We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
TripAdvisor
Healdsburg
Post
Inbox
Search

Holiday Rentals with Pools in Healdsburg

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    AU$1,870 Average
    |||
    |||
    AU$0AU$1,000+
    Suitability
    More filters
    Travellers to Healdsburg are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    13 Matching Rentals in HealdsburgView all 39 rentals
    Sort by:
    Default
    Stunning Wine Country Gated Estate w/ in-ground pool & spa1 / 25
    (22)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    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
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dry Creek Retreat Discover the luxuries of wine country living at Dry Creek Retreat, an exquisite 55-acre vineyard, 5,000-case state-of-the-art winery, and luxury home in the rolling hills of Healdsburg. Not only does this vineyard make world-class wines, but it also offers access to a gorgeous...
    View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Upscale, Modern four bedroom, three bath home1 / 20
    (5)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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,...
    View all property information
    Location Information
    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
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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
    See all reviews
    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,...
    View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    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...
    View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Save time - get the best Healdsburg rentals sent straight to your email!
    Get the List
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    List your property
    Owner log in