Caribbean Islands Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Princess Heights Luxury Boutique Condo Hotel

Save 100% on your flight

per person

Aug 6 - Aug 11

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Philipsburg (SXM)

Stay at this 3.5-star 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.

La Playa Orient Bay

Save 100% on your flight

per person

Aug 6 - Aug 11

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Philipsburg (SXM)

Stay at this 4-star 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.

Simpson Bay Resort, Marina & Spa

per person

Aug 1 - Aug 6

found 17 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Philipsburg (SXM)

Stay at this 4-star 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.

Sapphire Beach Club Resort

Save 100% on your flight

per person

Aug 6 - Aug 11

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Philipsburg (SXM)

Stay at this 3-star 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.

The Morgan Resort Spa Village

Save 100% on your flight

per person

Aug 6 - Aug 11

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Philipsburg (SXM)

Stay at this 4-star 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.

Holland House Beach Hotel

Save 100% on your flight

per person

Aug 6 - Aug 11

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Philipsburg (SXM)

Stay at this 4-star 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.

The Villas at Simpson Bay Resort

per person

Jul 17 - Jul 21

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Philipsburg (SXM)

Stay at this 4-star 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.

Oceans at Divi Little Bay

Save 100% on your flight

per person

Aug 31 - Sep 5

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Philipsburg (SXM)

Stay at this 4-star 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.

Caribbean Islands Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.

Simpson Bay Resort, Marina & Spa

Pelican Key

per person

Aug 5 - Aug 8

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)