Holiday rentals with a pool in Lake Winnebago

Private Pool - Hot Tub - Game Room - 20 min DT

🔹Private fenced in backyard w/ heated pool w/ pool toys & HOT TUB 🔸Outdoor living w/ lounge seating on the deck, gas grill, outdoor dining & fire pit 🔹Sleeps families & groups - 3 King, 4 Queen 🔸Game room w/ pool table, smart tv, board games, & gas fireplace 🔹5 min to Sun Prairie restaurants & shopping 🔸Pets welcome 🔹Highchair & pack n’ play on site 🔸You'll find "The Kohl Center, UW-Madison, Camp Randall Stadium, State Street, The Capitol, & The Alliant Energy Center" within 20min

Lakefront Condo, Private Beach/Pools, Walk to Town

Elkhart Lake’s beauty awaits year-round! This 3BR/3BA condo boasts a 600 ft private beach, pools (indoor/outdoor), hot tub, water sports rentals, and easy access to nearby Osthoff Lake Deck, hiking, golfing, and town. Fall brings vibrant foliage, trail hiking, and golf on scenic courses. Winter offers cross-country skiing, snowshoeing, ice skating, sledding and trail hiking, while spring delights with blooming wildflowers, birdwatching, and farmers markets. Experience nature’s magic any season!

4 Miles to Road America-Home-Hot Tub-Heated Pool

Private Craftsman home in Plymouth, WI—just 4 miles from Road America. Ideal for race teams and families, this two-story home offers 4 bedrooms, 2 baths, a private outdoor hot tub, and a seasonal heated inground pool. Free on-street parking plus a garage and shared driveway provide convenient vehicle access. Located in a quiet neighborhood near grocery stores, dining, and local attractions. No pets. Summers, Holidays, & RA race weekends require 3 night min. Longer stays (7+ nights) by request.

Modern Cabin with pool, hot tub and outdoor sauna

Forget your worries in this spacious and serene space. Secluded yet close to a big city (Maddison and Wisconsin Dells) and lots of entertainment! 20 min away from 2 ski resorts, an amazing winery and distillery, spas, restaurants, casino! 3 mile away from lake Wisconsin. Hiking trailers, 24 hour ferry service across the lake and more. This luxurious villa combines comfort and style, you won't want to leave it, but the area is full of enviting places to go to, so plan for a few extra days!

The Lake Street Kickback in Elkhart Lake!

Welcome to The Lake Street Kickback! This privately owned studio condo is located at The Elkhart Lake Beach Resort (Formerly The Shore Club of Wisconsin) & has access to all resort amenities. During your stay enjoy the outdoor pool/hot tub, resort beach, Tiki bar & indoor pool. A unique blend of updates, convenience, comfort & relaxation. Just steps away from local favorites including village restaurants, bars, farmers market, shops & neighboring resorts like Osthoff and Siebkens Resorts.

Epic 6BR w/ Movie Theater + Pool + Dock Access

At this 6BR Wisconsin Dells countryside retreat, you can spend the day skiing, paddling, or riding waterslides—and still be home in time to feed the goats. Kids of all ages will head straight to the petting zoo or pool upon arrival, while grownups kick back in the 7 person hot tub, grill under the gazebo, or wind down in the private movie theater. A lake lot a mile away offers dock access, kayaks, and canoes, while the spacious home lets big groups spread out, reconnect, and have fun.

2-acre retreat steps from Nagawicka Lake

Private Lake Country Retreat on 2 Acres | Pool, Park & Prime Location Relax at this private Lake Country retreat on 2 secluded acres surrounded by mature trees. Enjoy a private outdoor pool, spacious yard, and peaceful setting just steps from a county park with trails and a public beach. A nearby boat launch makes lake days easy, while shopping, restaurants, and coffee spots are only minutes away. Perfect for families, couples, or extended stays seeking privacy with convenience.

Camper Retreat @ Emrick Lake

Camper Stay with Resort Perks! Escape to this cozy camper in a vibrant campground with two pools, a swim-up bar, and pond with an inflatable aquapark. Explore scenic trails, enjoy fishing, kayaking, canoeing, or paddle boating in the private lake. The campground also offers pickleball, petting zoo, jumping pad, frisbee golf, bar/restaurant, game room, and themed weekends. Whether for family fun or a couples retreat, make lasting memories during an unforgettable getaway!

Exec Retreat Heated Pool 7 Beds; 2.5 Bath 6000 sf

The perfect place to relax, play and explore. Three levels of luxury and drenched with natural light. Wolf/Sub Zero/Miele kitchen. Kohler fixtures and spacious tiled showers for self pampering. Restoration Hardware furniture & two 77” TV's 5 Deck Areas: sip coffee, sun bathe, read, yoga sessions * Pickleball * Clearlight Infrared 4 person Sauna * 9 Person Hot Tub * In-ground Pool 48' x 24' with Sun Deck * 13 acres * Nearby ski, golf, Wis. Dells, Madison

A Sweet Suite in Freedom! Country Comfort!

Visiting friends or family in Freedom? Why bother them for an air mattress when you can stay right in town!? Going to a Packer Game and looking for a comfy place to stay with a super short drive? Found it! Ask about using the game room, golf simulator, or pool while you're here too! There's not a FULL kitchen!! Just one burner, and a flat griddle. There's also a microwave and small refrigerator/freezer, but overall, it's a suite. We think you'll LOVE it!

Premier Lakefront Escape Exclusive Pool near Dells

Ideally located 30 minutes from the Wisconsin Dells and about 20 minutes from Cascade Mountain. Experience refined relaxation with family and friends at this tranquil lakeside residence, complete with a private pool. From sunrise coffee to glowing sunsets and fireside s’mores, every moment is designed for relaxation. Created for memorable getaways, this home delivers a rich variety of experiences for guests of every generation.

Brewers Hill Gem w/hot tub & seasonal shared pool

Your family will be close to everything when you stay at this centrally-located place. Walking distance to Brady Street, the Milwaukee River Walk, shops, restaurants and coffee houses. Less than a mile from Fiserv Forum, downtown Milwaukee and just minutes from Bradford Beach. This pet friendly unit has a private fenced in yard, BBQ grill, off street parking for your vehicles and motorcycles, and a hot tub for your use.