Vacation rentals in South Portland

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Top-rated vacation rentals in South Portland

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Top guest favourite
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.
Apartment in Ferry Village
5 out of 5 average rating, 123 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.

Guest favourite
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.
Apartment in South Portland
4.93 out of 5 average rating, 174 reviews

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.

Top guest favourite
An open-concept studio space features sloped ceilings and warm hardwood floors. A dining area includes a wooden table and chairs. A colorful floral armchair is positioned beside a television, which faces a spacious sleeping alcove with a queen bed covered in light bedding.
Apartment in South Portland
4.91 out of 5 average rating, 239 reviews

Willard Square - The View

5 minutes to the beach , private deck , cozy apartment just a stone's throw from Scratch Bakery. Grab a bagel, or my personal fave, almond horseshoe, and relax on the deck stroll to the beach. One bedroom apartment on the third floor, fully equipped kitchen. Everything you need for a weekend or a winter rental. The stairs are steep and may not be appropriate if you have mobility issues. sloped ceilings . First response is alaways , "It's so much bigger than the photos show. Fast wifi .

Guest favourite
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.
Guest suite in Ferry Village
4.92 out of 5 average rating, 386 reviews

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.

Top guest favourite
A modern kitchen is highlighted by sleek cabinetry and a dark countertop. A black refrigerator, microwave, and stove are visible. Natural light enters through two windows, illuminating a vase of sunflowers beside a small potted plant. A textured area rug adds warmth to the space.
Apartment in Ferry Village
4.95 out of 5 average rating, 274 reviews

Luxury Apt, 7 min to Old Port, W/D, Parking

A sunny, private, spacious, recently renovated 1 BD apartment in a quiet neighborhood in South Portland. New kitchen and 2 luxury bathrooms with shared seasonal back patio. Enjoy the new Second Rodeo Cafe next door. Minutes to the beach and downtown Portland. Enjoy Bug Light Park, the Eastern Greenway Trail, and Scratch Bakery; you are close to it all. Please note: From December through March, we have off-street parking space for only one vehicle. We are owner-operated. Lic#2764

Top guest favourite
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
4.96 out of 5 average rating, 203 reviews

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!

Guest favourite
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.
Apartment in Knightville
4.94 out of 5 average rating, 129 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.

Top guest favourite
The airy living area features a neutral-toned sofa, complemented by two stylish chairs and a round glass coffee table. Soft light enters through two windows, and a vibrant abstract painting is displayed on the wall. Decorative lamps add subtle illumination.
Apartment in Cape Elizabeth
4.99 out of 5 average rating, 285 reviews

Cape Elizabeth Garden Apt+Beach+Close to Portland!

Bright, airy, two-story, 1000 sf apartment, with view of gardens. Off-street parking and private entrance. First floor living area with kitchenette, and sofa-bed, for additional guests. Second floor king bedroom with full bath. Ideally located a short walk to Kettle Cove Beach, and just minutes from Two Lights State Park, Crescent Beach, Higgins Beach and Robinson Woods Trail. Portland - voted the best restaurant city in the US - is a 10 minute drive. STR Permit #210701.

Top guest favourite
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.
Apartment in South Portland
4.9 out of 5 average rating, 217 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.

Top guest favourite
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.
Guest suite in Ferry Village
5 out of 5 average rating, 284 reviews

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.

Top guest favourite
A private deck is visible, featuring two comfortable chairs and a round table. Beyond the railing, a grassy area leads to a tranquil waterfront, framed by trees. The scene captures a peaceful outdoor setting, ideal for relaxation while enjoying views of the water.
Guesthouse in Portland
4.96 out of 5 average rating, 327 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 so if you'd like to book please introduce yourselves and let us know who is coming. 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
A queen-size bed is dressed in crisp white linens, complemented by decorative pillows in rich hues. A textured throw blanket adds warmth across the foot of the bed. Soft natural light filters in through a nearby window, highlighting the cozy atmosphere.
Apartment in Cumberland Mills
4.9 out of 5 average rating, 220 reviews

Cozy 2 BR Apt in Walking Distance to Restaurants

This is a private two bedroom apartment in a great location (15 minutes to downtown Portland). The apartment is in walking distance to eateries, Riverbank Park, grocery stores and local breweries. It is also located across the street from the police station on a dead end street. The unit is child friendly and has a pack 'n Play and high chair. (Please note that linens are not provided for the Pack n’ Play.)

Popular amenities for South Portland vacation rentals

When is the best time to visit South Portland?

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Avg. price$187 CAD$190 CAD$193 CAD$233 CAD$262 CAD$307 CAD$354 CAD$373 CAD$311 CAD$279 CAD$225 CAD$199 CAD
Avg. temp-4 °C-3 °C1 °C7 °C13 °C18 °C21 °C21 °C16 °C10 °C4 °C-1 °C

Frequently Asked Questions

  • Where should I stay in South Portland?

    Make yourself at home in South Portland by choosing from our most frequently booked neighborhoods. We have over 1,540 vacation rentals in West End, over 1,420 vacation rentals in Downtown Portland, and over 1,420 vacation rentals in Waterfront District.

  • Are there vacation rentals with a dedicated workspace in South Portland?

    Yes! Work meets play with ease at over 310 vacation rentals in South Portland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in South Portland?

    Four-legged friends are welcome in South Portland. Choose from more than 190 vacation rentals for guests traveling with pets.

  • Are there South Portland vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in South Portland, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in house rentals in South Portland?

    Experience the best of South Portland with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly townhouse rentals in South Portland?

    South Portland has more than 10 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in South Portland have a bbq area?

    Absolutely! We offer over 40 house rentals with a bbq area in South Portland. Enjoy a tailored experience with all the comforts you desire.

  • Do boutique hotel rentals in South Portland have wifi?

    Absolutely! We offer over 30 boutique hotel rentals with wifi in South Portland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in South Portland have a gym?

    Absolutely! We offer over 20 house rentals with a gym in South Portland. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in South Portland?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 260 homes with wifi, over 30 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in South Portland

  • Total vacation rentals

    Explore 600 vacation rentals in South Portland

  • Nightly prices starting at

    South Portland vacation rentals start at $56 CAD per night before taxes and fees

  • Verified guest reviews

    Over 71,030 verified reviews to help you choose

  • Family-friendly vacation rentals

    280 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 190 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    310 properties have a dedicated workspace

  • Wifi availability

    590 of South Portland vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across South Portland rentals

  • 4.9 Average rating

    South Portland stays are highly rated by guests—averaging 4.9 out of 5!

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