Holiday rentals with a pool in Kenwood

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Top-rated rentals with a pool in Kenwood

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

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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 serene courtyard features a circular firepit surrounded by four wicker chairs, inviting relaxation. Sunlight filters through the trees, creating a warm ambiance. Lush greenery and a vineyard view extend beyond the enclosure, enhancing the tranquil outdoor space.
Guest suite in Napa
4.96 out of 5 average rating, 199 reviews

Sherrie's Vineyard View Retreat-Pool, Spa, N.Napa

Enjoy our vineyard view and a glass of wine by the firepit! Relax in our ONE BEDROOM SUITE, ON THE LOWER LEVEL OF OUR TRI-LEVEL HOME. Conveniently located in N. Napa, we're near Alston Park for hiking, wineries, places to eat & shop. Enjoy a fresh-baked BREAKFAST, a dip in the pool (heated mid-June to Sept), spa (year-round) & many places for relaxing. Our suite is well appointed with a comfortable bed, fine linens, duvet, robes & slippers. DRIVING SERVICES may be added to enhance your tours.

Guest favourite
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.
Home in Santa Rosa
4.93 out of 5 average rating, 149 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.

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.

Guest favourite
Villa in Santa Rosa
4.97 out of 5 average rating, 131 reviews

Private 1+ acre, Bocce, Waterfall, Free Pool Heat

With over 1 acre of flat wooded land, this private gated country estate is still just a few minutes from conveniences like Whole Foods and Safeway. And with a full-size bocce court, pool table, and dining pavilion, you might not want to leave. Our new saltwater pool and spa are gas-heated to be comfortable all year, at no extra charge. A rock river and pool waterfall add to the sound of rushing water. The house is a few minutes from downtown, and within 20 minutes of the highlights of Sonoma.

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 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.
Guesthouse in Santa Rosa
4.9 out of 5 average rating, 211 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.

Guest favourite
A beautifully landscaped garden features a pathway bordered by gravel and decorative plants. White wicker chairs surround a small table, inviting relaxation. The wooden deck and spa pool are visible in the background, complementing the modern home adorned with solar panels.
Home in Glen Ellen
4.91 out of 5 average rating, 198 reviews

Luxury home, heated spa tub, walk to restaurants

Luna Lodge, a 3 bedroom 2 bath Glen Ellen village luxury home in the heart of Sonoma wine country. The home has a beautiful garden with spa pool by a peaceful creek. Everything you need for a great vacation is at your fingertips. Situated on a quiet lane, 5 min walk to wine tasting rooms, top restaurants, food markets. Enjoy a gourmet private chef dinner while at the home. Let us know if you are interested and we will help you arrange a very special dining experience.

Top Guest favourite
A serene pool area is surrounded by lush green trees and tropical plants, providing a natural setting. The clear water reflects the blue sky, while a hot tub is positioned next to the pool. Poolside tiles add a decorative touch to the paved deck.
Guesthouse in Petaluma
4.89 out of 5 average rating, 278 reviews

Historic D Street Private Bungalow!

You will enjoy easy access to everything from this centrally located place. The right pets welcome, but unfortunately we can’t have dogs swimming because it affects the pool negatively— so sorry! We have a 3-year old + Aussie named Luna and she’s good with other dogs, but can be territorial at first. Please cover couch and bed & cleanup after pets —I don’t charge a pet fee so please be mindful of keeping the bungalow clean. Much appreciated.

Top Guest favourite
A modern cottage is set against a backdrop of vibrant landscaping, showcasing a large, clear salt-water pool. Various outdoor seating areas are visible, complemented by lush trees and greenery that enhance the serene environment.
Guesthouse in Sonoma
4.95 out of 5 average rating, 271 reviews

Wine Country Gem - Sonoma Cottage with Pool Oasis

Charming Sonoma cottage perfect for a romantic getaway, girls’ trip, or family stay. Explore Sonoma, Glen Ellen & Napa with ease. The private unit has gourmet appliances, a minimalist-country style, and its own deck with dining + lounge seating. The peaceful 1-acre property features vineyards, a large saltwater pool, a veggie + herb garden, and fruit trees. Relax, recharge, and enjoy the best of wine country living. TOT #3140N

Top Guest favourite
Home in Glen Ellen
4.96 out of 5 average rating, 193 reviews

Vineyard Home • Press Pick • Walk to Wineries

WHY YOU'LL LOVE IT - Stroll your own private Sonoma vineyard - Resort-style outdoor living: pool, hot tub & bocce court with vineyard views - Prime location: minutes to top wineries, dining, spas & shops - Exclusive perk: complimentary tasting at the estate winery next door - Stylish modern interior with thoughtful amenities - Chef-ready, fully stocked kitchen - Ultra-fast, reliable WiFi - Attentive, responsive host

Popular amenities for Kenwood rentals with a pool

When is the best time to visit Kenwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$832 NZD$801 NZD$806 NZD$860 NZD$914 NZD$1,071 NZD$959 NZD$1,001 NZD$991 NZD$1,483 NZD$1,500 NZD$1,265 NZD
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Quick stats about holiday rentals with a pool in Kenwood

  • Total holiday rentals

    Explore 40 holiday rentals in Kenwood

  • Nightly prices starting at

    Kenwood holiday rentals start at $227 NZD per night before taxes and fees

  • Verified guest reviews

    Over 690 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Kenwood holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Kenwood rentals

  • 4.9 Average rating

    Kenwood stays are highly rated by guests—averaging 4.9 out of 5!

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