
Holiday rentals with a pool in Upper Peninsula
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Top-rated rentals with a pool in Upper Peninsula
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

DoorCo Happy Place @Landmark Resort
Welcome to this wonderful, full of positive energy and relaxing resort! The condo is a great place to relax, explore and rejuvenate! 1 bedroom with a queen size bed and queen sleeper sofa in the living room and fully equipped kitchen make enough room for 4 guests. The resort is a great place to enjoy- 1 indoor pool, exercise room and a game room located in the main building, hot tub, sauna in each building, 3 HEATED outdoor pools open seasonally (May- August), tennis court, playground, a trail.

Evergreen Hill B Whirlpool Condo by Pen State Park
It’s all about location and this is the perfect central location for your Door County adventure! All 3 B rental condos are set on a lovely, peaceful street in Fish Creek. On warm days, enjoy hiking, swimming, biking, boating, camping, picnicking, fishing, and golf. When snow is on the ground, spend time cross-country skiing, snow shoeing, snowmobiling, and sledding. Daily housekeeping is not included. You can add it for $24 per day if you would like, just let us know when you pick up your key.

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!

Furnace Lake Overlook - near Pictured Rocks!
Pictured Rocks Family Rentals welcomes you to Furnace Lake Overlook. Beautiful home with 2 bedrooms, 2 baths. Bedroom 1 has king bed and bunk beds with a sliding barn door separating them, while bedroom 2 has a queen bed. This home has a beautiful view overlooking Furnace Lake, but does not have lake access. The home has a nice deck on back with a heated 4' above ground pool that is open from Memorial Day to Labor Day (9/15/25 this year). Less than 5 miles from Munising, the beginning of PRNL

Rare Beachfront Condo on Pvt Round Lake Petoskey
Relax on the deck or sandy beach just footsteps from your door, at desirable Lakeside Condo's, on beautiful/private Round Lake. This comfortable studio condo location offers loads of nearby summer, (3.5 Miles to Nubs and Boyne Highlands Ski Resorts) and colorful autumn and snowy events, shopping and area attractions in Petoskey, Harbor Springs and Charlevoix. Just a 5 minute walk to the fabulous Toski Sands market for your food and beverage needs. Enjoy the indoor pool and hot tub year round.

Stunning Waterfront, Updated TC Condo with Pool!
Have this updated, waterfront condo be your home away from home while visiting the Traverse City area! This condo sits on East Bay with unobstructed views of the water. In the summer, hang poolside between exploring Traverse City hot spots. This condo offers one bedroom with a King bed with an additional queen sleeper sofa in the living room. Full kitchen is perfect for making up any meal and enjoying it on the balcony overlooking the water. Long day of hiking? Soak in the complex hot tub.

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)

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.

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.

Secluded Cabin w/ Loft & Fireplace at Schuss Mtn.
This 2 bedroom updated cabin with bonus loft (3 bed total) for additional sleeping space is located on a quiet cul-de-sac at Schuss Mountain in Shanty Creek Resort. The resort includes year round excitement including 5 golf courses, restaurants, skiing, hiking trails, and multiple indoor/outdoor pools. The town itself has unique shops as well as great local food and beverage options. Bellaire is also near popular destinations including Traverse City, Petoskey, and Charlevoix.

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.

Beachfront Oasis | Pool+Hot Tub
Escape to paradise in our luxurious beachfront condo, where the sugary sand and lake are just steps away from your door. Perfect for couples and families, this condo promises a memorable and comfortable vacation. Wake up to the sound of waves, breathe in fresh air from your private balcony, take a dip in the pool and relax in the hot tub. Pamper yourself with a soak in the soaker bathroom tub. Come create unforgettable memories at your beachfront oasis!
Popular amenities for Upper Peninsula rentals with a pool
House rentals with a pool

Waterfront 3 bedroom home with Island view

Camp Evan- Shanty Creek, Schuss Mtn

70s Retro Escape | Hot Tub, Sauna & Arcade Games

Mini Michigan Paradise

Long Lake/Lakeside Jacuzzi/Fenced yard for pets

House in Sault Ste. Marie, ON

Glamping Galore

PineHaus - Game Room, Fireplace, Private Sauna
Apartment rentals with a pool

Leelanau Townhouse Retreat at Sugarloaf

Luxury Rental on Boyne Mountain, 5 bedrooms/4 bath

1 Bedrm Loft ShantyCreek Northern Escape Condo

Treetop Escape - Stunning Lake Views All Year

Sauna Beach Haven 106: Beach Access|Tart Trail

Beachside 213 Luxury Condo on the Beach

Valleys Chalet - Harbor Springs/Petoskey Condo

344 Edgewater Inn
Other holiday rentals with a pool

1 Bedroom Suite in a World-Class Swedish Resort

Latitude 44

The Cozy Office— walkable to downtown

Spacious Cabin • Hot Tub • Game Room • No Bunkbeds

Shanty Creek Condo w/ Stunning Lake Bellaire Views

Couple’s Cozy Retreat

Waterfront/Pool/Hot Tub/Firepit/Game Room

Cozy A-Frame Cabin • 3 Min to Schuss Ski Lift
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