Holiday rentals in Islandia

Tranquility Getaway, Private Luxe Suite & Backyard

🌿 Welcome to Tranquility Getaway — a luxurious retreat nestled in the heart of Smithtown. Indulge in our Modern Newly Designed 2-bedroom Private Basement Luxe Suite, located on the left side of the property with a short staircase leading to your exclusive entrance on the lower level. Unwind in your private outdoor haven, featuring refined seating for four, a stone-top fire pit, and a solar-lit umbrella. THIS IS NOT THE ENTIRE HOUSE‼️ PLEASE REVIEW 📸 PHOTOS & HOUSE RULES BEFORE BOOKING‼️

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

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Hotel-Style Studio in Ronkonkoma

Suite 2283, a hotel-inspired studio apartment in Ronkonkoma, is a guest suite for one person. Featuring a private entrance, private fenced-in yard, patio with bistro set, onsite parking, AC, kitchen, Roku TV and free Wi-Fi, it's ideal for traveling medical and business professionals. And, it's just minutes from the airport, hospitals, corporate parks, major roadways, restaurants, parks, the mall, and nightlife at the new Station Yards complex at the LIRR hub.

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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.

Harbor House Stony Brook Village

Welcome to The Harbor House — a stunning luxury home nestled in the heart of Stony Brook Village. This beautifully custom-built retreat features a private pool, hot tub, sauna, and gym for the ultimate relaxation and comfort. Walk to the charming village center filled with shops, restaurants, and beaches, or reach Stony Brook University and Hospital in just minutes. Perfect for families or groups seeking a modern coastal escape with style and space.

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Ronkonkoma Residence by the Lake

Discover the enchanting allure of our stunning lake house retreat nestled in the quaint town of Lake Ronkonkoma. A 9 min drive to the Smith Haven Mall and variety of grocery stores within 10 min drives from the house, assortment of restaurants, etc. All close by the house and a 10 min. drive to MacArthur Airport. This charming and modern house is the perfect place in any season for families or groups of friends to indulge in a relaxing getaway.

Stylish 2BR Pet-Friendly Suite Near Islip Airport!

Kick back and relax in this stylish, newly renovated 2-bedroom basement apartment with beautiful white floors throughout. Perfect for work trips, court visits, sports tournaments, or weekend getaways. Enjoy two cozy bedrooms, a comfortable sofa bed, Smart TVs, fast Wi-Fi, and a modern bathroom with a Bluetooth speaker. Clean, comfortable, and thoughtfully designed to make you feel right at home during your stay.

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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.

Cozy apartment with private entrance

Cozy apartment for single or couple in the heart of Long Island. This new listing is located on the first floor of a 2 story house with its own entrance. As you walking you are greeted with a nice living room with a pull sofa, a dining table a well equipped kitchen and a nice size bathroom. The bedroom has a queen size with comfortable bed set for a wonderful night.

Summer Retreat: Heated Pool, Game Room, Playground

POOL CLOSES 1st-2nd WEEK OF OCTOBER 2026: Escape to the ultimate summer retreat! Enjoy a private saltwater heated pool, fire pit, game room, and family-friendly fun in this spacious Long Island oasis. Just minutes from Cedar Beach and perfect for groups, families, or couples. Relax, play, and make unforgettable memories—your perfect getaway starts here!

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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.

Large 1 bedroom apartment

Relax with the whole family at this peaceful place to stay. This is a one bedroom apartment which includes a kitchen, bathroom w/ tub, living room, refrigerator, stove, oven, large bedroom w/ closet. There is a closet in the living room available as well. Sofá bed queen size in the living room.