Holiday rentals with a pool in Fire Island

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

Stylish+Modern Cape Beach House nestled in Hampton Bays South of the highway, 5 min drive to beaches. Heated Saltwater Pool. 4 Bedrooms+Crib room & Office. 2 Bathrooms. Outdoor deck w/family dining+BBQ. Fully fenced tree-lined back yard w/ beautiful sunsets. Upstairs King bedroom w/ensuite bthrm + Twin bedroom directly off master. Main floor has another King bedroom+Twin bedroom, master bath, lounge+kitchen w/huge sit-around island. TV Den. Central AC. 15 min walk/ 2 min drive to shops+train.

Best Studio-Private Entrance+Parking-Close To All

Make yourself at home! This Deer Park Den is your perfect suburban getaway in the heart of Long Island, close to everything and right in the middle of all the fun. Walking distance to lots of great restaurants that give you plenty of great options for ordering in or dining out. Other local destinations include: - Tanger outlets (1 Mile) - Heartland Golf Park (1.5 Miles) - Edgewood Oak Brush Plains Preserve (0.5 Mile) - Robert Moses state park (12 Miles) - Sunken Meadow state park (12 miles)

East Hampton Village Fringe, Renovated with Pool

This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!

STAY. SOMEWHERE. DIFFERENT. This isn’t just a stay—it’s an experience. Welcome to THE GOOD VIBEZ HOUSE! Your private escape in the heart of Long Island. This smart home is located in a safe, quiet neighborhood, this unique retreat is the perfect getaway from the hustle and bustle of the city or everyday life. From the moment you arrive, it feels like vacation. As Superhosts, we go beyond hosting—with warm hospitality, thoughtful touches, and a five-star atmosphere you won’t forget.

Ultimate House with Heated Pool, Hot Tub and Sauna

Ultimate house with 4 Bds, 3 Baths, finished basement with entertainment area and gym. Minutes from the Hamptons and North Fork. Everything for your rest in any weather and season. Yamaha piano, Japanese massage chair, karaoke, drum set, electric guitars, ping pong, fossball and pool tables,board games. Fully landscaped backyard with flowering plants, outdoor lights. 2 BBQ areas, Gazebo with fireplace and projector. Easy access to beaches, restaurants, farms, vineyards and shopping.

Luxury modern farmhouse with heated pool & hot tub

*pool is now open! This beautiful modern farmhouse is located on a one-acre lot and features a custom designed open-concept living space with vaulted ceilings that opens directly into a pool area. Hidden behind a bookshelf, you'll find a gorgeous game room with a piano and a pool table that can be easily converted into a ping pong table or working space. Please note that we do not allow weddings and events at this time.

Exclusive Sag Harbor Compound

A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

Classic Southampton Village Home w/ Pool

Newly renovated Southampton village home with great light, offering the best of indoor-outdoor living. A beautiful backyard with a pool surrounded by lush privet hedges for privacy. Perfectly situated in the heart of the village, one block from restaurants, shopping, and one mile from the ocean beaches. Perfect with space to spread out, play or work remotely! Ask about special rates for long-term summer rental!