Simpson Bay Villas & Vacation Rentals with Swimming Pool - 495 Rentals Available.
495 Vacation rentals
Filters applied: Swimming pool
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
$658.00
from $658.00 / 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
- Nearest beach 0 mi
- Swimming pool
$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
$916.00
from $916.00 / 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
- Beach/lakeside relaxation
- Swimming pool
- Air conditioning
$500.00
from $500.00 / 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
- Nearest beach 0 mi
- Swimming pool
$558.00
from $558.00 / 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
$229.00
from $229.00 / 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
- Nearest beach 0 mi
- Swimming pool
$398.00
from $398.00 / night
CASA DE BELLA... Great location at a great price!!
Simpson Bay House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$258.00
from $258.00 / 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
- Nearest beach 0 mi
- Swimming pool
$229.00
from $229.00 / 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
$558.00
from $558.00 / 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
$483.00
from $483.00 / 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
- Nearest beach 0 mi
- Swimming pool
$772.00
from $772.00 / 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
- Nearest beach 0 mi
- Swimming pool
$350.00
from $350.00 / 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
- Nearest beach 0 mi
- Swimming pool
$472.00
from $472.00 / night
LA DI DA...4BR Hilltop Villa Overlooking Pelican Key
Simpson Bay Villa
- 6 bedrooms 6
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$643.00
from $643.00 / night
SURFSONG... 6BR fall in love again! Breathtaking sunsets, directly on ocean!
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,678.00
from $1,678.00 / night
LIFE'S A BEACH... Indeed! Remodeled beachfront, great location on Simpson Bay
Simpson Bay Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$343.00
from $343.00 / night
BEACH SECRET... Modern 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
- Nearest beach 0 mi
- Swimming pool
$943.00
from $943.00 / 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
INFINITY AT OCEAN EDGE...3 BR Condo Beacon Hill, St. Maarten
Simpson Bay Condo
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$772.00
from $772.00 / night
FAJA LOBIE... Competly New and offers Great rates for a beachfront villa on Bour
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
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
$3,163.00
from $3,163.00 / 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
$358.00
from $358.00 / 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
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$483.00
from $483.00 / night
Your search has been expanded 5.8 miles to include more rentals
LIGHTHOUSE 6B... penthouse with spectacular views, resort amenities of OBBR
Oyster Pond Condo - 5.8 miles away
- 2 bedrooms 2
- 3 bathrooms
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Air conditioning
$558.00
from $558.00 / night
GISELLE.. Lovely sunsets, short walk to Plum Baie beach!!
Terres Basses House - 3.4 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$1,143.00
from $1,143.00 / night
IT'S LIFE ... WOW !! Spectacular 6 BR Beachfront Beauty on Plum Bay, Terres Ba
Terres Basses House - 3.7 miles away
- 6 bedrooms 6
- 7 bathrooms
- sleeps 12 12
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$4,715.00
from $4,715.00 / night
ARTIMINO...3 BR condo, located in Porto Cupecoy, St Maarten
Cupecoy Bay Apartment - 2.6 miles away
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$408.00
from $408.00 / night
EMVIE... Contemporary 3 BR Beauty overlooking Orient Bay, Full AC, Gym, Jacuzzi,
Grand Case House - 5.6 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$629.00
from $629.00 / night
GRAND PALMS...Modern 3 BR villa w/ full AC, steps from Plum Baie Beach!
Terres Basses House - 3.6 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$816.00
from $816.00 / night
CARIBBEAN PARADISE... Affordable 2BR condo at Rainbow Beach Club on the shores o
Cupecoy Bay Apartment - 2.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$180.00
from $180.00 / night
SKI BEACH CONDO... romantic beach front condo on Nettle Bay beach
Baie Nettle Apartment - 1.7 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$170.00
from $170.00 / night
AMBIANCE... Fabulous villa!! 4 Huge equal bedrooms, the PERFECT couples villa!
Terres Basses House - 3.1 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 8 8
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$1,143.00
from $1,143.00 / night
L'OASIS... Heavenly, Super Deluxe beachfront estate has everything!!
Terres Basses Villa - 3.1 miles away
- 7 bedrooms 7
- 7 bathrooms
- sleeps 12 12
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$4,518.00
from $4,518.00 / night
LIFE IN BLUE ... Stunning New 2 BR Luxury Beach Front Villa on Baie Rouge
Terres Basses House - 2.7 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Air conditioning
$1,500.00
from $1,500.00 / night
GRAND BLEU... The name says it all! Fabulous 4BR contemporary villa, walk to Plu
Terres Basses House - 3.4 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0.5 mi
- Swimming pool
$1,000.00
from $1,000.00 / night
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