Holiday rentals with a pool in Santa Rosa

4.91 out of 5 average rating, 417 reviews

A spacious studio apartment features a king size bed with a colorful patterned quilt. Nightstands with lamps are positioned on either side. A kitchenette area is visible with open shelving and a small dining cart. Light wood flooring complements the bright, neutral walls.

Guest suite in Sonoma

Wildwood Retreat and Pool

The Wildwood Retreat is located on a wooded 2 acre country property in the hills above Sonoma just minutes from the Historic Downtown Sonoma Plaza. The newly remodeled studio apt is very private on a separate level below the main house conveniently close to the pool. Amenities include a king size bed, kitchenette, private bath,sunny deck,pool access and convenient parking. Great walks are just outside your door. This tranquil retreat is ideally located for enjoying all the Wine Country offers.

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.

4.93 out of 5 average rating, 151 reviews

PrivateWarm&Cozy+Spa+Pool+FirePit+Wifi!

Your home base for Sonoma, Napa, the Russian River and Sonoma Coast! A quiet neighborhood home within easy walking distance to shops and restaurants with many more options just a short drive away. Hundreds of wineries, breweries, and distilleries are here. Dozens of state and regional parks are waiting for you to explore. There's even a great neighborhood park just behind the house! Wondering what to do on your visit? My co-host Brenna and I are happy to help plan your trip to Wine Country.

4.98 out of 5 average rating, 178 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

Enjoy a tranquil art filled garden escape at our pet friendly home! Whether you are soaking in the hot tub after a day of wine tasting or having dinner with friends this indoor/outdoor living retreat will leave you feeling relaxed. Well stocked kitchen, fast wifi and walking distance to downtown. Great restaurants and breweries nearby. Well behaved non destructive pets are welcome in this home. It may not be a fit if you have severe allergies though we do our best to clean very thoroughly.

Guest suite in Indian Valley

A framed black and white photograph depicts six individuals arranged casually in a natural setting under a large tree. Instruments such as a guitar are visible, while varied chairs and a rustic box add to the composition.

4.88 out of 5 average rating, 113 reviews

1 BR suite in Rock & Roll History

A gated driveway and private entryway greets you as your arrive at your bucolic getaway. We are located next to a popular Open Space preserve great for hiking or biking. Both San Francisco and the Wine Country are 45 minutes away! Crosby, Stills, Nash & Young lived on this property when they produced their classic "Deja Vu" album in the early 70's. The album cover photo was taken under our special and majestic oak tree and the photo was developed in the dark room that is now the bedroom.

4.99 out of 5 average rating, 267 reviews

A cozy living area is furnished with a light-colored sectional sofa adorned with colorful accent pillows. A wooden coffee table holds snacks and glasses, while a lamp illuminates the space. Natural light enters through shutters, creating a warm ambiance.

Cottage in Kenwood

Winter special on now in beautiful Sonoma Valley!

Escape to your home-away-from-home on a private residential compound: the perfect getaway spot in the heart of beautiful Sonoma Valley! 🏡 Why You’ll Love It: ✔️ Minutes to 25+ wineries & great restaurants ✔️ Easy drives to Sonoma, Calistoga, Healdsburg, Napa & the Coast ✔️ Great hiking in nearby parks ✔️ Birdwatching in the garden ✔️ Saltwater pool & bocce court ✔️ Stunning Mountain views ✔️ Private patio with gas grill & outdoor dining ✔️ Full kitchen, separate bedroom with ensuite bath

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, 462 reviews

Pony Ranch Vineyard Estate with Pool

Guest House with private entrance on gorgeous gated Vineyard Estate. Overlooks pool and vineyards with views to Mount St. Helena. Gas fireplace, refrigerator, microwave, Keurig coffee maker, queen bed. Seasonal private pool with fabulous views, occasionally shared with owners. Toilet and sink separate from shower. 8 minutes to the Healdsburg Plaza. Less than a mile from 3 wineries, very close to dozens more. Agricultural Education Programs available. Sonoma County TOT Certificate 1362N

Superhost

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.

Home in Montgomery Village

4.87 out of 5 average rating, 244 reviews

Cozy Home w/ Hot Tub/Pool- near Shops, Wine, Food

Escape to our cozy Mid-Century Modern home in the heart of Sonoma Wine Country. A 10 min drive to some of the best wineries in the world! Relax in the large pool & hot tub, grill on the Traeger for BBQ dinners + pets are welcome! Walking distance to Howarth Park, Spring Lake, in the neighborhood of Annadel State Park for hiking & biking. One block from Montgomery Village, full of boutique shops & Wine-Country restaurants. A 20 minute drive to Sonoma, & near Healdsburg, Kenwood + Bodega Bay.

4.98 out of 5 average rating, 427 reviews

A cozy studio space features vaulted beam ceilings and warm wooden accents. A spacious bed sits against a backdrop of art, while a massage chair and a wall-mounted TV are visible. The area is complemented by decorative lighting and a welcoming atmosphere.

Guest suite in Petaluma

Petaluma Wine Country relaxing get away w/pool/spa

Your own studio guest house retreat complete w/ Cal king bed, large bathroom w/ walk-in tiled shower, vaulted beam ceilings, wall fireplace, A/C/heater, 2nd bed sleeper sofa for adult/kids,, Wi-Fi, 60 “TV w/swing arm for in bed movies, walk-in closet, , pool, spa, outdoor furniture, refrig, high top table. Walk to downtown, restaurants, theater district. Hiking 2 blocks away. Washer/dryer *during off Summer months outdoor cushions removed due to the weather. Pool/spa hrs 9am-9pm

5 out of 5 average rating, 687 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

**Very Important** Please read description below and “Other things to note” at the bottom of this section before contacting us. • Adults Only • Private Sunny 1 Bedroom, 2 full bathroom 900 sq ft stand alone home • Private Backyard with Pool, Sauna, Outdoor Shower, and Outdoor Bathtub • Luxurious Modern Farmhouse Style • Created to feel like a boutique hotel experience • In the heart of wine country Sebastopol/ West Sonoma • Eco-Friendly products used • Strict cleaning protocols

4.9 out of 5 average rating, 212 reviews

A spacious outdoor space features a shimmering pool surrounded by wooden decking. A covered seating area with comfortable furniture is visible nearby, alongside a barbeque setup. Lush greenery encompasses the area, creating a tranquil retreat. A water slide adjoins the pool for added fun.

Guesthouse in Santa Rosa

2 Wine Country Gem 2 Bedroom Upstairs

Looking for a place to stay in Santa Rosa that offers comfort, convenience, and charm? Look no further than our cozy guest house, located in a private gated property. You’ll have your own entrance and access to a shared laundry room with supplies. Enjoy the use of our pool, barbeque, and outdoor kitchen and seating area, where you can relax and soak up the sun. And as a special treat, you’ll get to savor our private tiffin service that delivers delicious home-cooked meals too.

A Mediterranean-inspired house is set amidst lush gardens and rolling hills. The round swimming pool is surrounded by colorful landscaping and lounge chairs, inviting relaxation. The exterior features warm stucco walls and a tiled roof, showcasing a harmonious blend with the natural surroundings.

5 out of 5 average rating, 124 reviews

Wine Country Luxury Retreat - Pool Sauna Spa Views

Welcome to Sonoma Valley Retreat! The Luxury Mediterranean-inspired resort style house in the middle of a world-class wine country. 3600 Square feet House is located in the world-famous Sonoma Valley and is perfect for all your vacation needs. It's where style and sophistication meets entertainment and fun. Enjoy stunning outdoor amenities; one of a kind round soaking pool private pool with spa, pine wood sauna and breathtaking garden, mountain views

4.97 out of 5 average rating, 213 reviews

Happy House Getaway - Pool, Hot Tub & Wine Country

Welcome to Your Relaxing Getaway! My home is a comfortable, clean, and happy space—perfect for unwinding and enjoying all that Sonoma County and the Bay Area have to offer. 🌿 Spacious Backyard: Large yard with a pool (heated by the sun) 6-person hot tub (kept at 102°F) Easy parking 🍽 Fully Stocked Chef’s Kitchen 🛋 Seasonal Note: Outdoor cushions/umbrellas stored late Oct to mid-May Come stay—you’ll love it! Happy House Permit # SVR25-160

Popular amenities for Santa Rosa rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A relaxing outdoor space features a sunny pool area surrounded by palm trees. Two loungers with bright cushions are positioned beside the pool, which reflects the blue sky. An umbrella provides shade nearby, completing this inviting retreat in a tropical setting.

4.85 out of 5 average rating, 133 reviews

Tropical Oasis with Pool & Hot Tub 30min to Sonoma

4.9 out of 5 average rating, 188 reviews

The exterior of a two-story California Craftsman home is shown, featuring a gabled roof and a welcoming front porch. Green lawn and garden beds with shrubs and flowers frame the pathway leading to the entrance, emphasizing the home's charming design.

Home in Junior College

Historic 1880's Craftsman Style Home with Pool.

4.97 out of 5 average rating, 105 reviews

A modern kitchen features a spacious island with three woven bar stools. Hexagon-tiled walls in a soothing grey tone complement open shelving displaying dishware. Large windows allow natural light to fill the space, with greenery visible outside.

Home in Sonoma

Modern wine country stunner!

4.92 out of 5 average rating, 125 reviews

A natural stone pool is surrounded by vibrant foliage, showcasing a mix of green and fiery red leaves. Two wooden lounge chairs face the pool, complemented by a bright red umbrella. Scenic views of the rolling landscape extend into the distance.

Home in Sonoma

Spectacular Stone Pool/Spa with Views; Near Plaza

4.84 out of 5 average rating, 188 reviews

This classic vacation home features a low-maintenance exterior surrounded by neatly trimmed bushes. A gravel pathway leads to the entrance, while a covered carport provides shaded parking. Lush greenery and trees can be seen in the background, creating a serene setting.

Home in Guerneville

STAY AWHiLE Guerneville Hot Tub Fireplace Yard

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

4.91 out of 5 average rating, 120 reviews

A spacious outdoor area features a large pool surrounded by natural stone walls. Comfortable lounge chairs are positioned for relaxation, and green umbrellas provide shade. Lush landscaping enhances the serene environment, with trees and plants framing the scene.

Home in Sebastopol

Luxury home (+ pool house) with views, pool & spa

4.86 out of 5 average rating, 118 reviews

A modern hillside lodge is surrounded by lush greenery, featuring a wrap-around deck adorned with string lights. Steps lead up to the entrance, with multiple levels of wooden decking providing serene outdoor spaces.

Home in Guerneville

Leo’s Lodge - Lux Retreat with Pool and Hot Tub

Condo rentals with a pool

The image showcases a scenic view of the Silverado Resort grounds, featuring well-maintained grassy areas and a sparkling pool surrounded by trees. The backdrop includes distant mountains and a clear blue sky, providing a tranquil outdoor setting.

4.99 out of 5 average rating, 492 reviews

Silverado! Luxe 1BR King Suite This View! Balcony

4.99 out of 5 average rating, 158 reviews

Romantic Winter Escape • Cozy 1BR at Silverado

An open concept living and dining area showcases wooden flooring and a spacious dining table surrounded by woven chairs. A comfortable seating space features a large rug and a bright blue accent chair. Large glass doors offer views of the outdoor area with greenery.

4.95 out of 5 average rating, 111 reviews

Wine Country Living at it's best at Silverado CC

The exterior of a private cottage is displayed, featuring a inviting entrance framed by shrubs and trees. Sunlight filters through the branches, casting a warm glow on the cottage dimensions. A pathway leads to the door, complementing the landscaped surroundings.

4.94 out of 5 average rating, 121 reviews

Casa Vina at Silverado Resort and Spa | Fireplace

4.92 out of 5 average rating, 12 reviews

A modern living space is visible, featuring a black leather seating area with a large cushion. The dining area is furnished with a wooden table and chairs. A doorway leads to a bright kitchen, while the walls are painted in a light color, giving an airy feel.

Condo in San Rafael

Modern, bright 2 bedroom/1 bath 2nd story

The open-concept kitchen features modern appliances, including a microwave and oven, complemented by a large island with seating. Natural light floods the space, which seamlessly connects to the living area, revealing views of the outdoor patio through oversized windows.

4.93 out of 5 average rating, 137 reviews

Fairways Silverado Golf and Country

Superhost

A row of charming cottages is lined along a walkable path, featuring varied exterior colors including blue, yellow, and red. Each unit has large windows and decorative gables, surrounded by neatly trimmed hedges and lush green trees, enhancing the inviting neighborhood atmosphere.

4.73 out of 5 average rating, 2,565 reviews

One Bedroom Cottage Along the Napa River

4.78 out of 5 average rating, 277 reviews

1 bed | 1 bath | Silverado Resort Experience

Other holiday rentals with a pool

Shipping container in Santa Rosa

5 out of 5 average rating, 24 reviews

Luxury Container Home w Infinity Pool + 360 Views

4.98 out of 5 average rating, 129 reviews

A spacious bedroom features a luxurious bed with a tufted white comforter and colorful decorative pillows. Soft area rugs lay underfoot, while a mirrored closet door provides depth. Ambient lighting is created by bedside lamps, and a textured wall adds visual interest.

Apartment in Terra Linda

Private Mid-Century Luxury Near SF & Wine Country

Guest suite in San Rafael

A spacious guest studio features large windows that provide natural light and panoramic views. The room includes a comfortable queen bed with premium linens, a small dining table with two chairs, and a minimalist wooden dresser. A warm color palette enhances the cabin-like feel.

4.89 out of 5 average rating, 476 reviews

Romantic Mtn Studio - Pool, Sauna, Views!

The exterior of a beautifully designed house is presented, showcasing a light-colored facade with decorative shutters and a newly paved pathway. A stone fountain serves as a focal point amidst landscaped greenery, highlighting the inviting entrance and two stories of windows.

4.97 out of 5 average rating, 91 reviews

Wine County Opulent Villa Pool/Hot Tub-Upper Level

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, 99 reviews

Best View Wine Country Oasis: Pool-Hot tub-Sauna

4.97 out of 5 average rating, 142 reviews

A well-maintained pool area is showcased, with clear water reflecting the blue sky. Surrounding the pool, a spacious deck is visible with outdoor furniture and access to a raised deck. Lush trees provide natural shade to the area.

Home in Petaluma

Nice Wine Country Family Home

4.96 out of 5 average rating, 211 reviews

A spacious covered deck area features comfortable seating arrangements with natural woven textures. Light-colored drapes softly frame the space, allowing for views of lush greenery and an infinity pool nestled in the landscape. A round table sits in the center, adorned with a small floral arrangement.

Guest suite in Fairfax

Mountain View Retreat