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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Superhost
A serene infinity pool extends towards the horizon, bordered by lush greenery. Eight lounge chairs, with two umbrellas, face the pool, inviting relaxation. A wooden structure sits in the background, along with a staircase leading to the home, all under a soft, pastel sky.
Home in Santa Rosa
4.91 out of 5 average rating, 122 reviews

Farpoint: Heated Infinity Pool, Mountain Views

Nestled in the Mayacamas mountains, this elevated home offers a peaceful and luxurious retreat in the center of Sonoma wine country. The large infinity pool - gas-heated all year - perches over the magnificent view. Inside, the living room and dining room are furnished to comfortably seat 12 adults. A pool table, ping pong, three dining tables, 75" 4K TV, and large hot tub provide endless options. Hiking trails surround the house. Grocery stores and farmer’s markets are less than 8 minutes away.

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, 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 favorite
A modern home is showcased with large sliding glass doors that open to a spacious wooden deck. The inviting heated pool features a gentle curve, with sun loungers placed nearby. Lush greenery surrounds the property, enhancing the tranquil outdoor setting.
Home in Sonoma
4.95 out of 5 average rating, 515 reviews

Luxe WineCountry getaway with Pool, hottub & Bocce

Thornsberry House is a luxe Wine Country home nestled between the two oldest wineries in California while just 5 minutes from the Sonoma Square. Renovated to accommodate the most discerning traveler, it consists of two separate buildings connected by a breezeway and large deck. Situated on the east side of town, it offers a true escape where one can walk or bike down to Gundlach Bundschu at the end of our street, or soak up the afternoon light from the heated pool, hot tub or a game of bocce.

Top guest favorite
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.

Superhost
A serene infinity pool reflects vibrant sunset colors, with lounge chairs and umbrellas positioned nearby. The horizon displays a gradient of pinks and purples, creating a tranquil atmosphere against the backdrop of distant hills and valleys.
Home in Glen Ellen
4.89 out of 5 average rating, 140 reviews

Spectacular Sonoma: Views! Stars! Cielo.

Cielo is a modern, private 10 acre estate with 180 degree views of Sonoma Valley and miles of vineyards. See Sunsets and stars from the house, deck, hot tub and pool! Cielo is the perfect wine country retreat comfortably accommodating 8. Note: offering this beautiful property at nearly 50% off normal price, only 2 night min instead of 3, because Cavedale road suffered a mudslide. House accessible but adds 15 mins to drive. Arrive at this magical place, settle in and enjoy the bliss!

Top guest favorite
A private outdoor pool area features a sleek, blue pool surrounded by smooth stone tiles. Chaise lounges are positioned nearby, inviting relaxation. The setting is complemented by a rustic wooden structure and a charming home with a brick chimney, set against a colorful sunset sky.
Home in Sonoma
4.99 out of 5 average rating, 182 reviews

Vineyard-House Escape in Sonoma Wine Country

Gather your group and enjoy a stunning wine-country home just 5 minutes from vibrant downtown Sonoma. This 3 bedroom ensemble includes a main house + guest cottage, multiple outdoor lounges, pool, hot tub, fire pit, lightning fast Wi-Fi, Sonos Indoor/Outdoor sound system and gas fireplace — perfect for lively group days and quiet restful nights. Surrounded by vineyards, yet close to dining and town, this distinctive retreat invites you to book now and indulge in togetherness, and rejuvenation

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, 267 reviews

Cozy private getaway 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 favorite
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
4.97 out of 5 average rating, 103 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
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, 682 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
A round fire pit table stands at the center, surrounded by black wicker chairs. Flames flicker invitingly, adding warmth to the outdoor seating area near the heated pool. Lush greenery and palm trees provide a backdrop, enhancing the outdoor setting.
Home in Santa Rosa
4.84 out of 5 average rating, 191 reviews

Nice home, wineries, heated pool, hottub fire pit

This newly remodeled home is your perfect vacation rental. It features a heated pool for you to enjoy year round! There is also a brand new hot tub for an extra dose of relaxation. Enjoy your meal outside around the fire pit table or in the large open kitchen area of the home. If you want a little more privacy, there is an additional side yard with its own fire pit for you to sneak away to. With its prime location (only 20 min to Sonoma) this is the Wine Country home for you!

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, 322 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, 122 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

When is the best time to visit Kenwood?

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Avg. priceﺩ.ﺇ1,752ﺩ.ﺇ1,686ﺩ.ﺇ1,697ﺩ.ﺇ1,811ﺩ.ﺇ1,924ﺩ.ﺇ2,255ﺩ.ﺇ2,020ﺩ.ﺇ2,108ﺩ.ﺇ2,086ﺩ.ﺇ3,122ﺩ.ﺇ3,158ﺩ.ﺇ2,663
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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 ﺩ.ﺇ477 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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