Holiday rentals in Oakdale

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!

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 with a pull-out twin bed and seating - 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.

Riverfront Retreat in Oakdale

Forget your worries in this spacious and serene waterfront space. Beautiful riverfront location in historic Oakdale. Very private. Gorgeous landscaped yard, open and covered outdoor spaces, fire pit,fish pond, dock, outdoor shower, covered hot tub, 3 bedrooms and sleeping den, large living room, 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.boat at dock not for use.

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.

Joyful Beach House, viewing The Great South Bay

Amazing Great South Bay view with access to Shorefront and Rider Parks. This Ranch has an unobstructed view of the Shorefront Band Shell. Watch concerts and sunsets from the comfort of your patio. Walk down to the Patchogue Beach Club and enjoy the pool and beach. This open-concept home has 2 bedrooms, one bath, a remodeled bathroom, and a kitchen. The kitchen has stainless steel appliances, a farm sink, and a butcher block countertop with natural lighting that will brighten the home.

The Sunshine House

Enjoy your stay and visit the Bayard Cutting Arboretum, SUSA Orlin & Cohen Sports Complex, Robert Moses Beach; centrally located between The Hamptons Vineyard Wine Tours & Manhattan. This unique home was originally built in 1921 and has since undergone renovations with additions added to the original structure, including the three bedroom / bath guest wing with a private entrance from the main house. We provide beverages and continental breakfast. Please email us for more details!

The Harbor House: Beachfront Home 1 hour from NYC

FEATURED #1 on Refinery29's "11 Best Beach Houses Near NYC" Welcome to Long Island’s iconic Gold Coast! Wake up to sweeping waterfront views and, if you’re lucky, catch a glimpse of our local bald eagle family soaring overhead! Explore nearby gems like the Vanderbilt Mansion & Planetarium, Caumsett State Historic Park Preserve, Del Vino Vineyards, and the lively Paramount Theatre. Stroll through Downtown Huntington or Northport Village for boutique shopping, great 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!

Studio in Stony Brook

We have contactless check-in procedure & fully private entrance. Please contact with any questions! Large clean studio space that is totally private from the main residence. Private bathroom with toiletries included. Close to beaches, shopping, and SUNY hospital and campus by car or bus. Pull-out loveseat with twin size mattress available for an extra charge. (Book for “3 Guests” for this regardless of occupancy so we know to prepare the bed.)

4 Bedroom in Vibrant Patchogue Village!

Convenient location! A two minute drive to the town of Patchogue with vibrant restaurants, shops, and entertainment. 5 Minute drive to Fire Island Ferries, 3 minute drive to LIRR, and walking distance to a newly rennovated park and tennis courts. About 1 hour drive to NYC, about 30-45 mins to the Hamptons and wineries, and 10 Minutes to MacArthur Airport!

Charming “hotel inspired” Retreat

Relax and recharge at this peaceful, centrally located retreat. Your private room features a cozy QUEEN size bed, desk and chair for work or study, TV for entertainment, and a coffee station with microwave and mini fridge for quick bites. Enjoy the privacy of your own bathroom and entrance, with easy on-street parking right in front of the house.

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.