
Apartment holiday rentals in South Portland
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Top-rated apartment rentals in South Portland
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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!

Luxury Condo in Downtown Portland Old Port
Luxury Condo in the heart of Portland's Old Port. Enjoy your stay on a beautiful historical street tucked away just steps from many restaurants, the art museum, state theater, and many other things downtown Portland has to offer! Well furnished and very clean. Every part of the rental is well utilized. Kitchen table can fold away when not in use, and features built in closets and cabinets. A true gem in the heart of the city, whether you are here to escape, explore, or on business.

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

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!

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.

Luxury Beach Front Condo! Prime Location!
Special rate for single night 11/25✨ Condo is directly on beach ✨ Generally minimum night stay is 2 nights during the week and 3 nights over the weekend. Sometimes single nights are opened. If you see a 14 day minimum, it’s only to prevent the reservation from leaving a single night open. Unless the trip is within the next few weeks, we appreciate it if guests don't book trips that leave a single night open. ✨ ✨To simplify things we typically do not negotiate rates.✨

The Brunswick
Listen to the waves crash from your fully equipped oceanfront condo with large deck located on picturesque Old Orchard Beach. This is a 4th floor condo in the Brunswick building located directly on West Grand Ave and a short walk to the “center”. There are miles of sandy beach you can walk / jog / bike on or just relax on your oceanfront deck and watch the sunrise. There is an elevator for easy access and a door code so you don’t have to worry about losing keys.

Waterfront Two Master Suite Penthouse with Rooftop
2023 City of Portland Registration #20185280-ST Penthouse suite w/modern amenities, exposed beams and brick, poplar walls. Rooftop deck w/views of harbor and city. Separate master suites with custom showers and one with soaking tub. Gas-fired Jotul stove in living room. Washer/dryer in unit. Easy elevator access. Spacious kitchen with granite countertops and wine cooler. Please note: animals (including assistance animals) not allowed due to owner's health.

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.
Popular amenities for South Portland apartment rentals
Weekly apartment rentals

Beautiful Updated Condo Steps from the Beach

Brand new unit 45 Steps to the beach! Sleeps 4

Fresh & Modern Family Friendly Central 2 bed

Steps from the sandy beach! "Surf's Up"

Oceanfront condo with Breathtaking view remodeled

Central Spacious 4 Bedroom, 5 Bed, 2 free parking

3 Bedroom 2 Bath - On the Beach!

Boho Surf Studio: Steps from the Beach in OOB!
Pet-friendly apartment rentals

My Old Port Sanctuary - Lux by the water & dining

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

Charming 2-Bedroom Back Cove Retreat

Attractive 1 bedroom cabin only 50 ft from beach#1

Prime Location Old Port apartment

Ocean View! - Luxury Condo with Beach Access

Over 1000 Five Star Reviews! Walk to Dock Square !

Walk Everywhere | Free Parking | DogsOK | King Bed
Apartment rentals with a pool

Stylish Designer Retreat on Langsford with Pool

Stars And Stripes

LUXURY OCEANFRONT CONDO Best Location on the beach

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

Steps to Beach, Pier, Park | Condo with Pool • 3

Condo in Old Orchard Beach

RARE 3 bedroom at The Resort Goose Rocks Beach!

Ocean View Studio Beach Condo
When is the best time to visit South Portland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $193 SGD | $159 SGD | $141 SGD | $209 SGD | $263 SGD | $308 SGD | $367 SGD | $453 SGD | $320 SGD | $287 SGD | $212 SGD | $162 SGD |
| 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 apartment rentals in South Portland

Total holiday rentals
Explore 30 holiday rentals in South Portland

Nightly prices starting at
South Portland holiday rentals start at $65 SGD per night before taxes and fees

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

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of South Portland holiday rentals include wifi 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!
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- Apartment rentals Cumberland County
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- 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
- Pemaquid Point Lighthouse
- Dunegrass Golf Club
- Funtown Splashtown USA
- King Pine Ski Area
- Willard Beach
- Coastal Maine Botanical Gardens
- Wolfe's Neck Woods State Park
- Short Sands Beach
- Wentworth by the Sea Country Club
- Cliff House Beach
- Parsons Beach
- Ferry Beach
- Crescent Beach State Park
- Laudholm Beach




