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Vacations in Simpson Bay
2 travelers
Travelers
Unfortunately our partners limit offers to 6 travelers total. Please adjust your selection to continue.
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0 children selected
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Boston (BOS)
Simpson Bay
Mon 8/22
Thu 8/25
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Simpson Bay vacation information
Top vacation (Flight+Hotel)
$369
Family vacation (Flight+Hotel)
$369
Romantic vacation (Flight+Hotel)
$686
Most popular vacation deals in Simpson Bay
Beautiful Villa! Tamarind Hill Estates - Rent as 2, 3, 4 or 5BR
$4,949
3 nights + flight
View Deal
Rising Star Luxury villa
$4,679
3 nights + flight
View Deal
2 Bedroom 2 Condo in Oyster Bay
10.0
Excellent
2 reviews
$1,774
3 nights + flight
View Deal
The Westin Dawn Beach Resort & Spa, St. Maarten
$3,525
3 nights + flight
View Deal
Chincherry Drive
$290
3 nights + flight
View Deal
Dawn Beach Club St Maarten 3 Bedroom unit sleeps up to
$3,634
3 nights + flight
View Deal
La Vue Sxm - Modern Oceanfront Villa
10.0
Excellent
3 reviews
$4,702
3 nights + flight
View Deal
Deluxe Caribbean Condo with beautiful views of St. Barths
$1,375
3 nights + flight
View Deal
Villa Anegada Is A Magnificent Villa With Refined Luxury
2.0
Mediocre
1 review
$5,759
3 nights + flight
View Deal
Villa Flagrantia, Paradise At Your Pleasure
9.0
Excellent
2 reviews
$1,319
3 nights + flight
View Deal
View all deals
Other popular destinations
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Packages
Simpson Bay
Mon 8/22
Thu 8/25
Choose up to 3 origin airports
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Choose up to 3 airports
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Mon 8/22
Mon 8/29
Choose up to 3 origin airports
Location
Airports within
70 miles
25 miles
50 miles
70 miles
100 miles
150 miles
200 miles
Airport
Drive
Transit
Miles
Pop.
Enter a location to see nearby airports
OK
Choose up to 3 airports
Enter a location to see nearby airports
2 travelers
Travelers
Unfortunately our partners limit offers to 6 travelers total. Please adjust your selection to continue.
Adults
2 adults selected
Children
0 children selected
Age Child 1
Under 2 years
Under 2 years
2 years
3 years
4 years
5 years
6 years
7 years
8 years
9 years
10 years
11 years
12 years
13 years
14 years
15 years
16 years
17 years
Age Child 2
Under 2 years
Under 2 years
2 years
3 years
4 years
5 years
6 years
7 years
8 years
9 years
10 years
11 years
12 years
13 years
14 years
15 years
16 years
17 years
Age Child 3
Under 2 years
Under 2 years
2 years
3 years
4 years
5 years
6 years
7 years
8 years
9 years
10 years
11 years
12 years
13 years
14 years
15 years
16 years
17 years
Continue
Boston (BOS)
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Mon 8/22
Mon 8/29
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