Family-friendly holiday rentals in Highland Park

4.8 out of 5 average rating, 673 reviews

A cozy living space is highlighted by a patterned armchair and an ottoman, offering a relaxed seating option. The blue walls and natural light from two windows create a bright atmosphere. An electric fireplace and a wall-mounted TV add to the modern comforts.

Apartment in Midtown

1890's Midtown Townhouse

Hello! Our home is an 1890 Victorian mansion that we purchased in 2016 and lovingly renovated using a team of local craftspeople and myself. This space is a 2 bed, 2 bath that spans 2 stories with much of its original character preserved. Located in the heart of Midtown just one block from 15+ dining options, Shinola and way more. The space is designed with leisure stays, but also capable of accommodating business travelers. Coffee+Cocktails are now available downstairs, opened in 2023! 8AM-11PM

4.86 out of 5 average rating, 112 reviews

A private guest suite features a spacious bed with a dark blue coverlet, a cozy sofa, and a TV mounted on the wall. Natural light enters through large sliding doors, complemented by dark blue curtains. A small round table stands nearby, adding to the inviting atmosphere.

Guest suite in Windsor

Private/Quiet Perfect for professionals!

Discover comfort in this private guest suite w/ self-check-in and a separate entrance, located in the tranquil Southwood Lakes neighborhood. Close to golf courses and Devonshire Mall, it’s perfect for relaxation or exploring nearby amenities. Enjoy a swivel mount TV with Netflix and Amazon Prime from the cozy sofa or bed. Step into the spacious backyard with a stunning gazebo and elegant seating, ideal for unwinding. Luxury bathroom w/ supplies. Coffee bar! Book your peaceful escape today!

4.99 out of 5 average rating, 244 reviews

A comfortable living area features a stylish orange sofa and gray armchair, centered around a round area rug with a modern pattern. Natural light enters through two windows, highlighting a wooden coffee table decorated with a small plant and decorative items. A floor lamp stands nearby.

Home in Ferndale

Little Yellow House in Ferndale! Quiet, Cozy 3BR

FERNDALE FAVORITE!! Walk to downtown! All new furniture / decor, luxury bedding, memory foam beds, quartz countertops… super clean & well-cared for. This comfy, freshly updated house is on a quiet street just blocks from restaurants, bars, coffee shops & more. Centrally located w/ easy access to freeways, 10-15 min drive to other downtown areas (Royal Oak, Detroit, Birmingham). Ideal for couples, business travelers, LGBTQ+, and families with children. We also allow SMALL pets (under 20 lbs).

4.94 out of 5 average rating, 109 reviews

An inviting living space features a gas fireplace surrounded by a rustic wooden accent wall. Modern furnishings include a comfortable sofa, an armchair, and a red ottoman. A dining area and updated kitchen are visible, with natural light illuminating the wood floor.

Apartment in Windsor

Victoria Ave - 1 BR apartment w fireplace

Available for monthly rental. Not 420 friendly. No smoking of any kind in apartment or on property. Private, light filled, warm apt in a character home on prestigious Victoria Ave. Furnished in Mid-century modern and Hollywood Regency decor. Includes a queen bed, gas fire place, modern kitchen with wifi and shared laundry room. Easy free street parking. Quick drive to Detroit Tunnel. Perfect for one or two people. A short walk to Hospital - Ouelette Campus - ideal for a daytime rest.

4.89 out of 5 average rating, 149 reviews

A detached carriage house is visible, showcasing a combination of brick and wood siding with a pitched roof. Green foliage frames the entrance, while a garage door adds functionality. Seating is provided on the patio, surrounded by landscaped greenery and a view of a neighboring house.

Guesthouse in Arden Park

Historic carriage house with gated parking & patio

Kick back and relax in this calm, stylish space. You'll have a private space in a detached historic carriage house, sharing a yard with the host. We have a large yard with a patio near the carriage house, covered porch, grill, bbq pit, bocce court, and outdoor living room (summer). We have a dog that has yard access. Private, secured parking is available for 1 car. Families are welcome, as are pets. We recommend families 3+ contact us before booking to ensure the space will work for you.

4.84 out of 5 average rating, 339 reviews

An aerial view showcases the vibrant Detroit skyline at dusk, with illuminated buildings including the Little Caesars Arena. A bridge spans in the distance, and various styled blocks of housing are visible, highlighting the neighborhood's unique architecture.

Apartment in Brush Park

Quirky artist studio with a beautiful view

**Please read details about the space** My space is located 2 blocks from Comerica Park, Ford feild, and the new Little Caesars arena. One block east of the new Qline that can take you from downtown to new center. Enjoy the beautiful view of the city skyline outside every window. Its a very short walk to downtown, shopping, restaurants, transportation, and events. Prime location! NO WIFI IN UNIT Elevator access not guaranteed Keys will be left in a lockbox for your convenience

4.85 out of 5 average rating, 472 reviews

A bright kitchen features a refrigerator and a gas stove, accompanied by a wooden table with two patterned chairs. Natural light streams in through multiple windows, while colorful artwork and a potted plant add a touch of vibrancy to the green walls.

Home in Hamtramck

Uniquely designed, warm and cozy Detroit hideaway!

Welcome to our newly renovated unique home! Bordering aesthetically between steampunk chic and bohemian chill the home is filled with handmade furniture, art and a variety of features and comforts meant to both relax the body and satisfy the mind. From handcrafted silver knobs, custom built beds, lamps and other features everything was carefully built or imported from our various travels. Truly too many unique elements to list. Please let us share our home with you!

4.86 out of 5 average rating, 222 reviews

A modern loft living room features a grey sectional sofa arranged on a patterned area rug, complemented by a round ottoman. A kitchenette with wooden cabinetry is visible in the background, along with a skylight that provides natural light to the space.

Guest suite in Hamtramck

Loft close to everything

Keep it simple at this peaceful and centrally-located place. People live downstairs. Private keypad entry. Bathroom with shower. Kitchenette with mini fridge, sink, water filter and microwave. Loft living room with bedroom and full sized bed. Right off freeway. Close to downtown Detroit, equidistant to east, west side, downriver and Oakland county. Markets, coffee shops, good carry out, entertainment in walking distance. Across from park with a little backyard and deck.

Loft in Milwaukee Junction

The studio loft features exposed wooden beams and brick walls that retain the building's industrial charm. A spacious king bed is positioned next to large windows, while a cozy sofa and a coffee table provide a welcoming seating area. Bright area rug adds color to the hardwood floor.

4.84 out of 5 average rating, 1,038 reviews

Vibrant Industrial Loft *King bed* Private entry

The loft is located in a 1920’s automotive factory, and has retained some of those original elements like exposed brick, hardwood floors, wood pillars and other little details reminiscent of a Detroit’s automotive history. Located in an industrial area close to downtown and major freeways. Easily access popular Detroit locations in 3-10 min. I have been hosting people in Detroit for over a decade, and my lofts have been featured in Airbnb mag & Hour Detroit.

Guesthouse in Boston Edison East

An open-concept living area features a rustic wooden table at the center, surrounded by metal stools. A leather couch sits nearby, complemented by a patterned area rug. The kitchen, equipped with stainless steel appliances, is visible in the background, along with a laundry area.

4.85 out of 5 average rating, 123 reviews

Motown Blue Carriage House

Enjoy your getaway in this restored 2-bed, 2-bath full carriage house in Detroit’s historic Arden Park. This bright mid-century modern space has free parking, fully equipped stainless-steel kitchen, large concrete island, and full laundry. You’re 10-minutes from the heart of downtown Detroit with access to all the sports & entertainment Motor City has to offer! Bring your running shoes for a morning run through the beautiful historic neighborhood.

4.92 out of 5 average rating, 141 reviews

A living area features a grey sofa with yellow accent pillows, set against light grey walls. A wall clock is mounted on the wall, accompanied by a plant and a floral artwork that adds visual interest. A small dining table and chairs are positioned nearby.

Home in Hamtramck

Cozy 1 Bedroom Apartment 10 Minutes From Downtown

Enjoy easy access to the Metro Detroit area. 10 minutes from downtown Detroit. This centrally located, 1 bedroom unit is the perfect stay for a quick trip to the city, working from home or home away from home while exploring the city. Hamtramck is a 2-square-mile city. Small in size, but large in population and ethnic diversity. With around 22,000 residents, the city has much to offer and visit in a day.

4.98 out of 5 average rating, 244 reviews

A bright and spacious living area features a sectional couch adorned with patterned pillows and a soft throw blanket. A colorful striped rug lies beneath a modern coffee table, and light streams through sliding glass doors leading to the outdoor space.

Home in Hazel Park

The Little Hamster - Near Ferndale & RO w/ 2TVs

LOCATION, LOCATION, LOCATION! Heart of all major hubs in metro Detroit, quick access to DT Detroit, Royal Oak and Ferndale! Explore vibrant Metro-Detroit from our stylish, central home in up-and-coming Hazel Park! Sleep soundly on double & queen memory foam beds. Whip up delicious meals in the open kitchen with large island (think Eastern Market finds!). Perfect for leisure or business stays :)

Popular amenities for Highland Park family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.87 out of 5 average rating, 206 reviews

Villa in Windsor

4 Bedroom Waterfront Oasis Getaway with Hot Tub

Farm stay in Essex County

A covered outdoor seating area features a cozy arrangement of a sofa and decorative pillows, illuminated by string lights. The space is surrounded by lush greenery, with a landscaped patio and wooden railing adding to the inviting ambiance.

5 out of 5 average rating, 171 reviews

The Fir&Feather Tree Farm 1Bedroom Suite & Hot tub

4.97 out of 5 average rating, 148 reviews

An outdoor seating area is surrounded by lush greenery and illuminated by warm string lights. Four black chairs with orange cushions are arranged around a central fire pit. A patterned rug complements the space, creating a cozy ambiance as the sunset casts a warm glow.

Home in Ferndale

Hot tub + Fire pit + Luxury cozy home + Game Room

4.95 out of 5 average rating, 181 reviews

A hot tub is positioned in a well-lit corner of an entertainment area. Its water features colorful lighting reflections, creating an inviting ambiance. The surrounding walls are tiled in neutral tones, with a small rug beneath. A towel is neatly hung on a wall-mounted hook.

Home in Detroit

Adults-Only Cozy Getaway with Hot Tub (No Parties)

4.88 out of 5 average rating, 163 reviews

A well-appointed bedroom features a spacious bed adorned with decorative pillows and a light throw. A television is mounted on the wall, while a stylish dresser and a cozy seating area with a patterned chair are included. Soft lighting enhances the relaxing ambiance.

Home in Auburn Hills

Spacious Farmhouse with Breakfast - Ella's Place

4.96 out of 5 average rating, 113 reviews

A spacious backyard is presented, showcasing a hot tub situated on a concrete pad. Green grass lines the space, complemented by wooden fencing and ambient lighting. A small tree is visible in the corner, and utility lines are present in the sky against a colorful sunset backdrop.

Home in Walkerville

Modern Walkerville Gem | HotTub & Cozy Backyard

Home in White Lake charter Township

The exterior of the A-frame house is framed by lush trees, featuring a welcoming front porch and a distinct triangular roof. Inside, a spacious living area showcases large, open spaces with comfortable seating and a lofted balcony that overlooks the lower level, offering a bright and airy atmosphere.

4.95 out of 5 average rating, 212 reviews

Vintage 1964 A-frame with game room

4.97 out of 5 average rating, 138 reviews

A private outdoor patio features a hot tub surrounded by wooden fencing and a pergola. Comfortable seating is provided by two chairs, with a BBQ grill situated nearby. Natural light filters in through the overhead structure, enhancing the relaxing atmosphere.

Home in Riverside

Perfect hideaway with a hot tub and a fireplace

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 303 reviews

The exterior of the two-story property features light blue siding and a decorative gabled roof. A covered porch with a white railing and steps leads to the entrance. A wooden gate is visible to the side, providing access to the backyard.

Apartment in Walkerville

OLDE WALKERVILLE, Windsor, Ontario

4.97 out of 5 average rating, 101 reviews

The living room features a mix of pastel wall colors, including pink and blue. A modern gray sectional couch and a pink settee offer seating. A skylight brightens the space, and a decorative coffee table displays magazines and floral decor. Mirrors and playful accents contribute to a whimsical atmosphere.

Apartment in Ferndale

Downtown Ferndale- Pink Barbiecore Loft

4.93 out of 5 average rating, 139 reviews

A welcoming living area features a light grey sectional couch and a small round coffee table. Natural light filters through the windows, and a mirror hangs on the wall opposite a console table. A woven area rug adds texture to the hardwood floor.

Townhouse in Royal Oak

Cozy 2BR/1BA Steps From Downtown Royal Oak

4.94 out of 5 average rating, 116 reviews

An outdoor dining area is set with a red table and chairs under a retractable awning. The grey exterior of the lodge is framed by a manicured lawn and wooden fencing, creating a secluded and private atmosphere. Natural light enhances the inviting space.

Home in South Windsor

Luxury 2BR home with high ceilings and BBQ w/patio

4.98 out of 5 average rating, 132 reviews

The living room features a comfortable gray sofa with accent pillows, a wooden coffee table, and a patterned area rug. Natural light enters through a large window and sliding glass door, which opens to a balcony. A smart TV is mounted for entertainment, and a dining area is present.

Apartment in Canton

Bright & Cozy 1 Bdr Apt

4.88 out of 5 average rating, 195 reviews

A chic living space is highlighted by two black chairs with turquoise accents, positioned beside a small table. A counter with bar stools is visible in the background under pendant lighting. Natural light streams in through two windows with white blinds.

Bungalow in Royal Oak

Walkable Royal Oak Bungalow | Fenced Yard

4.94 out of 5 average rating, 121 reviews

A bright living room features two modern sofas facing a coffee table, with a large window dressed in sheer curtains allowing natural light. A functional bar area with stools is visible in the background, connecting to the kitchen, while light wood flooring enhances the space.

Home in Windsor

Family-Sized 3BR • 5 Beds • Near Downtown

Cottage in Madison Heights

4.99 out of 5 average rating, 141 reviews

*King bed+Pet Friendly+fenced yard*

Family-friendly home rentals with a pool

5 out of 5 average rating, 24 reviews

The heated indoor pool area is illuminated naturally by sunlight filtering through several windows. Colorful pool toys float atop the water, complementing the inviting turquoise hue. Lounge seating is positioned against the wall, with a smart TV mounted nearby for entertainment.

Home in Sterling Heights

Grandma's Family Fun House with Heated Indoor Pool

5 out of 5 average rating, 17 reviews

A private backyard oasis is featured, showcasing a heated seasonal pool surrounded by lounge chairs and vibrant rugs. Bistro lights illuminate the area against a colorful sunset backdrop, creating a tranquil atmosphere for relaxation and outdoor enjoyment.

Home in Clawson

Seasonal Heated Pool|Firepit|Walk to Parks + Eats

4.94 out of 5 average rating, 157 reviews

A spacious living area features a light-colored sectional sofa adorned with dark blue and white blankets. A rustic barn door, made of wood, adds character and leads to the bedroom. Two round mirrors are mounted on the wall, reflecting natural light.

Cottage in Lakeshore

Waterfront Luxurious Cottage in Lakeshore, Ontario

4.88 out of 5 average rating, 88 reviews

The Cedarwood Suite features a modern design with a spacious bed adorned with a patterned coverlet. A flat-screen television is mounted on the wall opposite. Natural light filters through curtains, illuminating a small dining area equipped with a table and chairs.

Guest suite in Windsor

Cozy Cedarwood Suite ☆Terrace ☆ heated salt pool

4.79 out of 5 average rating, 174 reviews

Apartment in Royal Oak

*the Michigander* Entire Queen BR suite!@MicroLux

4.83 out of 5 average rating, 107 reviews

A spacious studio apartment features a comfortable bed with crisp white linens and a cozy gray blanket. Soft lighting from bedside lamps illuminates the room, which includes a wooden dresser and armchair. An entryway is visible in the background, along with a kitchenette area.

Apartment in Detroit

Midtown Gem – Walkable & Bright Hotel Style Unit

4.92 out of 5 average rating, 118 reviews

The exterior of a two-story brick home features large windows framed by wooden shutters. A stone pathway leads to the entrance steps, which are flanked by neatly landscaped flower beds and ornamental plants in decorative pots. The entrance is inviting, with a warm color palette.

Home in Malden

The Ambassador Estate Inn