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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
Price was $881, price is now $547 per person
$547
per person
Sep 8 - Sep 12
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 Great Bay Beach and Orient Bay are located nearby.
Large and beautiful condo with a fantastic view

Reviewed on Jul 4, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $1,474, price is now $692 per person
$692
per person
Sep 8 - Sep 12
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 St. Martin Beaches are located nearby.
Stayed for 4 days and had the breakfast included in our stay. It is in a location where you can walk to local shops and restaurants. Great experience.

Reviewed on Jul 5, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,360, price is now $742 per person
$742
per person
Sep 16 - Sep 21
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 St. Martin Beaches are located nearby.
A

Reviewed on Jul 6, 2026

Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Save 100% on your flight
Price was $1,010, price is now $664 per person
$664
per person
Sep 8 - Sep 12
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 in-room massages. Popular attractions Maho Beach and St. Martin Beaches are located nearby.
Beautiful place would definitely recommend

Reviewed on Jul 2, 2026

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $863, price is now $572 per person
$572
per person
Sep 8 - Sep 12
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 and Great Bay Beach are located nearby.
Nice

Reviewed on Jul 6, 2026

Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

4 out of 5
Save 100% on your flight
Price was $1,632, price is now $1,142 per person
$1,142
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
Book a stay at this beach resort in Oyster Pond. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Orient Bay and Great Bay Beach are located nearby.
Coral Beach Club was a wonderful choice for my family. (Husband/Wife & 3 little ones)The property was meticulously kept, and the Villa was cleanly and spacious. The Staff was kind and attentive. Special thanks to Bernadette! We utilized our splash pool, and the nearby sister resort’s infinity pool and market place as well. The Big Fish Restaurant offered high end dining and an array of dishes for any palate to enjoy! The location is on Dawn Beach yet minutes away from Orient Beach, and many excellent restaurants on the French side! We definitely recommend and hope to visit again one day!

Reviewed on Jun 10, 2026

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,212, price is now $849 per person
$849
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip 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 Great Bay Beach and St. Martin Beaches are located nearby.
Amazing

Reviewed on Jun 27, 2026

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $933, price is now $680 per person
$680
per person
Sep 8 - Sep 12
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 Great Bay Beach are located nearby.
Great Resort!

Reviewed on Jul 3, 2026

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
Price was $881, price is now $547 per person
$547
per person
Sep 8 - Sep 12
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 $1,474, price is now $692 per person
$692
per person
Sep 8 - Sep 12
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 $1,192, price is now $604 per person
$604
per person
Sep 8 - Sep 12
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 $1,010, price is now $664 per person
$664
per person
Sep 8 - Sep 12
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 $1,398, price is now $813 per person
$813
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip 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 $2,831, price is now $1,147 per person
$1,147
per person
Aug 8 - Aug 15
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 $2,188, price is now $921 per person
$921
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,663, price is now $1,009 per person
$1,009
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)