Family-friendly holiday rentals in Highland Park

*Charming Studio, 3 Doors off Main+Private porch

3 doors off of Main Street, downtown Royal Oak, walking distance to everything Royal Oak has to offer. This 1924 home offers a cozy studio apartment with private entrance at the back of house. The Alfresco dining porch, perfect for enjoying the huge backyard. The fire pit is ideal for taking the chill off in this quiet, peaceful setting. In the morning, walk to BREAD by Crispellis for the best pastry in the area. Super hi-speed internet, 50" 4K Smart TV. Full suites available in the same home!

"Perfect 5-STAR” Condo in the Heart of Brush Park

(375) PERFECT 5★ reviews say it all! Airbnb recently named this boutique Brush Park condo to its exclusive "Guest Favorite" list. Centrally located between Downtown, Midtown, and Eastern Market - a lively atmosphere awaits as many of Detroit's award-winning restaurants, bars, cafes and stadiums are literally steps from our front door. We are part of a stunning residential community, with other homeowners both above and below us. Respect for those owners in the building is an absolute must.

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!

Eclectic industrial loft 5 Min to downtown

Feel the industrial vibes of Detroit in this gorgeous loft, located in a 1920's automotive factory. Some features like the wood floors, pillars and steam pipes are all original. It also has exposed brick, and tall windows letting the sun shine through Located in an industrial area near downtown and major freeways. Easily access popular Detroit locations in 3-10 min My lofts have been featured in Airbnb Magazine & Hour Detroit. I look forward to providing you a comfortable and memorable stay!

Mid-Century Modern+Secure Parking+Laundry+Walkable

Enjoy staying in a diverse neighborhood, where the textures of art, music, industry, foodie culture, and history all converge. The former attic of this historic home has been transformed into an apartment with a mid-century modern vibe and Detroit soul music memorabilia. The building is one block from the Q-Line (light rail) and two blocks from many great restaurants. Secure parking in the gated lot. Contactless self-check-in (no keys). We are available via phone should you need anything.

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.

Sky Carriage House: Light, Bright, Corktown Escape

You'll be staying in our newly constructed carriage house at the back of our property in the heart of Corktown - Detroit's oldest historic neighborhood. This private dwelling is accessed from the back alley entrance and offers high ceilings and a panoramic view of downtown and the surrounding neighborhood. The unit features 1 bedroom/1 bath, living, dining, laundry and a full kitchen. In warmer months a small cafe seating area is situated on the spanish rock drive along the green alley.

Walk to sports and concert venues! Single Price

Step out of your door and into the energy of downtown..This professionally maintained space offers the perfect home base for fans and theatre goers alike. Catch Tigers games, or watch your favorite band at one of many concert venues. After the final Whistle or the standing ovation, explore the culinary scene, featuring everything from world class restaurants to cozy hidden gem bars! Finally, retreat to a space designed for comfort. Professionally cleaned. Now with single price

Caroline Cottage

Unique one-room cottage on the bank of the Huron River. A half-mile walk to the pedestrian-friendly Village of Milford, known for its array of shops, restaurants, outside dining, concerts, and festivals. Perfect bungalow for single, couple, or small family. Living area has double sofa bed. Tiny home with many unique features. Fire pit at river's edge for relaxing or roasting marshmallows, and a gas grill on the dining patio. Two sit-in kayaks available May 15–Oct. 15.

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

This PS Grand Getaways location is an ADULTS-ONLY vacation home. We call it our "Staycation Grand". This IS NOT A PARTY HOME. Please rent a hall if needed. 10 persons max. This cozy home with a keypad gated driveway is only 10 Minutes from Downtown Detroit! It is ideal for MATURE couples or adults that need a place to get away and catch some staycation vibes! Enjoy the Detached, Heated/Airconditioned Entertainment Garage with a Hot Tub, and the firepit in the backyard!

Sunlit Ranch w/ Coffee Bar & Fenced Backyard

🌞 Sun-Filled Living Area – Relax in a cozy, well-lit space with modern decor and smart TV. 🍳 Fully Equipped Kitchen – Ideal for extended stays, with everything you need to cook like home. 📍 Prime Location – Minutes from downtown Ferndale, Royal Oak, Detroit attractions, and local dining spots. 📶 Fast Wi-Fi & Workspace – Stay connected for business or streaming. 🏡 Comfort for Everyone – Perfect for families, business travelers, and weekend getaways.

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.