Search Deals on
Oyster Pond Vacation Packages

Build your package with 2 more options

Oyster Pond Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $1,709, price is now $1,202 per person
$1,202
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Great Bay Beach are located nearby.

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $3,592, price is now $1,622 per person
$1,622
per person
Jan 11 - Jan 18
found 5 hours ago
Roundtrip 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.
Only the villas are decent and renovated. The other rooms are run down. Roaches in the restaurant. Hot water intermittent. Staff overall not very helpful or caring, minus the property manager.

Reviewed on Oct 30, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $3,617, price is now $1,855 per person
$1,855
per person
Jan 5 - Jan 10
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.
Loved staying at Simpson Bay! Will definitely stay again!

Reviewed on Oct 29, 2026

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Save 100% on your flight
Price was $2,412, price is now $1,345 per person
$1,345
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip 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 Port of St. Maarten and Great Bay Beach are located nearby.
My cousin and I had a great overnight stay @ your hotel. The staff was very helpful. Paul was great !!!

Reviewed on Oct 24, 2026

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $3,091, price is now $2,105 per person
$2,105
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip 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.
Wonderful location and view from my room. The room was very spacious

Reviewed on Oct 29, 2026

Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Save 100% on your flight
Price was $3,116, price is now $2,148 per person
$2,148
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip 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 Great Bay Beach are located nearby.
Room was clean and the view was amazing from the balcony. Staff are friendly and helpful. I would definitely stay here again.

Reviewed on Oct 28, 2026

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Save 100% on your flight
Price was $2,501, price is now $1,780 per person
$1,780
per person
Dec 19 - Dec 25
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 Maho Beach and Port of St. Maarten are located nearby.
The meals at Ocean were phenomenal!

Reviewed on Oct 12, 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $3,197, price is now $2,287 per person
$2,287
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The staff everywhere was incredibly helpful and nice. However the property just lacked overall. The room for being “the ocean front penthouse” was very lack luster for the $$$$. Food was just ok. Nothing special for the island. The pool is really the highlight of the property but you don’t have beach access. Overall I would not recommend or stay here again. Sorry Morgan.

Reviewed on Oct 28, 2026

Oyster Pond Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $2,231, price is now $1,021 per person
$1,021
per person
Jan 23 - Jan 27
found 7 hours ago
Roundtrip flight included
Baltimore (BWI) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $2,721, price is now $1,446 per person
$1,446
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $2,702, price is now $1,898 per person
$1,898
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $2,690, price is now $1,911 per person
$1,911
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)

Oyster Pond 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
Price was $1,852, price is now $1,023 per person
$1,023
per person
Jan 13 - Jan 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 $3,592, price is now $1,622 per person
$1,622
per person
Jan 11 - Jan 18
found 5 hours 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 $2,217, price is now $1,272 per person
$1,272
per person
Dec 14 - Dec 19
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)
The Atrium Beach Resort and Spa, an Ascend Collection Resort

The Atrium Beach Resort and Spa, an Ascend Collection Resort

3 out of 5
Price was $4,253, price is now $2,594 per person
$2,594
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)