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Compare 277 Vacation Homes in Pleasant Prairie with updated reviews, rates, and availability.

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
YOUR MORNING WAKE-UP CALL

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

10.0 out of 10, Exceptional, (232)
"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!!
Room

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)
Children's area

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"
The price is AED 735
AED 1,201 total
includes taxes & fees
28 Jan - 29 January 2025
Lake/Beach Getaway (Remodeled)
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Exterior

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

9.8 out of 10, Exceptional, (76)
"AMAZING PROPERTY!!!"
The price is AED 551
AED 1,992 total
includes taxes & fees
5 Jan - 6 January 2025
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Lakefront Home w/ Game Room, Theater & Dock!
Fox Lake Vacation Rental | 5BR | 4BA | 3 Stories | Stairs Required | 2,800 Sq Ft

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
Libertyville Vacation Rental | 3BR | 3BA | 2,700 Sq Ft | Step-Free Access

Riverfront Libertyville Retreat w/ Outdoor Kitchen

9.0 out of 10, Wonderful, (18)
"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
Living area

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!
Room to spread out, relax, and unwind.

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!
Interior

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

9.8 out of 10, Exceptional, (8)
"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
Property grounds

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
Living room & Eat in Kitchen

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
Room

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 AED 213
AED 367 total
includes taxes & fees
1 Jan - 2 January 2025
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Riverside Retreat-Hot tub, Kayaks, firepit
Fire pit with a river view

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
Pool

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.
Exterior

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.
Escape to Tranquility: Lovely Oasis 20 Minutes from Downtown Milwaukee
Dining

Escape to Tranquility: Lovely Oasis 20 Minutes from Downtown Milwaukee

10.0 out of 10, Exceptional, (11)
"Wonderful property to stay at. The owner was very accomodating tonis arriving earlier than planned. The house was in a quiet area outside of the city but still was only 20 minutes from downtown."
Escape to Tranquility: Lovely Oasis 20 Minutes from Downtown Milwaukee
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.
Exterior

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
Aerial View Click Video Tab above to see Drone Video

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
Welcome to our guest house, "A Little House on Prairie"!

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
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

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.
Dining

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

10.0 out of 10, Exceptional, (59)
"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.
New Years!! Hot Tub, Fishing Pond, Events! Winter Discounts! Weddings, Pool
Aerial View Click Video Tab above to see Drone Video

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
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.