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Cole Bay Vacation Packages

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Cole Bay Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,159, price is now $581 per person
$581
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $3,518, price is now $1,741 per person
$1,741
per person
Mar 12 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Philipsburg (SXM)
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Orient Bay Beach are located nearby.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Save 100% on your flight
Price was $2,123, price is now $1,245 per person
$1,245
per person
Mar 12 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Philipsburg (SXM)
Book a stay at this family-friendly hotel in Oyster Pond. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Save 100% on your flight
Price was $2,740, price is now $1,890 per person
$1,890
per person
Mar 12 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Philipsburg (SXM)
Stay at this hotel in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Maho Beach and Orient Bay Beach are located nearby.
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $2,539, price is now $1,762 per person
$1,762
per person
Mar 12 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Philipsburg (SXM)
Book a stay at this beach resort in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maho Beach and Orient Bay Beach are located nearby.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $1,417, price is now $992 per person
$992
per person
Mar 30 - Apr 5
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Book a stay at this beach resort in Oyster Pond. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Orient Bay Beach and Grand Case Beach are located nearby.
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Save 100% on your flight
Price was $2,105, price is now $1,497 per person
$1,497
per person
Mar 12 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Philipsburg (SXM)
Book a stay at this beach hotel in Philipsburg. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Orient Bay Beach and Maho Beach are located nearby.
La Vista Hotel

La Vista Hotel

3 out of 5
Price was $1,649, price is now $1,198 per person
$1,198
per person
Mar 30 - Apr 5
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Book a stay at this beach hotel in Simpson Bay. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

Cole Bay Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Save 100% on your flight
Price was $907, price is now $548 per person
$548
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
Price was $1,159, price is now $581 per person
$581
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Save 100% on your flight
Price was $1,505, price is now $850 per person
$850
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Save 100% on your flight
Price was $1,241, price is now $779 per person
$779
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)

Cole Bay Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $2,583, price is now $1,075 per person
$1,075
per person
Apr 15 - Apr 22
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $3,518, price is now $1,741 per person
$1,741
per person
Mar 12 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Save 100% on your flight
Price was $2,123, price is now $1,245 per person
$1,245
per person
Mar 12 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Save 100% on your flight
Price was $2,740, price is now $1,890 per person
$1,890
per person
Mar 12 - Mar 18
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Philipsburg (SXM)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Sun, Mar 1 - Sun, Mar 15
FLL
Fort Lauderdale - Hollywood Intl.
SXM
Princess Juliana Intl.
$238 Roundtrip, found 14 hours ago
$238
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Sun, Mar 1 from Fort Lauderdale - Hollywood Intl. to Princess Juliana Intl., returning Sun, Mar 15, priced at $238 found 14 hours ago
Spirit Airlines
Wed, Feb 25 - Wed, Mar 4
PHL
Philadelphia Intl.
SXM
Princess Juliana Intl.
$243 Roundtrip, found 6 days ago
$243
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Feb 25 from Philadelphia Intl. to Princess Juliana Intl., returning Wed, Mar 4, priced at $243 found 6 days ago
American Airlines
Wed, Feb 25 - Sat, Feb 28
MIA
Miami Intl.
SXM
Princess Juliana Intl.
$253 Roundtrip, found 10 hours ago
$253
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Wed, Feb 25 from Miami Intl. to Princess Juliana Intl., returning Sat, Feb 28, priced at $253 found 10 hours ago
Spirit Airlines
Tue, Mar 3 - Tue, Mar 10
EWR
Newark Liberty Intl. Airport
SXM
Princess Juliana Intl.
$260 Roundtrip, found 4 days ago
$260
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Mar 3 from Newark Liberty Intl. Airport to Princess Juliana Intl., returning Tue, Mar 10, priced at $260 found 4 days ago