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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 $1,328, price is now $910 per person
$910
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) 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 Grand Case Beach and Dawn Beach are located nearby.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $1,984, price is now $1,167 per person
$1,167
per person
Apr 13 - Apr 20
found 23 hours ago
Roundtrip non-stop flight included
Columbus (CMH) 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 Grand Case Beach and Oyster Bay Marina are located nearby.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,667, price is now $1,003 per person
$1,003
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) 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
Save 100% on your flight
Price was $1,578, price is now $975 per person
$975
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) 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.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,948, price is now $1,324 per person
$1,324
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 Grand Case Beach and Green Cay are located nearby.
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,369, price is now $1,020 per person
$1,020
per person
May 9 - May 12
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) 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.
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,374, price is now $1,031 per person
$1,031
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) 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 Maho Beach and Mullet Bay Beach are located nearby.
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,515, price is now $1,139 per person
$1,139
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) 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 Harbour Point Village 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
Price was $1,328, price is now $910 per person
$910
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) 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 $1,667, price is now $1,003 per person
$1,003
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) 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 $1,578, price is now $975 per person
$975
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,421, price is now $1,008 per person
$1,008
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop 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.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was $1,984, price is now $1,167 per person
$1,167
per person
Apr 13 - Apr 20
found 23 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $3,224, price is now $1,523 per person
$1,523
per person
Apr 13 - Apr 20
found 23 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $2,937, price is now $1,400 per person
$1,400
per person
Apr 13 - Apr 20
found 23 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was $2,181, price is now $1,267 per person
$1,267
per person
Apr 13 - Apr 20
found 23 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Philipsburg (SXM)