Oyster Pond Holiday Rentals

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Holiday Rentals in Oyster Pond

Fourteen at Mullet Bay
Deluxe Condo, 1 Bedroom, Balcony, Beach View | Terrace/patio
Fourteen at Mullet Bay
3.5 star property
9.6 out of 10, Exceptional, 125 reviews
"Nice property overlooking the mullet bay beach. 5 minute walk to the beach was very nice. Good security and parking. "
Fourteen at Mullet Bay
Dawn Beach Club Resort Sint Maarten
Sundeck
Dawn Beach Club Resort Sint Maarten
4.0 star property
8.6 out of 10, Excellent, 14 reviews
"Nice property, but far away from the airport and party area"
The price is NZ$1,220
includes taxes & fees
15 Jun - 16 Jun
Dawn Beach Club Resort Sint Maarten
July Apartments
Front of property
July Apartments
3.0 star property
9.2 out of 10, Wonderful, 73 reviews
"Probably one of the easiest parking on the island! Front desk staff is always present and very helpful and friendly. Easy to get to and a nice, clean stay."
The price is NZ$131
includes taxes & fees
18 Jun - 19 Jun
July Apartments
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Villa Little Paradise - BIG DISCOUNT MARCH - APRIL !!
Sun-loungers, beach towels
Villa Little Paradise - BIG DISCOUNT MARCH - APRIL !!
10.0 out of 10, Exceptional, 8 reviews
"The house was just as listed and the area was perfect. We enjoyed our stay and would recommend and will return!"
Villa Little Paradise - BIG DISCOUNT MARCH - APRIL !!
The Horny Toad Guesthouse
Orchid | View from room
The Horny Toad Guesthouse
3.0 star property
9.4 out of 10, Exceptional, 51 reviews
"Deb & Doug are accommodating and great to talk to to get ideas of things to do. Perfect place to stay!"
The price is NZ$359
includes taxes & fees
5 Jun - 6 Jun
The Horny Toad Guesthouse
The Hotel Porto Cupecoy
Beach nearby, white sand, sun-loungers, beach umbrellas
The Hotel Porto Cupecoy
3.5 star property
9.6 out of 10, Exceptional, 31 reviews
"Great and safe property. Big rooms"
The price is NZ$871
includes taxes & fees
5 Jun - 6 Jun
The Hotel Porto Cupecoy
Villa Bahia Blue - Four Bedroom Villa, Sleeps 8
Pool
Villa Bahia Blue - Four Bedroom Villa, Sleeps 8
10.0 out of 10, Exceptional, 12 reviews
"2 familes each with 2 kids had a great time. Very close to baie rouge. Pool was nice. Hot tub water seemed bad so we didnt use it. Housekeeper and concierge were really nice. Rented a car and drove all over the small island. Would recommend and would stay again"
Villa Bahia Blue - Four Bedroom Villa, Sleeps 8
Tradewinds at Simpson Bay
Exterior
Tradewinds at Simpson Bay
3.5 star property
8.6 out of 10, Excellent, 10 reviews
"The room was spacious and spotless . The staff were attentive and went out of their way to ensure that we were comfortable. Nothing was too much trouble.Will be back excellent stay "
Tradewinds at Simpson Bay
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste
Outdoor pool, an infinity pool
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste
10.0 out of 10, Exceptional, 66 reviews
""We had an incredible stay at Villa Namaste! The property is gorgeous, with every room beautifully appointed. The view from the patio is breathtaking—worth every penny. Sitting in the infinity edge pool, looking out over the bluest Caribbean waters while watching mega yachts sail by, was a highlight of our days. The villa is also conveniently located close to many cool restaurants, some even within walking distance, which was perfect for our evenings out. The staff, particularly Olive and...
One Hundred Million Dollar Yacht On Land 5 star Villa Namaste
Simpson Bay Suites
Beach nearby, white sand, sun-loungers, beach umbrellas
Simpson Bay Suites
3.5 star property
6.8 out of 10, 100 reviews
"Convenient location with the requisite amenities for local stay and business. Water pressure could be improved. Though clean and tidy furniture could be modernized. "
The price is NZ$220
includes taxes & fees
6 Jun - 7 Jun
Simpson Bay Suites
LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site
Outdoor pool
LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site
10.0 out of 10, Exceptional, 67 reviews
"From the moment we walked out of the airport everything was amazing. The resort had transportation waiting for us. There was no real check-in like most resorts, the taxi driver walked us right to our villa and vacation began. On this trip we chose not to rent a car so we hired Claudette Fritz to take us everywhere we wanted to go which was much cheaper than car rental. The house was amazing to say the least. The pool was very well kept and only a couple steps from the beautiful white sand. We...
LITERALLY OCEANFRONT VILLA ALABASTER, DAWN BEACH w private pool ~ Owners' site
Beachfront villa with pool in Cul de Sac
Property grounds
Beachfront villa with pool in Cul de Sac
9.8 out of 10, Exceptional, 60 reviews
"We lucked out on selecting this place since we've never been. The french side is the place to stay. The airport, the cruise ships and all the tourist shops are on the dutch side ands its packed all the time. On the french side its beautiful, less touristy an A"
Beachfront villa with pool in Cul de Sac
Beautiful Ocean Front Penthouse/New Furnishings/Stunning View/Private Beach!
Beach
Beautiful Ocean Front Penthouse/New Furnishings/Stunning View/Private Beach!
10.0 out of 10, Exceptional, 66 reviews
"This was our first time in St. Martin. I fell in love with the pictures of this unit. The pictures cannot capture how wonderful this place is. The unit was spotless. The beds were very comfortable. But the VIEW!!!! Oh my gosh!!! The view from the balcony and the private terrace cannot be described!!!! Absolutely breathtaking!!!! The pools were fantastic. Our own private beach! Communication with Susan, the owner, was immediate. She also was so helpful in suggesting places for us to eat and...
Beautiful Ocean Front Penthouse/New Furnishings/Stunning View/Private Beach!
FantaSea beachfront, Survived the hurricane, low low prices take advantage!
Beach/ocean view
FantaSea beachfront, Survived the hurricane, low low prices take advantage!
10.0 out of 10, Exceptional, 53 reviews
"This stay was a mixed bag for our group of 4 kids aged 6-15 and 5 adults. Our check in process was not smooth but the owner was apologetic and tried to make it right. And I feel for the owners because I am sure the issues are not so much neglect as not completing repairs after the hurricane. Still, the pictures do not reflect the current state of the home. It feels warn down. Pros The house is spacious with room for a big group. Direct beach access is a great feature. Views from the house and...
FantaSea beachfront, Survived the hurricane, low low prices take advantage!
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
Beach
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
10.0 out of 10, Exceptional, 24 reviews
"Our family of 5 (2-10yr old boys, 1-14yr old girl) were very pleased with the condo. The location was prime in Simpson Bay. Within walking distance to a few beach bars and walked over to Maho Beach too a few times. The pool was nice (warm) and had plenty of seating, always a few seats available. There are beach chairs, toys on the porch along with a beach umbrella. The kitchen was well equipped and left us not needing anything. Bath linens could use a refresh but was sufficient. The only...
Perfect beach front condo in Simpson Bay Beach🌴 2 bedroom+ Loft, 2.5 Baths.
The CLIFF - Luxury Beachfront Resort - Full Amenities --> Spa - Restaurant - etc
On the beach, sun-loungers, beach towels
The CLIFF - Luxury Beachfront Resort - Full Amenities --> Spa - Restaurant - etc
10.0 out of 10, Exceptional, 91 reviews
"Host was amazing. Our flight got canceled the morning of. He was very accommodating and understanding. Perfect views. Private beach. Perfect, clear water. Very little shade on beach with stairs. Friendly staff. Would recommend."
The CLIFF - Luxury Beachfront Resort - Full Amenities --> Spa - Restaurant - etc
Anchor House - Direct Oceanfront - Luxury & Modern Style
Property grounds
Anchor House - Direct Oceanfront - Luxury & Modern Style
10.0 out of 10, Exceptional, 125 reviews
"This property is simply stunning. Very clean. Safe area. Walkable to restaurants, bars, markets and the beach, however we did rent a car. Property manager Stacey was amazing. The pictures are spot on for this property and we are booking again in the coming months! I was a little worried that sometimes you aren’t sure what you are booking but this was amazingly perfect. Can’t wait to go back!"
Anchor House - Direct Oceanfront - Luxury & Modern Style
Luxury Villa w Spectacular Ocean Views, private pool/Hottub, Walk to Beach
Outdoor pool
Luxury Villa w Spectacular Ocean Views, private pool/Hottub, Walk to Beach
10.0 out of 10, Exceptional, 116 reviews
"We stayed at Villa Valhalla with our 3 teenage kids and another family of 4. The house was beautiful, clean, well stocked with stunning views! Plenty of room for us all. It’s located in a safe and quiet neighborhood overlooking Dawn Beach. Everything was as stated from the website, except the kitchen has been updated and looks great. We had excellent communication before and during the trip. We were able to walk to the beach, and had dinner at the new JW Marriott. It was nice to have a close...
Luxury Villa w Spectacular Ocean Views, private pool/Hottub, Walk to Beach
Oceanfront amazing 2 bedrooms Condo
Outdoor pool
Oceanfront amazing 2 bedrooms Condo
9.8 out of 10, Exceptional, 49 reviews
"The condo was very nice. The furnishings were as expected and very tastefully done. The only detractor was the cleanliness of the pool. It needs more attention than what it currently receives and it is full sun. There is no shaded area if you’re hoping to take a break from the sun."
Oceanfront amazing 2 bedrooms Condo
Beautiful beachfront at The Villas On Great Bay
Outdoor pool, an infinity pool
Beautiful beachfront at The Villas On Great Bay
10.0 out of 10, Exceptional, 107 reviews
"What a lovely villa! The pics don't do it justice! The bedrooms and living room are much more spacious. The location in the community is perfect as far as privacy. The owners have thought of absolutely everything one might need. We even loved the beach compared to the few others we saw on the island. It wasn't super-wide which would make for a long walk, it was completely uncrowded - most days we were the only ones there, and the water was gorgeous. Also, watching the cruise ships come in and go...
Beautiful beachfront at The Villas On Great Bay
Don't see what you're looking for?
See all available properties in Oyster Pond
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.

Other types of properties in Oyster Pond you may be interested in

Les Balcons d'Oyster Pond
Exclusive Cottage, Private Pool, Ocean View (1 or 2 Bedroom for 2 to 4 Guests) | Terrace/patio
Les Balcons d'Oyster Pond
9.6 out of 10, Exceptional, 31 reviews
"An absolutely beautiful place to stay, I would definitely come back again! Property has everything you need (refrigerator, microwave, plates, silverware, glasses, air conditioning, outdoor BBQ, outdoor lawn chairs on the wonderful large secluded patio). Pool is a nice relaxing feature after a long day at the multiple amazing beaches. Didn’t feel crowded at all. Very nice bistro/convenience store (Bread and Butter) 2 min walk away with fabulous breakfast, wine, things for a beach trip. Best food...
Les Balcons d'Oyster Pond
Colombus Résidence
Studio, 1 King Bed, Kitchenette, Pool View | Terrace/patio
Colombus Résidence
9.4 out of 10, Exceptional, 84 reviews
"I liked spacious dinning room and huge veranda with beautiful sea and hills view, kitchen, room furnishing, mini-hotel architecture . I would like to have a mosquito net on bedroom window. "
Colombus Résidence
Sonesta Maho Beach All Inclusive Resort Casino & Spa
View from property
Sonesta Maho Beach All Inclusive Resort Casino & Spa
4.0 star property
8.0 out of 10, Very good, 1,677 reviews
"Our trip was fun. We were at the Sonesta for 11 days. We always felt safe, there’s plenty of great food and shopping options within walking distance. In my opinion, the food at the hotel was not good so we ate out almost every meal. The rooms are fine, served their purpose of sleeping. The beds were not comfortable and were small. There were 4 of us (2 adults, adult child (19) and an 11 yr old) and we had to have a roll-a-way be brought in. The power in the entire resort went out at least once...
The price is NZ$440
includes taxes & fees
5 Jun - 6 Jun
Sonesta Maho Beach All Inclusive Resort Casino & Spa
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oyster Pond holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oyster Pond. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oyster Pond. Seeing all the best attractions is bound to make you fall in love with Oyster Pond. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oyster Pond short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Oyster Pond?

Yes, there are holiday rentals close to the most popular sights in Oyster Pond, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Oyster Pond is known for its marina and beaches. While you're in the area, grab a bite or have a drink at the restaurants and bars.

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

White Sands Retreat - Beachside at Beacon Hill: This holiday home rental outside of Oyster Pond is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals will I find in Oyster Pond?

Expedia has 14 holiday rentals for your stay in Oyster Pond.

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

While you're exploring the area, Coralita Beach and Dawn Beach are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Oyster Bay Marina and Guana Bay Beach.

What’s a holiday rental in Oyster Pond like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oyster Pond. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips or small group gatherings.

Recent reviews of Oyster Pond properties
Expedia verified reviews

Hommage Hotel & Residences

Hommage Hotel & Residences

5/5 Excellent
"Love it "
A verified traveller stayed at Hommage Hotel & Residences
Posted 2 days ago
Hommage Hotel & Residences