Family-friendly holiday rentals in Old Orchard Beach

Luxury Year-round Treehouse with private hot tub

Cliff House 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.

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.

Spacious 2 bedroom cabin, 50ft from the beach no.8

This spacious, charming cottage features two bedrooms. One bedroom has a queen bed and one has two bunk beds, for a total of 6 people maximum. The open kitchen, dining, living room area has cathedral ceilings. The bathroom offers his & her sinks, shower and whirlpool tub. Relax with the whole family at this peaceful place to stay. Fully equipped efficiency kitchenettes, with dishes, utensils, paper towels, and coffee provided Individually controlled heat & air conditioning All linens provided

Oceanfront w/ Stunning views and Private Deck☀️🏖

Welcome to the Beach House on the Rocks, your very own oceanfront retreat! This beautiful, 1350 sq ft house is nestled right next to the ocean. With panoramic views and the ocean just steps away, you won’t forget this one of a kind experience. Tucked away in the hidden gem of Camp Ellis, you’ll enjoy a lively beach scene in the summer and a tranquil retreat in the off season. Just a short trip away to Old Orchard Beach and 30 min to Portland you’ll never be in need of fun activities.

Beachside Penthouse Paradise on Old Orchard Beach

The views of Old Orchard Beach and beyond are spectacular from the private deck. And the beach is a just few steps from your door. This five room- 2 bedroom unit has everything you need. A short, easy walk to the Pier, Palace Playland and all the hubbub, yet just far enough away to enjoy the peace and quiet on beautiful, seaside Camp Comfort Ave. Head in the other direction for a short walk to Ocean Park. NOTE - Minimum age to rent is 25. Maximum number of guests is 4. Stairs are steep.

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

OOB Oasis: 5BR Home w/ Private Pool Near Beach

Welcome to our stunning home and your private oasis in Old Orchard Beach! Just 5 minutes from the ocean, this expansive custom-built home offers 3 suites (each with its own private bath), a gourmet kitchen with high-end appliances, a sprawling open floor plan, and ample parking for large groups. Step outside to enjoy a large fenced backyard, spacious deck with BBQ grill, and sparkling in-ground pool—perfect for summer fun, fall gatherings, or simply relaxing after a day at the beach.

Walk to Beach from Spacious 1920 Home

Welcome to our newly renovated beach home just a 2 minute walk to the pier! Enjoy our large (~3000sqft), open-concept 4 bed, 3 bath, with 2 spacious kitchens, 2x washer/dryer rooms, 2x dishwasher, & off street parking. Each bedroom has memory foam queen mattress, 2 couches with full size memory foam pull out and 1 with queen pull out, this place comfortably sleeps 12. Includes access to Netflix, Hulu, Disney plus & high-speed internet although we recommend relaxing on the beach.

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Luxury Beach Front Condo! Prime Location!

Special Rate April 26-28! ✨ Encourage reserving multiple nights to bring down the cost per night ✨ Minimum stay varies, typically 2 to 3 nights ✨ 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 ✨ If you see a 14 day minimum, it’s only to prevent the reservation from leaving a single night open. Just select different start date. ✨

#7 Summit Family Cottage

3 night Min. stay 6/1 to Labor Day. The Perfect 2 Bedroom Family Beach Cottage. Just a short walk to the pier and 7 miles of sandy beach, shopping and more. This cottage features a queen master bedroom and bunk beds in the second bedroom. Full size washer dryer and full size bathroom with tub and shower. Take advantage of the essentials stocked kitchen or grill outside on your private, fenced in patio. Heat and AC are included. Pets are welcome.

Old Orchard Beach Guest Suite

OOB Guest Suite is a remodeled space just 1 block from the downtown area. Walk to restaurants, shops, beach, arcade and amusement park. Free parking. Free wifi/Smart TV. Outdoor space with small deck with bistro table/chairs, new patio with picnic table and grill. Enjoy all that Old Orchard Beach has to offer! Summer reservations from June 29, 2024 through August 24, 2024, are required to be 7 nights, beginning and ending on Saturday.