Family-friendly holiday rentals in Harbor Springs

4.97 out of 5 average rating, 193 reviews

A bright and open kitchen features a white island with bar stools, stainless steel appliances, and modern fixtures. Skylights allow natural light to fill the space, highlighting the warm wooden ceiling and floor. A cozy seating area is included with a green couch near a wooden side table.

Loft in Harbor Springs

The Bird’s Nest

Welcome to the bird’s nest! A cozy open floor plan loft overlooking Main St. in the heart of downtown Harbor Springs. Built in 1881, this is one of the first structures built in Harbor Springs! Loaded with historical charm and character, and meticulously updated, this space lends itself to romantic dinners on the back deck or entertaining around the large kitchen island The property has been updated and offers modern amenities to include: new appliances, wi-fi, smart TV, and Sonos sound system.

KitchenIndoor spacesBeach

4.98 out of 5 average rating, 200 reviews

An A-frame cabin surrounded by vibrant autumn foliage, featuring an outdoor fire pit with two chairs positioned nearby. Pumpkins are scattered throughout the naturally landscaped area, adding a seasonal touch to the serene setting. The cabin's warm windows hint at comfort inside.

Chalet in Harbor Springs

Cozy Aframe on Tunnel of Trees Harbor Springs

Cozy A-frame perfectly located minutes from downtown Harbor Springs. Nestled in the trees across from a nature preserve so you get that “cabin-in-the-woods” feel while being close to everything the area has to offer. Perfect homebase for “Up North” adventuring: •5 min from downtown Harbor Springs •20 min from Petoskey •40 min to Mackinaw •10 min to Nubs Nob/Highlands •5 min to Tunnel of Trees M-119 Home Features: •2 bdrms w queen beds •Indoor & Outdoor firepit •Stocked kitchen •Front/back deck

Indoor spacesFamilyLocation

4.92 out of 5 average rating, 132 reviews

The Nature Retreat - NEW hot tub & piano

A unique experience for people who appreciate the simple things of life - like nature, a good book and music. Located in a peaceful neighborhood near the Tunnel of Trees, Pond Hill Farm, downtown Harbor Springs, 8 minutes to Boyne Highlands and other top northern Michigan attractions. LUXARY HOT TUB INSTALLED JULY 2025. Upright piano and ukulele. House = approx. 2,800 sq. ft. You must let us know if you would like to bring 1 dog or an 8th person. Guests must be comfortable with stairs.

FamilyKitchenCheckout

Apartment in Harbor Springs

The kitchen features modern white cabinetry and updated whirlpool appliances. A wooden dining table with blue placemats is positioned in the foreground, complemented by white chairs. Bright light is provided by overhead fixtures and a nearby window, contributing to an inviting atmosphere.

Lake Street Retreat - In town Harbor Springs

This Lake Street apartment is a one of a kind. The apartment is partially above commercial businesses, including your host, The Harbor Barber (no chemical services offered - so no funky odors from below). This space was 100% improved in 2021. The property is a short walk/bike-ride from the bike path, and iconic downtown Harbor Springs, the Lyric theatre, a dog beach, a bathing beach and so much more. Your host freely shares his knowledge of the history and current events happening around town.

Indoor spacesKitchenSleep quality

4.95 out of 5 average rating, 151 reviews

4.97 out of 5 average rating, 126 reviews

The exterior of the cabin showcases a rustic stone chimney alongside wooden siding. A deck area features a table with an umbrella and a BBQ grill. Surrounding trees provide a natural backdrop, while large windows offer views into the inviting interior.

Cabin in Harbor Springs

Little Moose Lodge overlooking Lake MI

Breathe in the tranquility that only comes from being surrounded by nature. With Lake Michigan in front and woods in back you get the best of both worlds during your stay at Little Moose Cabin. We are located on M119, the historic "Tunnel of Trees" highway less than 20 mins from Harbor Springs, The Highlands Resort, Nubs Nob Resort, and 45 minutes from Mackinaw Bridge. This classic 2 -bedroom 1 bath cabin has a woodstove, outdoor firepit, BBQ grill, and access to a private beach on Lake Mi.

KitchenIndoor spacesQuiet

Superhost

The two-story home is framed by a well-maintained lawn and surrounded by greenery. Soft outdoor lighting illuminates the spacious porch, inviting relaxation. A stone path leads to the entrance, while trees provide a natural backdrop to the charming exterior.

4.81 out of 5 average rating, 108 reviews

Harbor Retreat |Private Hot Tub|Game Room|Ski+Golf

Relax and getaway with friends and family at our peaceful, charming 5BR home. Sitting upon a hill just 4 mins outside of Harbor Springs, you can enjoy the serene feelings of the countryside while being just minutes from the city. Ample space for comfortability while enjoying family memories together. Equipped with a full game room, hot tub, fire pit and more to accommodate family fun. Harbor Springs-4mins Boyne Highlands-7mins Nubs Nob-9mins Petoskey state park-12mins Tunnel of trees-11mins

KitchenFamilyBarbecue

A comfortable living area features a dark brown sectional sofa with decorative throw pillows. A wooden coffee table is centered in front of a cozy fireplace with a stone surround. Large windows provide a view of the outdoor space, complemented by light-colored curtains.

4.98 out of 5 average rating, 100 reviews

***NEW!*** Relaxing Retreat with Amenities Galore!

Immerse yourself in the rustic serenity of Northern Michigan while enjoying the modernized amenities that this newly listed location offers. Relish in the relaxing comforts of home, including an open floor plan, well-appointed full kitchen, master bedroom with a spacious attached bath, washer/dryer, outdoor patio, and a warm fireplace for those snowy nights. The many amenities include indoor/outdoor pools, hot tubs, pickleball, tennis, fitness center, fishing ponds, hiking trails and more!

FamilyIndoor spacesParking

A spacious multi-level condo is nestled among the trees, featuring large windows that provide ample natural light. A wooden deck extends from the main structure, furnished with chairs for outdoor relaxation. The design reflects a modern aesthetic, blending harmoniously with the surrounding nature.

4.88 out of 5 average rating, 128 reviews

Coveside Retreat: Beach, Pools, Hiking, Skiing

This large, end-unit 5-bedroom, 3 bath condo is great for large families or gatherings of friends at Harbor Cove. Tucked into the woods with nature trails to hike, sandy lake Michigan shoreline and indoor/outdoor pools. Close to golf courses and wineries. 5 miles from Boyne Highlands and Nubs Nob, for winter enthusiasts who enjoy skiing and snowboarding. A short drive, or bike ride to downtown Harbor Springs and Petoskey for dining, movies and shopping. Note this is not a party house!

FamilyKitchenSleep quality

The exterior of the home features a light-colored facade with green shutters, surrounded by lush greenery and trees. A welcoming staircase leads to a front entrance, which is adorned with an American flag. The front yard is spacious, with well-maintained grass and landscaping.

4.94 out of 5 average rating, 103 reviews

Cozy retreat near local resorts, skiing/golf

Located just two minutes away from The Highlands and Nubs Nob ski/golf resorts, and only ten minutes away from the beautiful downtown shopping districts of both Harbor Springs and Petoskey, this charming Northern Michigan getaway is fully stocked for your vacation! This home away from home is fully outfitted to make your stay as comfortable as possible. We have also taken great care to ensure that it is one of the cleanest and tidiest homes available to you. Thank you for your consideration!

KitchenIndoor spacesLaundry

Apartment in Harbor Springs

An outdoor patio area features a gravel surface, surrounded by planters with vibrant flowers. A fire pit is centrally located, accompanied by several seating options in various colors. A grill stands nearby, with expansive green fields visible in the background under a clear sky.

Harbor Springs Farm Apartment

A recently remodeled lower level apartment on a farm in Harbor Springs. Located just miles from downtown, Lake Michigan, world class skiing and golf, biking and hiking trails, this is the perfect home base for any adventure. Enjoy breathtaking views of the sunrises and sunsets on the farm out the panoramic windows. We do live upstairs and you will be able to hear us through the floors. The entire apartment is private, with your own driveway, entrance, kitchen, bathroom, and living space.

KitchenFamilyPool

4.84 out of 5 average rating, 198 reviews

A cozy living room features a plush sofa adorned with decorative pillows. A patterned area rug adds warmth to the space, while a low coffee table is centered beneath an inviting lamp. A flat-screen TV is positioned across from the seating area, and stairs lead to the upper level.

4.98 out of 5 average rating, 128 reviews

The House Next Door: In-Town Harbor Springs

The House Next Door is a vintage-chic modern cottage in the heart of Harbor Springs. Nicely designed throughout, perfect for staying in or to be your home base for endless local activities, many without getting in your car. 8 minute walk to waterfront, restaurants and shopping. Minutes from hiking, biking, beaches. 10 minute drive to ski/golf resorts. A block back from the bluff, close to the hustle of our busy resort town but separated enough for peace and quiet and sounds of nature.

FamilyKitchenLocation

Guest suite in Harbor Springs

A gray house with a metal roof is framed by lush greenery and flowering shrubs. Windows are adorned with plants, while a wooden trellis adds an element of structure to the surrounding natural landscape.

Guest Suite near Cross Village

Enjoy summer days or wintry splendor. We are located in a rustic area of northwest Michigan, 15 miles north of Harbor Springs, within 2 miles of the Tunnel of Trees. We are conveniently located for nature preserves, hiking trails, beautiful beaches, ski slopes, and Mackinaw Island. Our home is attached to the guest suite but guests access their suite via a secured private entrance. Our equipped kitchen has a pantry, fresh farm eggs, butter, a home-baked item, ground coffee, and teas.

FamilyKitchenQuiet

5.0 out of 5 average rating, 223 reviews

Popular amenities for Harbor Springs family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The living area features a cozy sofa placed near a fireplace, with a large window allowing natural light to fill the space. A dining table with wooden chairs is positioned in the foreground, complemented by decorative artwork on the walls.

4.91 out of 5 average rating, 110 reviews

Relaxing Getaway in Harbor Springs!

KitchenIndoor spacesHiking

4.86 out of 5 average rating, 122 reviews

Resort – Pool (Indoor & Outdoor), Sauna & Fun!

Indoor spacesKitchenTV

4.84 out of 5 average rating, 252 reviews

The chalet's exterior is framed by lush greenery, showcasing a striking A-frame structure with large windows. The natural wood tones blend harmoniously with the surrounding trees, creating a serene woodland setting. A hint of a deck is visible beyond the foliage.

Chalet in Harbor Springs

Harbor Springs Vacation Rental-outdoor Hot Tub

FamilyIndoor spacesOutdoor spaces

The exterior of the end unit is presented, featuring a neutral-colored façade and a pathway leading to the front door. An American flag is displayed on the building, surrounded by lush greenery and well-maintained landscaping. Windows offer glimpses of the interior, enhancing the inviting appearance.

4.91 out of 5 average rating, 146 reviews

Spacious End Unit ~ Near Skiing, Indoor Pool

FamilyIndoor spacesOutdoor spaces

A spacious living area features two comfortable gray sofas adorned with yellow pillows and a central wooden coffee table. Large windows provide natural light, and a ceiling fan adds to the room's ambiance. Natural wood accents enhance the inviting atmosphere.

4.96 out of 5 average rating, 118 reviews

Cozy 5-Bed, 3-Bath Retreat 5 Min to Dwtn. Petoskey

Indoor spacesKitchenHot tub

4.86 out of 5 average rating, 189 reviews

A serene beach area is presented with several lounge chairs arranged along a sandy shore, facing a calm lake. A solitary tree provides shade, while gentle waves ripple in the distance under a clear sky.

Condo in Petoskey

Rare Beachfront Condo on Pvt Round Lake Petoskey

Indoor spacesKitchenSkiing

4.96 out of 5 average rating, 126 reviews

The exterior of a modern cabin is showcased, featuring a wooden façade with a dark metal roof. A single, black front door is framed by two windows. A small wooden porch leads to the entrance, enhanced by decorative rocks and greenery on either side.

Cabin in Petoskey

Hidden Acres- Austur Cabin- Close to town- Hot Tub

KitchenFamilyBackyard

Superhost

4.85 out of 5 average rating, 118 reviews

Modern Home of Style & Comfort | Private Hot Tub!

Indoor spacesFamilyAmenities

Family- and pet-friendly home rentals

Guest suite in Harbor Springs

A welcoming living area features a comfortable brown leather sofa paired with a cozy armchair. A wooden coffee table sits in front, and a flat-screen TV is mounted on the wall. Natural light enters through a window, enhancing the simplicity of the space.

Private 2BR Loft in Harbor Springs

FamilyIndoor spacesComfort

4.99 out of 5 average rating, 200 reviews

4.98 out of 5 average rating, 236 reviews

Tiny home in Boyne Falls

Tiny Farm Stay * 5 Min to Boyne Mountain

Indoor spacesKitchenSkiing

4.82 out of 5 average rating, 102 reviews

A charming wood-clad entrance features a welcoming front door with a tasteful wreath. A stone pathway leads to the porch, flanked by a lush green lawn and flower pots, inviting visitors into a cozy, alpine-inspired chalet.

Chalet in Harbor Springs

Gem of a Chalet - Walking distance to Nubs Nob

KitchenIndoor spacesBackyard

The house is viewed from above, showcasing a split-level structure with a brown roof. Surrounding it are well-maintained lawns and mature trees. The distant horizon features Little Traverse Bay under a partly cloudy sky, enhancing the serene neighborhood setting.

4.92 out of 5 average rating, 142 reviews

Petoskey’s “Peeks of the Bay”

FamilyKitchenSleep quality

4.9 out of 5 average rating, 204 reviews

A single-story country house is showcased against a backdrop of tall pine trees. The exterior features light-colored siding and a green metal roof. A well-maintained grassy area with patches of snow surrounds the house, creating a serene rural setting.

Home in Brutus

Rustic country home

Indoor spacesKitchenBackyard

4.85 out of 5 average rating, 465 reviews

A bright kitchen area is presented with white cabinetry and appliances, featuring a stove with an oven, a refrigerator, and a sink. Natural light floods the space through large windows, illuminating a dining table with four chairs, set against a view of the surrounding landscape.

Home in Levering

The Little House ~ Near Mackinac Island

KitchenIndoor spacesAccuracy

A cozy living area is furnished with a large gray sectional sofa, accented by decorative pillows. A wooden coffee table sits in the center, showcasing a small potted plant. A dining table with chairs is visible in the background, along with a water dispenser and colorful wall art.

4.94 out of 5 average rating, 287 reviews

Cozy Getaway! 2 Queen Beds/2 twin fold-ups

FamilyIndoor spacesWi-Fi

4.95 out of 5 average rating, 189 reviews

An outdoor seating area features four navy blue Adirondack chairs arranged around a circular fire pit, surrounded by a lush green lawn. Nearby, a small shed and blue kayaks are visible, set against a backdrop of trees and a cloudy sky.

Home in Alanson

Northern Michigan Getaway (Petoskey/ Harbor)

Indoor spacesKitchenLong stay

Family-friendly home rentals with a pool

Guest suite in Harbor Springs

A modern home is set on a forested hillside, surrounded by bare trees and a gentle slope. The structure is constructed from stone, with a multi-level appearance, and is positioned away from the road, providing a sense of seclusion.

Harbor Springs hilltop home.

Indoor spacesKitchenDecor

4.98 out of 5 average rating, 129 reviews

4.98 out of 5 average rating, 171 reviews

The outdoor area features a private hot tub with illuminated water, surrounded by trees. A wooden deck leads to a fire pit area with seating and a propane grill nearby. The serene lake reflects the surrounding nature, creating a peaceful ambiance.

Cottage in Gaylord

Lakefront Cottage: Hot Tub, Pool, Fire Pit, Kayaks

FamilyIndoor spacesTV

4.96 out of 5 average rating, 255 reviews

Chalet in Gaylord

Bear’s Den ~ Hot Tub, Kayaks, Skiing, Pet & Trails

KitchenIndoor spacesCleanliness

4.98 out of 5 average rating, 179 reviews

A striking log lodge is showcased with large windows reflecting the sunset. The spacious front deck is lined with loungers, while lush greenery surrounding the property adds a natural touch. The well-kept lawn enhances the outdoor space, creating a serene atmosphere.

Cabin in Traverse City

Luxury Lodge overlooking both Grand Traverse Bays.

FamilyKitchenAccess

4.98 out of 5 average rating, 176 reviews

Cabin in Boyne Falls

Modern Cabin-Mtn Views-Hot Tub-Pool-Game Room-Pets

KitchenIndoor spacesLaundry

4.98 out of 5 average rating, 102 reviews

The chalet stands among lush trees, featuring a wooden deck that wraps around the structure. Large windows create an open feel, allowing natural light to flood the interior. Outdoor seating is arranged on the deck, enhancing the connection with nature.

Chalet in Bellaire

Chalet | Shanty Creek | Golf | Torch Lake | Pool

KitchenIndoor spacesLong stay

A modern kitchen is equipped with commercial-grade appliances and a large island surrounded by high-backed chairs. Natural light illuminates the space, highlighting the cabinetry and decorative accents. The layout promotes an inviting atmosphere for cooking and gathering.

5.0 out of 5 average rating, 89 reviews

Harbor Cove-Northern MI Bliss-Pool-Private Beach

Indoor spacesKitchenPool

A spacious backyard patio features a circular arrangement of six wooden lounge chairs surrounding a firepit. Lush greenery and flowering shrubs provide a natural backdrop, while a neatly paved stone pathway leads to the setup.