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Simpson Bay Vacation Packages

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Simpson Bay Flight + Hotel Packages

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
Price was $616, price is now $429 per person
$429
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $3,122, price is now $1,386 per person
$1,386
per person
Mar 3 - Mar 9
found 2 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 $1,933, price is now $950 per person
$950
per person
Feb 17 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Save 100% on your flight
Price was $1,675, price is now $1,128 per person
$1,128
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 $1,573, price is now $1,073 per person
$1,073
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Aqua Vue by Island Properties Online

Aqua Vue by Island Properties Online

3.5 out of 5
Save 100% on your flight
Price was $2,176, price is now $1,616 per person
$1,616
per person
Mar 3 - Mar 9
found 2 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Stay at this condo in Lowlands. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Price was $894, price is now $668 per person
$668
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Book a stay at this beach resort in Lowlands. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Save 100% on your flight
Price was $1,179, price is now $892 per person
$892
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.

Simpson 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 $1,192, price is now $718 per person
$718
per person
Feb 17 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $1,933, price is now $950 per person
$950
per person
Feb 17 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 $2,043, price is now $1,067 per person
$1,067
per person
Jan 28 - Feb 1
just found
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $2,093, price is now $1,341 per person
$1,341
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)

Simpson Bay Vacation Packages 5-7 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 $1,671, price is now $1,051 per person
$1,051
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $3,122, price is now $1,386 per person
$1,386
per person
Mar 3 - Mar 9
found 2 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $3,070, price is now $1,531 per person
$1,531
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Save 100% on your flight
Price was $2,417, price is now $1,606 per person
$1,606
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)

Top Flight Deals

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

Spirit Airlines
Wed, Feb 25 - Wed, Mar 4
PHL
Philadelphia Intl.
SXM
Princess Juliana Intl.
$221 Roundtrip, found 1 day ago
$221
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Feb 25 from Philadelphia Intl. to Princess Juliana Intl., returning Wed, Mar 4, priced at $221 found 1 day ago
Spirit Airlines
Sat, Jan 10 - Sat, Jan 17
EWR
Newark Liberty Intl. Airport
SXM
Princess Juliana Intl.
$238 Roundtrip, found 1 day ago
$238
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Jan 10 from Newark Liberty Intl. Airport to Princess Juliana Intl., returning Sat, Jan 17, priced at $238 found 1 day ago
JetBlue Airways
Fri, Jan 30 - Sat, Feb 7
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$280 Roundtrip, found 1 day ago
$280
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Jan 30 from John F. Kennedy Intl. to Princess Juliana Intl., returning Sat, Feb 7, priced at $280 found 1 day ago
United
Mon, Mar 9 - Wed, Mar 11
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$297 Roundtrip, found 1 day ago
$297
Roundtrip
found 1 day ago
Select United flight, departing Mon, Mar 9 from Logan Intl. to Princess Juliana Intl., returning Wed, Mar 11, priced at $297 found 1 day ago