Simpson Bay Villa Rentals - 770 Rentals Available.
770 Vacation rentals
Filters applied: Villa

TARA... Affordable oceanfront villa, walk to beach
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$843.00
from $843.00 / night

BEAU RIVAGE... Comfortable home on Burgeoux Bay beach, walk to Maho or Simpson B
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$858.00
from $858.00 / night

CARIBBEAN BLUE... 5BR beachfront home in Pelican Key
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,272.00
from $1,272.00 / night

SAPPHIRE... A casual, comfortable villa with ocean views in Pelican Key!
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$572.00
from $572.00 / 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
SMART VILLA...Beachfront at Pelican Key
Simpson Bay Villa
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Child friendly
- Air conditioning
$429.00
from $429.00 / night
LA CASITA...charming, comfortable oceanfront villa in Beacon Hill, St Maarten
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$543.00
from $543.00 / night
Beautiful 5 bedroom contemporary villa
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,143.00
from $1,143.00 / 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
$3,001.00
from $3,001.00 / 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
- Swimming pool
- Child friendly
- Air conditioning
$729.00
from $729.00 / 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
- Swimming pool
- Child friendly
- Air conditioning
$1,386.00
from $1,386.00 / night
Beautiful beachfront 5 bedroom villa
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Ask about pets
$850.00
from $850.00 / 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
$613.00
from $613.00 / 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
- Swimming pool
- Child friendly
- Air conditioning
$729.00
from $729.00 / night
Villa Amaryllis | Waterfront - Located in Stunning Simpson Bay with Private Po
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$766.00
from $766.00 / night
Your search has been expanded 13.5 miles to include more rentals
NEW SANDCASTLE BEACH HOUSE + Jeep Wrangler + Pool & Jacuzzi
The Valley Villa - 13.5 miles away
- 3 bedrooms 3
- 5 bathrooms
- sleeps 6 6
- min stay varies
- Air conditioning
- Pet friendly
- Private garden
Responds fast! Avg. 1 hour 24 minutes
$1,432.00
from $1,432.00 / night
La Casita Villa - Oceanfront Vacation Rental
St Martin / St Maarten Villa - 1.1 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0.32 mi
- Swimming pool
$428.00
from $428.00 / night
Your Paradise Villa
Orient Bay Villa - 5.6 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0.5 mi
- Swimming pool
$638.00
from $638.00 / night
Villa La Bella Casa | Ocean View - Located in Exquisite Terres Basses with Pri
Terres Basses Villa - 2.7 miles away
- 7 bedrooms 7
- 7 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
$1,671.00
from $1,671.00 / night
Villa La Sarabande | Ocean View - Located in Fabulous Orient Bay with Private
Orient Bay Villa - 5.9 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$488.00
from $488.00 / night
Villa Oceane | Ocean View - Located in Exquisite Terres Basses with Private Po
Terres Basses Villa - 3.5 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
$613.00
from $613.00 / night
A Gift For You. Stay 7 Nights Pay For 6! | Near Ocean - Located in Tropical Ter
Terres Basses Villa - 2.9 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$503.00
from $503.00 / night
Villa Grand Bleu | Ocean View - Located in Tropical Terres Basses with Private
Terres Basses Villa - 3.4 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$766.00
from $766.00 / night
Villa La Salamandre | Near Ocean - Located in Wonderful Terres Basses with Pri
Terres Basses Villa - 2.3 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,602.00
from $1,602.00 / night
Condo Acadia | Ocean Front - Located in Tropical Porto Cupecoy with House Clea
Cupecoy Bay Villa - 2 miles away
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$418.00
from $418.00 / night
Villa Giselle | Ocean View - Located in Exquisite Terres Basses with Private P
Terres Basses Villa - 3.4 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,114.00
from $1,114.00 / night
Villa Azur Dream | Ocean View - Located in Tropical Terres Basses with Private
Terres Basses Villa - 2.6 miles away
- 1 bedroom 1
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,254.00
from $1,254.00 / night
Villa La Hacienda | Ocean View - Located in Beautiful Terres Basses with Privat
Terres Basses Villa - 2.7 miles away
- 1 bedroom 1
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$620.00
from $620.00 / night
Villa La Bella Casa | Ocean View - Located in Wonderful Terres Basses with Priv
Terres Basses Villa - 2.7 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
$1,462.00
from $1,462.00 / night
Villa Grand Palms | Near Ocean - Located in Beautiful Terres Basses with Priva
Terres Basses Villa - 3.6 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$654.00
from $654.00 / night
Villa Terrasse De Mer | Beach View - Located in Exquisite Terres Basses with P
Terres Basses Villa - 2.7 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$794.00
from $794.00 / night
Villa Mariposa | Ocean View - Located in Tropical Terres Basses with Private Po
Terres Basses Villa - 3.6 miles away
- 1 bedroom 1
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$605.00
from $605.00 / night
Villa Etoile De Mer | Ocean View - Located in Fabulous Cupecoy with Private Po
Cupecoy Bay Villa - 2.6 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$907.00
from $907.00 / night
Villa Happy Bay | Beach View - Located in Tropical Happy Bay with Private Pool
La Savane Villa - 4.3 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$724.00
from $724.00 / night
Villa La Hacienda | Ocean View - Located in Tropical Terres Basses with Private
Terres Basses Villa - 2.7 miles away
- 1 bedroom 1
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$682.00
from $682.00 / night
SPECIAL CHRISTMAS PRICING IN EFFECT NOW At Villa Le Mas Des Sables!! | Ocean V
Terres Basses Villa - 2.5 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$696.00
from $696.00 / night
Villa Dreamin Blue | Ocean View - Located in Tropical Happy Bay with Private P
La Savane Villa - 4.3 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$836.00
from $836.00 / night
Villa Lune De Miel | Near Ocean - Located in Tropical Terres Basses with Priva
Terres Basses Villa - 3.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$529.00
from $529.00 / night
Villa Happy Bay | Beach View - Located in Magnificent Happy Bay with Private P
La Savane Villa - 4.3 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$682.00
from $682.00 / night
Villa La Magnolia | Ocean View - Located in Exquisite Terres Basses with Privat
Terres Basses Villa - 2.9 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$488.00
from $488.00 / night
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