Holiday rentals in Oakdale

Great South Bay Cottage

Fantastic private cottage on Long Island's South Shore. Great access to the best beaches in the world (walk to bay, ferries to ocean). Short train ride to/from NYC, Wineries & The Hampton's. Experience the Island’s charm and culture. Enjoy Long Island summers. Maintained by professional cleaners. NOTE: Increased prices reflect a policy change from Airbnb where the host is imposed a service fee, where before it was put on the guest. At the end of the day, your total costs will not have changed.

Modern Large 3-Bedroom Apartment in Islip, NY

Enjoy this stylish, family-friendly space. Dine at the solid wood table for eight and cook in a modern kitchen with stainless steel appliances. 3 bedrooms all W with modern furniture and 65" smart TVs all including cable .5 star sheets all down pillows master W king / walk-in closet, 2nd bedroom has a bunk bed with a full bed below the twin, third has a queen bed. living room with a silver sectional modern art / drapes / area rugs/ on a spacious 1/2 acre property. A/C Bluetooth stereo / bidet

Riverfront Retreat in Oakdale

Forget your worries at this beautiful riverfront location in historic Oakdale. Gorgeous landscaped yard, open and covered outdoor spaces, gas fire pit, fish pond, dock, outdoor shower, covered hot tub, 4 bedrooms, large L/R and kitchen, close to Connetquot Park, fishing,kayaking,Bayard Arboretum, shopping, restaurants ,bars,and Fire Island ferries. Owner has use of lower level apartment and garage, shared dock space. Just added 2026, waterfront woodburning stone firepit w/large seating area!

Bayport-2 Bedrooms 1 Bath Modern Coastal Retreat

Welcome to your modern Bayport getaway! This stylish 2-bedroom, 1-bath oasis (Entire 2nd floor of home) offers a bright, open layout with contemporary furnishings, a fully equipped kitchen, and a living area perfect for relaxing. The property is protected with Ring security camera to ensure safety Located minutes from beautiful beaches, a popular winery, Fire Island ferries, lively neighboring towns, local shops, and restaurants. This retreat blends comfort, convenience, and coastal charm!

Charming Secluded Waterfront Retreat

Unwind and enjoy in this stunning 1 bedroom waterfront oasis. It's on a secluded tree covered road leading to a private bridge and free off-street parking. Keep an eye out for beautiful wildlife! Welcome to your cozy beach styled apartment with fully equipped kitchen, full bath and water views from every window Abundant amenities, and in close proximity to airport, ferries, trains, state parks ,beaches kayaking, fishing and fine dining. Experience the best of Long Island has to offer!!

Waterfront Round House View

A unique little beach house on the south shore of long island with the most beautiful view. The house is located on a canal. Dock is available! **We have Paddle Boards, Surf Boards and 3- 2 person Kayaks onsite for you to use during your stay. You can get to the Great South Bay by paddling to the mouth of the canal. And you can get to Fire Island by hiring a Water Taxi to pick you up! The octagon house was built in the 1970s. It's recently been refreshed with all new beds & linens.

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

Hamptons Style Cottage close to everything!

Hamptons style cottage home is family friendly with a wonderful, fully equipped, kitchen to cook-in and spa inspired marble bathroom with huge shower and soaking tub to relax in. Rear patio with nicely landscaped yard shaded or unshaded by a large retractable awing. Located in Patchogue on a quiet block just a short walk to the fire island ocean ferries, restaurants, town's bustling main street, local bay beaches, and parks. Perfect for a weekend getaway or an extended stay!

Near all 1 BR - Full Kitchen, Backyard & Fire Pit!

Come stay at this beautifully renovated 1 bedroom apartment! Well-appointed for long-term stays or quick trips. ~ Propane Fire Pit ~ Private Sun-soaked backyard. ~ Full kitchen ~ Living room with sofa/futon for a 3rd guest ~ Queen bed ~ Full bathroom ~ Off-street parking for 1 car. This is a first-floor, ground-level apartment that gets lots of natural light. It is not a basement! :) Located in a quiet neighborhood and near all major highways. SmartTV. No cable TV. 21+

Cozy studio w/ private entrance

Perfect for solo travelers or couples.This new, cozy studio is part of a larger home but fully self-contained w/ its own entrance. Inside, you’ll find: - A comfy living area - A kitchen with essentials for light cooking - A private bathroom with shower, towels, and toiletries - High-speed Wi-Fi and a flat-screen TV Though attached to our home, your space is private. Located in a quiet neighborhood, close to attractions, restaurants, and transportation.

A little getaway!

The whole group will enjoy easy access to everything from this centrally located place. Just a short distance from the center of town and the Fire Island ferries. Close to grocery stores and shopping centers. Also, the LIRR is less than 1 mile away. NO PARTIES!!! AND ABSOLUTELY NO SMOKING!!! Please leave all towels on the floor of the bathroom and take out the garbage. The garbage pails are on the side of the house.

Bay Shore Boat House

Waterfront retreat with stunning views, a designer kitchen, serene interiors, and outdoor amenities including a fire pit, bluestone raised patio, and cabana bar. Ideal for couples and families. Walking distance to downtown Bay Shore, close to Fire Island Ferries and Captain Bill's. Unwind, fish off the dock, and witness unforgettable sunsets. Your perfect escape awaits.