Holiday rentals with a pool in Santa Rosa

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Top-rated rentals with a pool in Santa Rosa

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
Home in Santa Rosa
4.96 out of 5 average rating, 115 reviews

Wine Country Retreat- Privacy-Spa/Pool/Games

Take it easy at this unique & tranquil getaway in the middle of wine country! Feel worlds away but just minutes to world-class wineries, restaurants & shopping. Enjoy your own private pool, spa & game room. The large private property is perfect for your family getaway, couples retreat, or those looking for their own slice of heaven with thoughtful amenities. You'll want to come back year after year! Separate 1/1 guest house not included in price but available upon request at time of booking.

Guest favourite
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
4.91 out of 5 average rating, 416 reviews

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.

Top guest favourite
A shaded outdoor lounging area is framed by vibrant orange flowers, featuring a covered seating arrangement surrounding a central table. The stone-accented pool reflects the natural greenery, creating a serene environment for relaxation.
Guest suite in Santa Rosa
4.99 out of 5 average rating, 191 reviews

Wine Country Retreat w Pool & Spa-1 Acre Grounds

This one-acre estate offers the quiet and convenience of beautiful Bennett Valley. Just a short drive to the east you will find beautiful vineyards, wine tasting, and farm-fresh cuisine in Sonoma Valley. North 20 minutes up hwy 101 you will find spectacular vineyards in Alexander Valley, Dry Creek Valley, as well as elegant tasting rooms and shops in the town of Healdsburg. Located minutes from shopping and local sites, but you will feel worlds away in an upscale, quiet, peaceful neighborhood.

Top guest favourite
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
4.98 out of 5 average rating, 178 reviews

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.

Top guest favourite
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.
Guest suite in Indian Valley
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.

Top guest favourite
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
4.99 out of 5 average rating, 267 reviews

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

Top guest favourite
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.
Guest suite in Healdsburg
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, 243 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.

Guest favourite
A serene pool area is illuminated by soft landscape lighting, surrounded by lush greenery. A hot tub is positioned nearby, and a stylish lounge chair complements the outdoor setting. The sky displays vibrant hues of orange and pink, signaling a tranquil sunset.
Home in Sebastopol
4.91 out of 5 average rating, 137 reviews

The Deer Retreat – Privacy and Comfort

At the end of a private road (recently redone), the Deer Retreat offers privacy to enjoy the newly renovated pool, the hot tub, and the full outdoor kitchen. With sprawling views of a large private backyard, you will be sure to spot some deers or wild turkeys who call this peaceful place home. When staying inside, you will enjoy the privacy of the 2 large en-suite master bedrooms which are located at opposite ends of the house, or regroup in the large vaulted living room with open kitchen.

Top guest favourite
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
4.98 out of 5 average rating, 425 reviews

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

Top guest favourite
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
5 out of 5 average rating, 684 reviews

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

Guest favourite
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.
Guest house in Santa Rosa
4.9 out of 5 average rating, 212 reviews

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.

Popular amenities for Santa Rosa rentals with a pool

When is the best time to visit Santa Rosa?

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Avg. price$409 SGD$412 SGD$462 SGD$454 SGD$541 SGD$515 SGD$588 SGD$536 SGD$498 SGD$579 SGD$515 SGD$438 SGD
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Quick stats about holiday rentals with a pool in Santa Rosa

  • Total holiday rentals

    Explore 130 holiday rentals in Santa Rosa

  • Nightly prices starting at

    Santa Rosa holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 7,480 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    130 of Santa Rosa holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Santa Rosa rentals

  • 4.9 Average rating

    Santa Rosa stays are highly rated by guests – averaging 4.9 out of 5!

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