Holiday rentals with outdoor seating in Lake Montauk

Montauk Private Beach Bungalow

Beautiful secluded cottage tucked away at the end of cul-de-sac and surrounded by a nature preserve. Montauk’s finest waterfront dining and bars are less than a mile. The house has a large living room with a fireplace, king bed in one and a full bed with a twin bunk in the other, a full bath, and an eat-in kitchen with dining for 6. There is a large very private patio with a grill, dining table and lounge area. The private beach is stunning and a 3 minute walk from the house. Pets are welcome.

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Montauk Cottage Escape

EH Town Rental Registry: 23-483 Escape to Montauk’s Quiet Side- Enjoy the peaceful beauty of Montauk in the off-season from this updated, spacious, comfortable home - close to town, beaches, and scenic trails. Between cozy nights in and crisp coastal walks, this is the perfect retreat for a weekend getaway or a work-from-home reset. Reliable Wi-Fi and a fully equipped kitchen make it easy to settle in for a few days—or weeks. Dogs are welcome with prior approval (Additional pet fee applies.)

Montauk Waterfront Condo w/ Sunset Views

Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool / sauna / jacuzzi only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

Twin Pond Ocean View Studio 3

Semi-private path to one of the best beaches in Montauk. Imagine not having to deal with Ditch parking but beach passes included! Twin Pond is a compound on 2.5 acres on Old Montauk Highway. Studio is one of 7 units—galley kitchen (no cooktop) with 180 degree views (1) Qn Size Bed. Walk to Town & restaurants. Modern chic with flat screen TV and WiFi. Ideal for couples/single. Outdoor furniture and a gas grill. Dog fee is $250 per dog. Only small to medium size dogs. No cats or other animals.

5 Star Rated Private Cottage Southampton/Sag Hrbr

The Honeycomb Cottage is a little retreat located on a lush acre of evergreens in Southampton rated 5 Star by every guest that has stayed. One block to Peconic Bay Beach - perfect for a day in the sun. A cozy space with TV, WiFi and Sun Deck. Luxury soaps provided, amazing shower and crisp white linens. Exclusive use of the Hot Tub for Cottage guests. Easy parking and located 15 minutes drive to Sag Harbor or Southampton Village. Koi pond with waterfall will sooth the mind and spirit.

Montauk Beach Bungalow East Apt.

Charming, clean, private, quiet, 2 bed 1 bath ocean view apartment across from ocean beach via through dunes path. Check the surf from the living room window. Dine in or out with the moon rising over the ocean. Includes BBQ and fire pit, outside table. Private entrance, lawn, outdoor shower, storage space for bikes, etc. Perfect vacation rental. Full kitchen with stove oven, fridge, sink, coffee maker, toaster, microwave, pots pans dishes etc - monthly discounts. Small bathrm & shower

Modern Montauk retreat with wood stove by Harbor

Scandinavia meets Montauk in this sophisticated, comfy, all-season getaway with open-plan interior & large, private fenced yard. • 950 sq ft, 2 BRs (compact but comfy), 1 Ba, full high-end kitchen, W/D, A/C • Wood stove, Solo stove, patio, outdoor shower, high-end linens & furnishings/decor • Steps to LI Sound & Harbor. 3 mi to ocean/Town • Owner is in a private studio w/ own entrance in the house. No shared spaces! • Ask about dogs & flexible rental periods CLICK MORE for IMPORTANT INFO!

3 BR/Pool. Walk to Beach & Town!

Welcome to Good Tauk – a cheerful, retro-inspired 3BR, 2BA cottage tucked in the heart of Montauk and walkable to town and the beach. Thoughtfully renovated and full of personality, it’s perfect for families or longer stays. The vibe is fun, relaxed, and unmistakably Montauk. Outside, unwind in your private backyard with a pool, grill, and dining patio—ideal for lazy afternoons and sunset dinners. Just minutes from the beach, town, and everything that makes Montauk magical.

Coastline View Studio

This sun drenched studio apartment is perfect for families, couples or friends looking to get away and discover Montauk! Located in Montauk's harbor district. This unit is perfectly located to experience all that Montauk has to offer... Sit back on the balcony and enjoy a glass of wine as the sun sets perfectly over Culloden Point. A short walk to the Harbor, the Dock, Gosmans, TTs, Salivars, Sunday Funday, La Fin, Viking Fleet (fishing, Whale watching & Ferry).

Ocean Shire Coastal Cottage + Beach Pass

Welcome to this modern spotless beach cottage, 5 mins from amazing Watch Hill and Misquamicut beaches. Beach pass included. Kids most welcome. 🏖️ Watch Hill/Beaches: 5 mins ⚓ Historic Mystic: 18 mins 🏰 Newport: 50 mins ✈️ Block Island flight : 5 mins Cottage on 1.4 acres total privacy surrounded by trees with lavish gardens to enjoy morning coffee. Easy access to downtown, stores, restaurants, and wineries. Water sports and beach life at your doorstep.

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.