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Holiday Rentals with Pools in Healdsburg

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    ₹ 90,182 Average
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    ₹ 0₹ 71,000+
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    Travellers to Healdsburg are booking November dates now. Secure your holiday home today, and have the perfect trip.
    13 Matching Rentals in HealdsburgView all 39 rentals
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    Stunning Wine Country Gated Estate w/ in-ground pool & spa1 / 25
    (22)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)1 / 29
    (4)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • DVD Player
    • Parking
    • Internet Access
    • Washer
    • Grill
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2016
    I loved it and I'd love to come back again. I love Sonoma County.The rooms were very comfortable. I just adored the pool. The weather was perfect. I can't wait til next year.
    Reviewed 11 July 2016
    This is a wonderful house for groups. The common space offers many seats. The hot tub is large enough for 7 people. There is a BBQ and lots of outdoor seating for families to...
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    About this property
    Nestled on 10 acres in the prestigious Chalk Hill appellation of the Alexander Valley, this rustic, beautifully renovated and newly furnished, 5br/4.5ba, 3200 sq. ft., two-story lovely home with central heat/AC, sits on a wooded knoll just above the vineyards. A separate pool house on the opposite...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Upscale, Modern four bedroom, three bath home1 / 20
    (5)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2016
    I rented this house with a group of 7 and it was PERFECT! The property is secluded, the pool is amazing and the beds are comfortable. The location is removed from Santa Rosa...
    Reviewed 11 September 2014
    I was staying at Bella Gia with my husband and a few friends. We were in Healdsburg for our friends' wedding. The house is in an extremely convenient location to downtown...
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    About this property
    Enjoy the best of two worlds, the peace and tranquility of ‘country living’ among the vineyards and wineries of the Russian River Valley, and the convenience of being only five minutes from the historic Healdsburg’s Plaza. Bella Terra Healdsburg is an upscale, and modern appointed four bedroom,...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Limerick Lane / Stunning, Quiet, Contemporary, Single-Level, Eco-Friendly1 / 25
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Grill
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 2016
    the house is fabulous and the location is perfect.minutes to town and lots of wineriespeaceful setting and cool clean house
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    About this property
    Location, location location! Perfectly situated only 3 miles (a 5-7 minute drive) from the charming and historic Healdsburg Plaza, this fabulous, custom three-bedroom home abounds with special eco-friendly features. You will be wowed by this modern home’s beautiful open-beamed cathedral ceiling,...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private and in the country near the Dry Creek and Russian River Valleys and yet only 10 minutes to the Healdsburg Plaza Square. Main house is 3BR/3BA and cottage is studio and full bath with plenty of outdoor furniture. NOTE: Pool heated in high season only. Enter through private gate and wind up a...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Washer
    • Air Conditioning
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW A lavish retreat for the ultimate group getaway, this stunning 3BR/3BA home with a guest suite is hedged by expansive vineyards and mature trees. Spend an easy afternoon lounging poolside or relaxing in the hot tub. Then enjoy an evening gathered around the fire pit telling...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Riverstone Ranch is truely a multi-family property. A location which caters to several generations with traditional main house, or modern 2BR/2BA 'coup' or 'Oak Tree House', each offers something a little different, all against gorgeous Russian River views and less than 5 minutes to downtown...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Parking
    • Hot Tub
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning gated modern ranch house is nestled on one acre among the vineyards, and very well located at the north end of Healdsburg on Alexander Valley Road. Just remodeled, professionally decorated and furnished, this single story, 2000 sq. ft., 3 bedroom, 2.5 bath home sits under the shade of...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Washer
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Grill
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bask in the warmth and beauty of Tuscany — in Sonoma County! Set atop rolling hills among the vineyards, this exquisite estate invites you to transcend beyond everyday routine. You will feel expansive, enjoy a sense of calm, and elevate your perspective. Comfortable luxury welcomes you indoors...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly remodeled vacation rental home is wonderfully located less than 10 minutes north of downtown Healdsburg. It is nestled on the rolling hills of Dry Creek Valley with views looking towards Alexander Valley. Recently refreshed with stylish furnishings, fixtures and lighting system, the home...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Air Conditioning
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    HEALDSBURG VILLA This sprawling estate home offers easy access to every wine country amenity imaginable. Watch hot air balloons take off from the rear veranda while surrounded by acres of vines. Minutes to river fun and a walk to world class wineries. Relaxing seclusion to intense action at the...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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