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Caribbean Islands Vacation Packages

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Caribbean Islands 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
Save 100% on your flight
Price was $1,253, price is now $659 per person
$659
per person
Apr 13 - Apr 18
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 $1,707, price is now $714 per person
$714
per person
Apr 20 - Apr 24
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 Mullet Bay Beach are located nearby.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $2,299, price is now $1,150 per person
$1,150
per person
Apr 13 - Apr 18
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.
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Save 100% on your flight
Price was $1,806, price is now $1,040 per person
$1,040
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Book a stay at this luxury aparthotel in Philipsburg. Enjoy free WiFi, free parking, and onsite spa services. Popular attractions Maho Beach and Orient Bay Beach are located nearby.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,119, price is now $663 per person
$663
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,610, price is now $996 per person
$996
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Book a stay at this beach hotel in Orient Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff 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 $1,668, price is now $1,045 per person
$1,045
per person
Apr 13 - Apr 18
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 $1,488, price is now $946 per person
$946
per person
Apr 13 - Apr 18
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.

Caribbean Islands 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 $1,060, price is now $582 per person
$582
per person
Apr 20 - Apr 24
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 $1,707, price is now $714 per person
$714
per person
Apr 20 - Apr 24
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
Pelican Key
Save 100% on your flight
Price was $1,942, price is now $1,011 per person
$1,011
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 $1,502, price is now $890 per person
$890
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)

Caribbean Islands 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 $1,253, price is now $659 per person
$659
per person
Apr 13 - Apr 18
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 $1,845, price is now $757 per person
$757
per person
Apr 17 - Apr 22
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
Pelican Key
Price was $2,982, price is now $1,451 per person
$1,451
per person
Mar 3 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 $1,781, price is now $1,014 per person
$1,014
per person
Mar 3 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)