Vacation rentals in Simi, CA

Best vacation rentals and Airbnb offers in Simi, CA

Dreamy Fairy Tale Hut Rental with Pool and Sauna Access at Retreat in Sonoma County

Holiday Home, Simi

Dreamy Fairy Tale Hut Rental with Pool and Sauna Access at Retreat in Sonoma County is a holiday home in Simi, with pet-friendly space, pool access, and a quieter setting. This stay gives…

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About Dreamy Fairy Tale Hut Rental with Pool and Sauna Access at Retreat in Sonoma County

Dreamy Fairy Tale Hut Rental with Pool and Sauna Access at Retreat in Sonoma County is a holiday home in Simi, with pet-friendly space, pool access, 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, pool, pet friendly, pets friendly, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $871.

From$124/night

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Exclusivas chozas cerca de San Francisco, California

Holiday Home, Simi

Exclusivas chozas cerca de San Francisco, California is a holiday home in Simi, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Exclusivas chozas cerca de San Francisco, California

Exclusivas chozas cerca de San Francisco, California is a holiday home in Simi, with pet-friendly space and 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, pet friendly, pets friendly, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $918.

From$131/night

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Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine

Cottage, Simi

Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine is a cottage in Simi, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area,…

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About Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine

Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine is a cottage in Simi, 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, pet friendly, pets friendly, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,690.

From$241/night

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Healdsburg Hilltop Retreat :: Craftsman detail, modern comforts & stunning VIEWS

Holiday Home, Simi

Healdsburg Hilltop Retreat :: Craftsman detail, modern comforts & stunning VIEWS is a holiday home in Simi, with kitchen access and a quieter setting. This stay gives travelers a…

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About Healdsburg Hilltop Retreat :: Craftsman detail, modern comforts & stunning VIEWS

Healdsburg Hilltop Retreat :: Craftsman detail, modern comforts & stunning VIEWS is a holiday home in Simi, with kitchen access 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, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,067.

From$295/night

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Vacation rentals with a pool in Simi, CA

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

Minutes to Dozens of World Class Wineries - 2 Bedroom / 2 Bath - Sleeps 6

Condo, Simi

Minutes to Dozens of World Class Wineries - 2 Bedroom / 2 Bath - Sleeps 6 is a condo in Simi, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Minutes to Dozens of World Class Wineries - 2 Bedroom / 2 Bath - Sleeps 6

Minutes to Dozens of World Class Wineries - 2 Bedroom / 2 Bath - Sleeps 6 is a condo in Simi, with pool access, 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, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,005.

From$286/night

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Hidden Pocket: Pool + Spa, Private Retreat, 1.5 Fenced Acres, Healdsburg

Holiday Home, Simi

Hidden Pocket: Pool + Spa, Private Retreat, 1.5 Fenced Acres, Healdsburg is a holiday home in Simi, with pool access and a quieter setting. This stay gives travelers a comfortable base for…

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About Hidden Pocket: Pool + Spa, Private Retreat, 1.5 Fenced Acres, Healdsburg

Hidden Pocket: Pool + Spa, Private Retreat, 1.5 Fenced Acres, Healdsburg is a holiday home in Simi, with pool access 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,696.

From$1,099/night

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Heart of Healdsburg Cottage for 4, Pool, Spa, Fire Pit, WIFI, BBQ

Cottage, Simi

Heart of Healdsburg Cottage for 4, Pool, Spa, Fire Pit, WIFI, BBQ is a cottage in Simi, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Heart of Healdsburg Cottage for 4, Pool, Spa, Fire Pit, WIFI, BBQ

Heart of Healdsburg Cottage for 4, Pool, Spa, Fire Pit, WIFI, BBQ is a cottage in Simi, 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 $7,744.

From$1,106/night

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Lytton Station Vineyard - Stunning 360-degree vineyard views

Holiday Home, Simi

Lytton Station Vineyard - Stunning 360-degree vineyard views is a holiday home in Simi, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring…

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About Lytton Station Vineyard - Stunning 360-degree vineyard views

Lytton Station Vineyard - Stunning 360-degree vineyard views is a holiday home in Simi, with pet-friendly space and 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,419.

From$1,203/night

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Vacation rentals with parking in Simi, CA

Find vacation rentals that make arriving by car easier.

Charming Sonoma Wine Country Home Base w/ Extras

Holiday Home, Simi

Charming Sonoma Wine Country Home Base w/ Extras is a holiday home in Simi, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Charming Sonoma Wine Country Home Base w/ Extras

Charming Sonoma Wine Country Home Base w/ Extras is a holiday home in Simi, 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 $1,150.

From$164/night

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Quaint 2 Bedroom Flat Downtown

Apartment, Simi

Quaint 2 Bedroom Flat Downtown is a apartment in Simi, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Quaint 2 Bedroom Flat Downtown

Quaint 2 Bedroom Flat Downtown is a apartment in Simi, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,635.

From$234/night

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Whimsical Wilderness: Wonderful Yurt Stay

Cabin, Simi

Whimsical Wilderness: Wonderful Yurt Stay is a cabin in Simi, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Whimsical Wilderness: Wonderful Yurt Stay

Whimsical Wilderness: Wonderful Yurt Stay is a cabin in Simi, 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 $1,862.

From$266/night

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Russian River Forest Retreat with Unique Studio

Holiday Home, Simi

Russian River Forest Retreat with Unique Studio is a holiday home in Simi, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Russian River Forest Retreat with Unique Studio

Russian River Forest Retreat with Unique Studio is a holiday home in Simi, with parking, kitchen access, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,236.

From$319/night

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Pet-friendly vacation rentals in Simi, CA

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

Rio Nido Retreat

Holiday Home, Simi

Rio Nido Retreat is a holiday home in Simi, with pet-friendly space, parking, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Rio Nido Retreat

Rio Nido Retreat is a holiday home in Simi, with pet-friendly space, parking, 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, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,380.

From$218/night

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Relaxing Retreat •Hot Tub• Yard • Near Russian River • Dog–Guerneville Escape

Holiday Home, Simi

Relaxing Retreat · Hot Tub · Yard · Near Russian River · Dog–Guerneville Escape is a holiday home in Simi, with pet-friendly space, kitchen access, and a quieter setting. This stay gives…

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About Relaxing Retreat •Hot Tub• Yard • Near Russian River • Dog–Guerneville Escape

Relaxing Retreat · Hot Tub · Yard · Near Russian River · Dog–Guerneville Escape is a holiday home in Simi, with pet-friendly space, kitchen access, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,057.

From$294/night

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Rio Nido Dog-Friendly Redwood Canyon Cabin with Fenced Yard

Holiday Home, Simi

Rio Nido Dog-Friendly Redwood Canyon Cabin with Fenced Yard is a holiday home in Simi, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Rio Nido Dog-Friendly Redwood Canyon Cabin with Fenced Yard

Rio Nido Dog-Friendly Redwood Canyon Cabin with Fenced Yard is a holiday home in Simi, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,212.

From$316/night

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Forestville Dog-Friendly Forest Cabin with Hot Tub

Holiday Home, Simi

Forestville Dog-Friendly Forest Cabin with Hot Tub is a holiday home in Simi, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Forestville Dog-Friendly Forest Cabin with Hot Tub

Forestville Dog-Friendly Forest Cabin with Hot Tub is a holiday home in Simi, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,271.

From$324/night

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Vacation rentals with a kitchen in Simi, CA

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

Guerneville Redwood Canyon Retreat with Patio & Grill

Holiday Home, Simi

Guerneville Redwood Canyon Retreat with Patio & Grill is a holiday home in Simi, with outdoor space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Guerneville Redwood Canyon Retreat with Patio & Grill

Guerneville Redwood Canyon Retreat with Patio & Grill is a holiday home in Simi, with outdoor space, kitchen access, 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, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,270.

From$324/night

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Tariff Discount: Romantic Retreat w/ Spa

Holiday Home, Simi

Tariff Discount: Romantic Retreat w/ Spa is a holiday home in Simi, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Tariff Discount: Romantic Retreat w/ Spa

Tariff Discount: Romantic Retreat w/ Spa is a holiday home in Simi, with parking, kitchen access, 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,319.

From$331/night

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Breathtaking vineyard views on private estate

Country House, Simi

Breathtaking vineyard views on private estate is a country house in Simi, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Breathtaking vineyard views on private estate

Breathtaking vineyard views on private estate is a country house in Simi, with 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,388.

From$484/night

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Secluded Russian River Farmhouse: Vinyard Retreat, minutes from Healdsburg

Country House, Simi

Secluded Russian River Farmhouse: Vinyard Retreat, minutes from Healdsburg is a country house in Simi, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Secluded Russian River Farmhouse: Vinyard Retreat, minutes from Healdsburg

Secluded Russian River Farmhouse: Vinyard Retreat, minutes from Healdsburg is a country house in Simi, with parking, kitchen access, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,413.

From$488/night

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Family-friendly vacation rentals in Simi, CA

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

Charming Sonoma Wine Country Home Base w/ Extras

Cottage, Simi

Charming Sonoma Wine Country Home Base w/ Extras is a cottage in Simi, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Charming Sonoma Wine Country Home Base w/ Extras

Charming Sonoma Wine Country Home Base w/ Extras is a cottage in Simi, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,411.

From$147/night

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Premier Wine Country Getaway. Exclusive Bucher Vineyard Cottage on Westside Road

Cottage, Simi

Premier Wine Country Getaway. Exclusive Bucher Vineyard Cottage on Westside Road is a cottage in Simi. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Premier Wine Country Getaway. Exclusive Bucher Vineyard Cottage on Westside Road

Premier Wine Country Getaway. Exclusive Bucher Vineyard Cottage on Westside Road is a cottage in Simi. 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,255.

From$322/night

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Simple, Serene Wine Country Retreat In Alexander Valley, Sonoma County

Cottage, Simi

Simple, Serene Wine Country Retreat In Alexander Valley, Sonoma County is a cottage in Simi, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable…

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About Simple, Serene Wine Country Retreat In Alexander Valley, Sonoma County

Simple, Serene Wine Country Retreat In Alexander Valley, Sonoma County is a cottage in Simi, with parking, kitchen access, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,290.

From$327/night

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Luxury 1-br cottage on 30-acre vineyard property in enchanting Healdsburg

Cottage, Simi

Luxury 1-br cottage on 30-acre vineyard property in enchanting Healdsburg is a cottage in Simi, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Luxury 1-br cottage on 30-acre vineyard property in enchanting Healdsburg

Luxury 1-br cottage on 30-acre vineyard property in enchanting Healdsburg is a cottage in Simi, 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 $5,018.

From$717/night

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