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Holiday Rentals with Pools in Healdsburg

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    Travellers to Healdsburg are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    15 Matching Rentals in HealdsburgView all 44 rentals
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    Charming Apartment in Dry Creek Valley, Healdsburg1 / 20
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Tertulia at Amber Ridge - Stunning Wine Country Gated Estate with pool & spa1 / 24
    (22)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Chalk Hill Country Home - Wine Country Home - main house + pool house1 / 29
    (4)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Limerick Lane - Stunning, quiet, contemporary, single-level, eco-friendly home1 / 25
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • DVD Player
    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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    Location Information
    95448, Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Hot Tub
    • Air Conditioning
    • Grill
    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideally located on 7 hillside acres, in the famed Dry Creek Valley, this absolutely stunning, new, modern Wine Country home is a spectacular retreat nestled in Mother Nature’s paradise, with forever easterly views of the Dry Creek Valley. This magnificent architectural marvel was designed by John...
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    95448, Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    EastSide - Newly renovated 2-story custom Estate - 5br+/3.5ba home, sleeps 101 / 25
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very well located about 3.5 miles southeast of Healdsburg’s famed Plaza, the lovely Eastside Estate sits on 2+ beautifully manicured and wooded acres among the vineyards of the Russian River Valley appellation. Newly renovated, and professionally decorated and furnished, this Estate is nothing...
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    95448, Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    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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    95448, Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • 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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    95448, Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    Bella Terra Healdsburg - 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 10 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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    95448, Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4BR/4BA hm w/solar htd pool surrounded by vineyard1 / 30
    (10)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Mountain Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2015
    Mona was just as warm & welcoming as the photos showcased. Celebrating our Mother's 90th, it was the perfect location to enjoy time together as family- plenty of games to...
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    About this property
    'Mona, a name given to house by our daughter when she could not say 'Sonoma,' is a four bedroom/four bath, completely remodeled home including a one bedroom/one bath guest house in the heart of Dry Creek Valley in Healdsburg, California. Our vacation home sits on one acre nestled among the vines...
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    95448, Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Mountain Views
    • Patio
    • Private Garden
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cottage provides the true Dry Creek Valley wine country experience. with 270 degree views - from Mt. St. Helena in the east to the Pacific Coast Range in the west. Swim in the solar heated lap pool and then relax by the pool while soaking up the view. Walk through the vineyards and the rose...
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    95448, Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Parking
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW A lavish retreat for a picturesque wine country getaway, this 2BR/2BA is hedged on a lovely 3.5-acre vineyard and mature trees. Take a scenic walk through the charming neighborhood, or explore nearby downtown Healdsburg. Then spend an easy afternoon lounging poolside or relaxing...
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    95448, Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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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    95448, Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW The perfect retreat for a wine country getaway, this lovely 1BR cottage is nestled amongst lush vineyards. Pull up a rocking chair and take in garden views from the patio or spend the day lounging poolside. Go for scenic walks or bike rides through the charming neighborhood,...
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    95448, Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    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
    95448, Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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