Best Vacation Homes in Pleasant Springs
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $533/Night
For 7 Nights CA $3,733
1194.79 ft²
6 Guests
2 Bedrooms
1 Bathroom
House
- Private Beach
- Oceanfront
- Ocean View
CA $580/Night
For 7 Nights CA $4,061
CA $142/Night
For 7 Nights CA $994
6500 ft²
16 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $1,239/Night
For 7 Nights CA $8,675
CA $160/Night
For 7 Nights CA $1,118
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $325/Night
For 7 Nights CA $2,278
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Balcony/Terrace
- Kitchen
- Parking
CA $179/Night
For 7 Nights CA $1,250
600 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $255/Night
For 7 Nights CA $1,784
Pleasant Springs Luxury Rentals
2760 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $1,076/Night
For 7 Nights CA $7,534
16 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $988/Night
For 7 Nights CA $6,915
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $823/Night
For 7 Nights CA $5,765
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $702/Night
For 7 Nights CA $4,913
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $432/Night
For 7 Nights CA $3,025
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Kitchen
CA $390/Night
For 7 Nights CA $2,731
1500 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $377/Night
For 7 Nights CA $2,641
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
CA $344/Night
For 7 Nights CA $2,409
Pleasant Springs Pet Friendly Vacation Rentals
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
CA $318/Night
For 7 Nights CA $2,228
CA $76/Night
For 7 Nights CA $535
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
CA $674/Night
For 7 Nights CA $4,716
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
CA $191/Night
For 7 Nights CA $1,338
1400 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $448/Night
For 7 Nights CA $3,136
1400 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $518/Night
For 7 Nights CA $3,630
Pleasant Springs Large Vacation Homes
2350 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
CA $823/Night
For 7 Nights CA $5,758
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $723/Night
For 7 Nights CA $5,064
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
CA $665/Night
For 7 Nights CA $4,656
3200 ft²
14 Guests
6 Bedrooms
2 Bathrooms
Family Friendly
Other
- Hot Tub
- Fireplace/Heating
- Pool
CA $1,105/Night
For 7 Nights CA $7,738
Why Choose Rent By Owner for your Pleasant Springs Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Pleasant Springs
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as this destination's appeal varies with the seasons and regional climate conditions.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, you can experience pleasant weather and blooming landscapes in the region, making it ideal for outdoor activities and enjoying nature.
Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
Early Fall (September to October)
This season offers mild temperatures and vibrant fall foliage, perfect for exploring the area's scenic beauty and engaging in seasonal outdoor adventures.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Off-Season Highlights
Mid Winter (January to February)
The colder months bring fewer visitors, providing a peaceful retreat with opportunities for cozy stays and quiet exploration of the landscape.
Average Temperature Daytime: 20-30°F - Nighttime: 10-20°F
Late Fall (November to December)
As the region transitions into winter, the area becomes less crowded, offering a tranquil atmosphere before the holiday rush begins.
Average Temperature Daytime: 40-50°F - Nighttime: 25-35°F
Weekly Weather Forecast for Pleasant Springs
How to Book Your Pleasant Springs Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
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.
Explore and book the perfect rental in Pleasant Springs
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
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 spacious outdoor areas with private yards perfect for relaxing or outdoor dining.
- Take advantage of lakeside access or scenic waterfront views common in this region.
- Make the most of outdoor grilling stations to host your own cookouts amidst nature.
- Explore nearby trails and pathways suited for walking, jogging, or biking adventures.
- Relax on a charming porch or patio, ideal for soaking up the peaceful surroundings.
- Utilize outdoor fire pits or fireplaces for cozy evenings under starry skies.
- Benefit from well-maintained gardens or landscaped areas that enhance the outdoor experience.
Top Attractions Around Pleasant Springs
What attractions are nearby?
In this charming area, you can enjoy a variety of outdoor activities and scenic explorations that highlight the natural beauty of Wisconsin's landscape, providing memorable experiences just moments from your vacation rental.
Family Activities
- Pleasant Springs County Park: Enjoy outdoor fun by exploring scenic trails, fishing spots, and picnic areas right in the heart of the region.
- Local Farms and orchards: Visit nearby farms for family-friendly activities like pick-your-own fruit and guided tours that highlight the area's agricultural charm.
- Nature Center and Wildlife Viewing: Discover local flora and fauna at nature centers within easy reach, providing educational experiences for children and adults alike.
- Recreational Water Activities: Take advantage of lakes and waterways close to here for kayaking, paddleboarding, or relaxing by the shore with your loved ones.
Adult Activities
- Wine Tasting Tours: Experience the region's renowned wineries by exploring guided wine tasting tours that showcase local flavors and craftsmanship.
- Canoeing and Kayaking on Local Lakes: Enjoy the tranquility of nearby lakes through canoeing or kayaking adventures, offering a perfect way to connect with nature.
- Golfing at Area Courses: Play a round of golf at well-maintained courses nestled within the region, ideal for relaxing days on the fairways.
- Spa and Wellness Centers: Unwind with rejuvenating treatments at local spas that focus on relaxation and wellness in the area.
Other Places to Stay in Pleasant Springs, WI
Lake Kegonsa State Park
La Follette Beach
Pleasant Springs Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the area's event calendar to align your stay with local festivals or seasonal activities, enhancing your experience in Pleasant Springs.
- Explore Nearby Nature Trails: Take advantage of the region's scenic outdoor spaces by exploring walking or biking trails close to your vacation rental for a rejuvenating outdoor adventure.
- Utilize Local Recommendations: Seek out tips from hosts or locals about hidden gems and dining options that showcase the area's authentic charm during your visit.
- Visit During Off-Peak Seasons: Consider planning your trip during less busy times to enjoy more tranquility and better availability when booking your preferred stay.
Transportation Options
- Car Rental Services: Renting a car here offers the flexibility to explore the scenic countryside and local attractions at your own pace.
- Public Transit Options: Local bus routes provide convenient transportation within the area, making it easy to navigate without a vehicle.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing apps are readily available, offering quick and reliable transportation for your travels around this destination.
- Biking and Walking: The region features charming trails and walkable roads suitable for biking or exploring on foot, ideal for enjoying the natural beauty surrounding your stay.
Local Customs Options
- Local Fish Fry Tradition: Participating in the region’s beloved Friday night fish fry is a cherished custom that reflects the community’s appreciation for fresh seafood and camaraderie.
- Community Events and Festivals: Engaging in seasonal festivals and town gatherings offers a genuine glimpse into the area's friendly spirit and shared traditions.
- Respect for Nature and Outdoor Activities: Appreciating the local love for outdoor pursuits like fishing, boating, and hiking helps you connect with the region's scenic beauty and environmental values.
- Casual Hospitality and Friendly Greetings: Expect a warm, welcoming attitude from locals who often greet visitors with genuine friendliness, exemplifying the region’s hospitable customs.
Frequently Asked Questions About Pleasant Springs?
1. What are the top vacation rentals in Pleasant Springs?
There are a lot of options in Pleasant Springs. If you plan on staying in the Pleasant Springs area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pleasant Springs:
- Plan your reunion/gathering now in beautiful rural South Central Wisconsin
- Madison/Stoughton 3 BR/3 BA Lake Kegonsa Cottage
- Lake Kegonsa 1BR Cottage 15 Min.to Madison,Sleeps 3 ,Kayaks
- Two Bedroom Cottage with Great Lake Views!
- Lovely Waterfront Two Bedroom House
- Charming 4 Bed, 2.5 Bath home minutes from Madison perfect for any occasion.
- Boho & Rustic Getaway ~ King Bed ~ Close to Madison!
- Tiny house living with large fun experiences waiting for you
- Small Cottage. Huge Lake Views!
- Madison 3 BR Cottage on 3000 acre Lake Kegonsa. Kayaks & Pontoon
2. Which vacation homes in Pleasant Springs are best for families?
If you are looking for a family-friendly vacation home in Pleasant Springs, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Pleasant Springs:
3. How many Rentbyowner vacation rentals are available in Pleasant Springs?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 39 in the Pleasant Springs 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 Pleasant Springs.
4. What is the cancellation policy for vacation rentals in Pleasant Springs, Wisconsin?
Cancellation policies vary by listing, so it's important to review the specific terms on the property’s page or contact the owner directly to understand the refund and cancellation conditions for your stay.
5. How do I find available dates and book a vacation rental in Pleasant Springs?
You can easily check availability and make reservations by using the search feature on the booking site, selecting your preferred travel dates, and following the prompts to secure your stay in this region.
6. Are there any additional fees associated with booking a vacation rental here?
Additional fees such as cleaning charges, service fees, or taxes are itemized during the booking process. It’s advised to read the detailed fee breakdown on each listing before confirming your reservation.
7. Can I get a custom quote or inquire about special amenities for my stay?
Yes, most listings allow you to send a direct message to the property owner or manager to ask about custom requests or specific amenities to enhance your visit in this area.
8. What should I know about checking in and out of vacation rentals in Pleasant Springs?
Check-in and check-out times are specified on each property listing. For specific instructions or early/late arrangements, it’s best to communicate directly with the host prior to your arrival.
Pleasant Springs Top Rated Vacation Rentals
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Fireplace/Heating
- Pool
CA $101/Night
For 7 Nights CA $704
385.71 ft²
6 Bathrooms
Hotel
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $125/Night
For 7 Nights CA $872
CA $101/Night
For 7 Nights CA $706
CA $106/Night
For 7 Nights CA $745
