Condo vacation rentals in South Portland

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Top-rated condo rentals in South Portland

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Guest favorite

Condo in Kennebunk

4.89 out of 5 average rating, 200 reviews

Discover Dock Square…Surfs Up!

Free onsite parking for 1 car. Beautiful coastal décor and modern amenities makes this a perfect choice for your vacation. Walking distance to EVERYTHING! Dock Square is a 1 minutes walk. Music, Art and Fine Dining surrounds you. Lots of windows and a slider to the deck make this location bright and airy 2 private decks for your enjoyment, two bedrooms, 2 full bathrooms. Perfect for couples or families. Parking for one car in lot, added public park across s NO PARTIES Pets considered

Guest favorite

Condo in West End

4.94 out of 5 average rating, 111 reviews

Historic West End Condo 10 Minute Walk to Old Port

Our perfectly located condo in this brick federal building from 1848 is the ideal spot for your stay in Portland. Fully renovated and beyond comfortable. Walk to Old Port, Arts District or any restaurant/brewery you desire. Quite, top floor unit with self entry keypads and security cameras. Furnished and equipped with all the comforts of what you should expect and more. Interior offers lots of light, exposed brick, vaulted ceiling, stainless appliances, washer/dryer. Furniture is dialed in

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Condo in Old Orchard Beach

4.72 out of 5 average rating, 114 reviews

Attractive 1 bedroom cabin only 50 ft from beach#1

nestled in a restful pine grove just 50 feet from Maine’s finest beach. These 8 one & two bedroom charming Old Orchard Beach Cottages are decorated in a modern beach theme, providing guests with the modern conveniences of today. Conveniences include Smart TVs with Amazon Fire Sticks, Wi-Fi, individually controlled heat & air conditioning, fully equipped efficiency kitchenettes, & private baths. Ideal for group getaways! Enjoy the privacy of your own seaside cottage, oh, so close to the beach.

Guest favorite

Condo in Downtown Portland

4.89 out of 5 average rating, 177 reviews

Rustic Downtown Duplex with Private Deck

This condo is truly a unique & special space. Enjoy walking to the Portland Museum of Art, Merrill Auditorium, Arts District & the Old Port not to mention countless restaurants/bars/breweries just steps away. After a long day exploring come back to this relaxing two story rental & enjoy a beverage on your private deck. This condo is perfect for travelers that need extra space but don't want to sacrifice location. Bedrooms & Living space are on separate levels. Parking by request (small fee).

Guest favorite

Condo in Scarborough

4.96 out of 5 average rating, 337 reviews

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, full size sleeper sofa on ground level. 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.

Guest favorite

Condo in Downtown Portland

4.96 out of 5 average rating, 183 reviews

"Cornelia" Penthouse Waterfront Suite

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 heated bathroom floors; 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.

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Condo in Scarborough

4.77 out of 5 average rating, 260 reviews

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!

Guest favorite

Condo in Scarborough

4.96 out of 5 average rating, 214 reviews

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.

Guest favorite

Condo in South Portland

4.95 out of 5 average rating, 160 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. Ideal 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!

Superhost

Condo in East End

4.88 out of 5 average rating, 104 reviews

East Bayside/ Munjoy - Charming Downtown Escape

Walking distance to restaurants, craft breweries, and historic sites, this East Bayside condo will make the ideal home base for next trip to downtown Portland. This condo offers three comfortable bedrooms, a well-equipped, full kitchen, and a cozy living area with wall mounted TV's for streaming your favorite shows. You'll find everything you need here for rainy afternoons or relaxing evenings following days out on the town.

Guest favorite

Condo in Old Orchard Beach

4.9 out of 5 average rating, 391 reviews

Luxury Beach Front Condo! Prime Location!

Unless the trip is within the next few weeks, we appreciate it if guests don't book trips that leave a single night open. Generally minimum night stay is 2 nights during the week and 3 nights over the weekend. If you see a 14 day minimum, it’s only to prevent the reservation from leaving a single night open. To simplify things and to be fair to those that instant book, we typically do not negotiate rates. Thank you!

Superhost

Condo in Portland

4.93 out of 5 average rating, 172 reviews

Walk to downtown ! Free Parking! Private Entrance!

Sunny, large 1600 Sq Ft Condo. Walk to the Old Port, bars, restaurants, Farmer's Market, Portland Expo and Sea Dogs baseball stadium! All are welcome! - 5 queen beds plus sofa bed ! -Walk to Everything! - Parking off street for 2 or 3 cars! - Sunny front porch and backyard patio with BBQ grill ! -Smart TV ( Netflix Amazon, etc.) -Fully equipped kitchen - Smart lock self check in! -License Number STHR-000828-2018