
Family-friendly holiday rentals in Caledonia
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Top-rated family-friendly rentals in Caledonia
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for Caledonia family-friendly rentals
Family-friendly home rentals with a hot tub

Lakeside Getaway
Christine’s place was the perfect get-away for a family vacation close to home. The lake was beautiful and the place was spotless and inviting. It felt like you walked in to your own home. It’s close to places to eat and there is even a community space just a few houses down that is lively if the weather is nice. I’m hoping to come back again!

#4 Adorable Lake Cottage-Cypress Resort & Marine
This was our second visit to Amanda’s and just like the first time, it left my boys with fun memories. We will be back next summer.

6BR house, yard, hot tub - 5 min drive downtown
If i could give Paul and his home 6 stars I would. He was an excellent host. The home had everything and more than our group expected. It was close enough to down town but far enough to feel like we were away from the city.

Stylistic Condo Hot Tub Tosa Village 2 blocks away
Sarah was a wonderful host with a beautiful home! My friends and I had a great time at this spot. It was clean and comfortable. Sarah was accommodating and responsive. Also super easy to get around Tosa or easy to get downtown!

Restored Victorian w Hottub , 1block to shops
This house looks like it does in the photos. It is an easy walk to downtown in a safe area. Had a great stay overall!

Amazing view, Modern Space
This place was súper clean and beautiful. We were very comfortable and never heard the neighbors downstairs. The only thing that happened was the that the thermostat stopped working and they weren’t able to come and fix it. Then the bathroom switch kept tripping and we had to find the fuse box and various times the light didn’t work. But it was such a nice place and I would totally stay there again. We had a very comfortable experience.

The Retreat on Lake Michigan 6 bd/4bth 4000 sq ft
We had a wonderful stay at Daniel’s place! The house is beautiful and the view is stunning. It was really clean and felt very welcoming. We traveled with grandparents and kids and everyone found something to enjoy. The pool table was a huge hit, as was the badminton set and the multiple outdoor seating areas. This one is highly recommended!

Beautiful Lakehouse sleeps 12 Boat/Pets/HotTub/Ski
We had a great stay here. We had a large party but felt like there was plenty of space to relax and spend time together. Kitchen was well equipped with appliances. Sound system was great! Lots of great games to play inside and amenities for the lake as well to use outside. Surrounding area is peaceful and relatively quiet. Easy to get to stores/shops via short drive.
Family- and pet-friendly home rentals

HGTV Renovated Home with GREAT backyard!
This place was stunning and Jenni was fabulous to work with. Literally zero complaints! Thank you so so much for everything ❤️

Peaceful weekend or extended stay, full amenities
Cute stay! We had a wedding at Homestead Hollow and this place was perfect! Cute and fresh baked cookies on arrival. Entrance is on the backside of the house, but the host was super helpful on finding it. Plenty of room to spread out. Also exactly as described. It is a working farm with the family living there, but the space is as described. Although, it’s in the country - it’s also fairly close to lots of shopping, restaurants and parks.

Historic Home Sleeps 16 in MKEs Best Neighborhood
Always love staying with Daniel and Anne's place! Not only are they always super responsive, but their property is beautiful and well set up for large groups. walk friendly, and lots of nearby food options. 100% would recommend, and we definitely hope to be back in the future!

This Must Be the Place- Bayview Bohemian Vibes
Easy to access beautiful home which looks just like the photos. The host was extremely responsive when I had questions - would absolutely stay again.

Riverwest Loft with city skyline view
What a great stay! This is such a colorful and unique loft and really was a great experience. The location was close to a lot of things, and plenty of street parking if you need an extra space. We had such a great time!

Best location in Milwaukee! Lower Duplex Unit
everything you need. just a few steps from one of the greatest streets in the world

Allis in Dairyland-2 Bdm flat in heart of Bay View
The perfect location for my stay!! The hosts were quick to respond if I had any issues and the actual place itself was so cute.

WAVES : Steps to the Harbor ~ Crash Here!
We really enjoyed our stay. Very convenient and could walk to the water. The little deck in back was a nice spot to have coffee.
Family-friendly home rentals with a pool

2 BD 2 BA Abbey Villa with Pool
Great spot! The condo was clean, comfortable, and quiet. It was a short walk to the beach and restaurants. Mandy’s detailed directions and instructions made checking in a breeze. Our group of four had a fantastic time.

2 Bedroom Villa at Lake Geneva's GRAND Resort
What a lovely and hospitable place! We loved our time there. The level of comfort was unmatched. We would happily return. Truly a wonderful experience!

Abbey Spring Resort Home |North Shore Hideaway
We had a fantastic time here! The property has an incredible deck that extends into the surrounding forest. We had breakfast outside every morning! If you love wildlife, you'll love this place.

Flexible rental In Lake Geneva Area
Charming and comfortable - In the heart of Geneva close to cute shops and many restaurants! Very clean with convenient parking. Wonderful stay!

Luxury Log Cabin retreat home
Debbie was fabulous to work with. Communication and helpful instructions were provided at both check in and check out. Would to come down this house as it exceeded expectations.

Beautiful 137 Year Old Farm Home (3night min)
Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!

Lakeview at CasaCome
We took an unexpected trip to the lake and needed a peaceful, relaxing place to stay. Regina’s house was perfect. The condo is fully stocked with all you’ll need including a beautiful view of the lake. Regina gave great recommendations and was very responsive.

NEW! Updated Lake Geneva Resort Luxury Suite
Krissy was very helpful with questions and her place is very homey. We will definitely book with her again if she allows us to. We had a lovely 5 year Anniversary.
Destinations to explore
- Downtown Chicago Holiday rentals
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- Lake Geneva Holiday rentals
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- Rentals with a washing machine and dryer Caledonia
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- Six Flags Great America
- Erin Hills Golf Course
- Alpine Valley Resort
- Milwaukee Public Museum
- Geneva National Resort & Club
- Illinois Beach State Park
- Bradford Beach
- Moraine Hills State Park
- Racine North Beach
- Harrington Beach State Park
- Milwaukee County Zoo
- Grand Geneva Resort & Spa
- Richard Bong State Recreation Area
- Wilmot Mountain Ski Resort
- Milwaukee Country Club
- West Bend Country Club
- Discovery World
- Heiliger Huegel Ski Club
- Springs Water Park
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Old Elm Club
- Shoreacres
- Sunburst
- Blue Mound Golf and Country Club