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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 $1,138, price is now $708 per person
$708
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 Port of St. Maarten and Orient Bay are located nearby.

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $1,926, price is now $888 per person
$888
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
This resort was amazing. Walking distance to many restaurants and club. They call taxis for you 24/7 to where ever and back. Property is also very beautiful. I only tried one restaurant on property, Juliettes Bistro for breakfast, it was really good and the staff were really nice. I will definitely be back.

Reviewed on Sep 12, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,729, price is now $829 per person
$829
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $1,710, price is now $1,022 per person
$1,022
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Book a stay at this spa resort in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

4 out of 5
Price was $1,776, price is now $1,290 per person
$1,290
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Book a stay at this spa resort in Oyster Pond. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Orient Bay and Port of St. Maarten are located nearby.
The condo and property was clean and well decorated and maintained. We had an awesome stay and will return.

Reviewed on Jul 19, 2026

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $961, price is now $725 per person
$725
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Book a stay at this spa 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 Port of St. Maarten are located nearby.

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
Price was $2,543, price is now $1,921 per person
$1,921
per person
Nov 1 - Nov 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Book a stay at this beach property in Lowlands. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
There was a water issue, no hot water.

Reviewed on Sep 13, 2026

Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,228, price is now $930 per person
$930
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 Port of St. Maarten 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 $1,138, price is now $708 per person
$708
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $1,926, price is now $888 per person
$888
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,729, price is now $829 per person
$829
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $1,710, price is now $1,022 per person
$1,022
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,291, price is now $721 per person
$721
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $2,266, price is now $930 per person
$930
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $1,993, price is now $853 per person
$853
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $2,021, price is now $1,060 per person
$1,060
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)