Pleasant Prairie Vacation Rentals

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Browse Select Pleasant Prairie Vacation Homes

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Property grounds

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

10.0 out of 10, Exceptional, (231)
"I booked this property for a reunion with some old friends, with the intention that we would be spending a lot of time hanging out. This property was perfect for that -- lots of beds and bathrooms. A beautiful view of the lake from the main living area and two of the bedrooms. Lots of amenities/activities including a pool table, ping pong, a fire pit, etc. But perhaps the best feature was the openness of the kitchen/dining room/pool table/family room, which meant that you feel connected to...
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
New Your Home Away From Home! - Near Great Lakes Naval Base!!
TV

New Your Home Away From Home! - Near Great Lakes Naval Base!!

9.4 out of 10, Exceptional, (17)
"Very clean"
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Lake/Beach Getaway (Remodeled)
Property grounds

Lake/Beach Getaway (Remodeled)

9.8 out of 10, Exceptional, (28)
"excellent location - very clean - close to everything we wanted to visit - owners very helpful only 20 min from Antioch where we had our family reunion - this is the 2nd year we have stayed here - very happy - lake visable from front windows - beds comfy - kitchen completely stocked - great sunsets - easy walking in the area - shopping close by wonderful rental"
Lake/Beach Getaway (Remodeled)
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Terrace/patio

Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!

9.8 out of 10, Exceptional, (74)
"AMAZING PROPERTY!!!"
The price is CA $215
CA $778 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Lakefront Home w/ Game Room, Theater & Dock!
Pool

Lakefront Home w/ Game Room, Theater & Dock!

9.8 out of 10, Exceptional, (20)
"Perfect 4th of July weekend! We loved using the patio and the grill. Great location and great stay, would recommend!"
Lakefront Home w/ Game Room, Theater & Dock!
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Interior

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.8 out of 10, Excellent, (16)
"We rented this house to stay for my daughter’s graduation from Navy Boot Camp. It was an easy drive in and ample room for everyone. The host was awesome and attentive to our needs. Honestly, we didn’t really have any needs, but we used party poppers in the house and wanted to be able to clean them up, but we couldn’t find the broom. Being from California, I was super nervous about being cold, but as soon as we walked in the house, it was super warm and felt so cozy. The heated floors are...
Riverfront Libertyville Retreat w/ Outdoor Kitchen
3-bedroom house WiFi in lovely Waukegan Near Gurnee
Fridge, microwave, oven, stovetop

3-bedroom house WiFi in lovely Waukegan Near Gurnee

2.0 star property
4.6 out of 10, (12)
"Cute little house at all the necessities convenient to Naval base where we spent most of our time"
3-bedroom house WiFi in lovely Waukegan Near Gurnee
Beautiful and spacious lakefront home! Close to everything!
Terrace/patio

Beautiful and spacious lakefront home! Close to everything!

9.6 out of 10, Exceptional, (36)
"This was an amazing property! We kept commenting how the house was so well designed to fully appreciate the beautiful lake. It was amazing! The living room, sun room, kitchen and dining room all took advantage of fantastic views. Though in a neighborhood, we felt like it was in the country. Everything was wonderful - from the beds to the space, to the views, to the quiet setting. Couldn't have been better! "
Beautiful and spacious lakefront home! Close to everything!
Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!
Fridge, microwave, oven, stovetop

Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!

9.8 out of 10, Exceptional, (7)
"Overall listing was spot on. Clean overall, a little on the chilly side upon arrival and one trash can was not empty. Couple items it could use are hand towels for rhe bathrooms, additional dish towels and dish cloths in the kitchen. Aybe add some board games? Other then a few additionas it was a great locations and perfect for what we needed. "
Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!
Cozy Lakehouse Views on a hill, Hot tub, water activities, pier, & optional boat
Marina

Cozy Lakehouse Views on a hill, Hot tub, water activities, pier, & optional boat

10.0 out of 10, Exceptional, (9)
"Mario and Katie have a beautiful home with all the bells and whistles. We enjoyed the home, the hot tub, multiple patios, the lake and the low key vibe. The introduction to Luke at Luke's Float and Boat for our pontoon was a great add! Enjoy your time at the lake!"
Cozy Lakehouse Views on a hill, Hot tub, water activities, pier, & optional boat
IVP Manor House Close to Lake Beach & Naval Base
Fridge, microwave, oven, stovetop

IVP Manor House Close to Lake Beach & Naval Base

9.6 out of 10, Exceptional, (51)
"We needed a good centralized location for Thanksgiving with our relatives. This house was the perfect location, was very spacious, very clean, and comfortable beds and pillows. Would definitely stay again, thank you for your hospitality! "
IVP Manor House Close to Lake Beach & Naval Base
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Property grounds

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

9.6 out of 10, Exceptional, (78)
"It was a very nice place. Clean and cute. It would have helped to have the porch light on since arrived at night. We were a little unsure of where to go but figured it out because of the pictures. "
The price is CA $83
CA $143 total
includes taxes & fees
Dec 26 - Dec 27
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Riverside Retreat-Hot tub, Kayaks, firepit
Interior

Riverside Retreat-Hot tub, Kayaks, firepit

9.6 out of 10, Exceptional, (10)
"We enjoyed a quiet weekend on the river with lots of options inside and out for relaxing and spending time with family!"
Riverside Retreat-Hot tub, Kayaks, firepit
Gorgeous Lakefront Estate, Chain O'Lakes Gem~POOL
Interior

Gorgeous Lakefront Estate, Chain O'Lakes Gem~POOL

10.0 out of 10, Exceptional, (1)
"It was beautiful"
Gorgeous Lakefront Estate, Chain O'Lakes Gem~POOL
Cozy Bungalow, one car garage, walking distance to beaches, downtown.
Outdoor dining

Cozy Bungalow, one car garage, walking distance to beaches, downtown.

8.0 out of 10, Very good, (1)
"The house was extremely close to the water and the beach area was great! Easy to get around town and locate restaurants and stores. Only issue we had was there were so many spiders outside, we could not enjoy the patio/deck. We thought about having a fire but the spiders were everywhere. I personally don’t know the city of Racine but the road the house is on is noisy. Lots of cars and dogs barking through the night. If you’re a light sleeper, bring ear plugs! "
Cozy Bungalow, one car garage, walking distance to beaches, downtown.
Cozy Wauk-Townhse near navy base
Living area

Cozy Wauk-Townhse near navy base

2.0 star property
10.0 out of 10, Exceptional, (1)
"The neighborhood is quiet and well established. You are close to many places, especially the Naval base. The water gets hot quickly. Plenty of towels and blankets. Just needs more sitting room in living area. I would definitely stay again. Greats snacks too. e to many places, especially to Great Lakes base."
Cozy Wauk-Townhse near navy base
Peaceful Lindenhurst Dog-Friendly Retreat. Near Mall, Six Flags, Naval Base.
Fridge, microwave, oven, stovetop

Peaceful Lindenhurst Dog-Friendly Retreat. Near Mall, Six Flags, Naval Base.

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great house! Great stay! Thanks!"
Peaceful Lindenhurst Dog-Friendly Retreat. Near Mall, Six Flags, Naval Base.
New Years!! Hot Tub, Fishing Pond, Events! Winter Discounts! Weddings, Pool
Outdoor pool, a heated pool

New Years!! Hot Tub, Fishing Pond, Events! Winter Discounts! Weddings, Pool

9.8 out of 10, Exceptional, (194)
"We stayed here for the weekend and it was wonderful! The kids loved the playset outside and the game room! Definitely would recommend to other groups and families. "
New Years!! Hot Tub, Fishing Pond, Events! Winter Discounts! Weddings, Pool
Quaint Bungalow, near Great Lakes Naval Base
TV, books

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (56)
"Got to stay in this wonderful home while visiting my son and his family. I loved it!"
Quaint Bungalow, near Great Lakes Naval Base
Roxan Corner
Terrace/patio

Roxan Corner

8.4 out of 10, Very good, (29)
"Came to see my son graduate bootcamp"
Roxan Corner
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Pleasant Prairie

Modern Lakeside Villa
Outdoor spa tub

Modern Lakeside Villa

10.0 out of 10, Exceptional, (15)
"Great home and beautiful location. Thank you!"
Modern Lakeside Villa
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Miscellaneous

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

10.0 out of 10, Exceptional, (58)
"I needed a place to stay for work. Thus lake house was well done! Cute, cozy and great views. The hosts were excellent and responded when needed. I will definitely be staying again when Im in the area!"
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Property grounds

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

10.0 out of 10, Exceptional, (231)
"I booked this property for a reunion with some old friends, with the intention that we would be spending a lot of time hanging out. This property was perfect for that -- lots of beds and bathrooms. A beautiful view of the lake from the main living area and two of the bedrooms. Lots of amenities/activities including a pool table, ping pong, a fire pit, etc. But perhaps the best feature was the openness of the kitchen/dining room/pool table/family room, which meant that you feel connected to...
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.