- sleeps 8 8
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$786.00
from $786.00 / night
VILLA VITTORIA... Spectaculer, RARE 6BR villa sits directly on Simpson Bay Beach
Simpson Bay Villa
- 6 bedrooms 6
- 5 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,143.00
from $1,143.00 / night
MARY'S BEACH ESTATE... a plane watcher's dream! Huge observation deck at this be
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- sleeps 14 14
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$1,522.00
from $1,522.00 / night
LITTLE SEAGULL... Pelican Key, St Maarten
Simpson Bay Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$300.00
from $300.00 / night
FAJA LOBIE... 3 BR Offers Great rates for a beachfront villa
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$700.00
from $700.00 / night
CARIBBEAN BLUE... 4BR beachfront home in Pelican Key
Simpson Bay Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$814.00
from $814.00 / night
BELLA VITA... Stunning Super Deluxe 7BR, Breathtaking Views, Full AC, and Tons
Simpson Bay Villa
- 7 bedrooms 7
- 8 bathrooms
- sleeps 14 14
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$2,215.00
from $2,215.00 / night
COCO BEACH HOUSE... Charming refurbished 2BR on Simpson Bay Beach
Simpson Bay Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$357.00
from $357.00 / night
THE DREAM at Los Arenas... Fabulous Beachfront Penthouse on Simpson Bay!
Simpson Bay Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$471.00
from $471.00 / night
Your search has been expanded 19.7 miles to include more rentals
Colony Club
Gustavia Villa - 19.4 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 5 nights min
- Swimming pool
- Air conditioning
$314.00
from $314.00 / night
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