Simpson Bay 4+ bedroom Villas, Vacation Rentals & More - 270 Rentals Available.
270 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
$3,000.00
from $3,000.00 / 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
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
$747.00
from $747.00 / 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 19.7 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
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. 58 minutes
$2,176.00
from $2,176.00 / night
Villa Mer Soleil | Ocean View - Located in Exquisite Terres Basses with Privat
Terres Basses Villa - 2.8 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$842.00
from $842.00 / night
Villa The View | Ocean View - Located in Magnificent Colombier with Private Po
Anse des Flamands Villa - 18.3 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,714.00
from $2,714.00 / night
Villa Kir Royal | Ocean Front - Located in Exquisite Saint Jean with Private P
St. Jean Villa - 19.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,018.00
from $1,018.00 / night
Villa Amancaya | Ocean View - Located in Wonderful Anse des Cayes with Private
Anse des Cayes Villa - 18.7 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$4,139.00
from $4,139.00 / night
Villa K | Ocean View - Located in Beautiful Anse des Cayes with Private Pool
Anse des Cayes Villa - 18.5 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,307.00
from $2,307.00 / night
Villa Fabrizia | Ocean View - Located in Exquisite Gustavia with Private Pool
Gustavia Villa - 19.5 miles away
- 7 bedrooms 7
- 7 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$3,529.00
from $3,529.00 / night
Villa Le Chateau Des Palmiers | Beach Front - Located in Wonderful Lowlands
Terres Basses Villa - 3.6 miles away
- 9 bedrooms 9
- 9 bathrooms
- sleeps 18 18
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$6,108.00
from $6,108.00 / night
Villa Encore | Near Ocean - Located in Tropical Terres Basses with Private Poo
Terres Basses Villa - 3.3 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,065.00
from $1,065.00 / night
Villa Fabrizia | Ocean View - Located in Stunning Gustavia with Private Pool
Gustavia Villa - 19.5 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$3,257.00
from $3,257.00 / night
Villa La Bella Casa | Ocean View - Located in Magnificent Terres Basses with P
Terres Basses Villa - 2.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
$1,017.00
from $1,017.00 / night
Villa La Hacienda | Ocean View - Located in Magnificent Terres Basses with Priv
Terres Basses Villa - 2.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$706.00
from $706.00 / night
Villa Terrasse De Mer | Beach View - Located in Tropical Terres Basses with Pr
Terres Basses Villa - 2.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$910.00
from $910.00 / night
Villa Ambiance | Ocean View - Located in Magnificent Terres Basses with Privat
Terres Basses Villa - 3.1 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$950.00
from $950.00 / night
Villa SandCastle | Beach Front - Located in Fabulous Limestone Bay with Privat
The Valley Villa - 13.5 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,805.00
from $1,805.00 / night
Villa Bakea | Ocean View - Located in Tropical Anse des Cayes with Private Poo
Anse des Cayes Villa - 18.8 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,036.00
from $2,036.00 / night
Villa Vitti | Ocean Front - Located in Exquisite Shell Beach with Private Pool
Gustavia Villa - 19.5 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$4,343.00
from $4,343.00 / night
Villa Always | Ocean View - Located in Exquisite Terres Basses with Private Poo
Terres Basses Villa - 2.9 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
$1,629.00
from $1,629.00 / night
Villa Aventura | Ocean View - Located in Fabulous Flamands with Private Pool
Anse des Flamands Villa - 18.2 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,086.00
from $1,086.00 / night
Villa Ushuaia | Ocean Front - Located in Wonderful Flamands with Private Pool
Anse des Flamands Villa - 17.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,221.00
from $1,221.00 / night
Villa Cascades | Ocean View - Located in Wonderful Terres Basses with Private
Terres Basses Villa - 3.5 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$679.00
from $679.00 / night
Villa Sur Le Port | Near Ocean - Located in Stunning Gustavia with Private Poo
Gustavia Villa - 19.4 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,154.00
from $1,154.00 / night
Villa Lital | Ocean View - Located in Tropical Anse des Cayes with Private Pool
Anse des Cayes Villa - 19.1 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$5,294.00
from $5,294.00 / night
Villa La Bella Casa | Ocean View - Located in Magnificent Terres Basses with P
Terres Basses Villa - 2.7 miles away
- 9 bedrooms 9
- 9 bathrooms
- sleeps 18 18
- min stay varies
- Swimming pool
- Child friendly
$2,036.00
from $2,036.00 / night
Villa Ecume Des Jours | Beach Front - Located in Wonderful Plum Bay with Priva
Terres Basses Villa - 3.8 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
$1,168.00
from $1,168.00 / night
Villa Fabrizia | Ocean View - Located in Stunning Gustavia with Private Pool
Gustavia Villa - 19.5 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,714.00
from $2,714.00 / 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
$1,628.00
from $1,628.00 / night
Villa Mer Soleil | Ocean View - Located in Tropical Terres Basses with Private
Terres Basses Villa - 2.9 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$950.00
from $950.00 / 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
$883.00
from $883.00 / 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
$1,561.00
from $1,561.00 / night
Villa Grand Bleu | Ocean View - Located in Fabulous Terres Basses with Private
Terres Basses Villa - 3.4 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
$950.00
from $950.00 / night
Villa Fabrizia | Ocean View - Located in Magnificent Gustavia with Private Poo
Gustavia Villa - 19.5 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,986.00
from $2,986.00 / night
Villa Fabrizia | Ocean View - Located in Exquisite Gustavia with Private Pool
Gustavia Villa - 19.5 miles away
- 8 bedrooms 8
- 9 bathrooms
- sleeps 18 18
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$3,937.00
from $3,937.00 / night
What is Travelers’ Choice award?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.