Vacation rentals in Oakville

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Top-rated vacation rentals in Oakville

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Guest favorite

Guesthouse in Glen Ellen

4.91 out of 5 average rating, 931 reviews

Crow Cottage ~ 3 min walk to town - restaurants

Crow Cottage is newly rebuilt and decorated in an eclectic whimsical style by the artist owners. It is light and airy with a private shade deck and sunny patio. The Cottage has a queen bed. There is a portable A/C. The cottage is well insulated so it doesn't get too hot in the summer. There is also a fan. Set on a country lane just a 3 min walk to great restaurants & a gourmet market. While we do have rescued cats in our yard we don't let them in any of the rooms. If highly allergic, reconsider.

Nov 21 – 28

G$28,354 GYD per night

Guest favorite

Guesthouse in Kenwood

4.94 out of 5 average rating, 198 reviews

Casa de Vincenzi

Beautiful, immaculate private studio, situated in Kenwood village with separate entrance and garden patio offers a quiet retreat in the heart of Sonoma Valley. Walking distance to world class tasting rooms and restaurants. Close to Sonoma, Glen Ellen and fave parks. Enjoy your ensuite bathroom with fluffy towels and toiletries. Indoor or outdoor dining to enjoy wine, tea, conversation, TV or wifi. Sleep in the quiet of your comfy queen size bed. TOT (Transient Occupancy Tax) included. TOT #3720N

Jun 17 – 24

G$29,263 GYD per night

Guest favorite

Condo in Napa

4.99 out of 5 average rating, 134 reviews

Coastal Vibes at Resort: Balcony, Pool Access

Come experience a comfortable and relaxing retreat in the amenity-rich Silverado resort community and convenient to Napa Valley attractions. Everything you need is here – from a well-equipped kitchen to cozy bedroom, 2 king beds, fireplace, and balcony overlooking the condominium pool. You’ll enjoy access to resort amenities – restaurants, pool, Tesla charging station, laundry, and more. Guests rave about cleanliness, coastal decor, and responsive host. Launch your wine-country exploration here!

Jul 10 – 17

G$77,602 GYD per night

Guest favorite

Condo in Napa

4.99 out of 5 average rating, 152 reviews

Chic 1 BR Condo Par Excellence at Silverado Resort

Distinctly modern and exquisitely curated, this newly-remodeled 2nd floor condo at Silverado Resort is sleek, subdued, and moody. It’s perfect for a couple's retreat, a girls' getaway, or a quiet place to stay after enjoying one of the many events hosted at this famed property! Blending urban sophistication with Wine Country charm, this exquisite condo features upscale amenities, 100% bamboo linens, a posh sleeper sofa, two fireplaces, and a premium King size mattress for next level sleep bliss.

Jun 26 – Jul 3

G$93,731 GYD per night

Guest favorite

Condo in Napa

4.99 out of 5 average rating, 323 reviews

Silverado Resort! Large 1BR Mountain View, Balcony

Apartment with views! Top floor Silverado Resort true 1 bedroom (not studio), 1ba 676 sq. ft. w/ rare mountain views from the balcony, living and dining rooms. Wood burning fireplace. *Price includes tax. Walk to pool, market, dining, lounge at mansion. Newly remodeled, modern appliances, ready for your relaxation. Luxurious fine Italian linens from Frette. Just like a 5-star hotel. Roku streaming,Directv Hike or hang out in relaxing grounds! Solid surfaces, knobs sanitized during cleaning.

Aug 8 – 15

G$78,708 GYD per night

Guest favorite

Apartment in Napa

4.96 out of 5 average rating, 776 reviews

Carriage House at Main Street Farmhouse!

Clean, comfortable, space on this Farmhouse property dating back to 1880. Enter exact number of guests for correct pricing $60 per person after 2. Studio apartment with queen bed, full bathroom, kitchenette with microwave, electric sautée pan, toaster, coffee and tea, (no full oven or stove) dinette, tv area and sofa/sleeper. Beautiful patio with fire pit. Not suitable for children under the age of 12. Community fee (local lodging tax of 15%) is added to reservation when confirmed by guest.

Nov 12 – 19

G$58,650 GYD per night

Guest favorite

Apartment in Napa

5.0 out of 5 average rating, 317 reviews

Mendez on Main #2 / King Bed/1 bath Walk to town

Indulge in Napa's finest restaurants, wine tasting, and nightlife from our beautifully restored and remodeled apartment in our Victorian home, just a 10-minute stroll from downtown. Our apartment is fully equipped with all the amenities you'd expect, (*No stove) creating a comfortable space for your stay. For the peace and relaxation of all guests, please note that we do not allow pets or children under 12. You can book with confidence knowing that we have a Use Permit from the City of Napa.

Apr 2 – 9

G$68,546 GYD per night

Guest favorite

Villa in Napa

4.96 out of 5 average rating, 102 reviews

An Italian Villa in the heart of Napa Valley!

Villa RayEl was inspired by the farmhouses and small villas of Italy. Located midway between downtown Napa and Yountville, this property sits on 2 acres providing great privacy. It sits next to a year-round creek with a view of a vineyard and nightly sunsets. It has a pool and an attached hot tub. Located 5 minutes off Highway 29, 8 minutes to Downtown Napa and 8 minutes to Yountville. It is convenient to great wineries, restaurants. Its the perfect getaway for families and friends!

Jan 31 – Feb 7

G$184,112 GYD per night

Guest favorite

Guest suite in Glen Ellen

4.96 out of 5 average rating, 190 reviews

Hummingbird Hideaway, Glen Ellen in Sonoma Valley

Hummingbird Hideaway is the perfect location to enjoy everything wine country has to offer. Located in the heart of Glen Ellen in the Sonoma Valley, you can stroll to wine tasting, restaurants, French Bakery, gourmet market and historic saloon for a night cap. Hiking the trails at the Jack London State Park is just minutes up the road. When you're ready to venture further, Sonoma is a short 15 minute drive, Kenwood is 10 minutes and just an hour to Bodega Bay on the Coast.

Sep 26 – Oct 3

G$33,013 GYD per night

Guest favorite

Home in Napa

4.98 out of 5 average rating, 320 reviews

Vineyard House In The Heart Of Napa Valley

La Casita Megandina will create a memorable vacation experience for you and your family. Our house is centrally located in the heart of the Napa Valley only minutes from wineries and world famous restaurants. Our slogan is “Come Experience the Napa Valley Lifestyle at its Finest”. The house borders on a vineyard which give you an amazing view in a quiet neighborhood. Guests from around the world have enjoyed staying with us and we would like to share our house with you.

Feb 25 – Mar 4

G$83,943 GYD per night

Guest favorite

Guest suite in Napa

4.97 out of 5 average rating, 155 reviews

Luxury Private Poolside Suite

Walk past the fountain to a private entrance. The room has a king size bed, full private bath, a small kitchenette with dining space. We are located 5 minutes from wineries and 10 minutes from downtown Napa. Mature trees with horses and vineyards surround the 2-acre property including the shared pool, hot tub, outdoor fireplace, covered seating, deck & hillside seating. There's a semi-private patio space just for you. Vacation Rental Permit #VR17-050.

Aug 21 – 28

G$40,071 GYD per night

Guest favorite

Guest suite in Napa

4.97 out of 5 average rating, 344 reviews

Perfect Location w/ Charm

Permitted by the city of Napa: #VR16-0008 Our guest suite with private entrance in our charming Napa cottage style home provides you with a comfortable home away from home. Your room and bathroom is completely private and there are no shared spaces in the house. The backyard is shared with us. It's bright and sunny, and you are perfectly located for walking downtown or exploring the valley.

Jul 11 – 18

G$37,547 GYD per night