Kid-friendly vacation rentals in Portland

Guesthouse in Portland

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.

May 27 – Jun 3

Apartment in Portland

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

Guest suite in Portland

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

Oct 13 – 20

Apartment in Portland

Quiet Retreat in the Heart of Portland's West End

Our charming, historic home is perfectly located in Portland's West End, just steps away from Downtown, the Old Port, and all of the city's best restaurants and bars, shops, museums, and activities. The central location of this first floor apartment makes it the perfect home base for your time in Portland. We provide a guest manual in the apartment with all of our favorite places to eat and local things to do, so you can get the most out of your time in Portland.

Nov 3 – 10

Apartment in Portland

Adorable getaway on the Eastern Promenade

Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.

Nov 7 – 14

Guest suite in South Portland

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.

Dec 6 – 13

Guest suite in Freeport

Weather's Edge, Freeport

Come enjoy the historic charm of South Freeport. This antique home and cozy accommodation await you, featuring a private entrance, private room, private full bath, t.v. with cable, and wi-fi. This is a second-floor room, accessed from a dramatic original (steep) staircase, and is conveniently located in an area of lovely homes, with Freeport Village just five minutes away.

May 18 – 25

Home in Lisbon

Unplug at a Beachy Bolthole with Classic New England Style

Chill on the porch after exploring a scenic local walking trail and soak up the serenity of this breezy blue and white hideaway. Striped oars, starfish, smooth shells, and ocean scenes blend with shades of teal and aqua for a thoroughly calm space. There are EV chargers behind the post office. It’s around a block and a half.

Feb 7 – 14

Loft in South Portland

Serene studio apartment, close to everything.

Welcome to South Portland! Your spacious studio apartment with private entrance is a short walk to Fore River Brewing, Lincoln & Main/Electric Bike Cafe & Winery and the Greenbelt Walkway. A 10-min Uber ride will take you to the Old Port and South Portland staples like Willard Beach and Scratch bakery.