Family-friendly holiday rentals in Portland

Quiet Comfy Victorian Escape

Spend your vacation, work-trip, or weekend getaway in this lovely renovated cozy 2 bedroom unit. Apartment 2 is located on the second floor of a three family house where you have access to all the modern appliances: refrigerator, W/D, microwave and TV in the living room. A brand new queen bed each bedroom, with seat in cozy seating in the living room. Located in the very central Oakdale neighborhood, this unit is steps from Deering Park, Sea Dogs stadium, USM Law School and Portland's Old Port.

PRlVATE SUlTE in the Heart of East End Portland

Private Suite in the Heart of East End Portland. Sunny, elegant, Victorian studio with private entrance, bathroom and mini-kitchen area. This location is walkable to award winning restaurants, excellent cafes, the East End Beach where you can rent kayaks, ferries to the islands and more! A perfect romantic getaway close to anything you want to come to Portland to see and do, yet in the quiet, tree lined neighborhood of Munjoy Hill and the scenic East End. See guidebook included in this listing:)

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Your crew will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, no loud partying after 10 pm. City of Portland License #: STHR-004465-2022

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Sopo Abode

Welcome to your garden oasis. Your home away from home. This elegantly styled garden level apartment in South Portland's crown jewel neighborhood, Sylvan Sites, is spacious, calm, and inviting. Have a sit in your private sauna, and take in the abundant birdsong of the neighborhood from your private back patio while you sip your morning coffee. Just down the road (5 minutes) to downtown Portland, Willard Beach, or Knightville, and 10-15 minutes to Scarborough and Cape Elizabeth beaches.

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!

Private Garden Retreat on Munjoy Hill

This well-appointed, new space is located on first floor of a modern, new home on Munjoy Hill - Portland’s most charming neighborhood. This convenient suite has a separate, private entrance with a private outdoor seating area. The location is perfect for walking - just minutes to excellent restaurants, coffee shops, gourmet market, Eastern Promenade, St. Lawrence Arts Center and Washington Avenue. Portland’s Old Port and bustling harbor is just a 10 - 15 minute walk down the Hill.

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Peaks Island Master Bedroom Suite

Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

Mary J. Eastburn House - Baxter Suite

City of Portland Reg. No. : STHR-002888-2021 Perched on a quiet street corner on Portland's Western Promenade, this historic residence enjoys what Longfellow called the "rarefied air of this little town by the sea," spectacular sunsets, and commanding views of the White Mountains. Built in 1891, the Mary J. Eastburn House now offers 3 private and exclusive guest suites for those who enjoy the grandeur of the past, updated with the luxuries and technology of the present.

West End Private One Bed/Bath

Perfectly located with off-street parking just two blocks away, this spacious first-floor studio offers a quiet, private retreat in a beautiful, owner-occupied Victorian home. Fully self-contained, it’s the ideal place to relax after exploring Portland’s vibrant food, arts, and culture scene. Includes one dedicated parking space. Please note that while the bedroom room is spacious, the bathroom is tiny!

Modern & Sunny East End House. Private Parking!

This modern single-family home is just steps away from Portland's Eastern Promenade with its glorious views of Casco Bay and the islands. Many of the city's best restaurants, cafes, breweries & distilleries are all within a few blocks from the house. Park your car in the private parking spot behind the house and forget about it for a while and enjoy the city!