Family-friendly holiday rentals in Drakes Island Beach

Birch Sea

This new, very private apartment attached to our home is in a quiet and picturesque environment minutes away from Dock Square. It's great for couples, solo adventurers and families with one child. If you are seeking to spend the day at one of the beautiful Kennebunk beaches they are just minutes away. We are committed to environmental sustainability and the apartment is powered by solar energy. A new outdoor hot tub was recently installed in February, 2024! We look forward to your visit!

Family · Indoor spaces · Checkout

Luxurious 5 bedroom on the ocean, w/ dock & kayaks

Historic 1735 home on a spacious one-acre property overlooking the ocean. Enjoy swimming from the dock in Cape Porpoise’s protected cove. Two kayaks provided for exploring the lighthouse & picnicking on nearby islands. Stroll past picturesque lobster boats to the town pier, where restaurants serve fresh local lobster & drinks. Walk to morning coffee, pastries, a local grocery store, athe renowned Nunan’s Lobster Hut. Just two miles from Kennebunkport and a nine-minute drive to Goose Rocks Beach.

Family · Indoor spaces · Hospitality

Secluded Coastal Home & Cottage 3 Minutes to Beach

Escape to Thistle Pond Cottage, a peaceful coastal retreat in southern Maine. Nestled on 2 acres with pond views, lush gardens, and local wildlife, it’s minutes from beaches and Portland. Every stay begins with homemade bread from our kitchen and thoughtful, locally sourced welcome accompaniments. Weather and seasonal permitting, guests may occasionally savor a host-prepared wood-fired pizza made with fresh garden ingredients. Cozy, bright, and full of garden-to-table charm and seasonal delight.

Indoor spaces · Family · Beach

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

Welcome to your Ogunquit Oasis, a luxurious 5-bedroom beach house located on the edge of Ogunquit Village. Walk to the beach, restaurants, Perkins Cove, Marginal Way & everything in Ogunquit! The house features a heated pool that reaches 104 degrees, ideal for all seasons. Built in 2014, the house includes central air, three Ultra HD TVs, and wireless speakers. The dining table seats 10, with an outdoor living room, grill, & gas firepit. Each spacious bedroom offers plush bedding & ceiling fans.

Indoor spaces · Kitchen · Backyard

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.

Kitchen · Family · Location

Immaculate Moody Beach House

Steps from private Moody Beach, this stunning 3-level coastal home sleeps 12 and offers ocean views on one side and marsh views on the other. Enjoy 5 bedrooms, 10 private decks, a giant party deck overlooking Rachel Carson Wildlife Refuge, billiard room, fireplaces for cozy nights in, and a huge open living space with gourmet kitchen and wraparound sofa. Private parking for 6 cars. Perfect year-round getaway close to Ogunquit, York Wild Kingdom, Kittery shopping outlets, and Kennebunkport.

Indoor spaces · Family · Walkability

Family Beach House, Wells Beach, Maine

Family Beach House on the Harbor/River of Wells Beach. House Sleeps 8 adults, plus 3 - 4 children. Full kitchen, 4 bedrooms plus Sleeping Loft, 3 baths, Dining Room, large deck, patio, laundry, outdoor shower, fire pit. Private access back beach. Bring your kayaks, paddle boards, surf boards, or boat. Water behind house at High Tide. Approx. 100 yard walk across Atlantic Ave to beach. Parking for 5 cars Max. Optional in-law apartment available, sleeps 5, for $115 per night/$800 per week

Kitchen · Indoor spaces · Sleep quality

Cozy Cottage with Ocean Views, Wells Maine

Ocean breezes, panoramic views of the Atlantic, comfortable cottage to relax & enjoy your time in Maine, what more could you ask for on a getaway?! This cozy cottage for 6 boasts near panoramic views of the Rachel Carlson preserve and the Atlantic Ocean. Tastefully decorated and newly updated, our cottage offers AC/heat, ceiling fans, fully equipped kitchen with dishwasher, outdoor gas grill, cable TV in all rooms, WiFi, cabled phone, skylights, in unit W/D & a large screened in porch.

Indoor spaces · Family · Bathroom

Classic, calm river view & centrally located home

We are happy to share with you our coastal, colonial home set on eight acres along the Kennebunk River. Enjoy our quaint, warm home just 5 min to the beach and 3 minutes to Cape Arundel Golf Club. Our 4 bdrm, 2.5 bathroom suits short or long term stays. The location is ideal: 6 min from Kennebunkport, 15 min from Biddeford, and 30 min from Portland or Portsmouth! We hope to make you feel at home with the morning birds chirping and the calmness of the river just in back of the property.

Kitchen · Indoor spaces · Condition

The Copper Fox Treehouse

Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse

Indoor spaces · Kitchen · Skiing

★"Life~at~Sea"★I mi to beach★W/D★Park★2 full baths

• Open floor plan/first floor bedroom+full bath • Fully stocked kitchen with coffee & tea bar • Peaceful neighborhood close to Dock Square & less than 1 mile to KBK Beaches • Shaded back+side yard/patio/grill/outdoor shower • Netflix+Sling+Hulu+HBO+Amazon Video+4 TVs • 1 car garage parking+driveway parking for 2-3 cars • washer+dryer+towels+bed linens provided • board games, pack N plays x 2 • 2 KBK beach passes+boogie boards+beach towels+chairs

Family · Indoor spaces · Outdoor spaces

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.

Indoor spaces · Walkability · Check-in