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Family-friendly holiday rentals in Caledonia

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Caledonia family-friendly rentals

Family-friendly home rentals with a hot tub

Home in Lake Villa
4.84 out of 5 average rating, 44 reviews

Lakeside Getaway

AndreRating, 5 stars11 months ago
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!
Guest favourite
Cottage in Antioch
4.93 out of 5 average rating, 149 reviews

#4 Adorable Lake Cottage-Cypress Resort & Marine

JenniferRating, 5 stars10 months ago
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.
Guest favourite
Home in Milwaukee
4.95 out of 5 average rating, 235 reviews

6BR house, yard, hot tub - 5 min drive downtown

FrankRating, 5 stars3 weeks ago
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.
Condo in Wauwatosa
4.63 out of 5 average rating, 114 reviews

Stylistic Condo Hot Tub Tosa Village 2 blocks away

IrelandRating, 5 stars11 months ago
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!
Home in Lake Geneva
4.68 out of 5 average rating, 124 reviews

Restored Victorian w Hottub , 1block to shops

GraceRating, 5 stars1 week ago
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!
Guest favourite
Townhouse in Riverwest
4.92 out of 5 average rating, 245 reviews

Amazing view, Modern Space

TammyRating, 5 stars1 month ago
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.
Top Guest favourite
Home in Kenosha
4.94 out of 5 average rating, 152 reviews

The Retreat on Lake Michigan 6 bd/4bth 4000 sq ft

DianeRating, 5 stars3 weeks ago
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!
Superhost
Home in Bristol
4.85 out of 5 average rating, 111 reviews

Beautiful Lakehouse sleeps 12 Boat/Pets/HotTub/Ski

AbigailRating, 5 stars2 days ago
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

Guest favourite
Home in Walker's Point
4.93 out of 5 average rating, 188 reviews

HGTV Renovated Home with GREAT backyard!

JoshRating, 5 stars3 weeks ago
This place was stunning and Jenni was fabulous to work with. Literally zero complaints! Thank you so so much for everything ❤️
Top Guest favourite
Guesthouse in Richfield
4.94 out of 5 average rating, 257 reviews

Peaceful weekend or extended stay, full amenities

LauraRating, 5 stars1 month ago
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.
Superhost
Home in Walker's Point
4.89 out of 5 average rating, 231 reviews

Historic Home Sleeps 16 in MKEs Best Neighborhood

LynneRating, 5 stars8 months ago
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!
Guest favourite
Home in Bay View
4.95 out of 5 average rating, 116 reviews

This Must Be the Place- Bayview Bohemian Vibes

KristenRating, 5 stars2 weeks ago
Easy to access beautiful home which looks just like the photos. The host was extremely responsive when I had questions - would absolutely stay again.
Guest favourite
Apartment in Riverwest
4.87 out of 5 average rating, 420 reviews

Riverwest Loft with city skyline view

RhyomiRating, 5 stars2 weeks ago
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!
Superhost
Apartment in Lower East Side
4.82 out of 5 average rating, 276 reviews

Best location in Milwaukee! Lower Duplex Unit

JamesRating, 5 stars2 months ago
everything you need. just a few steps from one of the greatest streets in the world
Superhost
Apartment in Bay View
4.92 out of 5 average rating, 117 reviews

Allis in Dairyland-2 Bdm flat in heart of Bay View

ninaRating, 5 stars5 months ago
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.
Guest favourite
Apartment in Racine
4.9 out of 5 average rating, 292 reviews

WAVES : Steps to the Harbor ~ Crash Here!

MaryRating, 5 stars1 week ago
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

Guest favourite
Condo in Fontana-on-Geneva Lake
5 out of 5 average rating, 58 reviews

2 BD 2 BA Abbey Villa with Pool

GavinRating, 5 stars10 months ago
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.
Superhost
Villa in Lake Geneva
4.9 out of 5 average rating, 77 reviews

2 Bedroom Villa at Lake Geneva's GRAND Resort

LoriRating, 5 stars1 month ago
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!
Superhost
Home in Fontana
4.6 out of 5 average rating, 5 reviews

Abbey Spring Resort Home |North Shore Hideaway

MichelleRating, 5 stars11 months ago
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.
Condo in Lake Geneva
4.64 out of 5 average rating, 277 reviews

Flexible rental In Lake Geneva Area

LindseyRating, 5 stars2 months ago
Charming and comfortable - In the heart of Geneva close to cute shops and many restaurants! Very clean with convenient parking. Wonderful stay!
Guest favourite
Cabin in Lake Geneva
4.86 out of 5 average rating, 111 reviews

Luxury Log Cabin retreat home

AbbyRating, 5 stars3 days ago
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.
Superhost
Home in Lake Forest
4.9 out of 5 average rating, 63 reviews

Beautiful 137 Year Old Farm Home (3night min)

MaribethRating, 5 stars10 months ago
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!
Condo in Lake Geneva
4.9 out of 5 average rating, 200 reviews

Lakeview at CasaCome

ErinRating, 5 stars1 week ago
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.
Condo in Lake Geneva
4.6 out of 5 average rating, 141 reviews

NEW! Updated Lake Geneva Resort Luxury Suite

AmyRating, 5 stars3 days ago
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.

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