Family-friendly vacation rentals in South Portland

A spacious studio layout is visible, featuring a comfortable sectional sofa adorned with a mix of neutral and dark cushions. A large bed is situated in the background, accompanied by a soft area rug and warm wooden flooring, creating a relaxed atmosphere. Natural light enters through multiple windows.

4.98 out of 5 average rating, 162 reviews

Cozy South Portland studio with King bed! REG107

Welcome to our studio! Stocked with all you need! Short walk away from the green belt trail & ocean views. Just 5 minutes away from Fort Williams home to the most photographed light house in America. We are a walk away from bug light,and spring point and if you feel like a beach day Willard beach is 5 minutes away. Don't forget to stop at scratch bakery or the cookie jar for a coffee and treat. Portland's Old Port is just a 10 minute uber ride . FYI ,entrance is in back up a flight of stairs .

Indoor spacesKitchenParking

4.96 out of 5 average rating, 179 reviews

A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.

Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

You 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, quiet hours after 10 pm. No parties. City of Portland License #: STHR-004465-2022

Indoor spacesFamilyOutdoor spaces

The bedroom features a spacious bed dressed in light-colored linens, accompanied by a cozy seating area with a neutral-toned sofa. Two framed artworks are displayed on the wall, and a lamp provides soft illumination, creating a peaceful and restful environment.

4.98 out of 5 average rating, 156 reviews

Cozy SoPo Condo

Welcome to this cozy one-bedroom apartment in Ferry Village, South Portland, Maine. This charming neighborhood is located just across the Casco Bay from Portland, and it's the perfect place to relax and admire the natural beauty of Maine. Enjoy a tour of our gardens and relax on the string light lit patio. The apartment is located on a quiet street, less than a mile walk from Willard Beach. Take a walk on the Greenway to Bug Light park or towards Knightville for some food and drink options.

FamilyIndoor spacesCheck-in

Guest suite in South Portland

A serene beach scene is captured, featuring a gentle shoreline with soft sand. Small boats are anchored in the calm water, while a lush green landscape forms the backdrop under a partly cloudy sky. Sunlight reflects off the waves, creating a sparkling effect.

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.

KitchenFamilyWalkability

4.92 out of 5 average rating, 442 reviews

4.96 out of 5 average rating, 234 reviews

A cozy living area features a brown leather sofa and two woven armchairs flanking a wooden coffee table. Light flows in through two large windows with sheer curtains, creating a bright, inviting space. A decorative rug adds warmth to the floor.

Condo in South Portland

Rustic Willard Beach condo ten mins from Old Port!

Second-fl unit in historic 150-yr-old building one block from South Portland's premiere beach! Minutes away from historic Portland Head Light and Downtown Portland. Quaint, spacious and tucked away in charming Willard Square. Brand new kitchen and bathroom! Perfect for families, friends, or couples looking for a relaxing coastal retreat. World-famous Scratch Baking across the street, and the Old Port's incomparable restaurants, shopping and historic architecture across the Bay!

KitchenIndoor spacesCheck-in

A bright living area features a yellow loveseat, a gray circular chair, and a glass coffee table on a woven rug. A vibrant accent wall with colorful patterns adds a lively touch. A potted plant and a lamp complete the cozy ambiance.

4.94 out of 5 average rating, 182 reviews

Sunny Spot with Private Parking

This cozy, 1 bedroom apartment is located in the peaceful neighborhood of Knightville. The Portland Peninsula, which includes the historic Old Port and the downtown arts district, is less than a 10-minute drive across the bridge. The perfect spot for a couple or a fun friend getaway! Several excellent dining spots, coffee shops, and markets are all within walking distance from the house. Bike rentals are 2 blocks away! The local beach is a 5-minute drive /10-minute bike ride.

FamilyKitchenParking

A cozy sleeping area features a spacious bed dressed in a navy quilt, complemented by decorative pillows. The green walls are accented by a wooden wall art piece and hanging light fixtures. Nightstands with potted plants add a touch of greenery to the scene.

4.98 out of 5 average rating, 196 reviews

The Knightcap

Welcome to The Knightcap! Located in the wonderful area of Knightville, just across the bridge from Portland, Maine. In our neighborhood, you will find restaurants, a brewery, diner, grocery stores, and many shops. All within quick walking distances. Portland is a renowned foodie destination. We have everything here. Enjoy our beautiful working waterfront, great restaurants, shops, and the fantastic history and architecture. Or maybe have a relaxing night before a big hike.

FamilyIndoor spacesQuiet

The kitchen and living area feature warm wooden floors and reclaimed beams. A central island offers seating at two bar stools, while a round dining table with four chairs provides additional space. Large windows allow ample sunlight, highlighting the colorful decor and brick wall.

4.91 out of 5 average rating, 236 reviews

Sunny and beautiful brick house apartment

This beautiful and cozy apartment was renovated by our own hands, with energy efficiency and craft in mind. The space is an opened kitchen/living room with 2 bedrooms. Reclaimed beams and old wood mix with fun colors and gorgeous full sunlight. A lush organic garden surrounds the house with backyard chickens. Set on a quiet street, walking distance to Willard Beach & Scratch bakery, 5 minutes to Portland Headlight and 10 minutes to Portland's Old Port.

KitchenIndoor spacesGetting around

A bright bedroom features a queen bed with an ornate wooden headboard, flanked by two stylish wall lamps. Sliding glass doors provide access to the outdoors, while clerestory windows invite natural light. A cozy rug complements the wooden flooring, enhancing the spacious feel.

4.92 out of 5 average rating, 233 reviews

Sopo Abode

This elegantly styled garden level apartment in South Portland's crown jewel neighborhood, Sylvan Sites, is beautifully finished, spacious, 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.

FamilyIndoor spacesCheckout

Guest suite in South Portland

An elevated queen bed is showcased with a white comforter and a decorative pillow. Natural light filters through a large window above, accompanied by small potted plants. A wooden staircase leads to a different area, enhancing the studio's overall spacious feel.

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.

KitchenFamilyLaundry

4.99 out of 5 average rating, 333 reviews

A spacious bedroom features a large bed dressed in navy bedding. Natural light enters through two windows, illuminating the soft wood floors. A simple piece of wall art adds a subtle touch, while a modern chair is positioned nearby.

4.96 out of 5 average rating, 115 reviews

Peaceful Beach Getaway

Located steps away from the beautiful Willard Beach, this modern dwelling insures a peaceful getaway. Take a walk up the street for freshly baked bagels and mouth watering pastries, or down the Greenbelt Walkway for a lovely lighthouse excursion. Drive 10 minutes into Portland for a night-out on the town, and return to your newly-renovated one-bedroom suite for a restful night on a glorious king bed.

Indoor spacesKitchenHospitality

The image features a cozy hanging chair surrounded by decorative stones, set beneath a leafy structure. A beach scene is visible in the background, showcasing a sandy shoreline with umbrellas and the ocean. A simple living area is also highlighted with a neutral sofa, coffee table, and a shelf adorned with flowers.

4.91 out of 5 average rating, 281 reviews

Willard Beach–Apartment Near Portland & Parks

Many guests have remarked that this stylish, first floor apartment is much larger than it appears in the photos. Just a 4 minute walk to the beach and a ten minute drive to downtown Portland it’s the perfect home base for exploring everything the area has to offer! Jess is a fifth generation Mainer and is happy to answer any questions you may have as you plan your trip!

FamilyKitchenLocation

Popular amenities for South Portland family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Old Orchard Beach

The exterior of a modern oceanfront home is captured, showcasing a two-story structure with light gray siding and a charming front entrance. Lush landscaping and a paved driveway enhance the appeal. Panoramic views of the beach and ocean are visible in the background.

Unique and Stunning Beachfront property Greygoose

KitchenIndoor spacesOutdoor spaces

4.92 out of 5 average rating, 189 reviews

4.93 out of 5 average rating, 147 reviews

The outdoor area features a circular pool surrounded by reclining lounge chairs with blue and white stripes. A stone patio is adorned with a wooden table and chairs, while lush greenery and flowering shrubs frame the scene under a clear blue sky.

Guest suite in Portland

Resort-like 2 bed/1 bath - seasonal pool/hot tub

Indoor spacesFamilyAmenities

4.98 out of 5 average rating, 525 reviews

Apartment in Portland

Apt in Victorian Mansion w/ Hot Tub & Parking

FamilyIndoor spacesShared spaces

4.98 out of 5 average rating, 176 reviews

Home in Saco

Oceanfront Escape • Walk to Beach • Sleeps 14

Indoor spacesKitchenAccuracy

4.92 out of 5 average rating, 132 reviews

A hobbit house is nestled among lush green trees, with a sloping earth-covered roof adorned with grass and ferns. The rounded front features a large window framed in white, complemented by a natural stone border, emphasizing the home's connection with its woodland surroundings.

Earthen home in Sanford

Luxury Year-round Hobbit House w/ private hot tub

Indoor spacesFamilySleep quality

4.96 out of 5 average rating, 229 reviews

An aerial view captures the modern cabin surrounded by lush greenery, featuring warm string lights illuminating the outdoor area. A hot tub is positioned near a cozy seating arrangement, with a gravel path visible leading away from the cabin.

Cabin in Kennebunk

HotTub+Firepit/5 min to DockSquare, Dining, Beach

Indoor spacesKitchenLayout

4.99 out of 5 average rating, 394 reviews

An open space features a vaulted wooden ceiling with beams and skylights. A cozy seating area includes a brown sofa and a modern coffee table. A wood stove adds warmth, while a well-equipped kitchen with dark green cabinets is visible in the background.

Tiny home in Freeport

Cozy Rock Cabin #thewaylifeshouldbe

FamilyIndoor spacesValue

4.9 out of 5 average rating, 331 reviews

A charming coastal home is showcased with light-colored siding and a bright blue front door. Surrounding greenery includes tall trees and manicured shrubs. The property is set back from a grassy area, adding to its inviting curb appeal.

Home in Falmouth

Amazing Bay View Home with Hot Tub

FamilyIndoor spacesParking

Family- and pet-friendly home rentals

5.0 out of 5 average rating, 115 reviews

An open living area is highlighted by large windows that frame scenic views of the marsh. A modern gas fireplace serves as a focal point, while a light-colored sofa and a small table with a plant create a welcoming ambiance. Bar seating for four extends to the kitchen.

Home in Higgins Beach

Higgins Beach *New* Beach Home & Private Offices

FamilyIndoor spacesValue

Apartment in Cape Elizabeth

A panoramic view of lush green land, featuring an array of colorful flowers. The coastline is visible in the distance, with water reflecting the clear blue sky. A shaded area with trees complements the vibrant plants, creating a serene outdoor environment.

Crescent Beach Gardens

Indoor spacesFamilyBeach

4.99 out of 5 average rating, 142 reviews

Apartment in Cape Elizabeth

A cozy living and dining area features comfortable seating, including a pair of light-colored armchairs and a round dining table. Soft lighting illuminates the space, and decorative accents, such as art and plants, create a welcoming atmosphere.

Portland + Cape Elizabeth + Beaches + luxurious!

FamilyKitchenAir conditioning

4.92 out of 5 average rating, 701 reviews

4.91 out of 5 average rating, 186 reviews

A welcoming covered porch features white rocking chairs and a light blue table, complemented by window shutters painted in a matching hue. An anchor decoration adds a nautical touch, while potted flowers introduce a hint of greenery.

Home in Scarborough

Pine Point Beach Getaway - Steps From the Beach!

Indoor spacesFamilyHeating

4.97 out of 5 average rating, 284 reviews

A cozy cottage is surrounded by lush trees and greenery. Two blue chairs are placed outside near the entrance, with a small table between them. A gas grill is positioned nearby, creating a welcoming space for outdoor relaxation and dining.

Cottage in Scarborough

Bright, clean, private cottage near Higgins Beach!

KitchenFamilyGrill

4.96 out of 5 average rating, 263 reviews

A relaxing outdoor area is shown, featuring several seating options around a fire pit. Two cabins can be seen, with one situated on a hill and the other by the water. A sun umbrella provides shade, surrounded by trees and nature.

Chalet in Standish

Blueberry Hill

Indoor spacesKitchenBackyard

Superhost

Apartment in West End

Cozy West End Victorian | EV Charging + Parking

FamilyKitchenCheckout

4.86 out of 5 average rating, 528 reviews

4.97 out of 5 average rating, 148 reviews

A modern kitchen is equipped with a stainless-steel microwave and stove beneath a stylish backsplash. The countertop features a sink and invites meal preparation. A comfortable nook with a raised twin bed can be seen in the background, surrounded by decorative plants.

Guest suite in Freeport

Studio Apartment in Freeport

FamilyKitchenHeating

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 116 reviews

A spacious suite is showcased with large windows allowing natural light. A comfortable couch faces a marble-topped coffee table, and a custom-built king bed is nestled against a natural pine headboard. The decor reflects minimalism, offering a peaceful setting for relaxation.

Apartment in Portland

Luxury Retreat In Back Cove | 10 Min to Downtown

FamilyKitchenHeating

4.95 out of 5 average rating, 702 reviews

The spacious loft is highlighted by 16-foot ceilings and multiple skylights. A queen bed is positioned near a cozy seating area, complemented by a wooden dining table. Eye-catching artwork adorns the walls, and natural light fills the room through large windows.

Loft in Falmouth

Loft Apartment on Tree-Lined Street in Falmouth

KitchenIndoor spacesAccess

4.9 out of 5 average rating, 120 reviews

Condo in Wells

Starfish Condo Wells Beach

KitchenFamilyPets

5.0 out of 5 average rating, 106 reviews

A heated pool is set within a stone patio, surrounded by lush greenery. Two lounge chairs are positioned nearby, while modern heating units stand along the patio's edge. The pool's clear water reflects the surrounding area, offering a serene outdoor retreat.

Home in Ogunquit

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

Indoor spacesFamilyGetting around

4.95 out of 5 average rating, 180 reviews

A bright kitchen area features modern white cabinetry and a spacious countertop. Barstools with woven seats are positioned at the counter. Natural light floods in through a nearby door, illuminating the polished wooden floor and light blue walls.

Cottage in Wells

Cozy Cottage with Ocean Views, Wells Maine

FamilyIndoor spacesPool

4.99 out of 5 average rating, 250 reviews

A charming exterior of the historic residence showcases a well-maintained garden filled with vibrant purple flowers and greenery. The pale yellow siding of the house complements the octagonal window and green door, offering a welcoming appearance.

Apartment in Brunswick

Charming Saltwater Farm apartment

KitchenFamilyTV

Home in Old Orchard Beach

A serene community pool is surrounded by a spacious deck with lounge chairs for relaxation. Tall trees in the background provide a natural setting, while neighboring homes are visible, enhancing the sense of community.

Faith Lane with community pool

KitchenFamilyCleanliness

4.96 out of 5 average rating, 123 reviews