Family-friendly holiday rentals in Peaks Island

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Top-rated family-friendly rentals in Peaks Island

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Guest house in Portland

4.95 out of 5 average rating, 300 reviews

Beautiful large studio on the ocean.

Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests to share our beautiful property so if you'd like to book please introduce yourselves and let us know about who is coming and some hopes for your trip. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.

Guest favourite

Home in Portland

4.86 out of 5 average rating, 165 reviews

Booking Now: Year-Round Peaceful Island Getaway

*Quiet and Peaceful *Easy Portland Access *Sparkling Bathroom Remote Downeast island experience just two hours from Boston ... Renovated home in the tranquil Tolman Heights section of Peaks (the island’s highest point) offers a modern kitchen and sparkling new bathroom. Sleeps 6-plus comfortably in bedrooms all equipped with ceiling fans. Spacious home is a short stroll to the Back Shore, with its dramatic views of Casco Bay and the open ocean. Great biking, hiking, swimming, and kayaking.

Guest favourite

Home in Portland

4.97 out of 5 average rating, 208 reviews

Stunning & Spacious 6BR Waterfront House + Hot Tub

A charming craftsman-style home with beautiful water views, comfort, and character! This house features six bedrooms, three bathrooms, ample common spaces, and a fully outfitted kitchen. Hardwood floors and original trim add warmth and charm to the space, and modern updates ensure a comfortable stay. Just minutes from Portland's Old Port, the house commands sweeping water views of Casco Bay and the Presumpscot River. Guests will enjoy the hot tub, private patio, yard and plenty of parking.

Guest favourite

Rental unit in Portland

4.96 out of 5 average rating, 244 reviews

"Percival" Penthouse Suite - Amazing Harbor Views

2023 City of Portland Registration #20182242-ST Private Old Port Penthouse w/Breathtaking Views + Your Own Cupola. Quiet + Secure. Gorgeous contemporary suite full of light located right across from the working waterfront. Lobster and seafood off the boat is 100 meters from your front door. Watch the ferries to the islands from the cupola. Smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.

Guest favourite

Treehouse in Georgetown

4.94 out of 5 average rating, 321 reviews

Tree Dwelling w/ Water Views & Cedar Hot Tub (I)

Experience the airiness of life up among the pines. This unique tree dwelling, with its own private attached wood-fired cedar hot tub, is perched atop a 21-acre wooded hillside sloping to beautiful water views. Enjoy the view from the wood-fired cedar hot-tub or the king size bed--through a wall of windows. This treehouse is cozy all year round, especially in winter. Located in a classic coastal Maine village with Reid State Park's beaches and the famed Five Islands Lobster Co.

Guest favourite

Guest suite in Portland

4.9 out of 5 average rating, 375 reviews

Garden Suite @ A Peaceful Oasis on Munjoy Hill

Spacious light-filled garden level suite set in an ideal location, close to the Eastern Prom, cafes, award-winning restaurants & the Old Port. Tasteful art, a mini kitchen (fridge, microwave, toaster, coffee maker, electric kettle with coffee/tea and condiments), bath with essentials, contemporary furnishings: queen bed and bedding, leather reclining loveseat. Set in a lush garden of stone walls, pond, & perennials, this private setting is a perfect home base.

Guest favourite

Cottage in Portland

4.89 out of 5 average rating, 534 reviews

Cozy & Quiet Modern Cottage

Modern studio cottage designed and maintained with sustainability and eco-friendliness in mind, located in a quiet Portland neighborhood only a 7-10 minute drive (and $10 Uber/Lyft ride) from downtown Portland, the Old Port, and all local visitor attractions. The cottage is a mile down the road from the Allagash Brewing complex and is within walking distance (.5 mi) of the restaurants and bars at Morrill's Corner. This is an LBGTQIA- and BIPOC-friendly space.

Guest favourite

Rental unit in Portland

4.9 out of 5 average rating, 384 reviews

Hip & Cozy, high end Modern Design

Hip, modern retreat. This is your pied a terre for your Portland visit. High quality new construction, private, sweet unit, with wide-plank white oak and concrete floors, huge windows, full kitchen, tasteful design. In Portland's coveted Munjoy Hill neighborhood, you will be a block and half from the spectacular eastern Promenade, 5 minute walk to shops and restaurants at the top of 'the Hill', and 20 minute walk to the Old Port and all Portland has to offer.

Guest favourite

Rental unit in Portland

4.79 out of 5 average rating, 346 reviews

Studio w/ Patio, Sauna & Onsite Massage

Cozy daylight basement studio in the center of Rosemont. Relax with your own private patio, sauna, on-site massage & facial. Just minutes to Portland's extensive trail system. Delicious restaurants and markets within a short walk and just 2.5 miles from the historical Old Port and artsy downtown! Perfect for business and leisure! Conveniently located just 10 minutes from the Portland Jetport and less than five minutes from I-295 and I-95. STHR-000170-2018

Guest favourite

Home in Portland

4.98 out of 5 average rating, 343 reviews

3 bedroom house in the heart of Portland

New urban 2000 sq ft home in Portland's vibrant up and coming East End/ Munjoy Hill neighborhood. Mid-century style decor. Open concept kitchen/dining/ living area, 3 spacious bedrooms plus a quiet office/study. 2 balconies with views west to Back Cove. 2 car garage and plenty of free off street parking. There are restaurants and bars with great food and live music close by. There is a convenience store around the corner for any last minute needs.

Guest favourite

Rental unit in Portland

4.93 out of 5 average rating, 536 reviews

Glorious Getaway on the Eastern Promenade

This first-floor apartment is just steps from beautiful Casco Bay! On a quiet residential street, there is plenty of on-street parking available. There are several wonderful restaurants and cafes right in the neighborhood within walking distance, along with many local breweries, distilleries, and shopping spots. The historical Old Port and Downtown Portland are a fifteen-minute walk or a quick Uber, so park your car and forget about it for a while!

Guest favourite

Guest suite in South Portland

4.92 out of 5 average rating, 244 reviews

Top of the Hill So Po In Law

Lovely In law apartment in desirable Meeting House Hill area of South Portland .We were recently the hottest real estate market in the country .Conveniently located , 10 minutes to Portland , and on the doorstep of local beaches, State parks , restaurants ,unique boutique shops ,amazing bakeries and coffee , lunch and antiquing .All you need for a home away from home . Your going to love this neighborhood !