
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.

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.

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.

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.

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.

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.

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

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

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.

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.

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.

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

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
House rentals with a pool

House on Broadway • Steps to Plaza + Pool

Farmhouse at Sonoma Oaks: Hot Tub · Pool · Bocce!

Tropical Oasis with Pool & Hot Tub 30min to Sonoma

Sonoma Country Club Wine Country w/ pool

Vineyard-House Escape in Sonoma Wine Country

Wine Country Retreat- Privacy-Spa/Pool/Games

Nice Wine Country Family Home

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views
Condo rentals with a pool

Silverado! Luxe 1BR King Suite This View! Balcony

Romantic Winter Escape • Cozy 1BR at Silverado

Wine Country Living at it's best at Silverado CC

Casa Vina at Silverado Resort and Spa | Fireplace

Fairways Silverado Golf and Country

*Fairway Retreat at Silverado

One Bedroom Cottage Along the Napa River

Your wine and wellness retreat at Silverado Resort
Other holiday rentals with a pool

707 BARREL LOUNGE Cottage

1 BR suite in Rock & Roll History

[Egg Farm Ranch] Heated Pool-Water Slide-Hot Tub

Ravenwood Wine County Retreat w/ Pool & Hot Tub!

Spacious wine country villa with pool

Pony Ranch Vineyard Estate with Pool

Peaceful 2BR 1.5BA Oasis, Seasonal Pool & Hot Tub

Red Pepper Retreat-heated pool + hiking trails
When is the best time to visit Kenwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| Avg. temp | 10°C | 10°C | 11°C | 11°C | 12°C | 13°C | 14°C | 14°C | 15°C | 13°C | 12°C | 10°C |
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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