Family-friendly holiday rentals in Windsor

Guest house in Healdsburg

A covered patio is framed by wooden beams, offering a view of expansive vineyard landscapes and distant hills. Outdoor seating, including a dining table and lounge chairs, is arranged on the deck, inviting relaxation amid the tranquil scenery.

4.99 out of 5 average rating, 121 reviews

Bucher Vineyard Cottage

Discover the Charm of Our Vineyard Cottage! Escape to the heart of wine country with a stay at our fantastic one-bedroom cottage, nestled on the renowned Bucher Vineyard. Large room with kitchen & cozy seating area. Enjoy a restful night in a comfy queen bed surrounded by a stunning Redwood wall. Covered patio with heaters and fan. Deck with spectacular views of our vineyard & the Russian River Valley. Gas fire pit near deck. Hosts John & Diane are farmers and winery owners live on the property.

4.94 out of 5 average rating, 109 reviews

A bright kitchen features sleek white cabinetry and a spacious island with a light marble countertop. Pendant lights hang above the island, while large windows allow natural light to fill the space. Stainless steel appliances add a modern touch to the overall design.

Home in Windsor

Gourmet Kitchen in Wine Country w/Hot Tub + Office

There is no better way to enjoy your stay in wine country than sipping on a glass of wine in this this stunning home! The 14ft bifold door invites out to the beautiful spacious yard where you can relax at any of the 4 sitting areas nestled under a beautiful display of lights. Featuring a chef kitchen, an office, large yard for children & pets, spacious bedrooms, stunning master bath, hot tub, fire table, games & more. Just minutes from elite award winning wineries, craft breweries & restaurants

4.99 out of 5 average rating, 132 reviews

The exterior of a charming Victorian house is visible, featuring a welcoming front porch with a green door. Lush greenery and colorful plants frame the entrance, and a rustic wooden cart is placed nearby on a gravel pathway, enhancing the inviting outdoor space.

Home in Windsor

Gorgeous Victorian in the HEART of Windsor

Gorgeous renovated Queen Anne Victorian located in the heart of Windsor, CA combines quality finishes, modern convenience & vintage details. With a stylish kitchen, high ceilings, 3 beds/2 baths on a single level, HVAC & a huge lot with a Bocce Court. Walking distance to the Town Green, restaurants, wine tasting rooms and shopping. Just 3.5 miles from the Sonoma County Airport (STS), 5 miles to downtown Healdsburg, in the heart of the Russian River Valley & just 57 miles from the Golden Gate.

A spacious living area is designed for relaxation, featuring a comfortable light-colored sofa with decorative throw pillows. A large window allows natural light to fill the space, highlighting the modern décor. A stylish coffee table rests in front of the seating, complemented by a vibrant area rug.

4.93 out of 5 average rating, 213 reviews

Wine Country Getaway | Hot Tub + Near Park

Located in Santa Rosa, this home is the perfect retreat for families, friends, and anyone looking to relax and enjoy the area. Just one block away, a fantastic new park features a playground for kids and a spacious dog park perfect for outdoor fun. Enjoy a game of billiards, unwind in the garage-turned-game room, or relax in the inviting living space. Step outside to the patio seating area and BBQ grill—ideal for dining under the stars and making unforgettable memories. SVR24-154 Permit 2024

A cozy living room features two seating areas with a gray sofa and a beige armchair. A coffee table sits in front of them, and a flat-screen TV is positioned across the room, complemented by a decorative artwork and large windows allowing natural light.

4.85 out of 5 average rating, 215 reviews

Spacious 3BD/2BA, ideal for families!

Located in a quiet residential neighborhood in Santa Rosa, this spacious single level house is in the heart of California's Wine Country. With 3 bedrooms, 2 bathrooms, an open-plan living room and fully equipped kitchen there is plenty of room to cater for friends and family. The property has parking for two cars and outdoor seating to enjoy the great California weather on the new patio. Enjoy a local wine tour, explore a Giant Redwood forest or explore the stunning coastline at your feet.

4.95 out of 5 average rating, 210 reviews

A wooden bridge connects the ground to a treehouse elevated among tall trees. The treehouse features large windows and a circular design, surrounded by lush greenery. A sturdy netting lines the sides of the walkway, ensuring safety while traversing to this unique retreat.

Treehouse in Bodega Bay

Eagle's Nest Treehouse Farm Stay

Eagle's Nest Treehouse Farm Stay is a tranquil, secluded, luxurious, romantic wilderness experience in a private forest on a 400 acre working ranch. Thirty feet above the forest floor you are nestled in a gorgeous, well-appointed suite of 1,000 year old polished redwood, with bathroom and amazing copper/glass forest-view shower. Explore hiking trails through the forest and learn about ranch operations (Highland cattle, goats and ducks). See guest comments in the space description.

4.92 out of 5 average rating, 127 reviews

A heated swimming pool reflects the early evening sky, surrounded by lush greenery. Comfortable lounge chairs are positioned around the pool, complemented by a shaded umbrella. The vineyard is visible in the background, enhancing the peaceful atmosphere of this outdoor space.

Home in Healdsburg

Vineyard Vista, Modern Farmhouse Cottage with Pool

Our architect remodeled (2021), five star, elegant Farmhouse with great room and fireplace, is simply perfect throughout. This unique wine country two-acre property, with heated swimming pool (for a fee), looks out to the beautiful Russian River vineyards and the never-ending Western panorama. Only minutes from award winning food and shopping in downtown Healdsburg, it’s within easy walking or bicycling distance of tasting rooms at J, Rodney Strong and other acclaimed Sonoma wineries.

Guest suite in Santa Rosa

A spacious private deck is seen with views overlooking the rolling hills and valleys. Comfortable green lounge chairs are positioned for relaxation. The deck features wooden railing and steps leading down, while a doorway connects to the guest suite.

4.97 out of 5 average rating, 377 reviews

Wikiup lookout retreat

We self-developed our rural property as a secluded retreat with dog-friendly gardens. To share our creation with you, we designed a private 2nd-floor guest suite (ok to bring your good dogs). Your suite includes secure parking, private entrance, deck, kitchen, dining, living, 3 beds (queen, double, twin), one bath & a fenced back yard. We are on a country road near Healdsburg, Windsor, Russian River, Sebastopol, Santa Rosa, Calistoga, Sonoma & Napa valleys, wineries & beaches.

4.97 out of 5 average rating, 677 reviews

The exterior of a rustic winery building is featured, characterized by its earthy tones and distinctive red door accents. Lush greenery and blooming purple flowers surround the structure, enhancing its natural setting. The building's design includes terracotta roofing and large windows that invite an abundance of natural light.

Farm stay in Healdsburg

Gracianna Winery Vineyard Loft - Farm Stay

Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile of Pinot Noir in Healdsburg includes equipped kitchen with new gas Wolf Range. Pick up breakfast needs before arriving. Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. LOFT AVAILABLE YEAR ROUND. TOT #3294N

Serviced apartment in Windsor

A three-story building is seen with a colorful facade displaying verdant green, red, and yellow hues, surrounded by trees. The outdoor pool area features lounge chairs along the water's edge, illuminated against a night sky. The interior image shows a kitchen with wooden cabinets and dining space.

4.87 out of 5 average rating, 193 reviews

Windsor 2 Bed/2 Bath Condo ~Pool~Hot Tub~Gym

**Condo: 1,023 square feet 2 bedroom/2 bath- King size bed in the master bedroom, two twin beds in the 2nd bedroom (can be put together to make a king), and one queen Murphy bed in the living room. Additional amenities include a full kitchen and dining area, gas fireplace, washer and dryer and a private terrace with gas barbecue. Maximum occupancy is six. *** twin beds in 2nd bedroom can be put together to make a king size bed. Please request in advance.

4.96 out of 5 average rating, 439 reviews

A spacious living area features a blue sofa adorned with a soft orange throw. A large area rug with intricate patterns anchors the space, while natural light floods in through large windows. A wooden coffee table rests centrally, complemented by decorative items.

Home in Windsor

Winelight Vineyard Home With Spa

Gated driveway, private, scenic, safe, secure, and impeccably clean. Unwind, prepare dinner on granite counter tops in this newly remodeled well-stocked gourmet kitchen. Enjoy plush amenities, fine decor, hot tub, romantic fireplace, French doors leading to outdoor decks, secluded rural vibe, reliably fast internet. Close to Sonoma County's best wineries, breweries and restaurants. There is a guest laundry, designer carport, and ample parking for guests.

The dining area features a circular white table surrounded by comfortable upholstered chairs, complemented by a modern lighting fixture above. A sliding glass door leads to a view of the outdoor space, while a flower arrangement adds a touch of color.

4.89 out of 5 average rating, 173 reviews

Grape Expectations: A Winemaker’s Country Retreat

Welcome to our warm and modern 3-bedroom, 2.5-bath retreat—where style meets eco-friendly convenience! Nestled in a peaceful neighborhood, this thoughtfully designed home comes equipped with a Tesla Universal EV charger, making it ideal for families, friends, or business travelers. Whether you’re here for a relaxing getaway, a weekend escape, or a work trip, you’ll find everything you need for a seamless and comfortable stay. PERMIT NUMBER: SVR25-025

Popular amenities for Windsor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 538 reviews

A modern home is showcased with large sliding glass doors that open to a spacious wooden deck. The inviting heated pool features a gentle curve, with sun loungers placed nearby. Lush greenery surrounds the property, enhancing the tranquil outdoor setting.

Home in Sonoma

Designer Sonoma Getaway with Pool, Hot Tub & Bocce

4.95 out of 5 average rating, 171 reviews

An outdoor space features a plunge pool surrounded by a sun deck with lounge chairs and a sun umbrella. The home, with its wood accents, is set against a backdrop of tall redwood trees, contributing to a serene, natural setting.

Home in Occidental

Modern mid-century-inspired, Deer Ranch

The outdoor space features a gazebo with a fire pit, surrounded by comfortable seating. Lounge chairs are positioned near an unheated pool, and a dining table with seating is visible in the background, creating a welcoming atmosphere for relaxation and gatherings.

4.94 out of 5 average rating, 171 reviews

Wine Country Escape: Pool & Hot Tub. Fast WiFi

The image showcases the Quail Roost property, featuring a spacious outdoor deck with a fire pit and pool. The interior highlights a cozy seating area with artful touches, large windows providing natural light, and elegant furnishings. The exterior view captures the pool and surrounding scenic landscape.

4.97 out of 5 average rating, 100 reviews

Pool - Hot Tub - Sauna | Wine Country Oasis Views

4.97 out of 5 average rating, 204 reviews

Cul-de-Sac | King | BBQ | Stocked | Washer+Dryer

4.98 out of 5 average rating, 189 reviews

A private outdoor area features a hot tub adjacent to a wooden deck. A white dining table is positioned for meals, surrounded by lush greenery. Soft lighting hangs above, adding to the relaxed setting. A window on the house offers natural light to the space.

Home in Junior College

Pacific Gardens Retreat

5 out of 5 average rating, 705 reviews

A private backyard features a solar heated swimming pool surrounded by lounge seating and potted plants. A tiki bar is visible in the background, with palm trees providing shade in the sunlight. The space combines relaxation and outdoor living for a serene atmosphere.

Home in Graton

Eco Luxury Private Sanctuary / The Farmhouse Oasis

4.92 out of 5 average rating, 210 reviews

A cozy treehouse retreat is surrounded by towering redwoods, resting on stilts above the forest floor. Large windows illuminate the structure, allowing natural light to flood the interior. A wooden deck extends outdoors, providing a relaxing space to enjoy the serene woodland environment.

Treehouse in Camp Meeker

Redwood Treehouse Retreat - Hot tub, fire pit

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 438 reviews

The exterior view of the cabin showcases a grey wooden façade, complemented by a vibrant red door. Two orange chairs are positioned on a wooden deck, surrounded by lush greenery and a decorative maple tree. Large windows allow natural light to illuminate the interior space.

Cabin in Guerneville

Velouria - Hot Tub, Woodstove, Redwoods.

An inviting living area features a large black sectional sofa complemented by a wooden coffee table atop a light area rug. Natural light streams through large windows adorned with sheer curtains, illuminating traditional wood accents and hardwood floors.

4.95 out of 5 average rating, 683 reviews

Craftsman 2 blocks from Russian River Brewery!

A spacious bedroom features a comfortable bed with soft linens and a decorative throw blanket. Nightstands flank the bed, with lamps providing a warm glow. A large window allows natural light, while a chest of drawers offers storage. A potted plant adds a touch of greenery.

4.95 out of 5 average rating, 144 reviews

Amazing Santa Rosa Wine Escape Home

4.96 out of 5 average rating, 198 reviews

Home in Forestville

Hilltop Wellness Retreat | Sauna + Hot Tub

Guest house in Sebastopol

A bright living area features a leather couch with orange cushions, complemented by a comfortable armchair. Natural light enters through large windows, illuminating a wooden coffee table stacked with magazines. A fan hangs from the ceiling, and a flat-screen TV is mounted on the wall.

4.93 out of 5 average rating, 830 reviews

Sun Drenched Flat

4.94 out of 5 average rating, 151 reviews

A spacious great room features a high wood-beamed ceiling and natural light pouring in through skylights. Comfortable lounge seating is arranged near a fireplace, with a large dining table designed to accommodate multiple guests, creating an inviting space for gatherings.

Cabin in Forestville

The Black Sheep - Wine Country • Hot Tub • Theater

4.95 out of 5 average rating, 817 reviews

An outdoor deck surrounded by lush greenery features a fire pit at its center, surrounded by seating options. A claw foot tub is positioned against the railing, while a small round table and folding chairs provide additional seating. Bright green cushions add color to the wooden lounge chairs.

Cottage in Occidental

The Perch - Outdoor Clawfoot Tub

4.93 out of 5 average rating, 643 reviews

Home in Healdsburg

Healdsburg Garden House

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 114 reviews

Spacious 5 BR 3BA Pool EV Charger Group Getaway

4.88 out of 5 average rating, 111 reviews

The serene pool area is surrounded by lush greenery, featuring modern lounge chairs and large umbrellas for shade. The sparkling water invites relaxation, while a covered outdoor space extends from the home, providing a seamless transition to the tranquil outdoor retreat.

Home in Sebastopol

Serene Wine Country Retreat with Pool & Hot Tub

Home in Montgomery Village

A hot tub bubbles gently, positioned next to a large swimming pool. Lush greenery surrounds the area, complemented by a vibrant sky with hues of orange and pink. A lounge chair and a sun umbrella are visible in the background, enhancing the outdoor relaxation space.

4.86 out of 5 average rating, 255 reviews

Charming Home w Pool+Hot Tub. Walk to Shops & Wine

Guest house in Santa Rosa

A refreshing pool is surrounded by lush greenery and vibrant potted plants. Two chairs are positioned nearby, offering a serene space for relaxation. The cottage, featuring a light exterior and classic window design, rests under the shade of large trees, enhancing the tranquil atmosphere.

4.86 out of 5 average rating, 114 reviews

Tranquil Private Cottage / Pool-house

4.97 out of 5 average rating, 154 reviews

An aerial view of a spacious single-level home surrounded by lush lawns and mature trees. Expansive grapevines extend across the property, offering a visual connection to the scenic landscape. The structure features a blend of modern solar panels and charming landscaping.

Home in Sonoma

Large Charming Home Surrounded by a Vineyard

Guest suite in Healdsburg

A spacious guest house is set within a picturesque vineyard estate, featuring a distinct architectural style with multiple gabled rooftops. The driveway leads to a well-maintained entrance, surrounded by lush landscaping and mature trees, providing a serene and welcoming arrival experience.

4.93 out of 5 average rating, 470 reviews

Pony Ranch Vineyard Estate with Pool

4.91 out of 5 average rating, 119 reviews

A spacious property sits atop a knoll, surrounded by lush greenery and vineyards. A private pool glistens in the sunlight, while lounge chairs are arranged nearby. The outdoor seating area features a cozy fire-pit, inviting relaxation amidst scenic views of rolling hills.

Home in Sebastopol

Naidu Vineyards - Views/Pool/Spa/Bocce/9 Acres