
Holiday rentals with a pool in Kenwood
Find and book unique homes with a pool on Airbnb
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.

Sonoma Valley Vacation Home with Seasonal Pool
Enjoy indoor/outdoor living in Sonoma Valley with tons of amenities! Our home has a comfy, modern interior with 3 private bedrooms, office room with twin daybed, 2 full baths, large dining room, fully equipped kitchen and breakfast/bar table. The backyard has a large pool (seasonal), gas bbq, fire table, seating and dining table. Minutes by car to Sonoma Square, Glen Ellen, wineries, hiking trails, spas, shopping, & eateries. Walking distance to a park, cafe, mexican restaurant, and 7-11 store.

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!

Enjoy autumn and beyond 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

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

Vineyard Retreat • Steps to Tastings • Press Pick
WHY YOU'LL LOVE IT -Stroll through your own private vineyard -Pool, hot tub & bocce in a stunning serene setting -Minutes to top wineries, restaurants spas & towns -Complimentary tastings at the Estate Winery next door -Stylish interior with thoughtful touches -Chef-ready fully stocked kitchen -Helpful host and quick communication AS FEATURED IN Condé Nast Traveler | House Beautiful | House & Garden | The Wine Daily | Esquire | The Bold Italic | Refinery 29| Bon Traveler | Sunset Magazine

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

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!

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.

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.

Happy House Getaway - Pool, Hot Tub & Wine Country
Welcome to Your Relaxing Getaway! My home is a comfortable, clean, and happy space—perfect for unwinding and enjoying all that Sonoma County and the Bay Area have to offer. 🌿 Spacious Backyard: Large yard with a pool (heated by the sun) 6-person hot tub (kept at 102°F) Easy parking 🍽 Fully Stocked Chef’s Kitchen 🛋 Seasonal Note: Outdoor cushions/umbrellas stored late Oct to mid-May Come stay—you’ll love it! Happy House Permit #: SVR24-194

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
Popular amenities for Kenwood rentals with a pool
House rentals with a pool

Vineyard Vista, Modern Farmhouse Cottage with Pool

Tropical Oasis with Pool & Hot Tub 30min to Sonoma

Luxury home (+ pool house) with views, pool & spa

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views

Leo’s Lodge - Lux Retreat with Pool and Hot Tub

Silverado Napa Breath Taking Remodel 3 bed 2 bath

The Deer Retreat – Privacy and Comfort

SoLEIL OPEN Friendsgiving! Cook's Kitchen+Hot Tub
Apartment rentals with a pool

Silverado! Luxe 1BR King Suite This View! Balcony

Wine Country Living at it's best at Silverado CC

Casa Vina at Silverado Resort and Spa | Fireplace

Golf Course Views, Pool, King Bed & Balcony

Fairways Silverado Golf and Country

*Fairway Retreat at Silverado

Your wine and wellness retreat at Silverado Resort

1 bed | 1 bath | Silverado Resort Experience
Other holiday rentals with a pool

Sky View: Heated Pool & Hot Tub, 5 Acres

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

Ravenwood Wine County Retreat w/ Pool & Hot Tub!

When in Glen Sonoma Panoramic Views 3bed 3bath

Oak Den - Secluded Charm in the Heart of Sonoma

Glen Ellen Gem-2 Bed/2 Bath Oasis + Stunning Pool

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

La Cava -Valley of the Moon
When is the best time to visit Kenwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $620 SGD | $596 SGD | $600 SGD | $640 SGD | $681 SGD | $798 SGD | $715 SGD | $746 SGD | $738 SGD | $1,104 SGD | $1,117 SGD | $942 SGD |
| 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 $169 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Kenwood holiday rentals include wifi 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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