Vacation 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 favorite
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, 413 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.

Guest favorite
The exterior scene captures a serene backyard featuring a newly remodeled saltwater pool surrounded by a stone waterfall and lush landscaping. Lounge chairs are positioned near the pool, and the home is partially nestled among tall trees, creating a peaceful ambiance during sunset.
Villa in Santa Rosa
4.97 out of 5 average rating, 123 reviews

Private 1+ acre, Bocce, New Heated Pool & Hot Tub

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 favorite
A serene outdoor space features a sparkling saltwater pool surrounded by lush greenery and colorful landscaping. A cozy cottage is positioned in the background, with a gray roof and welcoming entrance. Comfortable lounge chairs are arranged neatly beside the pool, inviting relaxation.
Cottage in Kenwood
4.99 out of 5 average rating, 264 reviews

Private Charming Poolside 1 BD/BA in 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 favorite
The image showcases a spacious swimming pool surrounded by a manicured lawn and lounge chairs. Two stylish cabanas are positioned beside the pool. Lush trees are visible in the background, complementing the modern design of the home with solar panels on the roof.
Home in Sonoma
4.97 out of 5 average rating, 99 reviews

Modern wine country stunner!

Enjoy the best of Sonoma from this recently remodeled home. On over 1 acre with mature beautiful landscaping. Just added pickle ball/sport court! New kitchen and baths. Designer finishes. Comfy beds. Spacious and private outside seating and dining. Gorgeous pool. Hot tub and bar area in converted container. Close to the finest wineries in Sonoma. 2 minutes from Sonoma Golf Club. 10 minutes to Sonoma Square, 20 on bike. 7 minutes to Glen Ellen. 10 minutes to Kenwood. Sonoma County TOT #4481N

Top guest favorite
The villa stands nestled among the trees, featuring a spacious driveway leading to a tri-garage. Its exterior combines warm tones with charming shutters. The picturesque hillside setting offers a blend of greenery and distant trees, contributing to a serene ambiance.
Home in Santa Rosa
4.92 out of 5 average rating, 104 reviews

Wine Country Opulent Villa-Brush Creek

Welcome to Brush Creek, a 20-minute drive from Sonoma, Napa, Russian River, Alexander, and Knight's Valleys. Our cozy villa offers five unique bedrooms, including a regal King Master suite. Complimentary EV charging. Healdsburg, Calistoga, and the trendy Barlow are easily accessible. Our attentive staff handles all the chores while you can enjoy the complimentary gourmet coffee. Brush Creek: where comfort, luxury, and character converge for an unforgettable wine country retreat. SVR25-100

Guest favorite
A serene outdoor space features two white Adirondack chairs positioned amidst neatly trimmed hedges. The sun sets on the horizon, casting a warm glow over the landscape, with expansive views of the rolling Sonoma Wine Country hills visible in the background.
Guesthouse in Santa Rosa
4.99 out of 5 average rating, 143 reviews

Sonoma Wine Country Estate Guest House

Are you intrigued by the historical 1917 Crane Canyon Estate in Sonoma Wine Country with the prohibition-era speakeasy and tales of grand Gatsby-like parties?... Or the incredible panoramic views of Sonoma Wine Country?... Or the generous hosts who'll happily point you to the best off-the-beaten-path Sonoma and Napa county treasures... (or just as happily stay out of your way ;) ?... TAKE A BREAK FROM LIFE. We are here to help you do that. ***We are UNABLE to accommodate SERVICE ANIMALS.

Superhost
The spacious farmhouse is set amidst lush greenery, showcasing a serene pool surrounded by a patio. The exterior glows softly in the evening light, accentuating the property's inviting architecture and tranquil atmosphere.
Home in Santa Rosa
4.89 out of 5 average rating, 112 reviews

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

Spread over 5 gorgeous, oak treed acres, this spacious + peaceful family estate welcomes groups to wine country with a Bocce court, pool, hot tub, and a seasonal creek. The stylishly appointed home features 4 King bedrooms, formal dining, expansive game room with Foosball table and 2 fireplaces. Bonus King bedded guest cottage included for 9+ guests. Wild turkeys and deer roam the property. Close to wineries. 10-15 min to Kenwood + Glen Ellen. 30 to Sonoma Square + Healdsburg.

Top guest favorite
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, 673 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 favorite
The outdoor area features a large swimming pool surrounded by lounge chairs and umbrellas. A spacious barn-like structure is visible in the background, nestled among trees, while a hot tub is situated adjacent to the pool, creating a serene and functional outdoor retreat.
Home in Santa Rosa
4.97 out of 5 average rating, 113 reviews

Sustainable Luxury Barn - Secluded Sonoma Retreat!

Relax in the most beautiful, secluded setting Sonoma County has to offer. Hilltop views, walking trails right next to the property, and wineries so close, there is one just across the access road to the property. Constructed from trees that once stood where the Barn now stands, makes this property blend in with the natural surroundings. The trees were milled and dried on site. All siding, beams, flooring, basically anything made of wood is sourced from the property.

Guest favorite
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
4.95 out of 5 average rating, 164 reviews

Modern mid-century-inspired, Deer Ranch

Deer Ranch is a remodeled 2 bedroom, 1 bathroom home sitting on four acres of private land, with outdoor decks, hot tub, and plunge pool. This contemporary Frank Lloyd Wright-styled-like home sits on top of a hill with meadows below and towering redwoods that add to a peaceful seclusion getaway, and still only minutes from the hamlet of Occidental (1.3 miles). The pool is open during the summer months only (late May-end of September). The hot tub is on all year-round.

Guest favorite
A tranquil pool reflects the vibrant hues of a sunset, bordered by lush greenery and palm trees. Comfortable seating areas are visible under shaded structures, enhancing an inviting outdoor space surrounded by colorful landscaping.
Guesthouse in Sonoma
4.91 out of 5 average rating, 320 reviews

Romantic Tropical Garden Casita

As you step through the entrance and under the arch, you are transformed into another time and place. We have been told by guests they feel it reminds them of Italy, France, and Spain. The Hacienda is very private, behind the walls of the early California style home. The gardens are lush and filled with birds of all kinds. There are several vignettes to relax and watch nature. Nights are cool so there is no need for A/C if you leave window open at night.

Top guest favorite
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.
Home in Santa Rosa
5 out of 5 average rating, 117 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

Popular amenities for Kenwood rentals with a pool

Quick stats about vacation rentals with a pool in Kenwood

  • Total vacation rentals

    Explore 40 vacation rentals in Kenwood

  • Nightly prices starting at

    Kenwood vacation rentals start at € 111 per night before taxes and fees

  • Verified guest reviews

    Over 690 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Kenwood vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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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