
Condo vacation rentals in South Portland
Find and book unique condos on Airbnb
Top-rated condo rentals in South Portland
Guests agree: these condos are highly rated for location, cleanliness, and more.

New 2BR 2King beds Private Apt Downtown Brunswick
Completely Newly Renovated 2 Bedroom Private Apartment Located 1 Minute Walk From Maine Street In Brunswick (Downtown). Great For Anyone Looking To Visit Or Explore Brunswick Including Bowdoin Parents, Potential Students, Vacationers. We have hard wood floor, granite counter top, open concept living room and kitchen, red retro fridge, and lots of windows lots of sunshine! Both bedrooms has a small closet and both beds are king sized with super comfortable memory foam mattress! Please Enjoy!

Elegant 1 bedroom cabin just 50ft from the beach#2
This beautiful cabin now features a new Queen size bed, a double futon in the living room & can accommodate up to 4 people. The cottage includes a fully equipped kitchenette with microwave, fridge, coffee maker, toaster, and dining area. Smart TV, WIFI. AC & Central heating. It also has a private full bath with tub/shower combo at this unique and tranquil getaway. Enjoy the privacy of your own seaside cottage close to the beach! BBQ grills and picnic tables with umbrellas dot the courtyard.

First Floor Portland Condo 3 Bed 2 Bath + Parking
A cozy getaway nestled in the Portland's Deering neighborhood. Enjoy the retreat that this beautiful light-filled condo has to offer, whilst being less than three miles from the Old Port! The space is bright, and open--filled with luxurious touches and local Maine art. With three bedrooms and two full bathrooms, there is plenty of space for a large group to stay. Also, enjoy three free parking spots during your stay. We can't wait to have you! 3.5 miles to Airport 3 miles to bus station

Luxury Beach Front Condo! Prime Location!
Halloween party downstairs at Brunswick 10/31, single night available! Please no parties ✨ Condo is directly on beach ✨ Generally minimum night stay is 2 nights during the week and 3 nights over the weekend. Unless the trip is within the next few weeks, we appreciate it if guests don't book trips that leave a single night open. If you see a 14 day minimum, it’s only to prevent the reservation from leaving a single night open.✨ ✨To simplify things we typically do not negotiate rates.

Renovated Exchange St. Loft w/Free Parking
This renovated loft-style condo is right in the heart of the Old Port. Located on Portland's bustling Exchange Street, the loft is central to everything the Peninsula has to offer. Elevator access will take you from the apartment to the secure lobby. From there, shops, restaurants, night life and the working waterfront are just steps outside the door. Free off street parking is available for one car a few blocks away or a convenient pay-to-park garage is located next to the building.

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!

Modern Industrial Beach Cottage
Time for a beach vacation! Newly renovated studio apartment, right across the street from Pine Point! Stroll the seven miles of quiet, sandy, residential beach, or bring your bike for a quick ride to the Pier at Old Orchard Beach. Located nearby is a market and deli, restaurants, and a gift shop. Just 20 minutes drive to the heart of Portland, you won't want to miss the local breweries and shopping in Old Port. Kayak rental nearby. Be sure to check out our other listings!

Cozy condo by the beach!
Cozy condo across the street from Maine's beautiful Pine Point beach. Private entrance with one on-site parking spot. Queen bed in lofted area is the only sleeping space. Efficient kitchen area with fridge, stove, and microwave for preparing small meals. Wifi and TV equipped with a streaming device. Perfect place for one or two people who will spend most of their time enjoying our local trails, beaches, and restaurants before returning to this comfortable and quiet space.

Comfy condo with loft by the beach!
Comfy condo with lofted bed across the street from Maine's beautiful Pine Point beach. Private entrance with one on-site parking spot. Queen bed in lofted area, efficient kitchen area with fridge and convection microwave for preparing snacks and small meals. Wifi and TV equipped with a streaming device. Perfect for one or two people comfortable sharing an intimate space after returning from a day exploring our local trails, beaches, and restaurants.

Portland 1 Bedroom Condo in the Arts District.
You’ll love my sunny, clean home because of its central PENINSULA location in the heart of Portland's arts district with floor-to-ceiling windows on the first floor of a charming red brick Victorian. Walk to restaurants, music venues, theaters, museums, and galleries from this abode full of period details like high ceilings, wood floors, built-ins, decorative fireplace, and a full kitchen with all the basics. A truly unique space for a getaway.

Top Of The Line Stay!
Are You Tired Of Staying At Dirty, Rundown Places?? Completely renovated two bedroom/one bathroom in East Deering. Beautifully appointed rental that features: hardwood/ceramic tile floors, granite, fully applianced kitchen, two queen size beds, washer/dryer in unit, porch, yard and a garage. Close to Old Port, Payson Park, Back Cove, neighborhood beach and Falmouth.

Two-Bedroom Condo on the Wells/Ogunquit town-line
New condo unit at Compass Pointe Club, located on the Wells/Ogunquit town-line. Only one mile to Footbridge Beach and a quick 3-minute drive to downtown Ogunquit. Short drive to the supermarket and to great restaurants. Beautiful views of the Ogunquit River basin, with the Atlantic ocean peaking out beyond. The location cannot be beat.
Popular amenities for South Portland condo rentals
Weekly condo rentals

Beautiful Updated Condo Steps from the Beach

The Single. In the heart of Kennebunkport

Endless Direct Beachfront Views! 2 Oversized Decks

Fresh & Modern Family Friendly Central 2 bed

Oceanfront condo with Breathtaking view remodeled

2-Bedroom Condo Close to Downtown

Walk to beach, NO cleaning fee, Spotless Condo

3 Bedroom 2 Bath - On the Beach!
Pet-friendly condo rentals

My Old Port Sanctuary - Lux by the water & dining

Romantic apt:West End +parking

Arlie's Digs! - One Block To Willard Beach!

Charming 2-Bedroom Back Cove Retreat

Condo in Old Orchard Beach

Prime Location Old Port apartment

Munjoy Hill Haus

Ocean View! - Luxury Condo with Beach Access
Condo rentals with a pool

Cozy Coastal Condo in Wells - Hot Tub & Pool!

Stylish Designer Retreat on Langsford with Pool

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

Our Happy Place!

The Ocean's Belle

Nautical Mile Resort #234_ King Bed_Pool/Hot Tub

Starfish Condo Wells Beach

Awesome get away spot in Wells!
When is the best time to visit South Portland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$30,941 GYD | G$25,506 GYD | G$22,579 GYD | G$33,450 GYD | G$42,022 GYD | G$49,339 GYD | G$68,781 GYD | G$66,482 GYD | G$58,956 GYD | G$45,994 GYD | G$33,868 GYD | G$25,924 GYD |
| Avg. temp | -4°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 21°C | 16°C | 10°C | 4°C | -1°C |
Quick stats about condo rentals in South Portland

Total vacation rentals
Explore 30 vacation rentals in South Portland

Nightly prices starting at
South Portland vacation rentals start at G$10,453 GYD per night before taxes and fees

Verified guest reviews
Over 4,270 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of South Portland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across South Portland rentals

4.8 Average rating
South Portland stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Quebec City Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- Jersey City Vacation rentals
- Island of Montreal Vacation rentals
- East Side Vacation rentals
- Rentals with a fire pit South Portland
- Fitness-friendly rentals South Portland
- Rentals with a fireplace South Portland
- Rentals with pools South Portland
- Rentals with beach access South Portland
- Beachfront rentals South Portland
- Pet-friendly rentals South Portland
- Rentals with a patio South Portland
- Rentals with breakfast South Portland
- Family-friendly rentals South Portland
- Rentals with a washer and dryer South Portland
- Waterfront rentals South Portland
- House rentals South Portland
- Boutique hotel rentals South Portland
- Apartment rentals South Portland
- Private suite rentals South Portland
- Rentals with outdoor seating South Portland
- Condo rentals Cumberland County
- Condo rentals Maine
- Condo rentals United States
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Long Sands Beach
- Popham Beach State Park
- Popham Beach, Phippsburg
- Pemaquid Beach
- East End Beach
- Dunegrass Golf Club
- Pemaquid Point Lighthouse
- Funtown Splashtown USA
- Willard Beach
- Coastal Maine Botanical Gardens
- Parsons Beach
- Short Sands Beach
- Wentworth by the Sea Country Club
- Wolfe's Neck Woods State Park
- Crescent Beach State Park
- Cliff House Beach
- Ferry Beach
- King Pine Ski Area
- Laudholm Beach