Discover Your Perfect Greenleaf Vacation Homes

Best Vacation Homes in Greenleaf

House
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like-icon10.0
Exceptional
(9 Reviews)
2 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
CA $580/Night 7 Nights - CA $4,058
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House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
2 Bedrooms 2 Baths 4 Guests 1334.72 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Parking
    Parking
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CA $464/Night 7 Nights - CA $3,248
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Bed & Breakfast
Map-icon
like-icon10.0
Exceptional
(19 Reviews)
1 Bedroom 1 Bath
  • Balcony/Terrace
    Balcony/Terrace
  • Breakfast
    Breakfast
More amenities
CA $1,776/Night 7 Nights - CA $12,435
Apartment
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
1 Bedroom 1 Bath 3 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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CA $431/Night 7 Nights - CA $3,018
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House
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like-icon10.0
Exceptional
(2 Reviews)
3 Bedrooms 2 Baths 8 Guests 1776.05 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
CA $472/Night 7 Nights - CA $3,303
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
2 Bedrooms 1 Bath 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
CA $456/Night 7 Nights - CA $3,195
Apartment
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
2 Bedrooms 1 Bath 5 Guests 1496 ft²
  • Fireplace/Heating
    Fireplace/Heating
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    Kitchen
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CA $194/Night 7 Nights - CA $1,355
House
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like-icon9.0
Exceptional
(6 Reviews)
2 Bedrooms 2 Baths 8 Guests 1500 ft²
  • Fireplace/Heating
    Fireplace/Heating
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    Balcony/Terrace
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CA $240/Night 7 Nights - CA $1,680

Greenleaf Luxury Rentals

House
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4 Bedrooms 2 Baths 11 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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Unlock the Best Price
House
Map-icon
4 Bedrooms 3 Baths 11 Guests 3196.88 ft²
  • Parking
    Parking
  • Air Conditioner
    Air Conditioner
More amenities
CA $6,314/Night 7 Nights - CA $44,199
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
7 Bedrooms 5 Baths 20 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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CA $5,672/Night 7 Nights - CA $39,706
House
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3 Bedrooms 1 Bath 6 Guests 1120 ft²
  • Fireplace/Heating
    Fireplace/Heating
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    Balcony/Terrace
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CA $3,989/Night 7 Nights - CA $27,924
House
Map-icon
like-icon10.0
Exceptional
(33 Reviews)
6 Bedrooms 4 Baths 30 Guests 5200 ft²
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
CA $3,194/Night 7 Nights - CA $22,355
House
Map-icon
like-icon10.0
Exceptional
(11 Reviews)
6 Bedrooms 3 Baths 20 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
CA $2,708/Night 7 Nights - CA $18,956
House
Map-icon
like-icon10.0
Exceptional
(14 Reviews)
5 Bedrooms 3 Baths 20 Guests
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
CA $2,669/Night 7 Nights - CA $18,683
House
Map-icon
like-icon8.8
Fabulous
(3 Reviews)
6 Bedrooms 3 Baths 14 Guests
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
CA $2,347/Night 7 Nights - CA $16,432

Greenleaf Pet Friendly Vacation Rentals

Apartment
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2 Bedrooms 1 Bath 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
CA $77/Night 7 Nights - CA $540
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Apartment
Map-icon
like-icon10.0
Exceptional
(1 Review)
2 Bedrooms 2 Baths 6 Guests 1603.82 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
CA $1,137/Night 7 Nights - CA $7,963
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Cottage
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1 Bedroom 1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
CA $839/Night 7 Nights - CA $5,872
Apartment
Map-icon
like-icon10.0
Exceptional
(13 Reviews)
2 Bedrooms 2 Baths 6 Guests 1700 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
CA $546/Night 7 Nights - CA $3,825
star-icons-4
Apartment
Map-icon
like-icon10.0
Exceptional
(1 Review)
2 Bedrooms 2 Baths 6 Guests 1700.7 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
CA $1,137/Night 7 Nights - CA $7,963
House
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
2 Bedrooms 2 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $406/Night 7 Nights - CA $2,840
Condo
Map-icon
like-icon9.8
Exceptional
(14 Reviews)
2 Bedrooms 2 Baths 6 Guests
  • Pet Friendly
    Pet Friendly
  • Kitchen
    Kitchen
More amenities
CA $566/Night 7 Nights - CA $3,965
Apartment
Map-icon
like-icon9.8
Exceptional
(6 Reviews)
2 Bedrooms 2 Baths 6 Guests 1600 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
CA $462/Night 7 Nights - CA $3,234

Greenleaf Large Vacation Homes

House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
5 Bedrooms 4 Baths 10 Guests
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
CA $2,084/Night 7 Nights - CA $14,586
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House
Map-icon
like-icon9.2
Exceptional
(9 Reviews)
4 Bedrooms 2 Baths 10 Guests 2195.84 ft²
  • View
    View
  • Pet Friendly
    Pet Friendly
More amenities
CA $261/Night 7 Nights - CA $1,827
House
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5 Bedrooms 3 Baths 11 Guests 3500 ft²
  • Fireplace/Heating
    Fireplace/Heating
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    Balcony/Terrace
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CA $702/Night 7 Nights - CA $4,912
House
Map-icon
4 Bedrooms 2 Baths 12 Guests 2798.62 ft²
  • Parking
    Parking
  • Air Conditioner
    Air Conditioner
More amenities
CA $888/Night 7 Nights - CA $6,214
House
Map-icon
like-icon10.0
Exceptional
(91 Reviews)
6 Bedrooms 4 Baths 14 Guests 5200 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
CA $1,567/Night 7 Nights - CA $10,970
House
Map-icon
like-icon10.0
Exceptional
(27 Reviews)
5 Bedrooms 4 Baths 10 Guests
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
CA $1,513/Night 7 Nights - CA $10,588
House
Map-icon
like-icon10.0
Exceptional
(20 Reviews)
5 Bedrooms 3 Baths 16 Guests 3035 ft²
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
CA $1,843/Night 7 Nights - CA $12,905
House
Map-icon
like-icon10.0
Exceptional
(12 Reviews)
3 Bedrooms 1 Bath 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $450/Night 7 Nights - CA $3,153

Why Choose Rent By Owner for your Greenleaf Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Greenleaf

When should you plan your Vacation Rentals stay?

To make the most of your getaway, consider visiting during the shoulder seasons when the region offers pleasant weather and fewer crowds, allowing you to enjoy the natural beauty and local charm at the ideal time for this destination.

Peak Season Highlights

summer
Summer (June to August)

During the warmer months, this destination sees a surge of visitors seeking outdoor activities and pleasant weather. Booking your vacation rentals early ensures you secure the best options for enjoying the season.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

Autumn offers vibrant foliage views and mild temperatures, attracting travelers looking for scenic beauty. Planning ahead allows you to enjoy this colorful season comfortably with well-chosen accommodations.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December to February)

The colder months are quieter here, providing a peaceful retreat from busier times. This is an ideal period for those seeking solitude and cozy lodging options.

Average Temperature Daytime: 20°F to 30°F - Nighttime: 10°F to 20°F
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Spring (March to May)

Springtime ushers in milder weather and blooming landscapes, making it a great time for selective travelers to explore without the crowds. Early booking can help you find the most comfortable rental options.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Greenleaf

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor grilling facilities to prepare meals while soaking up the natural surroundings.
  • Take advantage of spacious patios or decks perfect for relaxing and entertaining outdoors.
  • Make use of private or shared fire pits to enhance cozy evenings under the stars.
  • Discover well-maintained gardens or landscaped yards that add to the charm of your stay.
  • Utilize available picnic areas to dine al fresco amid scenic views.
  • Benefit from access to nearby lakes or rivers for fishing, kayaking, or paddleboarding.
  • Explore outdoor sports amenities such as tennis courts, golf courses, or hiking trails in the vicinity.
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Family Activities

  • Greenleaf County Park: Enjoy outdoor activities such as picnicking, hiking, and exploring nature trails suitable for all ages.
  • Local Nature Center: Engage your family in educational exhibits and interactive programs that highlight the region’s natural environment.
  • Community Recreation Area: Take advantage of sports fields, playgrounds, and open spaces perfect for active family fun during your stay.
  • Nearby Lakes and Beaches: Spend a relaxing day swimming, fishing, or building sandcastles by the scenic waters within easy reach of your accommodation.
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Adult Activities

  • Fishing at Lake Michigan: Enjoy a peaceful day of fishing along the shores of Lake Michigan, just a short drive from here, offering excellent opportunities for anglers of all skill levels.
  • Greenleaf Nature Trails: Explore scenic hiking and biking trails in the nearby nature preserves, providing a perfect setting for outdoor enthusiasts seeking tranquility and natural beauty.
  • Local Breweries Tour: Discover the region's craft beer scene by visiting local breweries, where you can sample unique brews in a relaxed and welcoming atmosphere.
  • Golfing at Greenleaf Golf Course: Spend your day on the lush greens of the local golf course, ideal for both beginners and seasoned players looking to enjoy a round amidst scenic surroundings.

Greenleaf Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead: Research the local amenities and activities available nearby to tailor your stay with the region’s best offerings.
  • Explore Local Cuisine: Take advantage of regional dining options to experience authentic flavors unique to this destination.
  • Utilize Exclusive Deals: Look for special discounts or packages on vacation rentals here to maximize your budget during your visit.
  • Connect with Hosts: Communicate directly with property owners to get personalized tips and ensure a memorable stay in this area.

Transportation Options

  • Greenleaf Transportation Services: Local shuttle and taxi options provide convenient, reliable transfers around the area and to nearby attractions.
  • Public Bus System: The regional bus network connects you to neighboring towns and cities, offering an affordable way to explore without a car.
  • Car Rentals: Several rental agencies operate here, giving you the flexibility to discover the region at your own pace with a comfortable vehicle.
  • Bike Rentals and Trails: For a more active approach, bike rentals are available for exploring scenic routes and enjoying the fresh air within this destination.

Local Customs Options

  • Polish Heritage Celebrations: Embrace the region's rich Polish roots through local festivals and traditional foods enjoyed by residents here.
  • Farmers' Market Traditions: You can experience the community’s agricultural heritage by visiting farmers' markets that highlight fresh, local Wisconsin produce.
  • Seasonal Festivities: Participating in seasonal events like fall harvests or summer fairs allows you to connect with local customs and the area's natural beauty.
  • Religious Practices: Respect for longstanding religious traditions is evident in the numerous churches that serve as cultural landmarks here.

Frequently Asked Questions About Greenleaf?

2. How many vacation rentals have private pools in Greenleaf?

3. Which vacation homes in Greenleaf are best for families?

If you are looking for a family-friendly vacation home in Greenleaf, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Greenleaf:

4. How many Rentbyowner vacation rentals are available in Greenleaf?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 328 in the Greenleaf area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Greenleaf. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the individual property owner. To ensure you understand the specific terms, please review the listing details or contact the host directly before booking.

6. Are there any special requirements or house rules I should be aware of when booking a stay here?

Each vacation rental may have its own house rules and requirements. Check the listing information carefully and communicate with the host if you have any questions to ensure your stay aligns with their guidelines.

7. How do I know if a vacation rental is available during my preferred dates?

Availability is updated regularly on the listing page. For the most accurate information, verify the dates directly through the booking platform or contact the host for confirmation.

8. What amenities are typically included in vacation rentals in this region?

Amenities can vary by property, but common features include Wi-Fi, fully equipped kitchens, outdoor spaces, and parking. Review each listing for detailed information about the amenities offered.

9. What is the process for confirming my reservation in Greenleaf's vacation rentals?

Reservations are typically confirmed once you complete the booking process and receive a confirmation from the host. Be sure to follow the instructions provided and contact the host if you need any assistance prior to arrival.

Greenleaf Top Rated Vacation Rentals

House
Map-icon
like-icon10.0
Exceptional
(9 Reviews)
5 Bedrooms 3 Baths 10 Guests 2500 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
CA $1,615/Night 7 Nights - CA $11,304
House
Map-icon
like-icon10.0
Exceptional
(5 Reviews)
5 Bedrooms 4 Baths 12 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
CA $924/Night 7 Nights - CA $6,466
Hotel
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
CA $246/Night 7 Nights - CA $1,724
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Hotel
Map-icon
like-icon9.4
Exceptional
(549 Reviews)
1 Bath
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $233/Night 7 Nights - CA $1,633
star-icons-3
Hotel
Map-icon
like-icon9.4
Exceptional
(536 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
CA $177/Night 7 Nights - CA $1,236
Hotel
Map-icon
like-icon9.4
Exceptional
(152 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
CA $152/Night 7 Nights - CA $1,066
star-icons-3
Hotel
Map-icon
like-icon9.3
Exceptional
(39 Reviews)
2 Baths 509.49 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
CA $226/Night 7 Nights - CA $1,581
Hotel
Map-icon
like-icon9.2
Exceptional
(1005 Reviews)
1 Bath
  • Hot Tub
    Hot Tub
  • Pool
    Pool
More amenities
CA $159/Night 7 Nights - CA $1,111