Vacation rentals with outdoor seating in Highland Park

The Pingree of Piety Hill_Home # 1

Come stay at our preserved 1912 half duplex, furnished with Detroit-honored art & literature throughout, and enriched with craftsman character & contemporary charm. Found in the peaceful Piety Hill neighborhood, so unfortunately we do NOT allow gatherings of more than 15 persons. This is a multi-family home, but ONLY YOU will have full access to the entire 1st floor and basement level of this property. The 2nd floor home will NOT be occupied during your stay; just maintenance and cleaning staff.

1890's Stone and Brick Garden Loft

Hello! Our home is an 1890 Victorian mansion that we purchased in 2016 and lovingly renovated over three years using a team of local craftspeople and myself. This space is a quirky 1 bedroom, 1 bath garden level loft with much of its original character preserved. Located in the heart of Midtown just one block from 15+ 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. Parking included

Rock House Detroit w 2 Kings Office Designer HGTV

A “magical getaway”, eye candy”, “a respite”, "the best Airbnb ever". Best porch in Ferndale. Ideal location in gorgeous historic Northwest Ferndale with unique homes and tree-lined sidewalks. Great art and rock n roll/eclectic decor. A few blocks to shop, pick up food, dine at one of our many foodie destinations (1/2 mile/8 min walk). Pilot episode HGTV’s “What You Get For The Money”, SEEN Magazine’s “5 Cool Detroit Airbnb’s”, interior design cover story “Detroit News Homestyle” magazine 3x!

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.

Walkerville Loft (Main floor unit)

Welcome to our charming loft nestled in the heart of a Walkerville in Windsor. This thoughtfully designed space combines modern comfort with historical charm. Perfect for couples or solo travelers, our cozy loft features fire place, high ceilings, and large windows. Enjoy the convenience of being centrally located, with iconic landmarks, local shops, and vibrant cafes just steps away. Immerse yourself in the city's rich history during the day and unwind in this stylish retreat at night.

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 and Zen garden in the backyard!

Lagom Living - 5min walk from energetic DT RO

*All bookings after 9/15/25 : ENJOY A NEWLY REMODLED BATHROOM!* Enjoy your visit to Royal Oak in our open and comfortable one bedroom apartment; just a 8 minute walk from downtown Royal Oak full of a variety of restaurants, bars, entertainment, coffee shops and more! Short or long stays welcome! Quiet walkable neighborhood close to many parks. Close to Royal Oak Music Theater, Royal Oak Beaumont, The Detroit Zoo, Downtown Detroit and freeways.

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 :)

Aveline's Abode - N. Corktown

Nestled in North Corktown, this newly renovated home is absolutely charming. Centrally located near Corktown, Downtown, and Midtown, you'll be close to amazing cafes, bars, restaurants, and venues. The design-focused home features an expansive ensuite primary bathroom, 10' & vaulted ceilings, private backyard, patio, and off-street parking. Perfect for a romantic getaway or special occasion!