Family-friendly holiday rentals in Southeast Portland

The charming exterior of the guest cottage is highlighted by warm orange siding and French doors that open onto a wooden deck. Two bright red chairs are positioned outside, complemented by potted plants. A glimpse of the cozy interior is visible through the open doors.

4.94 out of 5 average rating, 741 reviews

Cozy Garden Cottage in the Heart of Richmond

A serene Guest Cottage nestled in a garden and located within walking distance to the local foodie restaurants. You’ll love the location and how quiet it is! The perfect set up for couples, solo travelers or business travel. It's open and bright. French doors, plenty of windows, and skylights to bring in natural light for an open feel. You'll be set up with a comfy mattress, quality linens and plush towels. Nothing more cozy than that! Don't forget about the Smart TV, work desk, and essentials!

Indoor spacesFamilyParks

4.94 out of 5 average rating, 507 reviews

A sunlit open-plan living area features a spacious kitchen island with bar stools and stainless steel appliances. Comfortable seating is arranged around a television, with dining space for four visible. Large windows and French doors illuminate the area, leading to the private garden patio.

Bungalow in Portland

The Backyard Bungalow! Big Living; Small House

The Backyard Bungalow - featured on Portland's ADU tour - is the perfect hideaway amidst uncertain times. With its own secluded pathway, and detached from the main house, it offers as much privacy as desired. Once inside however, its 16ft vaulted ceiling and sunlit open-plan living area surprises with a sense of spaciousness and comfort. Its inner SE location is walking distance to Division St. restaurants and cafes, food carts, parks and playgrounds, as well as being a "biker's paradise".

FamilyKitchenOutdoor spaces

The open kitchen and living area feature vaulted ceilings and natural light. A fully equipped kitchen is highlighted by wood cabinetry, a gas stove, and a breakfast counter with three bar stools. Subtle green accents decorate the walls, complemented by modern furnishings.

4.82 out of 5 average rating, 204 reviews

Private Oasis! Cozy & Close to Everything!

Beautiful, one of a kind guest house nestled in one of Portland's most desirable locations! This chic and cozy space features vaulted ceilings, all new appliances, comfortable furniture, and tons of natural light! A quiet street, peaceful atmosphere (and awesome soaking tub) make this the perfect spot for relaxation. Enjoy exploring the surrounding neighborhood and easily walk to shops, restaurants, bars and Laurelhurst Park! Central location allows quick travel to other areas of the city!

Indoor spacesKitchenValue

A light-filled living area features two armchairs positioned beside large windows, showcasing views of surrounding greenery. A plush sofa offers a comfortable seating option, while a small, decorative table holds a plant. A television is mounted on the wall, enhancing the modern design.

5.0 out of 5 average rating, 124 reviews

Chic Belmont retreat w/tree views & king bed!

Experience weird and wonderful SE Portland from a serene, newly-built home in a walkable/bikeable neighborhood with king bed and lots of light! Wake up well rested and open curtain on floor to ceiling windows to morning light. Enjoy the full kitchen & soaker tub in a breathtaking architect-designed home perfect for foodies, couples, and remote work. Great location just steps from bakeries, shops, parks and taprooms. Discover the quirky character and trendy eats of Belmont-Hawthorne-Tabor!

Indoor spacesKitchenCondition

4.98 out of 5 average rating, 624 reviews

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.

Guesthouse in Woodstock

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 patio located behind the Airbnb. As an added bonus, breakfast items and home baked treats are provided.

Indoor spacesFamilyWi-Fi

A detached studio features a charming A-frame design, surrounded by lush greenery. A stone patio with outdoor seating complements the inviting entrance, where large windows allow natural light to fill the space. The setting provides a serene atmosphere, ideal for relaxation.

4.98 out of 5 average rating, 690 reviews

The Westmoreland Lighthouse - Private studio in SE

We've dubbed this stunning, fully detached studio the "Lighthouse" because of the way natural light pours through the 550-square-foot studio's many windows and dances off its walls and vaulted ceilings. An open loft offers soothing views. We are tucked into the Westmoreland neighborhood's quiet residential area, but are only a five minute walk from more than 20 restaurants and entertainment features. Westmoreland Park, Reed College and downtown Portland are just minutes away by car.

FamilyIndoor spacesSleep quality

A cozy bedroom features a spacious bed adorned with a patterned duvet and decorative pillows. A flat-screen TV is mounted on the wall, while a small dining table with two chairs is positioned nearby. Natural light filters in through the windows, highlighting the wooden floors.

4.96 out of 5 average rating, 567 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.

KitchenIndoor spacesCheck-in

4.88 out of 5 average rating, 239 reviews

The interior space features warm wood finishes and large windows allowing natural light to fill the area. A compact kitchen area is equipped with essential appliances, and a comfortable seating arrangement includes a reclining chair and a small table. A spiral staircase leads to the lofted sleeping area.

Treehouse in Mt. Tabor

Mt Tabor Tree House, Hidden Urban Retreat

Our Mt Tabor Treehouse is an incredible and unique escape that invites you to relax and connect with nature without sacrificing any modern amenities, all in the heart of the City of Roses. Nestled underneath towering Douglas Fir trees, this fully equipped tiny house in a tree is surrounded with nature, along with immediate access to miles of mixed use trails and walking distance to one of Portland’s best restaurant, coffee shop and local market “Coquine”

FamilyKitchenBathroom

A modern garden retreat with sleek black exterior features a welcoming entrance framed by natural greenery. Concrete pathways lead to a patio area with seating, and large windows invite light into the space. The surrounding wooden fence provides privacy in a serene outdoor setting.

4.99 out of 5 average rating, 418 reviews

Award-Winning Guest House with Private Entrance

Featured in Dwell Magazine; Winner of “Best Whole House Design” by Oregon Home Magazine, this spacious urban garden retreat has one-bedroom with a luxurious king bed, full bathroom, and fully equipped kitchen. Tucked away in a tranquil urban oasis, the space is filled with natural light and boasts a private garden entrance. Wake up refreshed in the crisp, white bedroom and slide open the rustic barn door for a coffee on the patio of this zen retreat.

FamilyKitchenOutdoor spaces

5.0 out of 5 average rating, 192 reviews

Tiny home in Portland

Hawthorne Schoolhouse

Nestled between the popular and bustling streets of Hawthorne and Division in SE Portland, this tiny home provides a playful retreat. Walking distance to many shops, restaurants, bars, and cafes. Across from Sewallcrest Park and only a few blocks from Bagdad Theater and Powells Bookstore. Equipped with 80 inch 4k smart projector. Shared back yard with sauna. LGBTQA and 420 friendly. A golden retriever lives on property but please no pets.

Indoor spacesFamilyBackyard

The kitchen features navy blue cabinetry paired with white countertops and a farmhouse sink. Shelves display glassware and flower arrangements, while a gas stove adds functionality. A microwave is housed within the cabinetry, and a colorful rug provides a warm touch to the space.

4.98 out of 5 average rating, 138 reviews

NowStayingPDX-Private-Walkable-Inner SE Portland

Private one bedroom ADU in the walkable SE Division and Clinton neighborhood. Second story unit with queen bed (firm mattress) walk-in shower, and easy access to shops, food, and parks. Parents and grandparents return often for the quiet setting. The backyard sitting area is not included in the rental. There are two small dogs on the property, but they do not have access to the guest pathway.

FamilyIndoor spacesValue

4.98 out of 5 average rating, 395 reviews

An open-concept kitchen area features modern appliances and light cabinetry, complemented by a two-person dining setup with blue metal chairs. The space is accented by a patterned area rug and warm wood flooring, creating a welcoming atmosphere for meal preparation and dining.

Cottage in Laurelhurst

Deluxe 5★ Guest House ❤️ Close-in Convenience

Enjoy modern amenities and close-in convenience at our Craftsman home in historic Laurelhurst. This spacious retreat is private, easy living for business visitors, pleasure seekers, and family fun. It’s a pleasant stroll to the best restaurants and shops, plus instant access to public transport. Read our stellar reviews and book with confidence. 10 minutes to Downtown; 15 to airport

Indoor spacesFamilyLong stay

Popular amenities for Southeast Portland family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The guest home is set behind a picturesque entrance adorned with an elegant gate and carefully arranged greenery. Paved stone pathways guide visitors through the lush surroundings, leading to the welcoming facade of the home, seamlessly integrated with the tranquil, tree-lined environment.

4.99 out of 5 average rating, 611 reviews

IndigoBirch: Luxurious Zen Garden Retreat: Hot Tub

FamilyKitchenBathroom

4.86 out of 5 average rating, 900 reviews

Guesthouse in Woodstock

Romantic Casita. HotTub and Firepit. Pets Welcome!

KitchenIndoor spacesCondition

A vibrant red couch is placed against a light-colored wall, accented by dynamic artwork mounted above it. A soft white throw blankets a nearby chair, complemented by a wooden side table and a lamp casting a warm glow. Natural light enters through a window, enhancing the lively decor.

4.97 out of 5 average rating, 559 reviews

Underground Art Suite

Indoor spacesKitchenCleanliness

Guesthouse in Ladd's Addition

A compact kitchen area is situated next to a cozy seating space, featuring a black couch with decorative pillows. Modern appliances and cabinetry are visible in the kitchen, and a small dining table with high chairs is positioned nearby. Warm lighting enhances the inviting feel.

4.96 out of 5 average rating, 321 reviews

Portland at your doorstep

KitchenFamilyParking

4.91 out of 5 average rating, 148 reviews

A fire pit is illuminated in the foreground, casting warm light on the surrounding stones. In the background, a colorful sunset paints the sky with shades of orange and pink, while trees and distant hills create a serene landscape.

Home in Happy Valley

RoofTop FirePit, HotTub & Outdoor Theater

Indoor spacesFamilyAccess

4.87 out of 5 average rating, 225 reviews

An open living space features a modern kitchen with wooden cabinetry and stainless steel appliances. A cozy seating area includes a blue sectional sofa and a small lamp, while a dining table with yellow chairs is set beside a large glass garage door, allowing natural light.

Guest suite in Mt. Tabor

Parkside Urban Oasis

FamilyIndoor spacesNearby

The bedroom features a cozy bed with decorative pillows and a rattan headboard. A bedside table with a lamp and plants adds to the inviting decor. A small desk sits against the wall, providing a dedicated workspace, while natural light enters through the window, partially covered by curtains.

4.98 out of 5 average rating, 127 reviews

Boho Chic Secret Garden Suite w/Hot Tub in SE PDX

KitchenIndoor spacesNearby

4.92 out of 5 average rating, 233 reviews

Apartment in Portland

Hip & Spacious: Mt. Tabor Haven with Hot Tub!

Indoor spacesKitchenNearby

Family- and pet-friendly home rentals

Apartment in Ladd's Addition

4.9 out of 5 average rating, 552 reviews

Hip 1BR • Retro-Modern Vibes • Prime SE Spot

Indoor spacesKitchenCondition

4.94 out of 5 average rating, 341 reviews

A modern studio space features a sleek sofa positioned across from a television on a stylish cabinet. The kitchen area is to the left, complemented by a small dining table with a striped rug underneath. Natural light enters through three narrow windows above.

Tiny home in Portland

Stumptown Cottage in Eastmoreland

Indoor spacesFamilyCheckout

The exterior of a charming blue guest house is framed by greenery and decorative stones. A welcoming entryway is highlighted with two white chairs, while a wooden awning provides shade over the entrance. The path to the door is lined with pavers and gravel.

4.99 out of 5 average rating, 224 reviews

Willow Tree Guesthouse

Indoor spacesFamilyTV

4.87 out of 5 average rating, 396 reviews

Home in Portland

Color Splash - Fast WiFi - Heart of Hawthorne

KitchenFamilyParks

4.94 out of 5 average rating, 950 reviews

A spacious studio cottage is bathed in natural light. Wooden beams adorn the vaulted ceiling, while a queen size bed with a floral green coverlet occupies one side. A kitchen area, a small table, and two chairs are visible, with warm yellow curtains framing the windows.

Guesthouse in Mt. Tabor

The Cedar Cottage

KitchenFamilyAmenities

Apartment in Ladd's Addition

4.9 out of 5 average rating, 605 reviews

Stylish Hawthorne 1BR w 90 WalkScore

KitchenIndoor spacesCleanliness

Superhost

Apartment in Portland

4.79 out of 5 average rating, 776 reviews

Sunnyside Wonderland - Coffee Shops, Bars & Parks

Indoor spacesFamilyWalkability

A cozy studio space is depicted, showcasing a comfortable seating area with a neutral-toned sofa. An open kitchen with bar seating is visible in the background, alongside large glass doors leading to a fenced backyard. A television stands against the wall, ready for entertainment.

4.96 out of 5 average rating, 276 reviews

Bright, Private & Cozy with Yard

FamilyKitchenLayout

Family-friendly home rentals with a pool

Guesthouse in Southwest Portland

4.99 out of 5 average rating, 100 reviews

Cottage

FamilyKitchenCheck-in

4.97 out of 5 average rating, 393 reviews

A cozy sleeping space features a spacious bed adorned with various patterned pillows and a chunky knit blanket. A small yellow ottoman sits beside the bed, while artwork in soft colors is displayed on the light gray walls. A light rug adds warmth to the floor.

Cottage in Portland

Sellwood Sanctuary Guest House

Indoor spacesFamilyAir conditioning

4.99 out of 5 average rating, 114 reviews

A spacious living area is highlighted by a warm brown leather seating arrangement, including two armchairs and a three-seat sofa. Natural light filters through the dual windows with rolled shades, complemented by two potted plants and a contemporary area rug.

Home in Portland

Corner of Heaven

KitchenIndoor spacesDecor

Guesthouse in Northwest Portland

The guest house is set against a lush backdrop of greenery, featuring large windows that provide views of the surrounding nature. A pool is positioned in front, accompanied by two wooden lounge chairs and a shaded umbrella, creating a serene outdoor relaxation area.

4.92 out of 5 average rating, 110 reviews

Poolhouse of Portland Architectural Gem

FamilyKitchenAir conditioning

4.91 out of 5 average rating, 122 reviews

Villa in Camas

The blueberry villa spa & heated pool

Indoor spacesFamilyLayout

Guest suite in Northeast Portland

A bright yellow door welcomes guests, set against exposed brick and green wall textures. Stone steps lead up towards the entrance, framed by potted plants. The inviting doormat displays the word 'WELCOME', enhancing the cheerful entrance to the apartment.

4.95 out of 5 average rating, 126 reviews

Garden Apartment in the Heart of Portland

Indoor spacesFamilyTV

4.92 out of 5 average rating, 854 reviews

The entrance to the tiny house features a vibrant green door framed by natural wood, leading to a small porch area. A chair sits to the side, with lush greenery surrounding the property, enhancing the connection with nature.

Tiny home in Damascus

Quaint Tiny House In The Trees. Damascus, Oregon.

FamilyKitchenAmenities