Vacation rentals in Oakdale, NY

12 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Oakdale, NY vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Oakdale, NY

Top Vacation Rentals for Families in Oakdale, NY

Booking a family-oriented vacation rental in Oakdale, NY keeps you close to top city attractions for a stress-free getaway.

'Dreams Of Paradise' Luxury Home W/ Pool! - Oakdale, NY
9.6 5 reviews
Oakdale, NY
07/16 – 07/20
$1523/nighttotal: $6092 (4 )

'Dreams Of Paradise' Luxury Home W/ Pool!

4 3
apartment , Lake Grove
This luxurious vacation rental is located in Lake Grove, Long Island, just 8 miles from Short Beach and a short walk from the mall, making it a convenient base for exploring the area. The property is ideal for families and groups, with 4 bedrooms, 4 bathrooms, and a bonus sleeping nook, comfortably accommodating up to 10 guests.
The spacious home features a private pool, a chef's kitchen, a game room, and a jetted tub, providing everything you need for a relaxing and enjoyable stay. Enjoy movie nights under the stars with the outdoor DVD player, or relax by the fire pit table on the spacious deck.
Private 1 Bedroom Apt In A Quiet Neighborhood, Close To All! - Oakdale, NY
9.6 26 reviews
Oakdale, NY
07/16 – 07/20
$536/nighttotal: $2144 (4 )

Private 1 Bedroom Apt In A Quiet Neighborhood, Close To All!

1 3
apartment , Centereach
This Centereach apartment is conveniently located just over 4 kilometers from Suffolk County Community College and 4.8 kilometers from Stony Brook University, making it a great choice for visitors with academic ties or those attending events at these institutions. The apartment has consistently received excellent user ratings, indicating a high level of satisfaction among previous guests.
The 500 square foot apartment comfortably accommodates up to 4 guests with one bedroom and one bathroom. Amenities include a fully equipped kitchen, a fireplace, free WiFi, a washing machine, a balcony, a fenced private yard, and on-site parking.
Exceptional & Central, Garden Suite, Top Amenities & Care! - Oakdale, NY
9.6 5 reviews
Oakdale, NY
07/16 – 07/20
$401/nighttotal: $1604 (4 )

Exceptional & Central, Garden Suite, Top Amenities & Care!

2 3
apartment , Central Islip
This recently renovated two-bedroom apartment in Central Islip, New York, is conveniently located approximately 26 miles from the Nassau Veterans Memorial Coliseum and 29 miles from Jones Beach.
The 2-bedroom unit sleeps 7 guests and offers free Wi-Fi, private parking, a fully equipped kitchen with a microwave and coffee maker, plus a continental and American breakfast, an on-site snack bar, and an outdoor seating area.
Game Room, Hot Tub! Family Getaway In Bayshore - Oakdale, NY
Oakdale, NY
07/16 – 07/20
$3246/nighttotal: $12984 (4 )

Game Room, Hot Tub! Family Getaway In Bayshore

7 3
apartment , West Bay Shore
This 8,000 sq ft 'President's Mansion' vacation rental in West Bay Shore is located by the sea, offering proximity to Sagtikos Manor (0.7 miles), Gardiner County Park (0.8 miles), and the Bay Shore LIRR Station with NYC service (2 miles).
This expansive home accommodates up to 28 guests with 7 bedrooms and 4 bathrooms, featuring a game room, home gym, hot tub, gas grill, and ample parking for 28 vehicles.

Best Oakdale, NY vacation rentals with parking

Oceanfront Renovated Home In Fi Pines, Stunning Views & Spacious Outdoor Oasis - Oakdale, NY
10 3 reviews
Oakdale, NY
07/16 – 07/20
$3513/nighttotal: $14052 (4 )

Oceanfront Renovated Home In Fi Pines, Stunning Views & Spacious Outdoor Oasis

4 3
apartment , Fire Island
This Sayville vacation home, less than 1.2 miles from the Great South Bay and within 3 miles of the Cherry Grove Community House and Theatre, offers easy access to Fire Island's attractions. This four-bedroom, three-bathroom house sleeps eight, boasting a private patio, swimming pool, jacuzzi, and fully equipped kitchen including a dishwasher; free Wi-Fi and pet-friendly.
Polskarican Suite - Oakdale, NY
Oakdale, NY
07/16 – 07/20
$266/nighttotal: $1064 (4 )

Polskarican Suite

1 3
apartment , Centereach
This private guest suite in Ronkonkoma offers a convenient location, situated 10 miles from MacArthur Airport, 4 miles from Ronkonkoma Train Station, and 7.8 miles from Stony Brook University/Hospital, with Splish Splash Water Park 24 miles away.
This 700-square-foot apartment accommodates up to 4 guests with 1 bedroom and 1 bathroom, featuring air conditioning, internet, a garden, and parking, and is located near shopping centers, restaurants, and family attractions such as AMF Centereach Lanes and BounceU Smithtown.
Bay Shore Vacation Rental W/ Shared Yard! - Oakdale, NY
9.8 15 reviews
Oakdale, NY
07/16 – 07/20
$664/nighttotal: $2656 (4 )

Bay Shore Vacation Rental W/ Shared Yard!

3 3
apartment , North Bay Shore
This North Bay Shore rental is conveniently located near Brentwood State Park, Sky Zone, Tanger Outlets, and the Hauppauge Industrial Park, all within three miles.
The 1,250-square-foot apartment features three bedrooms, one bathroom, and accommodates six guests, boasting a fully equipped kitchen, in-unit laundry, a private fenced yard, and stunning ocean views.
The Bay House Patchogue Bay & Town 15 Minutes Walk - Oakdale, NY
Oakdale, NY
07/16 – 07/20
$1350/nighttotal: $5400 (4 )

The Bay House Patchogue Bay & Town 15 Minutes Walk

1 3
apartment , Patchogue
This 4-bedroom house in Patchogue is located within 1 mile of Fire Island National Seashore and close to local entertainment venues like 89 North Music Venue and Gateway Playhouse.
This air-conditioned rental accommodates up to 10 guests with 4 bedrooms and 3 bathrooms, offering a comfortable retreat with proximity to wildlife refuges and performing arts centers.

Frequently Asked Questions about vacation rentals in Oakdale, NY

  • Which walking or cycling routes are the best in Oakdale, NY?

    Oakdale has a few nice walking and cycling paths. You can take a stroll along the scenic waterfront of the Nissequogue River, or explore the trails at the Caleb Smith State Park Preserve. For a longer ride, you can head over to the nearby Sunken Meadow State Park, which has over 3,000 acres of trails to explore.
  • What are the best Airbnb and vacation rentals in Oakdale, NY?

    Just A Cozy Stay, Beautifully Decorated1br Apartment - Full Kitchen - Private Backyard & Fire Pit and Great South Bay Cottage are the most popular Airbnb and vacation rentals in Oakdale, NY among travelers.

  • What sports or outdoor activites can visitors enjoy in and around Oakdale, NY?

    Oakdale is a great place for outdoor activities. You can go fishing on the Nissequogue River, kayaking in the bay, or swimming at the beach. There are also several golf courses in the area, including the Oakdale Golf Club, which is a great option for a challenging round of golf.
  • What are the most popular Airbnbs in Oakdale, NY?

  • What other towns or cities can be easily accessed from Oakdale, NY?

    Oakdale is conveniently located near several other towns and cities on Long Island. You can easily drive to Port Jefferson, which has a charming downtown area with shops and restaurants. You can also visit the historic town of Huntington, which is known for its beautiful Victorian architecture.
  • What are the best vacation rentals with a pool in Oakdale, NY?

    Just A Cozy Stay, Ronkonkoma Bsment - Big Yard - Ping-pong - Bbq and The Historic 1888 House are the best vacation rentals with a pool in Oakdale, NY.

  • What amenities are commonly available in vacation rentals in Oakdale, NY?

    Vacation rentals in Oakdale usually offer a variety of amenities, including kitchens, laundry facilities, and outdoor spaces like decks or patios. Many rentals also have access to private beaches or pools, depending on the location.
  • What are the best rentals for families and kids in Oakdale, NY?

  • What time of year is best to rent a vacation rental Oakdale, NY?

    The best time to rent a vacation rental in Oakdale is during the summer months, from June to August, when the weather is warm and sunny. However, you can also find great deals during the shoulder seasons, in the spring and fall, when the crowds are smaller and the prices are lower.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakdale, NY?

  • What are the local dishes in Oakdale, NY region?

    The local cuisine in Oakdale is a mix of classic American dishes with a Long Island twist. You can find fresh seafood, like clams, oysters, and lobster, at many restaurants. There are also plenty of Italian restaurants, as well as delis that serve classic New York sandwiches.

Destinations nearby

Best Vacation Rentals with Balconies in Oakdale, NY

Wake up to breathtaking views at these Oakdale, NY vacation rentals with balconies, perfect for your morning coffee.

The Pelican's Nest - Oakdale, NY
Oakdale, NY
07/16 – 07/20
$1632/nighttotal: $6528 (4 )

The Pelican's Nest

1 3
house , Fire Island
The Pelican's Nest is a beachfront house located in Ocean Bay Park, Fire Island, directly adjacent to Ocean Beach.
This 1030 square foot residence accommodates up to 15 guests with 3 bedrooms, 2 bathrooms, a living room, TV, and includes a kitchen with a fridge, microwave, and dishwasher, plus a terrace, balcony with sea views, garden, outdoor dining area, picnic area, and an on-site restaurant.

Best Oakdale, NY vacation rentals with air conditioning

Fire Island Pines Paradise. - Oakdale, NY
Oakdale, NY
07/16 – 07/20
$763/nighttotal: $3052 (4 )

Fire Island Pines Paradise.

2 3
apartment , Fire Island
This Fire Island accommodation offers a prime location, just a 2-minute walk to the beach and a 5-minute walk to the Pines ferry dock, dining, and shopping.
This newly refreshed two-bedroom condo accommodates up to 5 guests and features a private deck with an ocean view, a Jacuzzi hot tub, an outdoor shower, and high-speed internet.
Private 1-2 Bedroom Apartment (Bay) - Oakdale, NY
8.6 16 reviews
Oakdale, NY
07/16 – 07/20
$198/nighttotal: $792 (4 )

Private 1-2 Bedroom Apartment (Bay)

1 3
apartment , Central Islip
This Central Islip apartment rental offers a 2-bedroom, 1-bathroom unit sleeping up to four guests, featuring a queen bed and optional twin bed.
The apartment includes a kitchen with a refrigerator and microwave, air conditioning, parking, and internet access; a private entrance ensures guest privacy.
Unforgettable Stay On A 44ft Luxury Yacht - Oakdale, NY
Oakdale, NY
07/16 – 07/20
$3128/nighttotal: $12512 (4 )

Unforgettable Stay On A 44ft Luxury Yacht

2 3
boat , Fire Island
This 44-foot Rivarama yacht offers luxurious day boat experiences near Fire Island, providing easy access to the island's beaches and communities depending on its mooring location.
The vessel features two bedrooms, one bathroom, and accommodates three guests, boasting amenities such as a queen-size bed, Gaggenau electric grill, Bose surround sound system, and a teak swim platform with a hydraulic swim ladder.
Fire Island Beach House - Oakdale, NY
Oakdale, NY
07/16 – 07/20
$8751/nighttotal: $35004 (4 )

Fire Island Beach House

3 3
apartment , Fire Island
This modernist apartment offers a prime coastal location in Fire Island, situated just minutes from a magnificent beach.
This 3-bedroom, 3-bathroom residence accommodates up to 6 guests and features air conditioning, internet, and access to a heated swimming pool, all within an exclusive and tranquil setting.
©2026 cozycozy.com