Family-friendly holiday rentals in Long Island

Amazing Views! Perfect Location. Loft style feel.

Oh the VIEW! City views and a beautiful park like old cemetery. Cozy, sunny private apartment in a quiet, Owner Occupied building. Perfect East End location for exploring all of Portland Just 2 blocks from Duckfat, Eventide and many restaurants, breweries and distilleries Comfy living room with a 55" TV and seating to take in the view. Fully equipped eat in kitchen, tile shower and a wonderful King size bed to watch the sun rise Includes Reserved Off street parking. License #STHR-000980

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking: fridge, stovetop, sink, water, firepit & firewood. Outdoor shower. WiFi . Heater for cool spring nights. Ferry options on Casco Bay Lines or CTC Ferry. Host provides transport to/from ferry to the yurt.

Cozy & Convenient Cumberland Guest Cottage

Make yourself at home in this quaint, private guest cottage, perfectly nestled halfway between Portland and Freeport. This detached guest cottage makes a perfect overnight spot as you make your way up the coast, or a home base as you explore Portland, Freeport and the whole breathtaking Casco Bay area. With a kitchenette, bedroom and living area, the cottage is ideal for solo travelers, couples, or a pair of friends looking for a comfortable home base while they explore southern Maine.

Apartment Walking Distance to Willard Beach

Our South Portland in-law suite is on a private floor & has its own private entrance at the back of the house. It is a 1 bedroom, 1 bathroom space with a fully stocked kitchenette and free parking. You'll love being only a 5 minute walk from Willard Beach and walking distance to 2 different lighthouses: Spring Point and Bug Light. You'll also be a 10 minute drive to Old Port. You'll have access to a shared, fenced-in backyard. South Portland Short Term Rental License #: STR2020-0022.

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.

Walk-able Portland Studio

NEWLY RENOVATED! Cozy studio apartment in a historic building, located in Portland's East End Neighborhood. This location can't be beat! The Space features original hardwood floors, and large windows, subway tiled shower and thoughtful decor. Portland Food Co-Op is directly next door, as is the Walgreen's. Walking distance to Eventide, Honey Paw, Duck Fat, Hugos, Little Woodfords, LB Kitchen, Washington Ave Breweries and Distilleries and Old Port shopping district.

Portland Back Cove Hideaway-1 BR- With Patio

Our quiet residential Back Cove neighborhood is your perfect retreat from a busy day exploring Portland. Take a short drive to the center of the city, or enjoy the waterfront walking and biking trail which loops around the cove. Dine at Tipo or Woodford F&B, two neighborhood favorites. Come home to this newly renovated space and relax on the patio! Our space can accommodate four guests. Great for a family, or close friends! We look forward to hosting you!

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer, and cozy couch for lounging.

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

Downtown Historical Victorian 2 BR APT

The West End is one of Portland's most historical districts. The house is within walking distance of Long Fellow Square, and the Western Promenade. It is a great home base while exploring. From its rich history rooted in the Victorian era, to its parks and restaurants, Portland's West End is consistently ranked as a favorite local hotspot. New reno located on a popular street in a neighborhood filled with historic homes.

Oceanside Modern Victorian 2BR- East End/ Downtown

Classic New England style home, recently renovated and updated with modern amenities. A stone's throw from Portland's best public park, The Eastern Promenade. The Promenade boasts beautiful ocean views, a public beach, basketball & tennis courts & large playground. The neighborhood offers great restaurants and coffee shops. The Old Port and the rest of Downtown Portland is a 10 minute walk or 4 minute Uber ride away.