Holiday houses in Old Orchard Beach

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

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 Pine Grove

Newly rebuilt - the Pine Grove is air conditioned and features a 10 by 14 ft deck, a brand new bathroom with tub, bedroom closets, and a full kitchen. It is one half of two charming rustic cottages set on a single plot on a leafy side-street. This cottage is wedged in a "grove" of tall majestic pine trees that provide an abundant supply of shade and breeze, pine cones, needles and all. It is great for families with children and a short walk (.4 of a mile) through the neighborhood to the beach.

The Boardwalk: Lux Vintage - 5 min Walk to Beach

Come feast your eyes on Grand Old Orchard Beach! For 125 years it’s lured seaside dreamers with 7 miles of soft sand, a bustling boardwalk, bully eats, and the only oceanfront amusement park in the land. Our swell luxury home rests quiet as a Sunday morn—just 5 min walk to the surf, and 15 min walk to the thrills. Shell huntin’, coaster ridin’, lobster rolls, and leisure galore. And only 25 minutes by motorcar—Portland awaits, a proper foodie town of cobblestone, lighthouses, markets, and art.

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!!

King Bed, Views, Sleeps 6, Minutes to Pier

Quiet Top Floor 1 Bedroom, 1 Bath Condo One Block from the Beach, easy walk to everything Old Orchard has to offer! Situated directly behind Palace Playland and abutting Veterans Park this condo provides great privacy and spectacular views of the ocean, pier and amusement park. King size bedroom in spacious bedroom plus Queen murphy bed and pull out couch in living room. Full Size, Fully Equipped Kitchen with dishwasher, electric stove and refrigerator. Washer and Dryer in unit.

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 #4 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.

Tiny house near the beach!

Enjoy a wooded retreat just minutes from Maine's stunning Fortune's Rocks beach. This newly constructed tiny home welcomes you for a memorable stay near the coast. We strive to offer a thoughtful balance between modern amenities and a natural setting. This space is perfect for two guests, with a maximum of four who are comfortable sharing tiny accommodations. We are pet friendly for an additional fee - one dog maximum per reservation.

Luxury Beach Front Condo! Prime Location!

✨ 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 ✨

#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.

Woods Lane Golf and Beach Vacation

Directly across from Dunegrass Golf Course clubhouse, restaurant, and bar. Just built with gorgeous finishes. Open layout for kitchen, living, dining, mini bar. Just 7 minute drive to OOB pier and the beaches. 2 car garage. and driveway that fits 4 cars. Get away from the crazy and loud beach homes and relax in the golf course community. Patio with seating for 8 with gas grill.