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Holiday Rentals with Pools in Windsor

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    AU$1,135 Average
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    Travellers to Windsor are booking February dates now. Secure your holiday rental today, and have the perfect trip.
    22 Matching Rentals in the Windsor AreaView all 55 rentals
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    Windsor
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Windsor
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Windsor
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Windsor
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Children's Pool
    • Terrace
    • Hot Tub
    • Washer
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Each condo is outfitted with one king-sized bed in the master bedroom, plus queen-sized Murphy bed in the separate living area. Ideal for two to four guests, this comfortable rental features a fully equipped kitchen, private terrace or patio and gas fireplace. You'll also have high-speed Internet...
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    Windsor, Sonoma County 95492
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Windsor
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    • Central Heating
    • Wi-Fi
    • Washer
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and the...
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    Windsor, Sonoma County 95492
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Windsor
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • Patio
    • DVD Player
    • Washer
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and the...
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    Windsor, Sonoma County 95492
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    The following rentals are within 10 kilometres of Windsor.
    Stunning Wine Country Gated Estate w/ in-ground pool & spa1 / 24
    (22)Excellent
    Healdsburg
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 November 2016
    Tertulia at Amber Ridge brings the best of wine country into one location. The house is spacious for multiple families with dining options to include 20 friends. Every morning...
    Reviewed 10 November 2016
    We recently stayed at Tertulia with 4 other couples while on a tour of the wine country. Tertulia was AMAZING! The house was beautiful and the grounds and amenities were...
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    About this property
    Tertulia at Amber Ridge – where good friends and family gather in stunningly beautiful, peaceful surroundings to enjoy each other’s company over great food and wine. Deep relaxation, pleasant conversation, laughter and joy ensue! Tertulia is a fabulous two-acre Wine Country sanctuary surrounded on...
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    Healdsburg, Sonoma County 95492
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Charming Apartment in Dry Creek Valley, Healdsburg1 / 20
    (6)Very good
    Healdsburg
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 June 2018
    This is a fantastic location in the heart of the wine region of Healdsburg. Easy to access and a quick drive from SFO. Upper barn apartment sleeps 5 comfortably, one bathroom...
    Reviewed 19 September 2017
    We stayed here for nearly a week in July, and not only is it a relaxing home base for a wine country trip, but it is also a great location for the IM Santa Rosa race. It is...
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    About this property
    Our apt. is nestled in the heart of the gorgeous Dry Creek Valley wine country, 10 minutes away from Healdsburg and its many wineries, acclaimed restaurants, and shops galore. the apt. is 1150 Sq ft with 2 bedrooms, kitchen/great room, and deck/BBQ. We have 8 acres with organic gardens, raised...
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    Healdsburg, Sonoma County 95448
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Stunning, quiet, contemporary, single-level, eco-friendly home on 2.5 acres1 / 25
    (3)Excellent
    Healdsburg
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)1 / 29
    (4)Very good
    Healdsburg
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Parking
    • Washer
    • Hot Tub
    • DVD Player
    • Internet Access
    • Private Outdoor Pool (Unheated)
    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/3.5ba, 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
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    Newly renovated 2-story custom Estate - 5br+/3.5ba home, sleeps 101 / 25
    (2)Excellent
    Healdsburg
    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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Upscale, Modern four bedroom, three bath home1 / 20
    (5)Very good
    Healdsburg
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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
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    Healdsburg
    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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Healdsburg
    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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    Healdsburg
    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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Healdsburg
    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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Healdsburg
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Hot Tub
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Healdsburg
    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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Healdsburg
    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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Healdsburg
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • 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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Healdsburg
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • 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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Healdsburg
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the best destination in Healdsburg for extended families attending weddings, on summer or spring vacations, or for groups of adults on holiday to cycle or taste wines. Designed as a family compound on a gated estate by the shore of the Russian River, it offers unmatched privacy along with a...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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