Vacation rentals with a pool in Healdsburg

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Top-rated rentals with a pool in Healdsburg

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Guest favorite

Guest suite in Sonoma

4.91 out of 5 average rating, 344 reviews

Wildwood Retreat and Pool

The Wildwood Retreat is located on a wooded 2 acre country property in the hills above Sonoma just minutes from the Historic Downtown Sonoma Plaza. The newly remodeled studio apt is very private on a separate level below the main house conveniently close to the pool. Amenities include a king size bed, kitchenette, private bath,sunny deck,pool access and convenient parking. Great walks are just outside your door. This tranquil retreat is ideally located for enjoying all the Wine Country offers.

Oct 7 – 14

G$30,956 GYD per night

Guest favorite

Cottage in Sonoma

4.91 out of 5 average rating, 101 reviews

Farm Cottage With Private Pool

*NOTE: the pool is solar heated and is only open JUNE 1- OCTOBER 31. Private, quiet, peaceful family or couple-friendly rustic farm cottage, wine country retreat with a private pool minutes away from wineries, like Schug, Gloria Ferrar, Viansa, Ram's Gate and Sonoma town square. Solar-heated pool is open June-October. We are locked in by three dead-end roads, so it's very quiet. Large deck, large pool patio, kids' play structure, and more. Horses are our neighbors and life slows down here.

Oct 8 – 15

G$161,707 GYD per night

Guest favorite

Home in Sonoma

5.0 out of 5 average rating, 116 reviews

Sonoma Vineyard House with Pool close to Plaza

Enjoy your own retreat in the middle of the vineyards, yet close to all of downtown Sonoma's charms and conveniences Central location to many wineries & the Sonoma Plaza, but you may never want to leave this tranquil property surrounded by vineyards. *3 bd/2 ba *Gas Fireplace Heat, AC in house and pool house *Pool *HotTub *Fire pit *Multiple lawns and lawn games *Outdoor movie area *Outdoor bbq / dining area *Complimentary Sonoma wine *Includes 4 bikes *Sleeps a total of 8 guests.

Dec 9 – 16

G$169,904 GYD per night

Guest favorite

Home in Santa Rosa

4.98 out of 5 average rating, 101 reviews

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.

Dec 31 – Jan 7

G$59,744 GYD per night

Guest favorite

Home in Windsor

4.99 out of 5 average rating, 144 reviews

Luxury Wine Country Estate with pool & hot tub

Welcome to our amazing Wine Country oasis, perfect for your relaxing getaway! This home features a large chef’s kitchen, four spacious bedrooms, and two living rooms. Enjoy the outdoor amenities, including large pool, hot tub, outdoor kitchen, bathroom, and dining area. You can also play a game of pool or pingpong in the finished garage! This home is located close to the Sonoma County Airport, wineries, and world-class dining, making it the perfect choice for enjoying all wine country offers

Sep 4 – 11

G$136,659 GYD per night

Guest favorite

Guesthouse in Healdsburg

4.96 out of 5 average rating, 101 reviews

Dog Friendly Healdsburg / Dry Creek Valley Cottage

Surrounded by vineyards, this dog-friendly* cottage provides a secluded and scenic wine country experience. You will enjoy the privacy of our custom-built cottage overlooking Dry Creek Valley, on a 20-acre vineyard ranch. Views stretch from Mt. St. Helena in the east to the Pacific Coast Range in the west. Swim in the lap pool or just soak up the scenery. Year around birding and nature photography opportunities abound. You will think you are in Tuscany. We are happy to share it with you.

Mar 30 – Apr 6

G$107,068 GYD per night

Guest favorite

Guesthouse in Cloverdale

4.95 out of 5 average rating, 184 reviews

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

Feb 17 – 24

G$57,139 GYD per night

Guest favorite

Home in Graton

5.0 out of 5 average rating, 562 reviews

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 covid cleaning protocols

Oct 20 – 27

G$97,723 GYD per night

Guest favorite

Guest suite in Santa Rosa

4.99 out of 5 average rating, 142 reviews

Wine Country Retreat w Pool & Spa - Near Vineyards

This one-acre estate offers the quiet and convenience of beautiful Bennett Valley. Just a short drive to the east you will find beautiful vineyards, wine tasting, and farm-fresh cuisine in Sonoma Valley. North 20 minutes up highway 101 you will find spectacular vineyards in Alexander Valley, Dry Creek Valley, as well as elegant tasting rooms and shops in the town of Healdsburg. Located minutes from shopping and local sites, but you will feel worlds away in a quiet, peaceful setting.

Sep 28 – Oct 5

G$39,177 GYD per night

Guest favorite

Guesthouse in Sonoma

4.99 out of 5 average rating, 208 reviews

707 BARREL LOUNGE Cottage

LIVE ALOHA IN SONOMA! Enjoy this tropical Hawaiian Getaway in the Heart of Sonoma Wine Country. Sonoma is a great little town to eat, drink, shop, hike, bike, walk, swim, and relax. There is so much to do here! This cottage will put you in a vacation state of mind as soon as you arrive. Relax around the pool, enjoy a good book, walk into town or hire a car service and visit some of the many amazing wineries in the Sonoma-Napa-Alexander Valleys. COME ENJOY ALOHA IN SONOMA!

Aug 7 – 14

G$55,665 GYD per night

Guest favorite

Guesthouse in Sonoma

4.94 out of 5 average rating, 192 reviews

Modern Cottage with Pool in Heart of Wine Country

This charming cottage is ideally situated for exploring Sonoma, Glen Ellen and Napa. It's perfect for a romantic getaway, friend-trip, or family fun. The private unit has gourmet appliances and a minimalist-country style. It has its own deck with outdoor dining and lounge chairs where you can relax. The ~1 acre property has vineyards, a large salt water pool and patio, and a garden with fresh veggies and herbs as well as many fruit trees. TOT #3140N.

Sep 7 – 14

G$53,736 GYD per night

Guest favorite

Home in Windsor

4.93 out of 5 average rating, 147 reviews

Luxurious home and pool

Beautiful executive home loaded with sophisticated upgrades. This spacious open floor plan features 4 bedrooms, 3 baths, and a private pool with a fountain. The gourmet kitchen, hardwood floors, and granite counters are all part of the great room with fireplace. Centrally located in Sonoma county with more than 20 wineries within a 10 minute drive. This house is just 5 miles from Healdsburg and 20 miles from Calistoga.

Aug 17 – 24

G$118,964 GYD per night