
Holiday rentals with a pool in Cobb
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Top-rated rentals with a pool in Cobb
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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.

Pacific Gardens Retreat
Enjoy a tranquil art filled garden escape at our pet friendly home! Whether you are soaking in the hot tub after a day of wine tasting or having dinner with friends this indoor/outdoor living retreat will leave you feeling relaxed. Well stocked kitchen, fast wifi and walking distance to downtown. Great restaurants and breweries nearby. Well behaved non destructive pets are welcome in this home. It may not be a fit if you have severe allergies though we do our best to clean very thoroughly.

Serene 1 BR Condo at Silverado Resort
Calming, relaxing, and stylish, this newly-remodeled 2nd floor condo at Silverado Resort is modern, serene, and peaceful. It’s perfect for a couple's celebration, a special birthday, or a quiet place to stay after enjoying one of the many events hosted at this famed property! Blending urban sophistication with Wine Country charm, this exquisite condo features upscale amenities, 100% bamboo linens, a posh sleeper sofa, two fireplaces, and a premium King size mattress for next level sleep bliss.

Pony Ranch Vineyard Estate with Pool
Guest House with private entrance on gorgeous gated Vineyard Estate. Overlooks pool and vineyards with views to Mount St. Helena. Gas fireplace, refrigerator, microwave, Keurig coffee maker, queen bed. Seasonal private pool with fabulous views, occasionally shared with owners. Toilet and sink separate from shower. 8 minutes to the Healdsburg Plaza. Less than a mile from 3 wineries, very close to dozens more. Agricultural Education Programs available. Sonoma County TOT Certificate 1362N

Islands in the Sky, Views, Pool, Jacuzzi & Sauna
West of Cloverdale, 7 mi. Beautiful Yorkville, 1800 ft. elev. 164 ac. mountain ranch, vineyard & winery. Large private 2nd floor suite, 1-5 guests. 1 extra guest, have bed for 1 more. High ceilings, skylights & fans. Living rm, bedrm. area, kitchen, dining, full bath & balcony deck. Hardwood floors, Air cond. Heating. garden deck, hiking, pool, jacuzzi, sauna, cooling rm. 1/2 bath. Wine tasting by appoint. $25. per guest Rustic setting, valley views. Above the fogline, sunny & starry sky.

Cozy Home w/ Hot Tub/Pool- near Shops, Wine, Food
Escape to our cozy Mid-Century Modern home in the heart of Sonoma Wine Country. A 10 min drive to some of the best wineries in the world! Relax in the large pool & hot tub, grill on the Traeger for BBQ dinners + pets are welcome! Walking distance to Howarth Park, Spring Lake, in the neighborhood of Annadel State Park for hiking & biking. One block from Montgomery Village, full of boutique shops & Wine-Country restaurants. A 20 minute drive to Sonoma, & near Healdsburg, Kenwood + Bodega Bay.

Wing in Tuscan Villa with Vineyard and two bedrms
Beautiful Tuscan-inspired villa perched at the northern most corner of Alexander Valley and Sonoma County. Perfect abode to escape the city and experience the beautiful outdoors with luxurious amenities. Cloverdale, Healdsburg & Anderson Valley Wineries all within short drive on Highway 128 wine trail - 1 hour’s drive to coast and town of Mendocino. Modern private space with full kitchen and private bathroom with access to pool, jacuzzi, outdoor kitchen/grill, and fire pit. TOT# 2713N

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.

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.

Hot tub, lakeview w/family & friends
Relax with the whole family or friends at this peaceful private unique place to stay. Have fun or just enjoy quiet time. Swim or hang by the pool or hot tub. BBQ or cook in the kitchen and eat while you look at the lake view! There are smart phone jacks in each room, plenty of parking, a private fenced in yard and screen room. This property has all the added modern comforts of a forced air heating and cooling system, washer/dryer and safe play area for the kids!!

BungalowTerrace-HotTub/Arcade/MassageChair/Gym
Welcome to the Bungalow Terrace! Step away into a magical journey full of life & color. A living 1950's Fairytale tucked high above the Redwoods. A place to dream peacefully, Live by the sun & Love by the moon. Designed for couples/families and any and all looking to treat themselves somewhere over the rainbow. The Bungalow Terrace is a sanctuary of magic, fun, and tranquility that will provide memories for a lifetime.
Popular amenities for Cobb rentals with a pool
House rentals with a pool

Private, Warm & Cozy + Spa + Pool + Fire Pit + WiFi!

STAY AWHiLE Guerneville Hot Tub Fireplace Yard

Serene Wine Country Retreat with Pool & Hot Tub

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

Lakefront family retreat!

Happy House Getaway - Pool, Hot Tub & Wine Country

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views

Leo’s Lodge - Lux Retreat with Pool and Hot Tub
Condo rentals with a pool

*Silverado Condo Retreat near Wineries

Fairway Getaway

Silverado Resort Dual Suite golf course villa

Wine Country Living at it's best at Silverado CC

*Fairway Retreat at Silverado

Your wine and wellness retreat at Silverado Resort

1 bed | 1 bath | Silverado Resort Experience

Sip, Taste, Hot Tub - Repeat - 2 Bdrm Condo-Slps 6
Other holiday rentals with a pool

Stylish & Cozy ~ Stunning Lake Views ~ ♛Royal Beds

Spacious Two Bedroom Unit in Clearlake!

Wine Country Estate: Pool, Spa & Vineyard Views

Adventures surround this charming 2bedroom home.

Clear Lake 1 Bed Resort Condo ~Boat Storage/Launch

Elegant Vineyard Getaway Nestled in Healdsburg

Jago Bay - Vineyard Home with Pool and Hot Tub

Chianti | Luxury Ranch w/Pickleball, Pool, Hot Tub
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- Lake Berryessa
- Jenner Beach
- Goat Rock Beach
- Safari West
- Doran Beach
- Johnson's Beach
- Sonoma Coast State Park
- Trione-Annadel State Park
- Chateau St. Jean
- V. Sattui Winery
- Jack London State Historic Park
- Sugarloaf Ridge State Park
- Iron Horse Vineyards
- Napa Valley Wine Train Wine Shop
- Charles M. Schulz Museum
- St. Francis Winery and Vineyard
- Harbin Hot Springs
- Armstrong Redwoods State Natural Reserve
- Salt Point State Park
- VJB Vineyard & Cellars
- Healdsburg Plaza
- Sonoma State University
- Bodega Head
- Francis Ford Coppola Winery




