Condo vacation rentals in Windsor

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Popular amenities for Windsor condo rentals

Weekly condo rentals

Superhost
The exterior of the condo complex is highlighted, showcasing a well-maintained landscape with manicured green lawns and trees. Multiple balconies are visible on the buildings, providing outdoor spaces. Clear blue skies with scattered clouds enhance the inviting atmosphere of the surroundings.
Condo in Windsor
4.89 out of 5 average rating, 18 reviews

Wine Country Getaway - Bring your Friends - Slps 6

JoyRating, 5 stars4 months ago
Great central location for Sonoma and surrounding wineries. Options for great restaurants in Windsor or go to Big John’s in Healdsburg and pick up some dinner to bbq at the condo. Very comfortable and great service from the Worldmark staff.
Superhost
A well-maintained condo complex is set against a clear blue sky. Lush green lawns surround the buildings, which feature multiple balconies and porches. The architecture includes light-colored exteriors with white trim, enhancing the welcoming appearance of the community.
Condo in Windsor
5 out of 5 average rating, 13 reviews

Eat, Drink, Pool - Choose the Order -2 Bdrm-Slps 6

AaronRating, 5 stars11 months ago
Although Logan warned us that this is a Wyndham property, we were not prepared to face a relentless and rude sales person before being allowed access to the unit we’d already paid for. We were not allowed to “simply decline” the sales pitch. Instead, after politely declining to sit through a presentation at least five times, we were forced to act angry and rude ourselves before the awful sales person (McKayla, sp?) handed over our room access cards. Additionally, Wyndham charged us a $250 deposit instead of the $100 deposit that Logan mentioned. Not sure what that was about. Very frustrating check in experience after a very long day on the road. The unit itself was clean and had everything we needed including a great bbq grill. The property is nice and has a heated pool and several hot tubs onsite. Logan was polite and very responsive. Despite several positive aspects about this rental, we would not knowingly subject ourselves to another Wyndham check in process.
Guest favorite
A spacious lawn is framed by well-maintained landscaping, with several condo buildings displaying balconies on the upper levels. Lush green grass stretches across the foreground, while a clear blue sky with scattered clouds enhances the inviting atmosphere of the area.
Condo in Windsor
4.89 out of 5 average rating, 27 reviews

Perfect Friends and Family Getaway Instant Book

NicoleRating, 5 stars2 weeks ago
The unit was beautiful and had lots of amenities! We booked two units for a group of 8 girls. Lots of fun activities, comfortable rooms, fun recommendations, and plenty of beds. The only unfortunate part was no free WiFi as a guest, but this was fine for one night.
Top guest favorite
Condo in Napa
5 out of 5 average rating, 49 reviews

Spacious&PeacefulOasis!Beautiful!PerfectlyLocated!

TerryRating, 5 stars1 day ago
The place looks exactly like the pictures the owner is shown. It is very convenient to go to the popular wineries. They are all about 15-20 minutes away.
Superhost
An outdoor pool is surrounded by lounge chairs under the shade of umbrellas. Lush greenery is visible around the pool area, and multiple buildings are seen in the background, showcasing a blend of modern architecture and natural surroundings.
Condo in Windsor
5 out of 5 average rating, 3 reviews

Spacious 2 BDRM Condo in Sonoma Wine County

MosesRating, 5 stars14 months ago
Loved the rental! The area and location is perfect for surrounding wineries and restaurants. Great views and feels just like home away from home!
Superhost
A well-maintained resort features multiple buildings set amidst lush green lawns and manicured hedges. Balconies with white railings provide outdoor spaces for relaxation. The sky is bright with scattered clouds, creating a picturesque backdrop for the tranquil environment.
Condo in Windsor
4.88 out of 5 average rating, 16 reviews

Comforts of Home with Resort Amenities - Sleeps 6

RachelRating, 5 stars74 months ago
Nice space, great for groups! Call ahead to make sure they adjust the two twins into the queen. And the time share folks will push hard, stand firm!
Superhost
An outdoor swimming pool is surrounded by lounge chairs, set within a serene resort area. A large tree provides shade, while the gentle light of evening casts a warm glow across the scene. Buildings reflect a classic design style in the background.
Condo in Windsor
5 out of 5 average rating, 5 reviews

Windsor Resort 2bdr Queen

RebecaRating, 5 stars21 months ago
I loved staying here! There was so many things available to do in the area! Be warned though the welcome desk will try to talk you into going to a timeshare meeting. Overall it was a great place to stay!
Guest favorite
A spacious outdoor area is showcased, featuring well-maintained lawns and walkways. The condo building displays multiple balconies, framed by lush greenery and trees, creating a serene environment. Clear blue skies provide a bright backdrop to the inviting scene.
Condo in Windsor
4.92 out of 5 average rating, 51 reviews

Make This Your Best Vacation Ever - 2 Bdrm Condo

RosannaRating, 5 stars2 weeks ago
Our stay was really nice overall! I highly recommend this listing for anyone with kids. There were multiple pools with with kiddie pools (1 foot deep) and several hot tubs located throughout the resort property. There’s also a restaurant within walking distance. The only issue I had was the layout of the units we stayed in which is that the window to the bedroom with the two twins (where I had planned to have my children sleep) has a big window that faces out into the walkway. Our unit was street facing so anyone could come into the resort. The window locked and honestly the resort felt like it was in a fairly safe area so not a deal breaker, I just think it’s worth noting. Other than that, the unit was very clean and the beds were so comfortable! This is a timeshare so they did ask if I wanted to sit in on a presentation but I didn’t feel pressured at all. I would definitely stay here again.

Condo rentals with a pool

Superhost
The outdoor pool area features a spacious swimming pool, surrounded by lounge chairs and shaded by trees. Nearby buildings offer multiple balconies overlooking the pool, enhancing the communal atmosphere of the resort.
Condo in Windsor
4.89 out of 5 average rating, 18 reviews

Wine Country Getaway - Bring your Friends - Slps 6

JoyRating, 5 stars4 months ago
Great central location for Sonoma and surrounding wineries. Options for great restaurants in Windsor or go to Big John’s in Healdsburg and pick up some dinner to bbq at the condo. Very comfortable and great service from the Worldmark staff.
Superhost
Condo in Windsor
4.86 out of 5 average rating, 7 reviews

Wine Country Home Base - 2 Bdm Condo-Sleeps 6

AdrienneRating, 5 stars24 months ago
Second time staying and was happy once again. Only issue I had was getting pulled into trying to be talked into a time share presentation. I felt very pressured and signed up for a presentation that I didn’t want to do, gave my credit card for an unclear reason. I did cancel my spot at the presentation but then recently saw a charge on my credit card for some membership I never agreed to that turned out to be tied to the timeshare. The whole thing made me very uncomfortable and disappointed. Otherwise the stay and accommodations were great and I plan to continue yearly visits with my family.
Superhost
A large outdoor pool is surrounded by lounge chairs and shaded areas, inviting relaxation. Surrounding buildings feature balconies, providing a view of the pool area. A clear blue sky is visible above, enhancing the inviting atmosphere of the space.
Condo in Windsor
5 out of 5 average rating, 13 reviews

Eat, Drink, Pool - Choose the Order -2 Bdrm-Slps 6

AaronRating, 5 stars11 months ago
Although Logan warned us that this is a Wyndham property, we were not prepared to face a relentless and rude sales person before being allowed access to the unit we’d already paid for. We were not allowed to “simply decline” the sales pitch. Instead, after politely declining to sit through a presentation at least five times, we were forced to act angry and rude ourselves before the awful sales person (McKayla, sp?) handed over our room access cards. Additionally, Wyndham charged us a $250 deposit instead of the $100 deposit that Logan mentioned. Not sure what that was about. Very frustrating check in experience after a very long day on the road. The unit itself was clean and had everything we needed including a great bbq grill. The property is nice and has a heated pool and several hot tubs onsite. Logan was polite and very responsive. Despite several positive aspects about this rental, we would not knowingly subject ourselves to another Wyndham check in process.
Guest favorite
An inviting outdoor pool is surrounded by sun loungers, featuring a smooth, circular shape. Lush greenery and tall trees provide a natural backdrop. Multiple buildings with balconies are visible in the distance beneath a clear blue sky, enhancing the serene atmosphere.
Condo in Windsor
4.89 out of 5 average rating, 27 reviews

Perfect Friends and Family Getaway Instant Book

NicoleRating, 5 stars2 weeks ago
The unit was beautiful and had lots of amenities! We booked two units for a group of 8 girls. Lots of fun activities, comfortable rooms, fun recommendations, and plenty of beds. The only unfortunate part was no free WiFi as a guest, but this was fine for one night.
Superhost
An outdoor pool is featured, surrounded by lounge chairs positioned along the deck. Nearby, lush greenery adds a natural touch to the setting. The backdrop includes multiple buildings with a light-colored exterior, under a blue sky with scattered clouds.
Condo in Windsor
4.88 out of 5 average rating, 16 reviews

Comforts of Home with Resort Amenities - Sleeps 6

RachelRating, 5 stars74 months ago
Nice space, great for groups! Call ahead to make sure they adjust the two twins into the queen. And the time share folks will push hard, stand firm!
Superhost
The outdoor pool area is surrounded by lounge chairs and trees, creating a relaxing environment. The clear blue water invites guests for a refreshing swim. The backdrop features well-maintained condo buildings under a blue sky, enhancing the sense of space and tranquility.
Condo in Windsor
4.75 out of 5 average rating, 57 reviews

Wine Country Condo - Food, Wine & Hot Tubs - Slp 6

RobinRating, 5 stars24 months ago
Logan was great to work with. He was always quick to respond to emails. The condo was perfect for our visit, the pools were great and the location was what made this place somewhere we will come back to.
Superhost
A large outdoor swimming pool is depicted, surrounded by lounge chairs arranged neatly along the perimeter. Lush greenery and residential buildings provide a serene backdrop under a partly cloudy sky.
Condo in Windsor
4.84 out of 5 average rating, 32 reviews

Wine Country 2 Bdrm Condo w/ Pools & Hot Tubs

AmandaRating, 5 stars32 months ago
This location was perfect for my employees, who are working on a new home construction project in the area. They felt right at home and couldn't believe how accommodating everything & everyone was.
Superhost
An outdoor pool area is shown, featuring a large circular swimming pool surrounded by lounge chairs. Nearby, trees and buildings provide a landscaped backdrop under a clear blue sky.
Condo in Windsor
4.83 out of 5 average rating, 78 reviews

Create Your Own 5 Star Vacation - 2 Bdrm Condo

TonyRating, 5 stars12 months ago
This place was a breath of fresh air after trying out a few air Bnb stays in the surrounding towns and area .Exactly as described clean, flexible check in lots of amenities on site and a lot of restaurants nearby . Our host was super quick to respond with any questions or help we needed .We extended our stay as well 10/10 stars

Private condo rentals

Three-story buildings surround a spacious outdoor pool, featuring lounge chairs and umbrellas for guest relaxation. Balconies extend from the upper levels, providing additional seating areas with views of the pool. The clear blue water reflects the bright sky above.
Condo in Windsor
4.73 out of 5 average rating, 11 reviews

1bdm-Condo Windsor WorldMark Resort

JessicaRating, 5 stars35 months ago
Lories place was perfect. My family and I actually got 2 of her units so we could all be together leading up to my wedding. This resort is super kid friendly with lots to do including a grill on each balcony. Would def come back again.
An outdoor swimming pool is surrounded by lounge chairs and umbrellas, situated amidst well-maintained landscaping. Several buildings are visible in the background, featuring balconies that overlook the pool area. A clear blue sky with soft clouds enhances the serene atmosphere.
Condo in Windsor
4.75 out of 5 average rating, 8 reviews

WM Windsor 3 Bedroom Condo

HollyRating, 5 stars2 months ago
This was a beautiful, fun, clean place to stay with our extended family. The unit was lovely, grounds were beautiful, and my kids loved the basketball court, pool, and hot tub. We would def stay again!
Superhost
An outdoor swimming pool is visible, featuring clear turquoise water and surrounded by a spacious deck with lounge chairs. Shade is provided by umbrellas, and trees are positioned in the background, contributing to the relaxing atmosphere of the resort.
Condo in Windsor

Windsor Deluxe Resort 1bdr

JonRating, 5 stars20 months ago
Stay here as often as I can since I work as a moving contractor. Very lovely
An inviting outdoor swimming pool is surrounded by lounge chairs under shaded umbrellas, offering a relaxing atmosphere. Nearby, the resort buildings display a blend of architectural style, with balconies viewed from the pool area, set against a backdrop of clear blue skies.
Condo in Windsor
4.58 out of 5 average rating, 12 reviews

2 Bedroom Accessible @ Worldmark Windsor!

LisaRating, 5 stars6 months ago
We enjoyed the visit and had a great dinner at Charlie’s!
Guest favorite
Electric vehicle charging stations are positioned in a landscaped area, featuring two charging units next to a green sign indicating 'blink EV.' Surrounding greenery adds a natural touch, complemented by a stone-clad building in the background.
Condo in Windsor
4.86 out of 5 average rating, 36 reviews

WM Windsor 2 Bedroom Twin Condo. Sleeps 6

JohnRating, 5 stars5 months ago
We always enjoy the Windsor Worldmark. Great restaurants and wine bars in town. Also several breweries and distilleries in the area. The coast is not far. We always enjoy our stay. FYI check out here for 2025 is now at 11 o’clock. Not 10 o’clock.
Superhost
An outdoor swimming pool is surrounded by lounge chairs, with a large tree providing shade nearby. The pool's clear blue water reflects the evening sky, while the resort buildings are visible in the background, creating a welcoming atmosphere.
Condo in Windsor

Windsor Deluxe Resort 2bdr

CarolRating, 5 stars37 months ago
We had a great time at this simple, family Wyndham resort. The host was very easy to deal with and everything was as advertised.
Superhost
The two-story condo complex is surrounded by well-maintained lawns and landscaped greenery. Balconies are visible on the upper levels, while walkways provide access to each unit. A clear blue sky and soft clouds create a serene backdrop.
Condo in Windsor
4.81 out of 5 average rating, 16 reviews

Wine Country Is Open - 2 Bedroom Resort Condo

JulieRating, 5 stars31 months ago
Wonderful place to stay that was close to the wineries and restaurants. We really enjoyed the fireplace, comfy beds and all the facilities. Would definitely recommend.
A tranquil landscape is displayed, featuring a long bridge spanning across a calm blue lake. Rolling hills covered in greenery rise in the background, under a clear blue sky. The water's edge shows sandy banks, reflecting the natural beauty of the region.
Condo in Windsor
5 out of 5 average rating, 3 reviews

3bdm-Penthouse-Windsor WorldMark

NontwachRating, 5 stars115 months ago
Everything was perfect. Lorie was super host. Will go back for sure. Recommended.

Quick stats about condo rentals in Windsor

  • Total rentals

    130 properties

  • Nightly prices starting at

    G$14,640 GYD before taxes and fees

  • Total number of reviews

    1.6K reviews

  • Family-friendly rentals

    100 properties are a good fit for families

  • Rentals with a pool

    130 properties have a pool

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. California
  4. Sonoma County
  5. Windsor
  6. Condo rentals