Best Vacation Homes in Windwood
House
10.0(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
Fireplace/Heating
Pet Friendly
Kitchen
Parking
US $127/Night
7 Nights - US $889
House
10.0(3 Reviews)
4 Bedrooms
4 Baths
14 Guests
2895.49 ft²
Oceanfront
Pool
Ocean View
Balcony/Terrace
US $391/Night
7 Nights - US $2,737
Cottage
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $502/Night
7 Nights - US $3,513
House
10.0(3 Reviews)
2 Bedrooms
2 Baths
5 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $337/Night
7 Nights - US $2,359
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
1097.92 ft²
- Fireplace/Heating
- Parking
Air Conditioner
Internet
US $295/Night
7 Nights - US $2,065
Cottage
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $114/Night
7 Nights - US $798
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
1950 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $204/Night
7 Nights - US $1,428
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $185/Night
7 Nights - US $1,296
Windwood Luxury Rentals
House
10.0(1 Review)
4 Bedrooms
3 Baths
16 Guests
- Kitchen
- Air Conditioner
- Internet
Child Friendly
US $1,296/Night
7 Nights - US $9,072
House
4 Bedrooms
3 Baths
12 Guests
3025 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $821/Night
7 Nights - US $5,745
US $788/Night
7 Nights - US $5,519
House
2 Bedrooms
2 Baths
6 Guests
View- Pet Friendly
- Parking
- Air Conditioner
US $708/Night
7 Nights - US $4,958
House
2 Bedrooms
2 Baths
6 Guests
- View
- Pet Friendly
- Parking
- Air Conditioner
US $708/Night
7 Nights - US $4,958
Apartment
1 Bedroom
1 Bath
2 Guests
764.24 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $588/Night
7 Nights - US $4,116
House
1 Bedroom
5 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $581/Night
7 Nights - US $4,066
Apartment
2 Bedrooms
2 Baths
4 Guests
1108.68 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $541/Night
7 Nights - US $3,787
Windwood Pet Friendly Vacation Rentals
House
8.8(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
1950 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $234/Night
7 Nights - US $1,640
House
2 Bedrooms
3 Baths
5 Guests
2002.09 ft²
Spa- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $262/Night
7 Nights - US $1,834
US $211/Night
7 Nights - US $1,474
House
8.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $180/Night
7 Nights - US $1,262
House
2 Bedrooms
1 Bath
6 Guests
559.72 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $242/Night
7 Nights - US $1,696
Apartment
7.4(6 Reviews)
2 Bedrooms
2 Baths
5 Guests
1055 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $205/Night
7 Nights - US $1,434
Apartment
5.4(3 Reviews)
2 Bedrooms
2 Baths
5 Guests
1055 ft²
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
US $196/Night
7 Nights - US $1,371
Apartment
5.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1113 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $111/Night
7 Nights - US $779
Windwood Large Vacation Homes
House
10.0(8 Reviews)
5 Bedrooms
3 Baths
12 Guests
3800 ft²
Private Pool
Hot Tub- Fireplace/Heating
- Pool
US $468/Night
7 Nights - US $3,274
House
7.0(2 Reviews)
4 Bedrooms
2 Baths
16 Guests
2400.35 ft²
- Pool
- Kitchen
- Parking
- Air Conditioner
US $522/Night
7 Nights - US $3,654
House
9.4(6 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Child Friendly
US $482/Night
7 Nights - US $3,376
House
10.0(3 Reviews)
5 Bedrooms
4 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $215/Night
7 Nights - US $1,508
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $353/Night
7 Nights - US $2,471
House
9.8(7 Reviews)
4 Bedrooms
2 Baths
14 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $538/Night
7 Nights - US $3,766
House
9.4(6 Reviews)
4 Bedrooms
3 Baths
14 Guests
3300 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $537/Night
7 Nights - US $3,757
House
9.0(38 Reviews)
6 Bedrooms
2 Baths
18 Guests
2798 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $486/Night
7 Nights - US $3,401
Why Choose Rent By Owner for your Windwood Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Windwood
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this destination can greatly enhance your experience, as seasonal weather and local events in the area influence the ideal period for your stay in Cypress, Texas.
Peak Season Highlights
Spring (March to May)
During spring, this destination experiences warm weather and lush surroundings, making it an ideal time for outdoor activities and exploring the region's natural beauty. It’s a popular season for visitors seeking pleasant temperatures and vibrant scenery.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Autumn offers cooler temperatures and less humidity, providing a comfortable environment for sightseeing and outdoor pursuits. This period marks the peak season as travelers enjoy the mild climate and scenic fall foliage.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Summer (June to August)
Summer can bring higher temperatures and increased humidity, with many visitors preferring to avoid the heat by staying indoors or visiting during early mornings and late evenings. This is a quieter time for booking vacation rentals.
Average Temperature Daytime: 90°F to 100°F - Nighttime: 70°F to 75°F
Winter (December to February)
Winter sees milder temperatures and less tourist activity, offering a peaceful retreat for those looking to escape colder climates elsewhere. It’s a great off-peak period for affordable stays and quiet exploration.
Average Temperature Daytime: 55°F to 65°F - Nighttime: 40°F to 50°F
Weekly Weather Forecast for Windwood
How to Book Your Windwood Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windwood
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor living with a private swimming pool to relax and unwind.
- Experience the beauty of lush, landscaped gardens surrounding your outdoor space.
- Take advantage of a fully equipped patio or deck perfect for outdoor dining and gatherings.
- Make use of designated barbecue grills to enjoy grilling meals with family and friends.
- Benefit from shaded areas or pergolas providing comfort during sunny days.
- Engage in outdoor activities with access to tennis courts or nearby sports facilities.
- Discover scenic walking or biking trails just steps from your rental for outdoor adventures.
Top Attractions Around Windwood
What attractions are nearby?
In this vibrant region, you can explore a variety of outdoor activities and local attractions that showcase the best of what Cypress has to offer, ensuring your stay is full of memorable experiences just moments from your vacation rental.
Family Activities
- Splashtown Waterpark: Enjoy a fun-filled day with the family at this popular waterpark, offering slides and attractions suitable for all ages in the area.
- Cypress Top Historic Park: Explore local history through engaging exhibits and walking trails that make for an educational outing close to your vacation rental.
- Harris County Public Library - Cypress Branch: Spend a quiet afternoon participating in storytime sessions or exploring a wide selection of books perfect for children and teens.
- Berry Center Sports Complex: Cheer on local sports teams or engage in recreational activities like soccer and tennis at this family-friendly sports facility nearby.
Adult Activities
- Explore Cypress Lakes Golf Club: Enjoy a round of golf on the scenic courses that cater to all skill levels, offering a relaxing way to experience the region's natural beauty.
- Visit the Houston Premium Outlets: Shop for designer brands and enjoy exclusive deals in this popular retail destination just a short drive from here.
- Discover the Berry Center: Attend live sporting events, concerts, or community shows at this versatile venue, perfect for entertainment lovers seeking local excitement.
- Relax at Towne Lake Park: Take a leisurely walk or have a picnic around the picturesque lakeside setting, ideal for unwinding amidst the area's tranquil environment.
Windwood Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities in Advance: Explore the local scenery and amenities around your vacation rentals to maximize your time here, ensuring you experience the best this destination has to offer.
- Select a Strategic Location: Choose accommodations close to key attractions or conveniences to minimize travel time and enhance your overall stay in the region.
- Engage with Local Recommendations: Seek advice from hosts or neighbors near your vacation rentals for authentic dining options and hidden gems within this area.
- Travel During Off-Peak Seasons: Visiting during less busy times can help you enjoy a more relaxed atmosphere and possibly better rates on your vacation rentals here.
Transportation Options
- Personal Vehicle: You can conveniently explore the area with your own car, offering flexibility and ease when traveling between Windwood's scenic spots and amenities.
- Public Transit: Buses provide an affordable transportation option, connecting you to nearby neighborhoods and essential services here in Cypress.
- Rideshare Services: Apps like Uber and Lyft are readily available for quick, comfortable rides around this region, making local travel seamless.
- Taxi Services: Traditional taxis operate in the area, providing reliable transportation choice for short trips within Windwood and surrounding communities.
Local Customs Options
- Southern Hospitality: Visitors often experience the warm and welcoming attitude characteristic of this region, making your stay in Cypress feel like a true local experience.
Participating in community celebrations and festivals reflects the area's rich cultural traditions and is an easy way to connect with locals during your visit. - Respect for Nature and Outdoor Etiquette: When exploring nearby parks and natural areas, it’s customary to follow conservation practices and demonstrate respect for the environment here.
- Family-Oriented Social Norms: Engaging in social interactions with neighbors and fellow visitors often involves friendly conversations and courteous manners, typical within this community.
Windwood Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Windwood?
There are a lot of options in Windwood. If you plan on staying in the Windwood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windwood:
- Work n' Play Cypress- Spacious 5-bedroom house with a pool/spa in north Cypress
- Mama’s Modern House is family and pet friendly, large yard, quartz countertops
- Charming, BRAND NEW, complete guest house 2/1 w, Full kitchen, laundry, & living
- FIFA World Cup Home with Pool!
- Dog-Friendly Cypress Vacation Rental w/Lanai!
- 30 Miles to NRG Stadium - Family Home in Houston!
- Quiet & Relax Getaway- Pool Table, Grill, &Netflixnn
- Family Retreat: Patio, RokuTV, Sleeps 10
- Charming 2-bedroom cottage in Cypress with WiFi, AC, & privately gated driveway
- ♕Fancy Home near Cypress♕
2. How many vacation rentals have private pools in Windwood?
There are 8 vacation rentals with private pools near Windwood. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Windwood are best for families?
If you are looking for a family-friendly vacation home in Windwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windwood:
4. How many Rentbyowner vacation rentals are available in Windwood?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 191 in the Windwood area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windwood.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary depending on the individual listing. It is important to review the specific terms provided by the property owner when booking, as they can differ from one rental to another.
6. Are there any additional fees I should be aware of when booking a vacation rental nearby?
Additional fees such as cleaning fees, service charges, or security deposits are often outlined in the listing details. To understand the full cost, it’s best to read the description carefully or contact the host directly.
7. How do I confirm my reservation and what are the payment options?
Reservations are typically confirmed through the booking platform, with secure payment options available. Check the listing for specific payment methods accepted by the owner, and ensure all details are finalized before confirming your stay.
8. Is there a minimum stay requirement for properties here?
Minimum stay requirements can vary based on the property and the season. Be sure to check the individual listing for any minimum night stay restrictions before making your reservation.
9. What amenities are included in the vacation rentals in the region?
Amenities vary between properties but commonly include essentials such as Wi-Fi, parking, and kitchen access. For detailed information on specific amenities, review the listing description or contact the property owner directly.
Windwood Top Rated Vacation Rentals
House
10.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
1815 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $170/Night
7 Nights - US $1,192
Hotel
9.2(1003 Reviews)
1 Bath
- Pool
- Balcony/Terrace
Breakfast- Kitchen
US $133/Night
7 Nights - US $934
Hotel
8.8(751 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $167/Night
7 Nights - US $1,171
Hotel
8.8(750 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $143/Night
7 Nights - US $1,002
Hotel
8.8(491 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $133/Night
7 Nights - US $934
Hotel
8.7(397 Reviews)
10 Baths
420.87 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $104/Night
7 Nights - US $729
Hotel
8.6(1002 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $174/Night
7 Nights - US $1,220
US $90/Night
7 Nights - US $631
