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Pleasant Prairie Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
48 rentals in Pleasant Prairie.
LESS THAN 1 MILE OFF FREEWAY, holiday rental in Pleasant Prairie
LESS THAN 1 MILE OFF FREEWAY, holiday rental in Pleasant Prairie
LESS THAN 1 MILE OFF FREEWAY, holiday rental in Pleasant Prairie

LESS THAN 1 MILE OFF FREEWAY

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Trendy! Pro Cleaned, Self Check In - Sleeps 10, holiday rental in Pleasant Prairie
Trendy! Pro Cleaned, Self Check In - Sleeps 10, holiday rental in Pleasant Prairie
Trendy! Pro Cleaned, Self Check In - Sleeps 10, holiday rental in Pleasant Prairie

Trendy! Pro Cleaned, Self Check In - Sleeps 10

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful homes a, holiday rental in Pleasant Prairie
Beautiful homes a, holiday rental in Pleasant Prairie
Beautiful homes a, holiday rental in Pleasant Prairie

Beautiful homes a

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Modern Lakeside Villa, holiday rental in Pleasant Prairie
Modern Lakeside Villa, holiday rental in Pleasant Prairie
Modern Lakeside Villa, holiday rental in Pleasant Prairie

Modern Lakeside Villa

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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The Executive Home Away from Home, holiday rental in Pleasant Prairie
The Executive Home Away from Home, holiday rental in Pleasant Prairie
The Executive Home Away from Home, holiday rental in Pleasant Prairie

The Executive Home Away from Home

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Wisconsin Escape w/ Deck, Grill & Fire Pit!, holiday rental in Pleasant Prairie
Cozy Wisconsin Escape w/ Deck, Grill & Fire Pit!, holiday rental in Pleasant Prairie
Cozy Wisconsin Escape w/ Deck, Grill & Fire Pit!, holiday rental in Pleasant Prairie

Cozy Wisconsin Escape w/ Deck, Grill & Fire Pit!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The following properties within 20 miles of Pleasant Prairie match all your filters:
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft, holiday rental in Pleasant Prairie
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft, holiday rental in Pleasant Prairie
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft, holiday rental in Pleasant Prairie

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

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View, holiday rental in Pleasant Prairie
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View, holiday rental in Pleasant Prairie
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View, holiday rental in Pleasant Prairie

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming farmhouse in the country, holiday rental in Pleasant Prairie
Charming farmhouse in the country, holiday rental in Pleasant Prairie
Charming farmhouse in the country, holiday rental in Pleasant Prairie

Charming farmhouse in the country

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard., holiday rental in Pleasant Prairie
Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard., holiday rental in Pleasant Prairie
Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard., holiday rental in Pleasant Prairie

Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Outrageous! Near Microsoft Mt Pleasant - Sleeps 18, holiday rental in Pleasant Prairie
Outrageous! Near Microsoft Mt Pleasant - Sleeps 18, holiday rental in Pleasant Prairie
Outrageous! Near Microsoft Mt Pleasant - Sleeps 18, holiday rental in Pleasant Prairie

Outrageous! Near Microsoft Mt Pleasant - Sleeps 18

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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Tiny home in not so tiny Yard, holiday rental in Pleasant Prairie
Tiny home in not so tiny Yard, holiday rental in Pleasant Prairie
Tiny home in not so tiny Yard, holiday rental in Pleasant Prairie

Tiny home in not so tiny Yard

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Welcome to Captain’s Quarters, holiday rental in Pleasant Prairie
Welcome to Captain’s Quarters, holiday rental in Pleasant Prairie
Welcome to Captain’s Quarters, holiday rental in Pleasant Prairie

Welcome to Captain’s Quarters

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Furnished 2 Bedroom Ranch in Pleasant Prairie, holiday rental in Pleasant Prairie
Furnished 2 Bedroom Ranch in Pleasant Prairie, holiday rental in Pleasant Prairie
Furnished 2 Bedroom Ranch in Pleasant Prairie, holiday rental in Pleasant Prairie

Furnished 2 Bedroom Ranch in Pleasant Prairie

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Fabulous! Near Microsoft Mt Pleasant - Sleeps 4, holiday rental in Pleasant Prairie
Fabulous! Near Microsoft Mt Pleasant - Sleeps 4, holiday rental in Pleasant Prairie
Fabulous! Near Microsoft Mt Pleasant - Sleeps 4, holiday rental in Pleasant Prairie

Fabulous! Near Microsoft Mt Pleasant - Sleeps 4

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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fast wifi, perfect remote worker home, 6 acres of secluded nature, holiday rental in Pleasant Prairie
fast wifi, perfect remote worker home, 6 acres of secluded nature, holiday rental in Pleasant Prairie
fast wifi, perfect remote worker home, 6 acres of secluded nature, holiday rental in Pleasant Prairie

fast wifi, perfect remote worker home, 6 acres of secluded nature

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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☆2bdrm Apt near Naval Base - 6 Flags - Casino☆, holiday rental in Pleasant Prairie
☆2bdrm Apt near Naval Base - 6 Flags - Casino☆, holiday rental in Pleasant Prairie
☆2bdrm Apt near Naval Base - 6 Flags - Casino☆, holiday rental in Pleasant Prairie

☆2bdrm Apt near Naval Base - 6 Flags - Casino☆

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Retreat near Golf Course! Minutes from Lake Michigan! LongTerm-6 months+ Rental., holiday rental in Pleasant Prairie
Retreat near Golf Course! Minutes from Lake Michigan! LongTerm-6 months+ Rental., holiday rental in Pleasant Prairie
Retreat near Golf Course! Minutes from Lake Michigan! LongTerm-6 months+ Rental., holiday rental in Pleasant Prairie

Retreat near Golf Course! Minutes from Lake Michigan! LongTerm-6 months+ Rental.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Heavenly! Near Microsoft Mt Pleasant - Sleeps 6, holiday rental in Pleasant Prairie
Heavenly! Near Microsoft Mt Pleasant - Sleeps 6, holiday rental in Pleasant Prairie
Heavenly! Near Microsoft Mt Pleasant - Sleeps 6, holiday rental in Pleasant Prairie

Heavenly! Near Microsoft Mt Pleasant - Sleeps 6

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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****Game Room Included**** Cozy 3BR Home, holiday rental in Pleasant Prairie
****Game Room Included**** Cozy 3BR Home, holiday rental in Pleasant Prairie
****Game Room Included**** Cozy 3BR Home, holiday rental in Pleasant Prairie

****Game Room Included**** Cozy 3BR Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming! Near Microsoft Mt Pleasant - Sleeps 8, holiday rental in Pleasant Prairie
Charming! Near Microsoft Mt Pleasant - Sleeps 8, holiday rental in Pleasant Prairie
Charming! Near Microsoft Mt Pleasant - Sleeps 8, holiday rental in Pleasant Prairie

Charming! Near Microsoft Mt Pleasant - Sleeps 8

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Modern! Professionally Cleaned, Self Check In - Sleeps 10, holiday rental in Pleasant Prairie
Modern! Professionally Cleaned, Self Check In - Sleeps 10, holiday rental in Pleasant Prairie
Modern! Professionally Cleaned, Self Check In - Sleeps 10, holiday rental in Pleasant Prairie

Modern! Professionally Cleaned, Self Check In - Sleeps 10

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful! Near Microsoft Mt Pleasant Sleeps 8, holiday rental in Pleasant Prairie
Beautiful! Near Microsoft Mt Pleasant Sleeps 8, holiday rental in Pleasant Prairie
Beautiful! Near Microsoft Mt Pleasant Sleeps 8, holiday rental in Pleasant Prairie

Beautiful! Near Microsoft Mt Pleasant Sleeps 8

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lake Michigan Waterfront Kenosha Retreat For Eight People!!, holiday rental in Pleasant Prairie
Lake Michigan Waterfront Kenosha Retreat For Eight People!!, holiday rental in Pleasant Prairie
Lake Michigan Waterfront Kenosha Retreat For Eight People!!, holiday rental in Pleasant Prairie

Lake Michigan Waterfront Kenosha Retreat For Eight People!!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Welcome Familys!!, holiday rental in Pleasant Prairie
Welcome Familys!!, holiday rental in Pleasant Prairie
Welcome Familys!!, holiday rental in Pleasant Prairie

Welcome Familys!!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful and Cozy With 5 Bedrooms, holiday rental in Pleasant Prairie
Beautiful and Cozy With 5 Bedrooms, holiday rental in Pleasant Prairie
Beautiful and Cozy With 5 Bedrooms, holiday rental in Pleasant Prairie

Beautiful and Cozy With 5 Bedrooms

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Victorian! Professionally Cleaned, Self Check In - Sleeps 10, holiday rental in Pleasant Prairie
Victorian! Professionally Cleaned, Self Check In - Sleeps 10, holiday rental in Pleasant Prairie
Victorian! Professionally Cleaned, Self Check In - Sleeps 10, holiday rental in Pleasant Prairie

Victorian! Professionally Cleaned, Self Check In - Sleeps 10

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Bright, Airy Keno Home with Patio and Yard, holiday rental in Pleasant Prairie
Bright, Airy Keno Home with Patio and Yard, holiday rental in Pleasant Prairie
Bright, Airy Keno Home with Patio and Yard, holiday rental in Pleasant Prairie

Bright, Airy Keno Home with Patio and Yard

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Large home for group gatherings! Reunions. Business travel., holiday rental in Pleasant Prairie
Large home for group gatherings! Reunions. Business travel., holiday rental in Pleasant Prairie
Large home for group gatherings! Reunions. Business travel., holiday rental in Pleasant Prairie

Large home for group gatherings! Reunions. Business travel.

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Lake Michigan Vacation Rental w/ Private Beach!, holiday rental in Pleasant Prairie
Lake Michigan Vacation Rental w/ Private Beach!, holiday rental in Pleasant Prairie
Lake Michigan Vacation Rental w/ Private Beach!, holiday rental in Pleasant Prairie

Lake Michigan Vacation Rental w/ Private Beach!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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great home in Waukegan for navy graduate families close distance to navy base!!, holiday rental in Pleasant Prairie
great home in Waukegan for navy graduate families close distance to navy base!!, holiday rental in Pleasant Prairie
great home in Waukegan for navy graduate families close distance to navy base!!, holiday rental in Pleasant Prairie

great home in Waukegan for navy graduate families close distance to navy base!!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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The Victory Park Ranch, holiday rental in Pleasant Prairie
The Victory Park Ranch, holiday rental in Pleasant Prairie
The Victory Park Ranch, holiday rental in Pleasant Prairie

The Victory Park Ranch

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Harbor Haven/Game Room/Gym, holiday rental in Pleasant Prairie
Harbor Haven/Game Room/Gym, holiday rental in Pleasant Prairie
Harbor Haven/Game Room/Gym, holiday rental in Pleasant Prairie

Harbor Haven/Game Room/Gym

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Huge 6-bedroom house with WiFi, fitness, Games and Comfort in Great Lake, holiday rental in Pleasant Prairie
Huge 6-bedroom house with WiFi, fitness, Games and Comfort in Great Lake, holiday rental in Pleasant Prairie
Huge 6-bedroom house with WiFi, fitness, Games and Comfort in Great Lake, holiday rental in Pleasant Prairie

Huge 6-bedroom house with WiFi, fitness, Games and Comfort in Great Lake

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Family Ranch close to Naval Base, Great America, Casino and more, holiday rental in Pleasant Prairie
Cozy Family Ranch close to Naval Base, Great America, Casino and more, holiday rental in Pleasant Prairie
Cozy Family Ranch close to Naval Base, Great America, Casino and more, holiday rental in Pleasant Prairie

Cozy Family Ranch close to Naval Base, Great America, Casino and more

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Mid-Century Modern Dream Getaway, holiday rental in Pleasant Prairie
Mid-Century Modern Dream Getaway, holiday rental in Pleasant Prairie
Mid-Century Modern Dream Getaway, holiday rental in Pleasant Prairie

Mid-Century Modern Dream Getaway

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Cozy second floor deplex 2-bedroom in peaceful Kenosha with AC, heat and WiFi, holiday rental in Pleasant Prairie
Cozy second floor deplex 2-bedroom in peaceful Kenosha with AC, heat and WiFi, holiday rental in Pleasant Prairie
Cozy second floor deplex 2-bedroom in peaceful Kenosha with AC, heat and WiFi, holiday rental in Pleasant Prairie

Cozy second floor deplex 2-bedroom in peaceful Kenosha with AC, heat and WiFi

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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The Red Brick Flat- 15 minutes from Naval base!, holiday rental in Pleasant Prairie
The Red Brick Flat- 15 minutes from Naval base!, holiday rental in Pleasant Prairie
The Red Brick Flat- 15 minutes from Naval base!, holiday rental in Pleasant Prairie

The Red Brick Flat- 15 minutes from Naval base!

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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The Brick Arch- 3 bedroom home, holiday rental in Pleasant Prairie
The Brick Arch- 3 bedroom home, holiday rental in Pleasant Prairie
The Brick Arch- 3 bedroom home, holiday rental in Pleasant Prairie

The Brick Arch- 3 bedroom home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Carthage Lakehouse, holiday rental in Pleasant Prairie
Carthage Lakehouse, holiday rental in Pleasant Prairie
Carthage Lakehouse, holiday rental in Pleasant Prairie

Carthage Lakehouse

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2-bedroom house in peaceful Waukegan with WiFi, AC, holiday rental in Pleasant Prairie
2-bedroom house in peaceful Waukegan with WiFi, AC, holiday rental in Pleasant Prairie
2-bedroom house in peaceful Waukegan with WiFi, AC, holiday rental in Pleasant Prairie

2-bedroom house in peaceful Waukegan with WiFi, AC

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Entire 3 Bedroom Cozy Unit, holiday rental in Pleasant Prairie
Entire 3 Bedroom Cozy Unit, holiday rental in Pleasant Prairie
Entire 3 Bedroom Cozy Unit, holiday rental in Pleasant Prairie

Entire 3 Bedroom Cozy Unit

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Office Loft- 2 Bedroom, holiday rental in Pleasant Prairie
The Office Loft- 2 Bedroom, holiday rental in Pleasant Prairie
The Office Loft- 2 Bedroom, holiday rental in Pleasant Prairie

The Office Loft- 2 Bedroom

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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3-bedroom house WiFi in lovely Waukegan Near Gurnee, holiday rental in Pleasant Prairie
3-bedroom house WiFi in lovely Waukegan Near Gurnee, holiday rental in Pleasant Prairie
3-bedroom house WiFi in lovely Waukegan Near Gurnee, holiday rental in Pleasant Prairie

3-bedroom house WiFi in lovely Waukegan Near Gurnee

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy 2 bedroom home with a study., holiday rental in Pleasant Prairie
Cozy 2 bedroom home with a study., holiday rental in Pleasant Prairie
Cozy 2 bedroom home with a study., holiday rental in Pleasant Prairie

Cozy 2 bedroom home with a study.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious 5-bedroom home - amazing backyard with fire pit. Great for gatherings, holiday rental in Pleasant Prairie
Spacious 5-bedroom home - amazing backyard with fire pit. Great for gatherings, holiday rental in Pleasant Prairie
Spacious 5-bedroom home - amazing backyard with fire pit. Great for gatherings, holiday rental in Pleasant Prairie

Spacious 5-bedroom home - amazing backyard with fire pit. Great for gatherings

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Relaxing beach-style sanctuary in quiet area!, holiday rental in Pleasant Prairie
Relaxing beach-style sanctuary in quiet area!, holiday rental in Pleasant Prairie
Relaxing beach-style sanctuary in quiet area!, holiday rental in Pleasant Prairie

Relaxing beach-style sanctuary in quiet area!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
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3 Bedroom Home near Naval Base!, holiday rental in Pleasant Prairie
3 Bedroom Home near Naval Base!, holiday rental in Pleasant Prairie
3 Bedroom Home near Naval Base!, holiday rental in Pleasant Prairie

3 Bedroom Home near Naval Base!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Showing results 1-48 of 48
Frequently Asked Questions about Pleasant Prairie