Simpson Bay 4+ bedroom Villas, Vacation Rentals & More - 238 Rentals Available.
238 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
$657.00
from $657.00 / 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
$843.00
from $843.00 / night
WITENBLAUW... Magical Beach Front Estate on Pelican Key
Simpson Bay Villa
- 6 bedrooms 6
- 7 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,072.00
from $2,072.00 / 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
$643.00
from $643.00 / 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
$851.00
from $851.00 / 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
MARY'S BEACH ESTATE... a plane watcher's dream! Huge observation deck at this be
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,522.00
from $1,522.00 / night
CARIBBEAN BLUE... 4BR beachfront home in Pelican Key
Simpson Bay Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$743.00
from $743.00 / 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
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
- Swimming pool
- Child friendly
- Air conditioning
$2,215.00
from $2,215.00 / night
Your search has been expanded 19.7 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
$3,571.00
from $3,571.00 / night
The Harbor House
Gustavia Villa - 19.4 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Air conditioning
$1,214.00
from $1,214.00 / 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
beautiful Ring
Colombier Villa - 17.5 miles away
- 4 bedrooms 4
- 6 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Air conditioning
$1,714.00
from $1,714.00 / night
Sandcastle Villa - 10,000 sf Luxury Beachfront Villa + Chevy Tahoe (by owner)
The Valley Villa - 13.5 miles away
- 5 bedrooms 5
- 6 bathrooms
- sleeps 14 14
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 3 hours 54 minutes
$3,264.00
from $3,264.00 / night
NEW SANDCASTLE BEACH HOUSE + Jeep Wrangler + Pool & Jacuzzi
The Valley Villa - 13.5 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 8 8
- min stay varies
- Air conditioning
- Pet friendly
- Private garden
Responds fast! Avg. 3 hours 54 minutes
$2,119.00
from $2,119.00 / 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
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
Villa Globe Trotter | Ocean View - Located in Fabulous Lurin with Private Pool
Lurin Villa - 19.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,946.00
from $2,946.00 / night
Villa L'Oasis | Beach Front - Located in Stunning Terres Basses with Private P
Terres Basses Villa - 3 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$3,928.00
from $3,928.00 / night
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