Southeast Portland vacation rentals

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Top-rated vacation rentals in Southeast Portland

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

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Guest favorite

Guest suite in Portland

4.96 out of 5 average rating, 338 reviews

Hawthorne Hobbit Hole: special Portland experience

The Hobbit Hole is a cozy, comfortable sculpted suite to stay. It's an enchanting oasis, crafted with love and with guests in mind. This is a walking, biking, and transit paradise with easy curbside parking. We are around the corner from an organic grocery store, iconic restaurants, shopping, bike share programs and entertainment on perfectly Portland Hawthorne and Division streets. We are an open and affirming household who welcomes all. We do allow smoking/vaping outside, including cannabis

Dec 6 – 13

G$16,424 GYD per night

Guest favorite

Apartment in Portland

4.97 out of 5 average rating, 171 reviews

Hawthorne Area Artsy Home Away from Home

You’ll love our place because of its fantastic location! The Sunnyside neighborhood has been named one of the hottest in the country. We're close to so much: wonderful restaurants and pubs, Stumptown Coffee, McMenamin's movie theater and pub, grocery stores, beautiful parks. We're two miles from downtown with convenient public transportation. The comfortable, bright apartment has its own entry and kitchen is well-supplied. Our place is good for couples, solo adventurers, and business travelers.

Dec 7 – 14

G$23,651 GYD per night

Guest favorite

Guesthouse in Montavilla

4.95 out of 5 average rating, 391 reviews

Tabor Cottage: Detached Guest House SE Portland

Mt. Tabor Cottage is a quiet, cozy, detached one bedroom house.with a private, fenced patio. In the South Tabor neighborhood, we are close to Mt. Tabor park and walking distance to several restaurants. It's a 15 minute car ride to the airport or about 17-20 minutes to downtown Portland and only a 5 -7 minute drive to Montavilla, Division St and Hawthorne Blvd restaurants, bars and shopping. Street parking is always available on the block, often next to property or within 150ft, 30 second walk!

Jul 10 – 17

G$20,797 GYD per night

Guest favorite

Guest suite in Mt. Tabor

4.91 out of 5 average rating, 332 reviews

Fresh & Modern, Spacious 1 Bed/1 Bath Condo

Large, modern 700 sq ft condo with private entrance & lots of natural light. Washer & dryer, air conditioning and king-size memory foam bed. True cook’s kitchen with quartz countertop, full size appliances, and pots/pans. 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!

Oct 4 – 11

G$17,599 GYD per night

Guest favorite

Apartment in Ladd's Addition

5.0 out of 5 average rating, 130 reviews

Ladd's Addition Apartment in SE Portland

My Ladd's Addition apartment is well-positioned to allow you to explore Portland. Located in a quiet neighborhood halfway between the bustling streets of Hawthorne and Division; from here, you can easily walk to coffee shops, restaurants, bars, grocery stores, and a movie theater. Public transportation is readily available, as well as car, bike, and scooter shares. In just a few minutes, you can be downtown, the Moda center, the convention center, OMSI, or the waterfront esplanade.

Sep 22 – 29

G$21,769 GYD per night

Guest favorite

Guesthouse in Portland

4.95 out of 5 average rating, 384 reviews

Newly built studio in perfect SE location

A cozy newly renovated space with a modern motif. Plenty of natural light, high ceilings. Large walk in shower,walk in closet, washer +dryer and kitchenette with microwave. Queen size bed with European style bedding:fitted sheet, pillows and king size duvet with duvet cover, NO FLAT SHEET or TOP SHEET. The apartment is located in one of the best neighborhoods on the east side.Close to downtown, bus lines, bikes and scooters rental,shopping,casual and fine dining.

Jul 11 – 18

G$21,539 GYD per night

Guest favorite

Guesthouse in Laurelhurst

4.96 out of 5 average rating, 109 reviews

Modern and Bright Laurelhurst Abode

Our one bedroom cottage is completely private, accessible by a separate walkway, and has an outdoor patio. Extra time was spent choosing finishes and creating a modern, comfortable, and light-filled space. You’ll find everything you need for a weekend in Portland, or a long-term stay. We’ve outfitted a full kitchen, full bathroom with luxurious tub and plush towels, a bedroom with a queen mattress and soft bedding, washer and dryer, and lots of extra touches.

Oct 6 – 13

G$26,980 GYD per night

Guest favorite

Guesthouse in Mt. Tabor

4.94 out of 5 average rating, 116 reviews

Modern Urban Retreat + Sauna

Our modern urban guest house is a completely private space, accessible by a separate walkway, and has an outdoor patio. We designed the space to be light-filled and modern, feel roomy yet cozy, fitting a lot into a small space - with vaulted ceilings, a ceiling fan, full kitchen, bathroom, a bedroom with a comfy queen mattress and soft bedding and lots of extra touches. Our 335 sq ft guest house is fitted with all you'll need for your time in Portland.

Oct 1 – 8

G$25,198 GYD per night

Guest favorite

Loft in Portland

4.98 out of 5 average rating, 528 reviews

Charming Studio in SE PDX

Charming and bright private studio apartment in inner SE Portland, 4 blocks from "7-Corners". Walking distance to cafes, bakeries, shops, food carts, natural food markets, movie theater, restaurants and pubs. Bike friendly Washer/dryer Secure storage Private entrance Kitchen with pantry basics/refrigerator Freezer/ice WiFi Sleeps 2 in standard queen bed An air mattress is available upon request if more than two guests Hydronic radiant floor heat

Dec 10 – 17

G$18,990 GYD per night

Guest favorite

Guesthouse in Portland

4.97 out of 5 average rating, 123 reviews

The Perch PDX - Modern Studio on Division

A guesthouse in the SE Division/Hawthorne neighborhood that will make you feel right at home. The Perch PDX is light and bright. It's a short walk away from locally roasted coffee, farm-to-table fine dining, endless brunch options, a hip brewery and beer garden, bagels made fresh daily, authentic Mexican street tacos, a neighborhood wine bar, a fiercely independent movie theater, groceries, and some of the best Thai food in Portland.

Aug 31 – Sep 7

G$17,968 GYD per night

Guest favorite

Guesthouse in Woodstock

4.93 out of 5 average rating, 175 reviews

Charming, private 2-level guesthouse-Woodstock

**No list of chores to do at the end of your stay!** Vaulted ceilings, fully private 2 level home. Chef’s kitchen, AC, patio, designer decor and architecture. Contact-less, private self checkin. New Guest House in quiet residential area, upscale Eastmoreland-15 mins from downtown Portland. One bedroom/one bath. Within 10 minutes’ walk is Woodstock Ave-full of cafes, bars, bakeries, and shopping. Ample parking on the street.

Sep 21 – 28

G$24,145 GYD per night

Guest favorite

Guesthouse in Montavilla

4.94 out of 5 average rating, 306 reviews

The Artist’s Nest

You'll love this private and comfortable artist's studio complete with your own outdoor deck and pergola. Enjoy a King size Casper bed to relax on. You can walk to the Montavilla bars/restaurants or up to the top of Mt. Tabor and grab a city view while you picnic. Located conveniently near the airport, downtown, public transit and freeways, whatever you have planned for Portland, this is a perfect launchpad.

Sep 30 – Oct 7

G$21,833 GYD per night