Vacation rentals in Pleasant Springs, WI

35 available vacation rental offers

airbnbBooking.comVrboExpediaSonderpricelineTripadvisorTrip.comHomestayHotels.comOrbitz

Choose the perfect vacation accommodation

Price per night

Up to $100$100 - 200From $200

Accommodation type

Vacation rentals and Airbnb

Rating

Excellent 9+Very good 8+Good 7+All ratings

Best vacation rentals and Airbnb offers in Pleasant Springs, WI

Free Breakfast. Pool & Hot Tub. Near UW-Madison! - Pleasant Springs, WI

Free Breakfast. Pool & Hot Tub. Near UW-Madison!

Apartment, Pleasant Springs

Free Breakfast. Pool & Hot Tub. Near UW-Madison! is a apartment in Pleasant Springs, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Free Breakfast. Pool & Hot Tub. Near UW-Madison!

Free Breakfast. Pool & Hot Tub. Near UW-Madison! is a apartment in Pleasant Springs, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,111.

From$159/night
Show
King Suite. Free Breakfast. Pool. Near UW-Madison! - Pleasant Springs, WI

King Suite. Free Breakfast. Pool. Near UW-Madison!

Condo, Pleasant Springs

King Suite. Free Breakfast. Pool. Near UW-Madison! is a condo in Pleasant Springs, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About King Suite. Free Breakfast. Pool. Near UW-Madison!

King Suite. Free Breakfast. Pool. Near UW-Madison! is a condo in Pleasant Springs, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,237.

From$177/night
Show
Free Breakfast. Pool + Hot Tub. Near UW-Madison! - Pleasant Springs, WI

Free Breakfast. Pool + Hot Tub. Near UW-Madison!

Condo, Pleasant Springs

Free Breakfast. Pool + Hot Tub. Near UW-Madison! is a condo in Pleasant Springs, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Free Breakfast. Pool + Hot Tub. Near UW-Madison!

Free Breakfast. Pool + Hot Tub. Near UW-Madison! is a condo in Pleasant Springs, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,318.

From$188/night
Show
The Wilson - Pleasant Springs, WI

The Wilson

Apartment, Pleasant Springs

The Wilson is a apartment in Pleasant Springs, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

Read more

About The Wilson

The Wilson is a apartment in Pleasant Springs, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,558.

From$194/night
Show

Vacation rentals with a pool in Pleasant Springs, WI

Add a pool to the search when you want an easy place to cool off between outings.

Free Breakfast. Pool & Hot Tub. Near UW-Madison! - Pleasant Springs, WI

Free Breakfast. Pool & Hot Tub. Near UW-Madison!

Condo, Pleasant Springs

Free Breakfast. Pool & Hot Tub. Near UW-Madison! is a condo in Pleasant Springs, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Free Breakfast. Pool & Hot Tub. Near UW-Madison!

Free Breakfast. Pool & Hot Tub. Near UW-Madison! is a condo in Pleasant Springs, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,805.

From$258/night
Show
Free Breakfast. Pool & Hot Tub. Near UW-Madison! - Pleasant Springs, WI

Free Breakfast. Pool & Hot Tub. Near UW-Madison!

Condo, Pleasant Springs

Free Breakfast. Pool & Hot Tub. Near UW-Madison! is a condo in Pleasant Springs, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Free Breakfast. Pool & Hot Tub. Near UW-Madison!

Free Breakfast. Pool & Hot Tub. Near UW-Madison! is a condo in Pleasant Springs, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,952.

From$279/night
Show
Beautiful Lake Monona Home-Minutes to Downtown Madison - Pleasant Springs, WI

Beautiful Lake Monona Home-Minutes to Downtown Madison

Holiday Home, Pleasant Springs

Beautiful Lake Monona Home-Minutes to Downtown Madison is a holiday home in Pleasant Springs, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Beautiful Lake Monona Home-Minutes to Downtown Madison

Beautiful Lake Monona Home-Minutes to Downtown Madison is a holiday home in Pleasant Springs, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $19,551.

From$2,793/night
Show

Vacation rentals with parking in Pleasant Springs, WI

Find vacation rentals that make arriving by car easier.

Log Cabin at Lake Koshkonong - “The Overlook” - Pleasant Springs, WI

Log Cabin at Lake Koshkonong - “The Overlook”

Cabin, Pleasant Springs

Log Cabin at Lake Koshkonong - “The Overlook” is a cabin in Pleasant Springs, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

Read more

About Log Cabin at Lake Koshkonong - “The Overlook”

Log Cabin at Lake Koshkonong - “The Overlook” is a cabin in Pleasant Springs, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: parking, free parking, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,593.

From$228/night
Show
Lake Ko Bungalow, full home. Short walk to lake Koshkonong. Private fire pit. - Pleasant Springs, WI

Lake Ko Bungalow, full home. Short walk to lake Koshkonong. Private fire pit.

Holiday Home, Pleasant Springs

Lake Ko Bungalow, full home. Short walk to lake Koshkonong. Private fire pit. is a holiday home in Pleasant Springs, with parking. This stay gives travelers a comfortable base for exploring…

Read more

About Lake Ko Bungalow, full home. Short walk to lake Koshkonong. Private fire pit.

Lake Ko Bungalow, full home. Short walk to lake Koshkonong. Private fire pit. is a holiday home in Pleasant Springs, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,814.

From$259/night
Show
A Best Value! Nice 2+ bdrm home on Foxboro GC in Oregon.. 10 Minutes to Madison! - Pleasant Springs, WI

A Best Value! Nice 2+ bdrm home on Foxboro GC in Oregon.. 10 Minutes to Madison!

Holiday Home, Pleasant Springs

A Best Value! Nice 2+ bdrm home on Foxboro GC in Oregon.. 10 Minutes to Madison! is a holiday home in Pleasant Springs, with parking and kitchen access. This stay gives travelers a…

Read more

About A Best Value! Nice 2+ bdrm home on Foxboro GC in Oregon.. 10 Minutes to Madison!

A Best Value! Nice 2+ bdrm home on Foxboro GC in Oregon.. 10 Minutes to Madison! is a holiday home in Pleasant Springs, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,107.

From$301/night
Show
Renovated 4 BR Home Near Madison - Pleasant Springs, WI

Renovated 4 BR Home Near Madison

Holiday Home, Pleasant Springs

Renovated 4 BR Home Near Madison is a holiday home in Pleasant Springs, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

Read more

About Renovated 4 BR Home Near Madison

Renovated 4 BR Home Near Madison is a holiday home in Pleasant Springs, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,827.

From$404/night
Show

Pet-friendly vacation rentals in Pleasant Springs, WI

Bring your pet along with stays that welcome four-legged travelers.

Home in the Heart of Monona! - Pleasant Springs, WI

Home in the Heart of Monona!

Holiday Home, Pleasant Springs

Home in the Heart of Monona! is a holiday home in Pleasant Springs, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

Read more

About Home in the Heart of Monona!

Home in the Heart of Monona! is a holiday home in Pleasant Springs, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,907.

From$415/night
Show
Exceptional Comfort Quiet Clean 4 Bed 3 Bath next to woods - 21 min to Madison - Pleasant Springs, WI

Exceptional Comfort Quiet Clean 4 Bed 3 Bath next to woods - 21 min to Madison

Condo, Pleasant Springs

Exceptional Comfort Quiet Clean 4 Bed 3 Bath next to woods - 21 min to Madison is a condo in Pleasant Springs, with pet-friendly space and a quieter setting. This stay gives travelers a…

Read more

About Exceptional Comfort Quiet Clean 4 Bed 3 Bath next to woods - 21 min to Madison

Exceptional Comfort Quiet Clean 4 Bed 3 Bath next to woods - 21 min to Madison is a condo in Pleasant Springs, with pet-friendly space and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,673.

From$525/night
Show
Cozy 4+ Bed 3 Bath Screened in Porch, Fire Pit, yard games - 19 min to Madison - Pleasant Springs, WI

Cozy 4+ Bed 3 Bath Screened in Porch, Fire Pit, yard games - 19 min to Madison

Condo, Pleasant Springs

Cozy 4+ Bed 3 Bath Screened in Porch, Fire Pit, yard games - 19 min to Madison is a condo in Pleasant Springs, with pet-friendly space and kitchen access. This stay gives travelers a…

Read more

About Cozy 4+ Bed 3 Bath Screened in Porch, Fire Pit, yard games - 19 min to Madison

Cozy 4+ Bed 3 Bath Screened in Porch, Fire Pit, yard games - 19 min to Madison is a condo in Pleasant Springs, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,885.

From$555/night
Show
A-Frame Arbor One Block From The Beach-Four Beds and Four Bathrooms! - Pleasant Springs, WI

A-Frame Arbor One Block From The Beach-Four Beds and Four Bathrooms!

Holiday Home, Pleasant Springs

A-Frame Arbor One Block From The Beach-Four Beds and Four Bathrooms! is a holiday home in Pleasant Springs, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

Read more

About A-Frame Arbor One Block From The Beach-Four Beds and Four Bathrooms!

A-Frame Arbor One Block From The Beach-Four Beds and Four Bathrooms! is a holiday home in Pleasant Springs, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,622.

From$946/night
Show

Vacation rentals with a kitchen in Pleasant Springs, WI

Compare stays with kitchen access for longer trips and easier meals.

Charming 4-bedroom Lake house on Lake Ripley in Cambridge - Pleasant Springs, WI

Charming 4-bedroom Lake house on Lake Ripley in Cambridge

Holiday Home, Pleasant Springs

Charming 4-bedroom Lake house on Lake Ripley in Cambridge is a holiday home in Pleasant Springs, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

Read more

About Charming 4-bedroom Lake house on Lake Ripley in Cambridge

Charming 4-bedroom Lake house on Lake Ripley in Cambridge is a holiday home in Pleasant Springs, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,381.

From$483/night
Show
Remodeled 3 bedroom home in Monona. Close to Downtown! - Pleasant Springs, WI

Remodeled 3 bedroom home in Monona. Close to Downtown!

Holiday Home, Pleasant Springs

Remodeled 3 bedroom home in Monona. Close to Downtown! is a holiday home in Pleasant Springs, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

Read more

About Remodeled 3 bedroom home in Monona. Close to Downtown!

Remodeled 3 bedroom home in Monona. Close to Downtown! is a holiday home in Pleasant Springs, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,650.

From$521/night
Show
Madison & ~UW~-Madison Area Lakefront Home - Pleasant Springs, WI

Madison & ~UW~-Madison Area Lakefront Home

Cottage, Pleasant Springs

Madison & ~UW~-Madison Area Lakefront Home is a cottage in Pleasant Springs, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Madison & ~UW~-Madison Area Lakefront Home

Madison & ~UW~-Madison Area Lakefront Home is a cottage in Pleasant Springs, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,477.

From$640/night
Show
Family-Friendly 5BR Lakefront Cabin Near Madison WI • Sleeps the Whole Crew - Pleasant Springs, WI

Family-Friendly 5BR Lakefront Cabin Near Madison WI • Sleeps the Whole Crew

Holiday Home, Pleasant Springs

Family-Friendly 5BR Lakefront Cabin Near Madison WI · Sleeps the Whole Crew is a holiday home in Pleasant Springs, with parking, kitchen access, and room for a group. This stay gives…

Read more

About Family-Friendly 5BR Lakefront Cabin Near Madison WI • Sleeps the Whole Crew

Family-Friendly 5BR Lakefront Cabin Near Madison WI · Sleeps the Whole Crew is a holiday home in Pleasant Springs, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,908.

From$844/night
Show

Family-friendly vacation rentals in Pleasant Springs, WI

Plan a trip with stays that give families more room to spread out.

Cheerful 3-bedroom cottage 2 blocks from the lake - Pleasant Springs, WI

Cheerful 3-bedroom cottage 2 blocks from the lake

Cottage, Pleasant Springs

Cheerful 3-bedroom cottage 2 blocks from the lake is a cottage in Pleasant Springs, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the…

Read more

About Cheerful 3-bedroom cottage 2 blocks from the lake

Cheerful 3-bedroom cottage 2 blocks from the lake is a cottage in Pleasant Springs, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,069.

From$296/night
Show
Family-friendly Lake Waubesa Home: Boat + Swim! - Pleasant Springs, WI

Family-friendly Lake Waubesa Home: Boat + Swim!

Cottage, Pleasant Springs

Family-friendly Lake Waubesa Home: Boat + Swim! is a cottage in Pleasant Springs, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base…

Read more

About Family-friendly Lake Waubesa Home: Boat + Swim!

Family-friendly Lake Waubesa Home: Boat + Swim! is a cottage in Pleasant Springs, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,381.

From$382/night
Show
Entire duplex next to waterfront - Pleasant Springs, WI

Entire duplex next to waterfront

Holiday Home, Pleasant Springs

Entire duplex next to waterfront is a holiday home in Pleasant Springs, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Entire duplex next to waterfront

Entire duplex next to waterfront is a holiday home in Pleasant Springs, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,857.

From$408/night
Show
Family-Friendly Lake Waubesa Home: Boat + Swim! - Pleasant Springs, WI

Family-Friendly Lake Waubesa Home: Boat + Swim!

Holiday Home, Pleasant Springs

Family-Friendly Lake Waubesa Home: Boat + Swim! is a holiday home in Pleasant Springs, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Family-Friendly Lake Waubesa Home: Boat + Swim!

Family-Friendly Lake Waubesa Home: Boat + Swim! is a holiday home in Pleasant Springs, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,038.

From$434/night
Show