
Valparaiso vacation rentals
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Top-rated vacation rentals in Valparaiso
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Valparaiso vacation rentals
Other great vacation rentals in Valparaiso

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours
Was an absolutely relaxing stay. It was exactly what my husband and I were looking for. An extended weekend away with a bunch of things around us to do. It had a little bit of everything around us, including privacy. It was fantastic.

Great Living
The accommodation is nice. It is clean, and the space is cosy and well kept. Catch the sunset from the sitting rooms, they are beautiful.

Home near the lake with an inground pool
Clean house and will definitely book again for our needs. Very comfortable with everything.

Location location
I don’t think the pictures do this house any justice. House is tremendously big. Lots of space for large families. The views? Amazing. With the vineyard next door and the woods surrounding it, it was a great view. Very ample parking. Easy to find and close to the highway. There’s plenty of wineries near the house. Also grocery stores for any quick essentials. Back to the house. Very clean and big kitchen. Has everything you need from plates to cups. The living room is big. Tv is huge to keep the kids entertained. It was a little chilly so we stayed inside. But the deck looks really new and big with a girl. The backyard was huge. Rooms were big with nice beds and clean as well. All bathrooms were super clean and big. Basement had an entire other living area with rooms as well. Pool table kept everyone entertained. Dining room had a nice table for the large family dinners. In conclusion, I will definitely love to book this for the summer. You won’t regret it.

Designer Cottage Relax Beach Pool & Spa—Windjammer
Beautiful house, very well thought out for guests. Host and Co-Host were absolutely wonderful through the whole process. Lots to do in the area. Would highly recommend!

cozy new buffalo cabin, hot tub, 14m walk to beach
very fun relaxing experience, stayed in the back cabin. great time

Sprawling Retreat w/ Private Beach Access!
I had my family of 17 up to MI for this past Thanksgiving. I own a home about 100 yards from Monika’s and half my family stayed there. It was incredibly convenient and my family loved the house! Coffee in the sunroom, hot tubbing and hanging at the fire pit with a roaring fire. Heaven!!

Beautiful Home Oasis
Beautiful house and surroundings. Great place to relax with a large family gathering. Lots for kids to do inside and out. We enjoyed the pool, fire pit, and sports areas. Hosts were very responsive and friendly.
Quick stats about vacation rentals in Valparaiso
Total rentals
80 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
4.1K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
Frequently Asked Questions
Are there pet-friendly vacation rentals in Valparaiso?
Four-legged friends are welcome in Valparaiso. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Valparaiso?
Yes! Work meets play with ease at over 50 vacation rentals in Valparaiso featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Valparaiso vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Valparaiso, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Valparaiso have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Valparaiso. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Valparaiso?
Experience the best of Valparaiso with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly house rentals in Valparaiso?
Valparaiso has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Valparaiso have wireless internet?
Absolutely! We offer over 10 apartment rentals with wireless internet in Valparaiso. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Valparaiso?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
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