Holiday rentals in Old Orchard Beach

Newly Updated 2BR | Hot Tub|Fire Pit|Walk to Beach

Welcome to Surfside — a newly updated coastal retreat in Old Orchard Beach where the beach life follows you home. This bright, beautiful unit is made for people who want more than just a place to sleep. Outside, a brand new round hot tub and a custom stone fire pit set the scene for evenings you won't forget. An outdoor dining setup with a grill, table, and chairs means the fun doesn't have to end when the beach day does. It's the kind of place that feels like a vacation the moment you walk in.

Unique and Stunning Beachfront property Greygoose

Brand new hot tub open all year long Stunning inside out, this spectacular oceanfront property offers bold panoramic views of the Saco Bay! Imagine enjoying the morning sunrise from your private Master Bedroom deck or gathering with family and friends on the oceanfront deck or by the fire pit in the private patio courtyard. Fondly known as the ''GreyGoose'', this lovely home was extensively renovated in 2012 with impeccable attention to maximizing ocean views, and creating spacious living areas.

Peaceful & Updated Ocean Park 3BR Beach Cottage

Private and peaceful, this fully updated 3 BR beach cottage is situated on a quiet, dead-end street. Enjoy the serenity of the marsh while being conveniently located to Ocean Park beach. All the comforts of home -- full kitchen, dining, and living rooms. Air hockey table and spacious outdoor area are ideal for family fun. Comfortable sleeping arrangements for 8, with local Portland mattresses (2 kings and 2 queen beds). Quick 7-8-minute walk to the beach 0.5 miles from Ocean Park town center

The Saltwater Pearl

Come to the beach!!! Originally a seaside cottage, now a fully renovated 2-bedroom, 2-bath year round home! Sleeps 4, master bed has private bath, free WiFi, open concept, and literally 100-steps to the beach!!! Start your days with a peaceful walk on the beach and enjoy everything our cozy home offers! Parking for 2-vehicles, washer/dryer, BBQ grill, outdoor shower. Walk 10-minutes down the beach to the Pier and OOB main strip. Start planning your vacation now at the Saltwater Pearl!!

Charming Cottage in OOB

Welcome to your perfect Maine escape—just a short walk to the beach. This fully renovated cottage blends modern comfort with timeless sea captain charm. Step inside and enjoy a spacious living room, a fully-equipped kitchen, and three inviting bedrooms (two queens and two twins). Whether you're sipping coffee on the large porch or gathering in the backyard, this space was designed for relaxation. Come experience Maine the way it was meant to be—breezy, beautiful, and filled with charm.

Adorable Beach bungalow w/ arcade room & parking!

Enjoy this renovated bungalow in the heart of Old Orchard Beach! It's conveniently located half a mile from the beach, walkable to the pier, restaurants & shops. Only 20 min. to Kennebunk and 25 min to Portland. The cottage comfortably sleeps 7 people and has many amenities including a/c, free wi-fi, smart tvs, fully stocked kitchen, washer & dryer, 2 off street parking spots, fenced in backyard with patio, grill and arcade room with cocktail arcade machine, skee ball & foosball table.

Luxury Beach Front Condo! Prime Location!

last minute cancellation June 29th! special rate ✨ Encourage reserving multiple nights to bring down the cost per night ✨ Minimum stay varies, typically 2 to 3 nights ✨ If you see a longer minimun, it’s likely to prevent the reservation from leaving a single night open. Just select different start date. ✨ Much appreciated if guests book trips connected to other guest trips ✨ Unless the trip is within the next few weeks, please don't book a trip that leaves a single night open ✨

Romantic Mirror cabin in the woods

Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

160 East by the sea #5 Steps to the beach

You must be 21 years of age Steps to 7 miles of sandy beach. Walking distance from shops, restaurants, public transportation and more. 20 mInute Drive to Portland. One room unit with Kitchen, Bath, King bed and a Queen Sofa Bed. (360 sq. ft.) Accommodates family of 4 2 adults and 2 Children or 3 Adults max Parking for 1 vehicle. Yard with Picnic Tables and umbrellas (seasonal) Gas Grill No Smoking property No Pets Allowed.

#4 Vintage Cottage walk to the beach and Pier!

3 night Min. stay 6/1 to Labor Day. Cottage 4 is a 2 bedroom classic cottage with soothing beach colors and well appointed with comfortable furnishings. It is our only cottage with a claw foot bath tub. The cottage has a fully stocked kitchen with pots and pans. The cottage also has a private deck with a gas grill. A short walk, and you are at the 7 mile stretch of sandy beach and pier. Yes we allow pets.

Serenity

Relax with the whole family at this peaceful place to stay. Stroll to the beach or soak in the hot tub. You'll find everything you need here for a trip to the beach; chairs, umbrella, toys, boogie boards and a cart to haul it all in. In the evening you can sit on the porch, around the fire pit or in the hot tub. Lots of restaurants a short walk away. The beach is a short 6-7 minute walk!

HotTub+Firepit/5 min to DockSquare, Dining, Beach

Follow us on IG @anchorunwind. Escape to a hidden gem nestled in the heart of the Kennebunkport area, where modern comfort meets nature's serenity. Our cabin offers an unforgettable vacation experience. ✭"...A must stay location. The host’s were very helpful and genuine..." ✭"...We’ve travelled all around the world and this is in our top 3 Airbnbs we’ve stayed in."