Oyster Pond Vacation Rentals

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Check prices for these dates

Tonight
Dec 31 - Jan 1
Tomorrow
Jan 1 - Jan 2
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Oyster Pond vacation rentals

Pool
Lovely Studio Apartment with Pool & Nature Views!

Lovely Studio Apartment with Pool & Nature Views!

Lovely Studio Apartment with Pool & Nature Views!
Oyster Pond
8.0 out of 10, Very Good, (1)
"The feature of the unit is the view! For the price it’s a great deal - especially if you have a car. The unit is clean - but the shower only runs really hot. "
United States
Jennifer
The price is ￥14,817
￥21,797 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Lovely Studio Apartment with Pool & Nature Views!
Sundeck
Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten
4.0 star property
Oyster Pond
8.8 out of 10, Excellent, (21)
"Wonderful vacation spot in st maarten"
United States
Debasis
Dawn Beach Club Resort Sint Maarten
Beach
Singh Luxury Apartments With sea View, Apt.1

Singh Luxury Apartments With sea View, Apt.1

Singh Luxury Apartments With sea View, Apt.1
3.0 star property
Oyster Pond
The price is ￥70,558
￥85,784 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Singh Luxury Apartments With sea View, Apt.1
Pool
Villa Sophia: Oceanfront w/ Generator & Pool

Villa Sophia: Oceanfront w/ Generator & Pool

Villa Sophia: Oceanfront w/ Generator & Pool
Tamarind Hill Estates
The price is ￥231,110
￥380,851 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Villa Sophia: Oceanfront w/ Generator & Pool
Outdoor pool
Singh Luxury Apartments With sea View, Apt.2

Singh Luxury Apartments With sea View, Apt.2

Singh Luxury Apartments With sea View, Apt.2
3.5 star property
Oyster Pond
The price is ￥70,558
￥85,784 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Singh Luxury Apartments With sea View, Apt.2
Beach
Singh Luxury Apartments With sea View, Apt.3

Singh Luxury Apartments With sea View, Apt.3

Singh Luxury Apartments With sea View, Apt.3
3.0 star property
Oyster Pond
2.0 out of 10, (1)
The price is ￥130,866
￥149,107 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Singh Luxury Apartments With sea View, Apt.3
Outdoor dining
Tintamarre exclusive dinner and night at anchor

Tintamarre exclusive dinner and night at anchor

Tintamarre exclusive dinner and night at anchor
Grand-Case
10.0 out of 10, Exceptional, (2)
"Wow. We can’t say enough about this amazing experience. The hosts are wonderful. We were just on their fantastic boat for one night - the last night of our trip, but it was perfect. We had a sail out to Tintamarre, a pristine and beautiful little deserted (amd conservation protected) island. We snorkeled, had apps and Karim’s signature cocktail as the sun went down. Then Sophie served us a great dinner out on the deck of the boat, including her delicious homemade bread! We stargazed and slept...
United States
Sheri W.
The price is ￥401,630
￥401,630 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Tintamarre exclusive dinner and night at anchor
Outdoor dining
UNIQUE EXPERIENCE: OVERNIGHT ON A CATAMARAN WITH DINNER AND BREAKFAST INCLUDED

UNIQUE EXPERIENCE: OVERNIGHT ON A CATAMARAN WITH DINNER AND BREAKFAST INCLUDED

UNIQUE EXPERIENCE: OVERNIGHT ON A CATAMARAN WITH DINNER AND BREAKFAST INCLUDED
Grand-Case
The price is ￥161,570
￥190,983 total
includes taxes & fees
Jan 2 - Jan 3, 2026
UNIQUE EXPERIENCE: OVERNIGHT ON A CATAMARAN WITH DINNER AND BREAKFAST INCLUDED
Outdoor dining
Unusual night in catamaran with dinner

Unusual night in catamaran with dinner

Unusual night in catamaran with dinner
Grand-Case
The price is ￥185,209
￥185,209 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Unusual night in catamaran with dinner
Iron/ironing board, free WiFi
MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
5.0 out of 10, (2)
"You sent me a confirmed booking upon arriving there I didn't had a reservation. I need my card credited or refunded please."
United States
Ailsie
The price is ￥11,564
￥13,956 total
includes taxes & fees
Jan 1 - Jan 2, 2026
MIDTOWN MOTEL SXM
Amazing Top Floor Apartment | Balcony
The Hills Residence

The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.8 out of 10, Excellent, (62)
"Good location, walkable area, great views. "
United States
Tiffany
The Hills Residence
1 bedroom, iron/ironing board, WiFi, bed sheets
Lovely room in a nice villa , close to Friars bay and happy bay

Lovely room in a nice villa , close to Friars bay and happy bay

Lovely room in a nice villa , close to Friars bay and happy bay
Saint-martin
9.0 out of 10, Wonderful, (9)
"Great place to stay. Will definitely be staying again next year! "
United States
Kurt
The price is ￥11,940
￥15,247 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Lovely room in a nice villa , close to Friars bay and happy bay
Front of property
July Apartments

July Apartments

July Apartments
3.0 star property
Madame's Estate
9.2 out of 10, Wonderful, (160)
"Amazing place. "
United States
Cristina
The price is ￥11,963
￥12,562 total
includes taxes & fees
Jan 5 - Jan 6, 2026
July Apartments
Beach nearby, white sand, sun loungers, beach umbrellas
Simpson Bay Suites

Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.0 out of 10, Good, (127)
"No issues. Staff were very welcoming and accommodating. Was a pleasant stay. "
United States
Sharmain
The price is ￥26,428
￥29,599 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Simpson Bay Suites
Terrace/patio
Mullet Bay Suites: Your Luxury Stay Awaits

Mullet Bay Suites: Your Luxury Stay Awaits

Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
Maho
9.8 out of 10, Exceptional, (118)
"Great apartment and great location!"
United States
Miljan
The price is ￥40,190
￥58,507 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Mullet Bay Suites: Your Luxury Stay Awaits
Living area
Quiet cozy flat in the centre of the island.

Quiet cozy flat in the centre of the island.

Quiet cozy flat in the centre of the island.
Weymouth Hill, Sint Maarten
8.0 out of 10, Very Good, (1)
The price is ￥25,021
￥33,935 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Quiet cozy flat in the centre of the island.
Fridge, microwave, oven, stovetop
Large 2BR Condo - STEPS FROM BEACH!

Large 2BR Condo - STEPS FROM BEACH!

Large 2BR Condo - STEPS FROM BEACH!
Maho
10.0 out of 10, Exceptional, (1)
"What a perfect unit! She thought of every extra detail down to laundry detergent. The condo was clean, beautifully decorated, and perfect for our stay. The added amenities made it a joy. It was so close to the beach and the beach chairs and towels made it all so easy. Jean was available to answer every questions and to help us with our pre-trip planning. There are many grocery stores close and one of the most beautiful beaches on the island is a short walk away. Thank you for a beautiful...
United States
Cylinda N.
Large 2BR Condo - STEPS FROM BEACH!
On the beach, sun loungers, beach towels
Charming studio with splendid Caribbean Sea view & pool/beach access

Charming studio with splendid Caribbean Sea view & pool/beach access

Charming studio with splendid Caribbean Sea view & pool/beach access
Marigot
The price is ￥22,319
￥26,518 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Charming studio with splendid Caribbean Sea view & pool/beach access
Room, 2 Bedrooms | Balcony view
Sea Palace

Sea Palace

Sea Palace
3.0 star property
Downtown Philipsburg
8.6 out of 10, Excellent, (113)
"Great staff. Excellent room. Awesome views. The young lady with the glasses at the front desk is the best ever. Didn't get her name unfortunately. "
United States
Elizabeth
The price is ￥31,151
￥32,709 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Sea Palace
Outdoor pool, sun loungers
Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten
4.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (1167)
"Room was great, resort was great, staff was great"
Canada
Gisele
The price is ￥59,900
￥67,000 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hilton Vacation Club Royal Palm St. Maarten
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oyster Pond Hotel Reviews

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

10/10 Excellent
"All rooms with a View of the Bay. Very well maintained resort. "
Eric 9-night trip
Posted 3 days ago
The Villas at Simpson Bay Resort

Find out more about Oyster Pond

Search for holiday rentals in Oyster Pond on Expedia! You can easily find your home rentals, villas, holiday apartments in Oyster Pond using one of the methods below:

  • View our selection of featured holiday rentals in Oyster Pond
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Look no further and take a look at our great range of rental properties in Oyster Pond!

Frequently asked questions

Can I find a vacation rental in Oyster Pond?

Yes, we give you a choice of vacation rentals close to popular sights in Oyster Pond, or you can go with a secluded option if you're looking for relaxation. Visitors to Oyster Pond speak positively about the scenic seaside and top-notch restaurants in this destination. Make sure you have time to check out the cafes while you're in the area.

What are some of the best vacation rentals that Oyster Pond has to offer?

DawnBeach Club 4 Bed/4Bath Villa With Swimming Pool, Beach and Resorts Access. : This Oyster Pond vacation home rental offers an outdoor pool, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the terrace in this rental home to help you unwind. Our travelers also rate Tropical Oasis in St. Martin 5 min to beach! Huge private pool+panoramic views!! as a favorite home for rent in Oyster Pond.

How many vacation rentals are there in Oyster Pond?

Choose from 18 Expedia vacation rentals in Oyster Pond for a memorable vacation.

What’s there to see and do in Oyster Pond?

Dawn Beach and Guana Bay are a couple of lovely local spots to get outside and enjoy nature. While here, Oyster Bay Marina and Gibb's Bay Beach are other places worth a visit.

What’s a vacation rental in Oyster Pond like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Oyster Pond. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.