Holiday rentals in Head of the Harbor

Large and Beautiful Guest Suite

Large beautiful, bright guest suite in a private home. Separate driveway and private entrance. Cathedral ceiling, open floor plan, queen bed, full sofa bed, kitchenette with mini refrigerator, microwave/convection oven combo, Keurig coffee maker, TV with fire stick, gas fireplace (Nov.1 - April 1). Full bathroom with walk-in shower, towels. Washer/dryer. Beautiful covered back porch. Close to shopping, 2 miles from beach, 1 mile from SUNY Stony Brook, and LIRR. 5 miles from Port Jefferson ferry.

Cozy Apartment with King Bed - Separate Entrance

Enjoy your stay in this private, clean and comfy environment. Space offers a bedroom with a king size bed and a desk for at-home work. Living room includes a smart TV and a sectional. Unleash your inner chef! Access to kitchen utensils, dinnerware, and pots/pans. Free parking on premises. Convenient location with many necessities nearby (mall/gas station/restaurants). We are located 2 mins from I-495 and 15 mins from Macarthur airport. Great for visiting family in Port Jefferson, Patchogue, etc!

Beautiful Huge 1BR with Parking

Top floor cozy 1 bedroom with your private entrance & parking at the back of the house. In the best part of Stony Brook surrounded by nature. 5 min drive to beautiful beaches & 10 min walk to SBU. Super comfy queen size orthopedic mattress, pull out sofa bed, 2 walk in closets, WiFi, 60" smart TV with Netflix, amazing bathroom & kitchen. You are going to love staying here;) Coffee and green tea included. No: pets, smoking, food in bed, candles. No loud parties or checking in after 11pm.

Hotel-Style Studio in Ronkonkoma

Suite 2283 is a hotel-inspired studio apartment in Ronkonkoma. Thoughtfully designed, featuring a private entrance, private fenced-in yard, patio with bistro set, onsite parking, AC, kitchen, Roku TV and free Wi-Fi. This stylish apartment is ideal for traveling medical and business professionals. Just minutes from the airport, hospitals, corporate parks, major roadways, restaurants, parks, the mall, nightlife at the new Station Yards complex at the LIRR hub, and, of course, Lake Ronkonkoma!

Apartment with Separate entrance & parking

"Location, Location, We are located on the very border of Centereach and Lake Grove, 8 minutes away from Stony Brook Hospital & University, 18 minutes away from Port Jefferson Also 2 min away from Smith Haven Mall, 25 Min. to Riverhead Outlets, 12 Min. from LIRR Ronkonkoma Station ( you can catch express train to Manhattan) and so much more, everything is just steps away. We are near nice beaches and wineries. The apartment is located in a quiet residential neighborhood.

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.)

The Rosevale Studio Suite

Located just about 10 minutes from the Long Island Rail Road and Long Island Mac Arthur Airport is The Rosevale Studio Suite which combines modern finishes with a cozy, warm charm. Enjoy a lovely lunch in your private patio where the sun hits so perfectly or have a night out at one of the many surrounding restaurants! With shops, beaches and more all located under 5 miles away, our suite is just perfect for your little get away!

Private charming Studio Cottage in Nesconset

Escape to this cozy studio cottage, perfect for couples or solo travelers. Enjoy a comfortable full-sized bed, a well-equipped kitchenette, and a welcoming seating area. Located in a peaceful neighborhood, you're just minutes from local parks, shops, and eateries. P.S. Cleanliness is my top priority to make every guest happy all towels and sheets are sanitized and washed every guest checks in before they're arrival.

Modern style Spacious Getaway

This apartment offers a living room, dining area, bathroom, and a bedroom. The apartment is very spacious so you will never feel cramped and is stylish giving it a unique, creative vibe. The apartment is attached to the side of a house with the owners living on one side. The apartment is partitioned from the main house making it private. There is potential for noise sometimes. There are no hidden fees.

Cozy Riverside Cottage

This is a private cottage on its own lot with its own driveway and yard located in a quiet residential neighborhood. Several grocery stores and restaurants for delivery/pick up in the area. 400 MBPS Internet connection for those who need a reliable internet connection for work/movie streaming! Please note guest maximum is 4. There are no additional guests or visitors allowed.

Charming “hotel inspired” Retreat

Relax and recharge at this peaceful, centrally located retreat. Your private room features a cozy full-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.

Private New Apartment

Open concept living. Cathedral ceilings. 1 Bedroom, Full Bath. Private parking. Patio. 5 minutes from train, 15 minutes to MacArthur Airport. Close to Stony Brook, South shore ocean beaches, and the north shore of Long Island. Perfect if you are planning on heading out east to the wineries!