Holiday rentals in Southeast Portland

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Top-rated holiday rentals in Southeast Portland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A shaded patio area is featured, showcasing a set of three wicker chairs with cushions positioned around a small table. A pergola covered in vines provides natural cover, while a landscaped yard and colorful garden shed are visible in the background.
Guest house in Woodstock
4.98 out of 5 average rating, 842 reviews

Woodstock Tiny House

Detached, very small (300 sq ft) guest house in the Southeast Portland neighborhood of Woodstock. Lots of walkable eateries as well as New Seasons and Safeway within a 5 minute walk. Close to Reed College, Woodstock Village, Springwater Trail, Southeast Portland Neighborhoods, Public Transportation. You’ll love the location, the outdoors space, and the ambiance. Good for couples, solo adventurers, and business travelers. TV (Netflix enabled!), A/C (summer months), heat, coffee, fridge/freezer.

Top guest favourite
A welcoming exterior view of the cottage is shown, featuring a manicured front garden filled with various shrubs and seasonal flowers. The white brick façade of the home contrasts with the lush greenery, while large windows allow for ample natural light to enter the space.
Guest house in Woodstock
4.98 out of 5 average rating, 576 reviews

Cozy Guest Cottage in Woodstock Neighborhood

A bright and cozy cottage located near Reed College, Woodstock's restaurants/coffeehouses, Trader Joe's and public transit. This residential neighborhood is ideal for a quiet retreat for all visitors. The private guesthouse is outfitted to make your stay comfortable including a spacious bathroom with a walk in shower and a heated floor. Plus, you may want to enjoy a cup of coffee on your own patio located behind the Airbnb. As an added bonus, breakfast items and home baked treats are provided.

Top guest favourite
The exterior of a two-story studio is framed by lush greenery and trees. The building features a spiral staircase leading to a private balcony with black railings. A shared garden area is visible below, with a hammock and various plants around the space.
Guest house in Piedmont
4.98 out of 5 average rating, 244 reviews

Spacious, bright garden studio on Peninsula Park

Explore the world-class restaurants, coffee shops and bars in the nearby Williams and Mississippi districts. Take a stroll around the award winning (and oldest) rose garden in the City of Roses across the street in Peninsula Park. At home, this second story studio has extra space in the meditation loft, a full kitchen, fast internet, and projector for streaming. Enjoy your private deck over the shared garden with hammock and H/C outdoor shower. Bus and train nearby with ample on-street parking.

Top guest favourite
A modern two-story home with a light-colored exterior features large windows that invite natural light. The entrance is highlighted by a set of stairs leading to the front door, with a driveway visible in the foreground, surrounded by landscaped gardens.
Guest suite in South Tabor
4.92 out of 5 average rating, 407 reviews

Cozy & spacious like home with full kitchen & W/D

Fresh & Modern, Spacious 1 Bed/1 Bath Condo - 700 sq ft unit with private entrance & lots of natural light. Free washer & dryer, A/C, and king-size memory foam bed. Cook’s kitchen with quartz countertops & full size appliances. Lovely outdoor stone patio with picnic table. We're excited to host you at our Earth Advantage energy efficient home that's convenient to downtown, the airport, and many nearby restaurants. Just steps away from walking paths on Mt. Tabor with panoramic views!

Top guest favourite
A spacious studio is presented with a queen-sized bed featuring a patterned duvet. A comfortable sofa is positioned opposite, with stylish decor elements enhancing the ambiance. The room includes an area rug and has a kitchenette visible in the background.
Guest house in Foster-Powell
4.91 out of 5 average rating, 738 reviews

Studio Guesthouse SE Portland

Memory Foam Mattress, 43" TV on an adjustable wall mount AirBnB COVID-19 Cleaning in place w/cleaning supplies for your use. You will love our Southeast Studio with Private Entrance, patio, seating & garden. Near Mount Tabor Park, restaurants and bus stop. The Studio is great for couples, solo adventurers, business travel, and small families. Quiet neighborhood vibes. Yummy snacks, Coffee and Tea Portable A/C installed June - mid September Fan in unit after A/C removed

Top guest favourite
An open-space studio features high ceilings with wooden beams, enhancing the airy feel. A queen-sized bed is set against the wall with soft linens. A small kitchenette and dining area are visible, with a full bathroom enclosed in glass. Natural light brightens the interior.
Guest house in Woodstock
4.96 out of 5 average rating, 473 reviews

SE Portland Guest Cottage

The guest cottage offers self check-in. It is located in a quiet neighborhood in SE Portland. High ceilings make this studio airy and bright. We think of it as a perfect hotel room without the hotel. The small galley kitchen has everything you need to cook a gourmet meal including filtered water. There is a full bathroom with tub and shower. The cottage stands on its own making it perfect for coming and going as you please. City of Portland Permit #24 013532

Top guest favourite
Guest suite in Richmond
4.95 out of 5 average rating, 136 reviews

★ Modern Division Street Hideout ★

✅ 5 ⭐️ location! ✅ Modern finishes ✅ Sauna 🧖‍♀️ ✅ King Size Bed ✅ Fully stocked kitchen ✅ Washer + Dryer ✅ Roku Smart TV ✅ ecobee smart thermostat Bright one-bedroom flat with private access and patio located in the mix of all the restaurants, shops, galleries, and nightlife Division Street has to offer. Aside from the incredible location, you’ll have a fully stocked kitchen, Roku TV, washer + dryer, and a king size bed. Oh, and a sauna!! 😎

Top guest favourite
An open living space features a comfortable sitting area with a sofa and stylish chairs. A dining table accommodates four, while the kitchen area showcases modern appliances. Natural light filters through multiple windows, illuminating the spacious sleeping area with a large bed in the background.
Guest house in South Tabor
4.99 out of 5 average rating, 381 reviews

The Loft: Modern Open space in Southeast Portland

An open, airy, private, and stylish space located over a detached garage behind the main house. This is a great neighborhood that is close to public transportation and major roads. Easily walk to bike rentals, food carts, restaurants, local bars, and main shopping areas. We are looking to provide a safe and comfortable space. We love to give suggestions and recommendations on places and things to do while in Portland and Oregon.

Top guest favourite
A spacious studio apartment features a cozy sleeping area with a wooden bed frame and soft bedding. A dining table with chairs is nearby, along with a comfortable sofa. Large windows allow natural light, and entertainment options include a flat-screen TV. Kitchen appliances are neatly arranged along one wall.
Guest house in Buckman
4.98 out of 5 average rating, 898 reviews

Cozy Portland Studio Apartment

The space is a well appointed, comfortable studio apartment. It is an ADU at the back of the main house. All the amenities that one would desire are provided (wifi, internet, TV, washer & dryer, fridge, dishwasher, stove, microwave, AC, cooking utensils, etc., etc). It is also very modern and clean, with a private entrance and keyless entry. Close to many restaurants, bars and coffee shops.

Guest favourite
Flat in Sunnyside
4.92 out of 5 average rating, 170 reviews

Portland's Best in Hawthorne District

Step outside and explore the charm of Portland's Hawthorne neighborhood, filled with vintage shops, local bookstores, and cozy coffee spots full of character. Stroll past colorful murals, browse unique boutiques, and take in the laid-back, creative vibe. Whether you're here to relax, explore, or a little of both, this welcoming space is a great place to call home through your stay.

Top guest favourite
A cozy studio space features a queen size bed with soft linens, complemented by a plush blue couch and a small coffee table. Natural light enters through windows, while plants and a wall of shelves add a touch of greenery and warmth to the environment.
Guest house in Portland
4.99 out of 5 average rating, 323 reviews

Cozy Clinton Cottage (close-in SE off Division)

Our lovingly renovated guest cottage is detached from the main house, with a private entrance and outdoor seating area. Our central location is great for exploring all of the best that Portland has to offer, with easy access to public transit and bike routes. The space is very cozy and has everything you need for a fantastic Portland vacation or work trip.

Top guest favourite
A modern living area features a comfortable dark sofa and a light wood coffee table positioned on a plush red rug. Large windows allow natural light to fill the space, framing views of greenery outside. A sleek kitchen and dining area are visible in the background.
Guest house in Richmond
4.99 out of 5 average rating, 430 reviews

Modern Hawthorne Guesthouse - Close to Everything

A bright, stylish and modern home awaits you in the heart of Portland's Hawthorne District. Located only a few minutes from downtown but you may find yourself not wanting to leave the neighborhood. An easy stroll will take you to the Hawthorne, Division, and Belmont restaurant/shopping areas.

Popular amenities for Southeast Portland holiday rentals

When is the best time to visit Southeast Portland?

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Avg. price$121 SGD$121 SGD$125 SGD$126 SGD$128 SGD$137 SGD$146 SGD$147 SGD$138 SGD$133 SGD$134 SGD$134 SGD
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Quick stats about holiday rentals in Southeast Portland

  • Total holiday rentals

    Explore 1,860 holiday rentals in Southeast Portland

  • Verified guest reviews

    Over 209,460 verified reviews to help you choose

  • Family-friendly holiday rentals

    720 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 550 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    1,120 properties have a dedicated workspace

  • Wifi availability

    1,840 of Southeast Portland holiday rentals include wifi access

  • Popular amenities for guests

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

  • 4.9 Average rating

    Southeast Portland stays are highly rated by guests – averaging 4.9 out of 5!

  • Nearby attractions

    Southeast Portland’s top spots include Laurelhurst Park, Tom McCall Waterfront Park and Portland Saturday Market

Destinations to explore

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