Simpson Bay 4+ bedroom Villas, Vacation Rentals & More - 311 Rentals Available.
311 Vacation rentals
Filters applied: 4+ Bedrooms
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
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
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
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 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
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
- Swimming pool
- Child friendly
- Air conditioning
$850.00
from $850.00 / night
Your search has been expanded 19.5 miles to include more rentals
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
Sandcastle Villa - 10,000 sf Luxury Beachfront Villa + Chevy Tahoe (by owner)
The Valley Villa - 13.5 miles away
- 4 bedrooms 4
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 1 hour 9 minutes
$2,176.00
from $2,176.00 / night
Champagne Shores
Blowing Point House - 9.2 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Air conditioning
$1,700.00
from $1,700.00 / night
Dream Island Views of Orient Bay - 4 Suites / Sleeps 8
Orient Bay House - 6.5 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 3 nights min
- Swimming pool
- Ask about children
- Air conditioning
$836.00
from $836.00 / night
10% OFF Special - Villa Belle Vue - Orient Bay
Orient Bay House - 5.5 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$836.00
from $836.00 / night
Villa Casa Sunshine - 10 Suites
Philipsburg House - 5 miles away
- 10 bedrooms 10
- 10 bathrooms
- sleeps 20 20
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$2,550.00
from $2,550.00 / night
Habitation Saint Louis
Corossol Villa - 18.4 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Air conditioning
$1,229.00
from $1,229.00 / night
Luxurious Cliffside Villa, perfect for a large group
Terres Basses Villa - 3.4 miles away
- 14 bedrooms 14
- 14 bathrooms
- sleeps 28 28
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$4,143.00
from $4,143.00 / night
4 Bedroom beautiful view Villa (Terres Basses)
Terres Basses Villa - 2.6 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,000.00
from $1,000.00 / night
Spacious and ideally Villa located within minutes of the Beach
Terres Basses Villa - 2.6 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$743.00
from $743.00 / night
Luxurious, private and staffed Villa
Terres Basses Villa - 2.6 miles away
- 9 bedrooms 9
- 9 bathrooms
- sleeps 18 18
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$6,429.00
from $6,429.00 / night
Fully renovated 6 bedroom villa with infinity pool and gorgeous views
Terres Basses Villa - 3.2 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,714.00
from $1,714.00 / night
5-bedroom villa with heated pool, sauna & tenniscourt within a minute walk from
Terres Basses Villa - 3.5 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,071.00
from $1,071.00 / night
Elegant 6 bedroom villa with a magnificent free-form pool
Terres Basses Villa - 2.4 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,470.00
from $1,470.00 / night
Colonial styled 4 bedroom villa with private pool
Terres Basses Villa - 2.6 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$643.00
from $643.00 / night
Beautiful Ocean view Villa with a large pool
Terres Basses Villa - 2.6 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$743.00
from $743.00 / night
6 bedroom villa at short walk from beach
Terres Basses Villa - 3.4 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$1,000.00
from $1,000.00 / night
VILLA AQUA at Indigo Bay... gorgeous, modern, fully air-conditioned ocean front
Cole Bay Villa - 2.4 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,765.00
from $1,765.00 / night
SEA VOUS PLAY... Private, comfortable 4BR villa with views to Saba and beyond
Terres Basses House - 3 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,072.00
from $2,072.00 / night
DEL MAR... Spacious 5BR villa Great for Families
Anse Marcel Villa - 6.3 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,143.00
from $2,143.00 / night
SUNRISE...Affordable 5 BR family villa within walking distance to beautiful Dawn
Oyster Pond Villa - 5.5 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$815.00
from $815.00 / night
VILLA IMAGINE... Lovely affordable 5 Br villa on gorgeous lot in Terres Basses
Terres Basses House - 2.5 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$972.00
from $972.00 / night
LA BELLA CASA... Huge 12 BR Luxury villa in Terres Basses, St Martin
Terres Basses House - 2.7 miles away
- 12 bedrooms 12
- 12 bathrooms
- sleeps 24 24
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,786.00
from $2,786.00 / night
ARCADIA...Charming hillside 3BR villa... wonderful sea & marina views
Oyster Pond House - 5.3 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$643.00
from $643.00 / night
MES AMIS...Spectacular Ultra Deluxe cliffside masterpiece! Breathtaking views! A
St Martin / St Maarten Villa - 3.2 miles away
- 14 bedrooms 14
- 14 bathrooms
- sleeps 26 26
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$12,858.00
from $12,858.00 / night
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