Vacation rentals near Cypresswood Golf and Country Club

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Choose the perfect vacation home within easy reach of Cypresswood Golf and Country Club. Vacation rentals provide the best amenities for your stay with friends, family, or just your pet, such as WiFi and a fireplace. You'll be able to choose a rental that has what everyone needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Cypresswood Golf and Country Club

Showing deals for:Jul 17 - Jul 24

Image gallery for Heated Pool, Arcade with PS5, 5min from Legoland-Stylish LakeHome

Living area
10 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)

Heated Pool, Arcade with PS5, 5min from Legoland-Stylish LakeHome

Winter Haven

8% off
Price is $363
$2,542 for 7 nights
All fees included
Heated Pool, Arcade with PS5, 5min from Legoland-Stylish LakeHome

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Find out more about Cypresswood Golf and Country Club

Why visit Cypresswood Golf and Country Club

  • Premier Golfing Experience: Enjoy top-notch golfing at the Cypresswood Golf Club with its well-maintained fairways and greens suitable for all skill levels.
  • Family-Friendly Activities: Explore nearby amusement parks and urban parks that cater to visitors of all ages for a fun-filled day.
  • Stunning Natural Landscapes: Take in the beauty of scenic lakes and lush surroundings, perfect for outdoor activities and relaxation.
  • Welcoming Neighborhoods: Experience the charm of Winter Haven's friendly communities, ideal for families and budget travelers.
  • Diverse Accommodation Options: Choose from a range of vacation rentals, from cozy homes to luxurious villas, with great amenities.

Popular types of accommodation around Cypresswood Golf and Country Club

Vrbo offers a variety of vacation rentals in Cypresswood Golf and Country Club, perfect for your getaway. Whether you prefer a private vacation home, a luxurious villa, or a comfortable condo, there's something for everyone. Enjoy access to top-notch amenities, including the Cypress Point Club, additional golf facilities, and a refreshing swimming pool. Plus, the nearby Winter Haven Golf Course ensures you'll have plenty of options to tee off during your stay.

  • Houses: This is the top choice among travelers seeking spacious and comfortable accommodations for families or groups at Cypresswood Golf and Country Club.
  • Villas: Often featuring luxurious amenities, villas provide an upscale experience for those looking to indulge during their stay.
  • Condos: These convenient options offer a blend of comfort and community, ideal for vacationers wanting access to shared facilities.
  • Apartments: A practical choice for visitors, apartments provide all the essentials for a home-like stay.
  • Cottages: Perfect for those seeking a quaint and cozy retreat, cottages offer charm and tranquility.**

Top attractions near Cypresswood Golf and Country Club

During your visit to Cypresswood Golf and Country Club in Winter Haven, Florida, you'll find a variety of attractions nearby, including scenic lakes, amusement parks, and urban parks. Enjoy outdoor activities and golfing at the Cypresswood Golf Club, or explore the beautiful landscapes and recreational opportunities in the area. Whether you're looking for a family outing or a relaxing day in nature, there's something for everyone to experience around Cypresswood.

  • LEGOLAND® Florida: This vibrant amusement park offers a world of adventure with themed rides, interactive attractions, and impressive LEGO structures. Perfect for families, it features water rides, roller coasters, and play areas inspired by popular LEGO sets, making it an exciting day out for all ages.
  • Bok Tower Gardens: A serene escape, this historic garden features stunning landscapes, beautiful flora, and the iconic Singing Tower. Experience the calming atmosphere, artful designs, and rich cultural heritage as you stroll through the lush gardens.
  • Peppa Pig Theme Park Florida: Tailored for younger visitors, this delightful theme park immerses families in the whimsical world of Peppa Pig. Enjoy rides, interactive play areas, and character meet-and-greets that promise endless fun and entertainment for the little ones.

Things to do recommended for couples

For a romantic getaway near Cypresswood Golf and Country Club, consider water sports at Chain Of Wakes, just 3 miles away, or feel the thrill of skydiving with Jump Florida, 5 miles away. For a luxurious experience, visit Ridgewood Lakes Golf and Country Club, 12 miles away.

Things to do recommended for families

Families visiting Cypresswood Golf and Country Club can explore Chain of Lakes Park for sports, enjoy family fun at Indigo's Billiards, Bowling & Games, or unwind at Sertoma Park, all offering unique experiences within a short drive.

Things to do recommended for groups

Explore the vibrant Northgate Shopping Center for shopping and entertainment, just a mile from Cypresswood Golf and Country Club. For golf enthusiasts, Winter Pines Golf Course offers outdoor sports experiences only 0.1 miles away, while Baytree Golf Club is a short 2-mile trip for more golfing fun.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Cypresswood Golf and Country Club

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your preferences when searching. Here are some helpful Vrbo booking tips for you.

  • Traveling to Cypresswood Golf and Country Club with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Cypresswood Golf and Country Club with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Cypresswood Golf and Country Club: For many families, a vacation isn't truly fulfilled without their furry companions. If you can relate, take a look at Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Cypresswood Golf and Country Club: If you're seeking vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Cypresswood Golf and Country Club

Exploring the area around Cypresswood Golf and Country Club in Winter Haven, Florida, offers a delightful mix of family-friendly activities and relaxing excursions. Experience some of the top public golf courses with nice fairways and good greens, perfect for both seasoned players and beginners. The welcoming neighborhoods provide a warm atmosphere, making it an ideal destination for families and budget-conscious travelers alike. Enjoy the charm of Winter Haven and its beautiful family homes during your stay.

  • Dundee: Located a mere 2 miles from Cypresswood Golf and Country Club, Dundee is a charming city known for its family-friendly atmosphere and outdoor adventures. Visitors can enjoy a variety of activities, including golfing and visiting nearby amusement parks and resorts. The town is situated close to local landmarks such as picturesque lakes and beautiful beaches, perfect for a day of fun in the sun or a relaxing afternoon by the water.
  • Lake Hamilton: Just 2 miles away from Cypresswood Golf and Country Club, Lake Hamilton is a quaint village that offers a delightful escape for families and outdoor enthusiasts. With its proximity to resorts, amusement parks, and golf courses, Lake Hamilton is ideal for those seeking adventure. Visitors can explore the nearby theme park, enjoy a day at the urban park, or take in the serene beauty of the local lakes, making it a perfect spot for a family outing.
  • Cypress Gardens: Situated 3 miles from Cypresswood Golf and Country Club, Cypress Gardens is a picturesque village that beckons families and adventure seekers alike. This area is known for its exciting amusement parks and golf venues. Nearby attractions include a stunning beach and a renowned film studio, offering a unique blend of recreational activities and entertainment. Whether you're relaxing by the beach or exploring the vibrant local attractions, Cypress Gardens promises a memorable getaway.

Best time to go to Cypresswood Golf and Country Club

If you're planning a trip to Cypresswood Golf and Country Club, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in February to March and July, while off-peak times, like September to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
February64.4°F (18.0°C)No Rain (Dry)Mostly SunnySlightly HighSlightly Low
March67.5°F (19.7°C)Light RainMostly SunnySlightly HighAverage
April72.9°F (22.7°C)Light RainMostly SunnyAverageSlightly High
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June80.6°F (27.0°C)Moderate RainMostly SunnyAverageAverage
July81.7°F (27.6°C)Moderate RainMostly SunnySlightly HighSlightly High
August81.9°F (27.7°C)Moderate RainMostly SunnyAverageAverage
September79.5°F (26.4°C)Moderate RainMostly SunnySlightly LowSlightly Low
October74.7°F (23.7°C)Light RainMostly SunnySlightly LowSlightly Low
November68.0°F (20.0°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December64.2°F (17.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can lead to significant savings, as prices tend to vary. Additionally, opting for an extended stay often results in even greater discounts. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash on the whole booking. Being the trip organizer truly has its perks. Sign up for our One Key rewards program to unlock exclusive member discounts and earn OneKeyCash on eligible stays. Join today and start reaping the benefits.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform for planning your travels. You can create new trips, resume planning from where you left off, or organize your existing plans all in one place. You’ll see your saved or booked properties neatly organized into categories: Potential, Upcoming, or Current Trips. To start exploring the Trip Boards, head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What are the best vacation rentals near Cypresswood Golf And Country Club?
The best vacation rentals near Cypresswood Golf And Country Club are typically found right in Winter Haven, Florida. You will find a great selection of private vacation homes and apartments available. These properties are often conveniently located, allowing easy access to the club. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties. You can find the best vacation rentals near Cypresswood Golf And Country Club that offer comfort and convenience.

Many of these properties feature desirable amenities such as private pools, which are great for relaxing after a day on the greens, and spacious patios or decks for outdoor enjoyment. These homes are ideal for golf enthusiasts, families, or groups looking for a relaxing stay.
Are there any cheap vacation rentals near Cypresswood Golf And Country Club?
There are several affordable vacation rentals near Cypresswood Golf And Country Club, especially if you are flexible with location and travel dates. Budget-friendly stays typically start around $100 per night. You might find great deals in October or February during the off-season. These properties often include amenities such as free WiFi, toiletries, and self-parking, which is great for those arriving by car. You can find cozy private vacation homes or efficient apartments, providing a comfortable base for your stay.

If you're willing to drive a bit further, renting around nearby areas can be an affordable option. This strategy allows guests to find properties that offer great value without sacrificing comfort. With a little planning, it is absolutely possible to find a comfortable stay near Cypresswood Golf And Country Club while keeping costs down.
What are the best pet-friendly vacation rentals near Cypresswood Golf And Country Club?
There are 16 pet-friendly vacation rentals near Cypresswood Golf And Country Club, primarily private vacation homes and some apartments, located in Winter Haven. These homes often feature amenities such as fully equipped kitchens, comfortable living areas, and sometimes even private outdoor spaces, ensuring a pleasant stay for both guests and their animal companions. Many properties specifically permit dogs and service animals, making them ideal for those traveling with pets.

When searching for the best pet-friendly vacation rentals near Cypresswood Golf And Country Club, remember to review individual property policies regarding pet size, breed restrictions, and any additional fees. Cypresswood Golf And Country Club itself is known to be pet-friendly, with designated areas where pets are welcome.
What are the top vacation rentals with pools near Cypresswood Golf And Country Club?
There are approximately 27 vacation rentals near Cypresswood Golf And Country Club that offer swimming pools. These properties primarily consist of private vacation homes, with a few apartments also available. Guests can find options with shared outdoor pools or private outdoor pools, many of which are heated for comfort. These homes are typically located within close proximity to the Country Club, making them convenient for guests. Standard amenities often include full kitchens, Wi-Fi, and areas for relaxation, making them suitable for families or groups seeking a comfortable stay.

When selecting your rental, consider whether a private pool for seclusion or a shared pool with potential access to additional community features better suits your needs. For stays during cooler months, properties with heated pools are a great option to ensure year-round enjoyment. Always check pool availability and heating status when making your reservation, especially for specific dates.
What are the best family vacation rentals near Cypresswood Golf And Country Club?
There are over 32 family-friendly vacation homes near Cypresswood Golf And Country Club, primarily private vacation homes and apartments, offering ample space and comfort for groups. These properties often boast multiple bedrooms and bathrooms, full kitchens for meal preparation, and washer/dryers for convenience. Many also feature outdoor play areas, yards, patios, and even pools, superb for family enjoyment. Guests can also find properties with entertainment options like games, video games, and books.

When selecting a vacation rental, consider properties that offer separate spaces for adults and children, such as multiple bedrooms or a sofa bed, ensuring everyone has room to relax. Look for practical amenities like a fully equipped kitchen to simplify meal times and laundry facilities to keep up with clothes.
Are there any luxury vacation rentals near Cypresswood Golf And Country Club?
Near Cypresswood Golf And Country Club, guests can find several luxury vacation rentals that combine the natural surroundings with sophisticated comfort. These properties often feature amenities such as private heated pools, private secured pools, fireplaces, and lake views. Many homes also boast gourmet kitchens and access to onsite golf and tennis.

These homes are ideal for families or larger groups seeking a refined stay. Many of these top-tier properties are managed by highly rated Vrbo hosts, ensuring a professional and premium experience.
How much is a vacation rental near Cypresswood Golf And Country Club?
Vacation rentals near Cypresswood Golf And Country Club offer a wide range of options suitable for different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties typically start around $100 per night, providing an affordable option such as simple apartments. Mid-range rentals, including private homes with standard amenities, are generally around $190 per night, offering more comfort and privacy. Upscale options can cost $310 or more per night, providing additional space, amenities like private pools, or premium locations.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.
Where should I stay when visiting Cypresswood Golf And Country Club?
When visiting Cypresswood Golf And Country Club, selecting the right vacation rental enhances your experience. The areas around Winter Haven offer excellent choices.

For those desiring close proximity to Cypresswood Golf And Country Club, properties in the immediate Winter Haven area provide convenient access to the greens and local amenities. Many homes here are designed for comfort and ease, superb for golf enthusiasts.

Alternatively, staying closer to downtown Winter Haven offers a different charm. Vacation rentals in this area provide easy access to local dining and attractions, while still being a short drive from Cypresswood Golf And Country Club. This allows guests to enjoy both recreational activities and the town's offerings.

For a quieter, more residential feel, properties on the outskirts of Winter Haven provide spacious homes and a relaxed setting. These rentals are well-suited for families or groups seeking a peaceful retreat after a day of golfing, with convenient routes to Cypresswood Golf And Country Club.
What is the cheapest month to stay near Cypresswood Golf And Country Club?
The cheapest time to find vacation rentals near Cypresswood Golf And Country Club is typically during the late Autumn (October) and late Winter (February). October and February are frequently the months where you can find the best deals on properties and homes. Guests can often find lower rates during these months, along with greater availability.
Are there any lakefront vacation rentals near Cypresswood Golf And Country Club
Lakefront vacation rentals are available near Cypresswood Golf And Country Club, predominantly found on the numerous lakes surrounding Winter Haven, such as Lake Eloise and Lake Winterset. These properties are a short drive from Cypresswood Golf And Country Club, offering convenient access to water activities like kayaking, fishing, motorboating, and relaxing by the shore. Many also provide direct access for swimming and other water sports.

These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy lake views and unwind in peaceful surroundings.
Are there any monthly vacation rentals near Cypresswood Golf And Country Club?
Vrbo offers excellent options for monthly vacation rentals near Cypresswood Golf And Country Club, making it a great choice for those who want to combine work and adventure. Monthly rentals often feel like a true home away from home, with fully furnished properties equipped with essential amenities like high-speed Wi-Fi, full kitchens, and comfortable workspaces, perfect for remote work or a summer vacation with the family. With flexible monthly rental options, Vrbo is a convenient and comfortable choice for extended stays near Cypresswood Golf And Country Club.
Are there any last-minute vacation rentals near Cypresswood Golf And Country Club?
Vrbo makes it simple to find last-minute vacation rentals near Cypresswood Golf And Country Club that blend comfort, style, and great value. Vrbo offers plenty of options for guests ready to pack up and go. Families and groups will find these deals especially appealing. Many spacious homes, complete with full kitchens, private pools, and multiple bedrooms, often become available when hosts want to fill open dates on their calendars.

Finding these stays is easy. Just enter your destination and travel dates, then use Vrbo's "Last Minute" or "Discounts" filter to uncover the best offers. You'll see reduced rates in the listings. Vrbo's last-minute rentals are a smart way to save while you explore. Whether you're planning a quick trip or a weekend getaway with friends, your last-minute escape is waiting, you just have to decide where to go next.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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