Vacation rentals with a pool in Gaylord

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Top-rated rentals with a pool in Gaylord

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite
A serene winter view showcases a snow-covered lakeside setting. A circular fire pit is surrounded by wooden chairs, while snow-draped trees reflect on the still water. A small dock is partially visible in the distance, enhancing the tranquil atmosphere.
Home in Gaylord
4.85 out of 5 average rating, 128 reviews

Snowmobile/ Ski Waterfront Haven | Private Hot tub

Come unwind at Channel Lodge! A cozy, newly updated 3 bedroom, 2 bath lakefront cabin, private hot tub tucked in the heart of Lake Arrowhead — a peaceful, private 640 acre community perfect for year round getaways. This beautiful all sports lake includes fishing, swimming, kayaking, etc. LA is always known for its adventurous trails for SxS & snowmobiles. We are conveniently located within 20-60 minute drive from various skiing resorts, including Boyne Mountain, Treetops, & Otsego Club Resort.

Top guest favorite
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.
Home in Gaylord
4.93 out of 5 average rating, 94 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.

Top guest favorite
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
4.97 out of 5 average rating, 156 reviews

Hot Tub, Wood Stove, Close to Skiing, Trails, Snow

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!

Top guest favorite
A charming chalet is nestled among snow-covered trees, surrounded by a serene winter landscape. The roof is blanketed with snow, and the scene is enhanced by a snow-laden evergreen tree nearby, creating a peaceful, wintry atmosphere.
Cabin in Elmira
4.96 out of 5 average rating, 23 reviews

Bear Bottoms Chalet in the Woods

Relax in this charming, quaint chalet located at Lakes of the North Resort w/golfing, campsites, lakes, restaurant, cross-country skiing, and an airport! Access to indoor swimming pool with hot tub, waterslide and gym. This 2 bedroom w/loft, 1 bath cabin is the ideal home base in the heart of Michigan. Centrally located to lakes, beaches, state parks, wineries, breweries, snowmobiling & skiing. No matter your sport or the season, this is the place for a fun family vacation or relaxing getaway!

Guest favorite
A cozy living area features a L-shaped sofa facing a modern fireplace. Earthy tones are accented by a large nature-themed artwork on the wall. A wooden table with a lamp and decorative elements is situated beside the seating, contributing to a warm ambiance.
Cabin in Boyne Falls
4.87 out of 5 average rating, 60 reviews

Cozy Cabin Condo Steps from Boyneland ski lift!

Enjoy a Vacation getaway to Boyne Mountain at this Cozy cabin Located just steps away from the Boyneland ski lift and Avalanche Bay Indoor Water park. Everything within walking distance of this wonderful home including trophy room, Forty acres tavern, ski and ice cream shops, and more. A very short drive will take you into the heart of Boyne city and to lake Charlevoix. 3 bed 3 Bath sleeps 9 comfortably. Wifi, streaming services, and full amenities included. Washer and dryer included in unit.

Guest favorite
Cabin in Gaylord
4.9 out of 5 average rating, 100 reviews

The Beige House in Lake Arrowhead

Experience the tranquility of a charming 4-bedroom cottage nestled in the picturesque Lake Arrowhead, featuring a refreshing atmosphere and abundant natural light. Enjoy a heated outdoor pool and access to all-sports Buhl Lake! Gaylord, Michigan offers something for everyone, with activities like swimming, boating, golfing in summer, and skiing and snowmobiling in winter. Boyne Mountain is just 30 minutes away, while Traverse City, Mackinaw Island, and Petoskey are all within an hour's drive!

Top guest favorite
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.
Condo in Harbor Springs
4.9 out of 5 average rating, 100 reviews

Relaxing Getaway in Harbor Springs!

Located in Harbor Springs, the perfect year-round getaway in Northern Michigan awaits. Tucked away in a peaceful location, Trout Creek condos are on 150 acres with many amenities for all to enjoy! Indoor & outdoor pools, tennis courts, gym, hiking trails and more! Enjoy area golf courses, ski hills, lakefront & restaurants. -Located next to Nubs Nob and The Highlands -Complimentary shuttle to Nubs Nob (weekends) -Close to Harbor Springs & Petoskey - Mackinac Island Bridge (30 miles)

Top guest favorite
A spacious bedroom is presented with large windows overlooking lush greenery. An inviting bed adorned with a patterned quilt is complemented by wooden furniture, including a dresser and mirror. A cozy seating area is visible next to the fireplace, creating a warm atmosphere.
Condo in Bellaire
4.96 out of 5 average rating, 224 reviews

Lakeview 🌅 Fireplace, Walk to Summit GC & Pools ⛳️

This 1 bedroom, 2 bed, 1 bath 605 sq. ft. condo sleeps 4 and is located in Summit Village. The condo features a full kitchen, wood burning fireplace, queen sleeper sofa, and private deck for stunning Lake Bellaire sunsets. Your stay includes access to the resort’s multiple indoor and outdoor pools and the indoor hot tub. Our condo is a short walk to the Summit Golf Course, Shanty Town and the Lakeview Restaurant. Staying here means you're right in the heart of Shanty Creek Resort!

Top guest favorite
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
4.99 out of 5 average rating, 99 reviews

We have snow! Pet Friendly Resort Home

Whether you enjoy skiing, snowmobiling, golfing, orv'ing, sightseeing, or just lying on the beach, we have it all. So come hit the trails or enjoy our golf course then when done for the day, head back to a flaming fireplace or watch the stars by the firepit in summer. Resort amenities including the beach, when open, are available at ADDITIONAL COST and registration. We are pet friendly with a 2 dog maximum, no cats. Security cameras are facing front porch,driveway and back door.

Guest favorite
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.
Home in Gaylord
4.98 out of 5 average rating, 121 reviews

Timber Valley Chalet Ask about seasonal discounts

Timber Valley Chalet provides 4 seasons of rest, relaxation and outdoor fun. 3 bd/2ba +basement to sleep 14 . 5G wifi, full kitchen, fireplace, deck, firepit, backyard that opens up to the woods...everything you need. Easy access to all outdoor activities: ski (downhill & x-country), golf, snowmobile, fish, hunt, hike, bike, boat, swim, atv, snowshoe, ice skate...all in Gaylord. Centrally located in the top of the Mitt, we are also an easy drive to much of northern Michigan.

Top guest favorite
A welcoming living area features large windows allowing natural light to brighten the space. A wooden coffee table sits in front of a comfortable sofa, with an armchair and a dining table nearby. A cozy fireplace adds a warm touch to the room.
Home in Boyne Falls
4.96 out of 5 average rating, 181 reviews

Family ski-in & ski- out 4B/4B Disciples Ridge

Clean and waiting for you and your family and friends! Beautiful, quiet, ski-in/ski-out condo located right on Boyneland Run...walk or ski to everything ANY season. We love Boyne Mountain and can't wait to share our home with you. Our 4 bedroom/4 bathroom (sleeps 14+) condo/home is comfy, clean (smoke-free/pet free) and fully stocked so you relax from the minute you arrive! Comfy beds and a fireplace make it perfect for resting after a day of fun in Northern Michigan.

Guest favorite
Chalet in Gaylord
4.96 out of 5 average rating, 241 reviews

Bear’s Den ~ Hot Tub, 2 Pools,Kayaks,Skiing&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.

Popular amenities for Gaylord rentals with a pool

Quick stats about vacation rentals with a pool in Gaylord

  • Total vacation rentals

    Explore 20 vacation rentals in Gaylord

  • Nightly prices starting at

    Gaylord vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

  • Verified guest reviews

    Over 720 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Wi-Fi availability

    20 of Gaylord vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Gaylord rentals

  • 4.8 Average rating

    Gaylord stays are highly rated by guests—averaging 4.8 out of 5!

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