Family-friendly holiday rentals in Highland Park

4.87 out of 5 average rating, 726 reviews

Apartment in Midtown

Victorian 1890's Midtown Home

Hello! Our home is an 1890 Victorian mansion that I purchased and lovingly renovated with a small team of local craftspeople. This space is a 1 bed, 1 bath with much of its original character preserved! Located in the heart of bustling Midtown just one block from 20+ bars and restaurants, DMC, Shinola and way more! The space is designed with leisure stays in mind but also capable of accommodating business travelers comfortably. Just opened in 2023, Coffee + Cocktails downstairs! Open: 8AM-11PM!

Superhost

A cozy studio space is displayed, featuring a comfortable bed with light bedding. A television is mounted on the wall, and two patterned chairs sit across from a small table. A floor lamp provides soft lighting, while a compact storage area holds towels and linens.

Apartment in North End

4.92 out of 5 average rating, 215 reviews

Cute & Cozy North End Studio

Welcome to Detroit’s North End! We are located minutes away from major freeways, Wayne State, Henry Ford Hospital, Little Caesars Arena, Ford Field, Comerica Park and more! Shops and restaurants are nearby. Hop on the Q Line to head Downtown or grab a city bike/scooter! If your plans take you far away, grab a car. This is the Motor City, after all. The North End is a neighborhood that is in transition. Here you will see the city’s history as well as its bright future. Come book with us today!

4.89 out of 5 average rating, 143 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.

4.89 out of 5 average rating, 107 reviews

A cozy kitchen area is highlighted by wooden cabinetry and modern lighting fixtures. A wooden dining chair is positioned near a warm wooden island. A calendar hangs on the wall alongside decorative items and a plant, contributing to the home's welcoming atmosphere.

Home in Hazel Park

Cozy Lovley Little Home!

Our place is a cute home in an up and coming, very safe community. We actually live here full time, and AirBnB it while traveling. WiFi is available. Kitchen is at your disposal. There is a dedicated workspace in the study. Yes, a whole room just for that. And of course a big tv to relax at night, unless you chose to go out and explore local nightlife! Please note that due to certain restrictions we are exempt from hosting guests with dogs or cats even if they are service animals.

4.85 out of 5 average rating, 464 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!

4.88 out of 5 average rating, 209 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 smart entry. Bathroom with shower. Kitchenette with mini fridge, sink, water filter and microwave. Loft living room with bedroom and full size 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.

4.97 out of 5 average rating, 158 reviews

A bright studio space features a queen bed with a colorful accent wall and a blue sofa bed. A wooden dining table is set with plates and rose decorations. Light fixtures create a warm ambiance, while mirrors and artwork enhance the decor.

Apartment in Henry Ford

Work/Play Base: Park Free, 10mins DTWN, Fast WiFi

Hey there, welcome to your cozy Midtown Detroit studio—your perfect home base for work or play. Unwind in style with plush furnishings, a comfy queen bed, and a full-size sofa bed for extra R&R. You’re super close to Henry Ford Hospital, Comerica Park, Ford Field, and the iconic Motown Museum. Need a break? Explore the Detroit Institute of Arts or Eastern Market, or grab a bite at Selden Standard. Work hard, explore harder—your Motor City stay starts here! 🚗✨

A spacious living area features a dark sectional couch, a white coffee table, and a TV stand with a flat-screen television. Soft lighting is provided by a floor lamp, while wall art and plants add a touch of color and warmth to the neutral-toned walls.

5 out of 5 average rating, 200 reviews

Little House on Laprairie

This cozy 1 story, 2 bedroom 1 bathroom bungalow has been recently renovated (2022) with all new appliances and updated finishes. A short walk to downtown Ferndale is where you’ll find plenty of shops, restaurants, coffee houses and bars. Downtown Detroit is 11 miles away and a quick 15 minute drive. Our home is perfect for couples, small families, business travelers and LGBT travelers. The large fenced backyard is perfect for your house trained dog.

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.

4.88 out of 5 average rating, 119 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.

4.95 out of 5 average rating, 139 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, 233 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 :)

4.88 out of 5 average rating, 122 reviews

A living area features a large blue sofa set accompanied by an ottoman, all placed on a light-colored area rug. A round dining table with chairs occupies one corner, while a wall-mounted television is visible across the room. Light enters through large windows.

Apartment in Midtown

VeMas Motown Retreat

Right in the heart of Downtown Detroit. The whole group will enjoy easy access to everything from this centrally spacious apartment. Walking distance to all Museums, Art Galleries, Stadiums/Arenas, Bars, Lounges, Prime shopping strip, and so much more. *1 bedroom, but can accommodate additional beds. Please ask.

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

4.97 out of 5 average rating, 155 reviews

A dining nook features a wooden table surrounded by four soft gray chairs. A bottle rack holding several wine bottles is mounted on the wall. Natural light filters in through a nearby window, complemented by decorative plants and a circular mirror.

Home in Berkley

The Pride of Berkley

4.84 out of 5 average rating, 189 reviews

A stylish living area features a modern electric fireplace beneath an elegantly detailed mantle. Natural light enters through a large window adorned with sheer curtains. A chandelier hangs from the ceiling, complementing a light-colored tufted sofa and accompanying chair.

Condo in Royal Oak

*Victoriana* - Entire upper King suite@MicroLux

Cottage in Waterford Township

A bright sunlit dining area features a table set with a colorful tablecloth. Breakfast items are arranged alongside a bowl of fresh fruit. Large windows offer a serene view of the lake, enhancing the inviting atmosphere of the space.

4.99 out of 5 average rating, 380 reviews

Hot Tub Kitch Lake Fireplaces Late Ck Out at GSL

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, 164 reviews

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

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.

4.96 out of 5 average rating, 141 reviews

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

4.95 out of 5 average rating, 172 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)

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, 205 reviews

Vintage 1964 A-frame with game room

4.93 out of 5 average rating, 401 reviews

A serene outdoor space features a salt-water pool surrounded by lush greenery, lounge chairs, and shaded seating areas. Natural stone accents are present near the water's edge, with steps leading up to a covered patio area. Tree silhouettes frame the background, enhancing the tranquil setting.

Guest suite in Windsor

Lakeshore Hidden Oasis (heated pool / jacuzzi)

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 294 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

A stone house is nestled among lush greenery, featuring a facade adorned with climbing vines and flowering plants. The inviting porch is illuminated by warm lights, creating a serene atmosphere. Surrounding foliage enhances the natural setting of this unique home.

4.99 out of 5 average rating, 252 reviews

Rock House Detroit w 2 Kings Office Designer HGTV

4.93 out of 5 average rating, 134 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

4.93 out of 5 average rating, 106 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, 122 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

The exterior of a charming brick home features a red door framed by large green shrubs. The surrounding lawn is neatly maintained. A cyclist is seen riding past, adding a sense of activity to the tranquil neighborhood setting.

4.96 out of 5 average rating, 113 reviews

Peaceful Pretty Art and Cinema Reclining Couches

A well-appointed bedroom features a queen-sized bed with a tufted orange headboard and crisp white bedding. Flanking the bed are two nightstands, each with a soft-glow lamp. Three textured wall art pieces in earthy tones add visual interest, complemented by a large window allowing natural light.

4.89 out of 5 average rating, 159 reviews

Park Side Studio-Pets Welcome!

Superhost

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

4.94 out of 5 average rating, 116 reviews

3BR Home Near Downtown w/ 5 Beds & Finished Basmnt

Family-friendly home rentals with a pool

5 out of 5 average rating, 14 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, 154 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

4.99 out of 5 average rating, 110 reviews

Barn in Kingsville

Cozy Forest Retreat w/ Sauna + Event Space

Superhost

The living area features a comfortable gray sofa and accent chairs in blue, arranged to foster conversation. A wall-mounted television is positioned for easy viewing, while a light-colored area rug adds texture. The space is brightened by natural light from the room's lighting and neutral paint.

Apartment in Rochester Hills

4.71 out of 5 average rating, 24 reviews

Peaceful & Trendy Unit Near Attractions

4.89 out of 5 average rating, 87 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

Loft in Village of Clarkston

A cozy sleeping area features a spacious bed dressed in a patterned quilt with neutral tones. Light filters through a nearby window, illuminating the soft, beige carpet. A nightstand is positioned beside the bed, creating a functional and relaxing space.

4.9 out of 5 average rating, 83 reviews

The Loft @ the Wickson Farmhouse

5 out of 5 average rating, 5 reviews

A spacious living area features a comfortable sofa and loveseat, complemented by decorative pillows. A wooden coffee table sits in front, with a remote control placed on top. Nearby, a dining table with four chairs is visible, alongside bar stools positioned at a countertop.

Apartment in Tecumseh

Impressive Furnished All-inclusive Apartment