Family-friendly holiday rentals in Gaylord

4.9 out of 5 average rating, 137 reviews

An aerial view captures the cottage surrounded by vibrant autumn foliage, with the tranquil lake reflecting colorful trees. The peaceful water is dotted with islands, enhancing the picturesque landscape, inviting outdoor exploration and relaxation.

Cottage in Gaylord

Iconic 5Bd Lakefront Cottage w Hot tub & Kayaks

Large family-friendly luxurious cottage sitting right on the shores of private Five Lakes w/ all seasons breathtaking views & clear water. Enjoy swimming, fishing, kayaking, and ice fishing on-site. Minutes from downtown attractions, golf resorts, snowmobiling, snowshoeing, and a short drive to Boyne Mountain Ski Resort & up north attractions. Cozy bedrooms, modern kitchen, dining room, comfortable living room, large deck, fire pit, gas grill, Billiard table & HOT TUB with gorgeous lake viewing.

Indoor spacesFamilyAccess

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

Welcome to Greenhouse Cottage! Relax in this lakefront home on all-sports Buhl Lake! This home is newly updated, professionally decorated & ready to host your favorite travel memories. Just under 20 min from Treetops & Otsego and under 30 min from Boyne & Schuss ski resorts for all your downhill thrills! Trail 4 Access. Mod furniture, hot tub, wood stove, fire pit, kayaks, paddle board, outdoor heated pool (Summer only), and ATV Trails await. Your ideal home away from home is waiting for you!

Indoor spacesKitchenHot tub

A two-story lodge style home is framed by lush greenery, featuring a wraparound deck with a warm wooden railing. A private balcony is visible on the upper floor. The exterior showcases a combination of natural stone and wooden siding, complemented by expansive windows.

4.93 out of 5 average rating, 113 reviews

Stunning Cabin - Arcade & Pickleball - sleeps 13

Welcome to Porcupine Lodge, relax with the family or enjoy some time away with your friends! Located 1 mile into Michaywé golf community and 12 minutes from Downtown Gaylord, our cottage provides ample privacy with empty lots on both sides, but easy access to 17 golf courses, 2 ski resorts, miles of snow mobile trails, along with dozens of bars and restaurants. Enjoy the multiple entertaining areas, brand new kitchen, natural gas grill and the Michaywé indoor/outdoor pools, hot tub and sauna.

FamilyKitchenOutdoor spaces

A serene lake view reflects vibrant autumn foliage and trees along the shoreline. The calm water mirrors the colorful landscape, creating a peaceful atmosphere. Clear blue skies complement the natural scenery, enhancing the tranquil setting of Kassuba Lake.

4.94 out of 5 average rating, 158 reviews

Kassuba Lake Retreat

Just minutes from Treetops Golf Resort, with hiking trails, fishing, & outdoor recreation nearby, our air conditioned lakefront ranch overlooks peaceful Kassuba Lake & sleeps six. Inside you'll find a king bedroom, a bunk room with two twin-over-full bunks, a full bath, and a stocked kitchen. Large windows fill the space with natural light. After a day of golfing, swimming, boating, or exploring, relax with a 58" Smart TV, HDMI hookup, DVD player & WiFi-perfect for a 4 season Up North getaway.

KitchenFamilyLayout

The A-frame cabin features a striking blue exterior and large windows that invite natural light. Surrounded by trees displaying autumn colors, the cabin sits on a grassy lot, enhancing the serene, wooded setting.

4.97 out of 5 average rating, 470 reviews

Hephzibah’s Haven: Up North cabin with Lake Access

Hephzibah's Haven is a cozy A-frame cabin in the heart of Northern Michigan. It is nestled in a neighborhood of cabins by Otsego Lake. Despite the vintage decor, the cabin offers modern conveniences and a great kitchen! Regardless of which season and level of adventure you are seeking, you will find Hephzibah's Haven to be a great home-base for your time Up North. Guests will have access to Otsego Lake, and all of the Northern Michigan favorites are within 45 minutes to 1.5 hours away!

Indoor spacesFamilyAmenities

A spacious living area features a comfortable gray sectional sofa paired with a blue accent chair. A round coffee table sits center stage on a decorative area rug. A large mirror hangs on the wall, reflecting natural light, while a dining area with a table is visible in the background.

4.94 out of 5 average rating, 185 reviews

Beautiful Sonshine Corner

Escape to serenity in this rental home located in the countryside less than two miles from Treetops and Otsego Resort, both offering premier skiing and golf. It is also walking distance from Sonshine Barn Wedding & Event Center, and has a three-mile access to shopping and restaurants. Includes: - Grill - Horse shoes - Ping pong table - Pool table - Fully stocked kitchen - Washer & dryer - Attached garage - Heat & A/C - Back deck with furniture - Bonfire pit with chairs and wood provided

FamilyIndoor spacesAccuracy

4.9 out of 5 average rating, 235 reviews

Happy Trails Haus, Lakeview Cabin for Fall Colors

Step into natures playground in Gaylord Michigan. This three bedroom one bath cabin is located steps to beautiful Otsego lake with access across the street where you can swim, fish or try out kayaking! With a cozy up north cabin feel you also have the amenities of home with Wi-Fi for streaming, a full kitchen, washer & dryer, and downtown Gaylord just a 9 minute drive away! There is an abundance of golf courses close by with some just up the road: Michaywe Pines, The Ridge, and The Loon!

KitchenIndoor spacesHospitality

An early autumn scene captures vibrant red and orange leaves on tall trees beside a peaceful lake. A cottage with a welcoming facade is visible, alongside a wooden deck and swing set. An American flag gently flutters against a clear blue sky.

4.82 out of 5 average rating, 152 reviews

Cottage 7 | Cozy Cabin for Two on the Lake

Fresh remodel - May 2025! Welcome to Cottage 7 on Heart Lake. This has 1 bed/1 bath accommodating up to 2 guests. The cottage includes a full kitchen stocked with all cookware, silverware, and dining utensils. In the summer guests will have access to shared kayaks, canoes, paddle boards, water trampoline, swim platform, and bonfire pit. In the winter, guests can access Trail 7, directly across the road, for snowmobile season. It's the perfect place for your northern Michigan getaway!

KitchenIndoor spacesAccess

4.8 out of 5 average rating, 223 reviews

The Main House

Welcome to The Main House. Location is everything when it comes to getting around Northern Michigan. Centrally located in Gaylord, quick access to local golf/ski resorts, short drive to many up north tourist activities, and even perfectly located in our Alpine Village. Walk to downtown and enjoy Gaylord's night life. Tastefully updated 5 bedroom home perfect for large groups and families. Enjoy our outdoor spaces as well, fenced back yard, large porches and beautiful flowers.

FamilyIndoor spacesAccess

4.99 out of 5 average rating, 183 reviews

Cabin in Johannesburg

True Nature Lodge | 10 Acres | Hot Tub | Groups

Private log-and-stone lodge on 10 secluded acres, 15 minutes from downtown Gaylord, Treetops golf course, and Otsego Resort and ski slopes. Ideal for groups, wedding guests, reunions, ski trips, ORV weekends, couples, families, and peaceful retreats. Sleeps 20, with hot tub, huge private yard, pond and stream, wide wooded trails, unique games and activities inside, and a fun, relaxing up-north feel. Weddings and family reunions welcome with prior approval. No ‘parties’.

KitchenIndoor spacesAccuracy

4.96 out of 5 average rating, 256 reviews

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

Leave your worries behind at this spacious and charming 3-bedroom chalet, set on a peaceful lake with a private outdoor hot tub. Just 6 miles from downtown Gaylord, this Alpine retreat is perfect for year-round family fun. Spend your days kayaking, swimming, fishing, or barbecuing on the deck, then unwind on the dock or soak in the hot tub as the sun sets over the water. Whether summer adventures or snowy getaways, this lakefront chalet is the perfect Up North escape.

Indoor spacesKitchenPool

4.99 out of 5 average rating, 105 reviews

A spacious deck overlooks Kassuba Lake, shaded by a large umbrella. Seating options include a wicker sofa with soft cushions, and five metal chairs arranged around a small table. A round area rug lies on the wooden floor, adding comfort to the outdoor setting.

Cottage in Gaylord

Scenic Lakefront Near Town w/Hot Tub and Lake Toys

Experience winter Up North at Blue Pearl Cottage on quiet Kassuba Lake! Your prime basecamp for snowshoeing, ice fishing, and quick drives to premier skiing at Treetops Resort, Otsego Resort, and Boyne Mountain. After hitting the powder, take in serene frozen lake views from the deck and wood swing, or cozy up inside. Only 3.8 miles to downtown Gaylord's dining and pubs. Includes a fully loaded kitchen, gas grill, and easy keyless self-check-in. Book today!

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Popular amenities for Gaylord family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 181 reviews

The mid-century A-frame cabin is set among trees, illuminated by string lights in the evening. A spacious deck features seating and an umbrella, providing a welcoming atmosphere for relaxation. The cabin's distinctive triangular roof highlights its architectural charm and rustic appeal.

Chalet in Johannesburg

MCM A-Frame | HOT TUB | Lake | Nature | Hike

Indoor spacesFamilyCheckout

4.95 out of 5 average rating, 253 reviews

The cabin features a modern A-frame structure with a striking blue roof and large glass windows. Surrounded by lush greenery, a gravel patio is designed with comfortable seating and subtle outdoor lighting. Tall trees provide privacy in the tranquil outdoor setting.

Cabin in Elmira

The Bear Cub Aframe

KitchenIndoor spacesLayout

A cozy living area features wooden beams and large windows that provide expansive views of the lake. Comfortable seating includes a sectional sofa and two armchairs. A wood-burning stove is positioned centrally, accompanied by a natural wood coffee table and light-colored area rug.

4.99 out of 5 average rating, 121 reviews

*Sunrise Vista*NEW AC/Lakefront/HotTub/Kayaks/Dock

Indoor spacesKitchenBarbecue

4.87 out of 5 average rating, 252 reviews

Ski~Golf Resorts*HotTub*Game Room*King bed

FamilyKitchenWi-Fi

An outdoor fire pit area is surrounded by a circular stone pathway, featuring four Adirondack chairs arranged for seating. In the background, the multi-level cabin is visible, with a green metal roof and a small balcony, amidst a natural wooded setting.

4.95 out of 5 average rating, 214 reviews

Big Lake Cabin W Hot Tub/ Kayaks/PngPong

FamilyKitchenOutdoor spaces

4.98 out of 5 average rating, 119 reviews

An indoor pool area features clear blue water and decorative palm trees. A yellow water slide spirals down into the pool beside several lounge chairs. Gentle water fountains create a soothing ambiance, while large windows provide natural light to the spacious environment.

Home in Elmira

Resort Home Pet friendly!

FamilyIndoor spacesTV

Shipping container in Mancelona

The modern shipping container home is surrounded by lush greenery, featuring a combination of black metal siding and warm wooden accents. A spacious rooftop deck is adorned with string lights, providing a cozy atmosphere. A gravel pathway leads to the entrance, enhancing the natural setting.

Steelhaven - Sleek, Modern Shipping Container Home

FamilyIndoor spacesAccess

4.94 out of 5 average rating, 212 reviews

A modern living area features a comfortable sofa and two wooden armchairs arranged on a patterned rug. A kitchen island with seating overlooks the space, and large windows provide natural light, illuminating the wood-paneled walls and floor.

5.0 out of 5 average rating, 100 reviews

Arch’s Hideaway on the trail Hot Tub!

Indoor spacesFamilyBathroom

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 237 reviews

Tiny home in Boyne Falls

Tiny Farm Stay * 5 Min to Boyne Mountain

KitchenFamilyView

A charming cabin is surrounded by trees, featuring a sloped roof and a deck. Colorful chairs in red and blue are arranged on the deck, offering a spot to relax outdoors. A fire pit is visible in the grassy area, enhancing the outdoor experience.

4.84 out of 5 average rating, 124 reviews

Place of Peace Cozy cabin in woods 20 acres/lake

KitchenFamilyComfort

A contemporary chalet is surrounded by vibrant autumn foliage, showcasing a large deck with wooden railing. Steps lead from the deck to the forest floor, while large windows offer views of the tranquil woodland. The structure exudes a welcoming charm within its natural setting.

4.98 out of 5 average rating, 124 reviews

Timber Valley Chalet Ask about seasonal discounts

FamilyKitchenSkiing

A charming A-frame cabin is set among tall trees, showcasing a triangular roofline. The front porch features a white railing and steps leading to a welcoming door. A mix of natural surroundings and a gravel pathway enhances the cabin's rustic appeal.

4.86 out of 5 average rating, 283 reviews

Morgan’s Cozy A-frame: near golf skiing & downtown

FamilyIndoor spacesGetting around

Cabin in Grayling/Gaylord

A rustic log cabin is framed by tall trees, surrounded by a blanket of autumn leaves. The cabin features a covered front porch with ample seating, and sunlight filters through the branches, creating a warm ambiance in the serene woodland setting.

Secluded log cabin with acreage + all the comforts

Indoor spacesKitchenWi-Fi

4.98 out of 5 average rating, 530 reviews

A vintage coffee maker in soft aqua color is placed on a patterned countertop, reflecting a cozy kitchen vibe. An antique car's rounded headlights are captured close-up, displaying vibrant yellow. A rustic wooden shelf is lined with neatly arranged books and a decorative item.

4.84 out of 5 average rating, 101 reviews

Retro Retreat right on Main Street Gaylord!

FamilyKitchenLaundry

4.98 out of 5 average rating, 192 reviews

The entrance to a rustic barn is framed by green grass and a blue sky. A red barn door complements the wooden exterior. A welcome mat lies in front of a white door, flanked by potted plants. A small bench is positioned to the side.

Barn in Grayling

Barn Studio Suite

FamilyKitchenOutdoor spaces

4.97 out of 5 average rating, 248 reviews

A cozy cabin is illuminated by warm lights, nestled among tall trees under a starry sky. The building features large windows and a welcoming entrance, with a snow-covered porch visible in the foreground.

Cabin in Frederic

Bonfire Holler (between Grayling and Gaylord)

Indoor spacesFamilyWalkability

Family-friendly home rentals with a pool

4.81 out of 5 average rating, 104 reviews

Condo in Boyne Falls

DownHill- Studio: Pool: Lake: Golf

FamilyKitchenDecor

4.9 out of 5 average rating, 114 reviews

Fallen Timbers Cottage in Lake Arrowhead

KitchenFamilyBiking

4.86 out of 5 average rating, 139 reviews

Lakefront Cottage for SidexSide & Golf Enthusiasts

KitchenIndoor spacesDecor

An open living area features high cathedral ceilings with large triangular windows allowing natural light to fill the space. A spacious sectional sofa is positioned on a patterned area rug. A staircase leads to the upper level, and a dining area is visible in the background.

4.93 out of 5 average rating, 137 reviews

Secluded 3 Br Luxury Chalet!

Indoor spacesKitchenTV

4.87 out of 5 average rating, 162 reviews

A spacious home exterior is showcased, featuring a combination of wood and stucco materials. A set of stairs leads to a welcoming entrance, flanked by lush greenery and decorative lighting. Large windows provide a glimpse of the interior, surrounded by well-maintained landscaping.

Condo in Boyne Falls

Luxury Rental on Boyne Mountain, 5 bedrooms/4 bath

Indoor spacesFamilyCheck-in

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

KitchenFamilyHospitality

4.98 out of 5 average rating, 100 reviews

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.

Condo in Harbor Springs

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

FamilyKitchenBeach