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Top 24 Hotels Near Cypresswood Golf & Country Club
1099 Clubhouse Rd Winter Haven, FL 33884
Courtyard by Marriott Winter Haven
The journey from Courtyard by Marriott Winter Haven to Cypresswood Golf & Country Club is a simple drive, a perk that contributes to a cohesive and convenient visit.
Upon entry, Courtyard guests encounter floral displays, bright finishes, and polished counters, cues that provide clarity and comfort. Each guest room includes smart TVs, ergonomic chairs, and Wi-Fi, ensuring productivity and entertainment remain seamless. The 24/7 Market offering drinks, packaged meals, and snacks ensures travelers maintain convenient access to essentials at any hour.
Amenities include The Bistro, complimentary Wi-Fi, indoor pools, and meeting spaces, combining convenience with daily consistency.
Home2 Suites by Hilton Winter Haven
The guest's journey from Home2 Suites by Hilton Winter Haven in Winter Haven to Cypresswood Golf & Country Club is a simple drive, enhancing the sense of being in a convenient location.
Guests visiting Home2 Suites find community tables in lobbies, providing convenient gathering points that encourage casual interaction. Each guest room highlights plush bedding, adjustable thermostats, and blackout curtains, ensuring quality sleep every evening. In the pool area, towels, loungers, and calm lighting provide families a consistent place for leisure and downtime during trips.
Amenities such as outdoor grills, laundry rooms, self-parking, and Wi-Fi support family routines while keeping travel flexible.
Best Western Plus Winter Haven Inn & Suites
When your visit to Winter Haven is anchored by Cypresswood Golf & Country Club, Best Western Plus Winter Haven Inn & Suites's location a short drive away allows for a seamless daily plan.
Best Western arranges sofa clusters, standing ledges, and café tables near outlets, creating quick huddle points while plans and messages settle. Each guest room may include blackout shades plus sheers, allowing flexible light control for late sleepers and early risers alike. Outdoor pools where available add shade and deck seating, letting families regroup without committing to long off-property breaks.
With Wi-Fi, business centers, meeting rooms, and EV charging where offered, teams coordinate work and travel while momentum stays intact.
Rodeway Inn & Suites Winter Haven Chain of Lakes
This convenient drive to Cypresswood Golf & Country Club from Rodeway Inn & Suites Winter Haven Chain of Lakes is a defining element, as it ensures the stay is built on simplicity.
Design details at Rodeway Inn are minimal but intentional, with basic flooring, standard lighting, and Choice branding visible at entry. All guest rooms come stocked with tissue boxes, wastebaskets, and mirror lighting to support hygiene and personal care needs each day. Reception areas with accessible furniture and uncluttered paths aid guests with mobility concerns without calling special attention.
Amenities include public vending, mini‑fridges, Wi‑Fi, on‑site laundry, coffee stations, and climate-controlled in-room comfort.
Economy Suites
From Economy Suites, the short drive to Cypresswood Golf & Country Club is a core benefit without a long commute before the day begins.
Economy Suites often provides practical check-in, available parking, and a simple lobby designed for straightforward guest arrivals. Each guest room may highlight tasteful interiors, hardwood finishes, and rainfall showers, supporting a polished yet modest stay. Facilities often highlight vending machines, modest lobbies, and laundry areas that emphasize simple and reliable daily guest routines.
Accommodations often feature Wi-Fi, breakfast counters, laundry facilities, and parking, reinforcing clear routines during visits.
Lake Roy Beach Inn
The brief drive from Lake Roy Beach Inn to Cypresswood Golf & Country Club in Winter Haven makes the connection between the two uncomplicated and fast.
At Lake Roy Beach Inn, arrivals may feature an efficient reception, complimentary parking, and basic lobby seating for quick convenience. Guest rooms often feature climate control, ergonomic seating, and Wi-Fi, helping ensure both comfort and productivity during visits. Public areas typically include breakfast counters, vending access, and compact seating that create practical support during visits.
A visit may present Wi-Fi, modest breakfast, vending machines, and guest laundry, giving travelers consistency throughout their stays.
Holiday Inn Express Lake Wales N-Winter Haven by IHG
This practical drive to Cypresswood Golf & Country Club from Holiday Inn Express Lake Wales N-Winter Haven by IHG is a key component, as it ensures a visit free of traffic concerns.
Concierge-style reception at Holiday Inn Express ensures orientation clarity, offering travelers confidence in their arrival process. All guest rooms offer flat-screen TVs, ergonomic chairs, and outlets, creating setups that balance comfort with everyday utility. Business centers with computer terminals, printers, and Wi-Fi access support productivity for travelers needing quick task completion.
Free Wi-Fi, complimentary breakfast, and fitness centers combine with indoor pools and business spaces, giving guests balanced routines.
Hampton Inn & Suites Lake Wales
Because Hampton Inn & Suites Lake Wales keeps Cypresswood Golf & Country Club a direct run, guests can opt on the travel method that best suits their needs.
Grab-and-go counters within Hampton Inn lobbies supply snacks and drinks, offering immediate convenience that reduces arrival stress. Guest rooms provide smart HDTVs, streaming services, and sofa seating, giving travelers dependable entertainment for evening downtime. Business centers with computer terminals, internet, and printers allow travelers to complete work efficiently during their visits.
Valet parking, complimentary breakfast, fitness studios, Wi-Fi, and Pavilion Pantry counters simplify routines with reliable convenience.
OYO Hotel Dundee by Crystal Lake
The direct drive from OYO Hotel Dundee by Crystal Lake to Cypresswood Golf & Country Club in Winter Haven ensures guests a simple and reliable way to get to their destination.
OYO's promise of a standardized experience begins in the lobby, which provides a clean, safe, and reliable first impression for guests. A commitment to cleanliness is evident in each room, with staff ensuring that all surfaces are sanitized for guest safety and peace of mind. Clean, uncluttered corridors are a brand standard, reflecting the overall commitment to providing a hygienic and orderly environment.
The hotel's practical offerings, from free parking and Wi-Fi to a clean bathroom and a television, cater to the needs of modern travelers.
Holiday Inn Winter Haven by IHG
For a visit that balances a key destination with broader travel, Holiday Inn Winter Haven by IHG keeps Cypresswood Golf & Country Club within easy reach.
Complimentary coffee points at Holiday Inn & Suites act as small courtesy touches, signaling attention to guest comfort on arrival. All guest rooms supply sofa seating, flat-screen TVs, and USB ports, allowing travelers to relax and stay connected with ease. Lobby lounges furnished with communal tables, natural light, and lounge chairs act as orientation points for arrivals and regrouping.
Meeting spaces, breakfast buffets, and Wi-Fi pair with fitness facilities and laundry, offering professional and leisure balance.
Hampton Inn Winter Haven
For guests in Winter Haven, Hampton Inn Winter Haven keeps Cypresswood Golf & Country Club an easy drive, a position that supports a variety of travel plans.
Hampton Inn breakfasts with reliable hot selections ensure mornings begin with consistent clarity, providing guests dependable routines. Each suite offers storage closets, luggage benches, and drawer units, providing guests practical solutions to stay organized on the road. Breakfast areas with omelet stations, fruit, and pastries provide consistency, giving mornings dependable rhythm and clarity for all guests.
On-site markets, complimentary internet, indoor pools, breakfast bags, and laundry services ensure ease that keeps daily travel smooth.
Howard Johnson by Wyndham Winter Haven FL
Guests at Howard Johnson by Wyndham Winter Haven FL can leverage Cypresswood Golf & Country Club being within easy reach, a perk that adds a relaxing touch to the stay.
At many sites, a 24/7 coffee station near reception at Howard Johnson supports early departures and late check-ins alike for tired travelers. Every guest room adds ironing gear, a hair dryer, and bath products, so routines stay familiar without extra errand runs after check-in. Hot tubs beside pool decks let small groups soak and chat, turning late afternoons into gentle downtime that resets energy for dinner.
With breakfast, Wi-Fi, and a fitness room, plus a market for forgotten items, travelers maintain balance without extra cross-town stops.
Staybridge Suites Winter Haven Auburndale by IHG
This uncomplicated drive to Cypresswood Golf & Country Club helps Staybridge Suites Winter Haven Auburndale by IHG guests get grounded in the local Winter Haven environment without a long journey.
With automatic doors and level thresholds, Staybridge Suites keeps carts and strollers moving smoothly through the vestibule at peaks. Each guest room provides an iron, ironing board, and hair dryer so outfits refresh quickly and mornings stay unhurried and neat. Pantry markets stock meal kits, snacks, and travel items for purchase 24/7, reducing off-site trips, with nearby microwaves.
EV charging at participating sites, parking, and lighting align with Wi-Fi and a lobby market, supporting efficient returns after errands.
Rodeway Inn Lake Wales - Winter Haven
As a convenient base, Rodeway Inn Lake Wales - Winter Haven is a central feature that elevates the convenience of the stay.
Rodeway Inn lobby zones are designed for efficiency, with minimal clutter and clearly labeled paths to guest rooms or elevators. Suites sometimes provide wet bars, second TVs, or extended seating, offering modest upgrades that suit longer or more social visits. Market coolers stocked with bottled water, frozen meals, or juices allow low-effort replenishment between major meals.
Features include coin laundry, air-conditioned rooms, flat‑screen TVs, vending access, free Wi‑Fi, and public coffee in shared zones.
Rodeway Inn & Suites Haines City - Winter Haven
From Rodeway Inn & Suites Haines City - Winter Haven, Cypresswood Golf & Country Club is an easy regional drive, a choice that makes for a well-planned trip.
Front desk agents at Rodeway Inn properties often provide printed Wi-Fi instructions during check-in, streamlining connectivity setup. Every guest room includes laminated surfaces, neutral tones, and light wall décor, creating a simple, distraction-free environment. Lobby TVs on news or sports channels create casual energy in shared spaces without overwhelming guest interactions or workflow.
Daily housekeeping, breakfast, TV access, snack vending, Wi‑Fi, and climate control ensure consistency across most property types.
Prince of Wales Motel
From Prince of Wales Motel, the easy regional drive to Cypresswood Golf & Country Club makes it a sensible hub for smart planning for your visit.
Prince of Wales Motel typically includes vending areas, modest desk service, and exterior parking that reinforce functional guest arrivals daily. Accommodations may present modest bathrooms, climate control, and Wi-Fi, helping sustain straightforward consistency for travelers. Shared spaces may highlight modest lobbies, vending areas, and compact breakfast counters that sustain practical routines each day.
Guests may encounter Wi-Fi, vending access, exterior parking, and pet-friendly policies, reinforcing consistency across budget motels.
Budget Inn
When the primary destination in the Winter Haven area is Cypresswood Golf & Country Club, Budget Inn's position as a convenient base allows the focus to remain on the visit.
Guests at Budget Inn may encounter a no-frills front desk, self-serve coffee, and parking options that support daily travel needs. Guest rooms may include curated décor, hardwood floors, and premium bedding that create a comfortable and stylish overnight experience. Shared spaces may present vending corners, modest lobbies, and laundry rooms that reinforce straightforward consistency for travelers.
Guests may encounter Wi-Fi, continental breakfast, laundry access, and vending areas, ensuring straightforward balance during travel.
Best Western Auburndale Inn & Suites
The journey from Best Western Auburndale Inn & Suites to Cypresswood Golf & Country Club is an easy regional drive, a benefit that contributes to an effortless visit.
Where airport or local shuttles run, Best Western marks pickup points near the doors, converting transfers into simple movement after check-in. Every guest room typically features a shower/tub combo, reliable water pressure, and refillable toiletries, making quick refreshes simple. Fitness rooms feature mirrors, mats, and space for stretches, supporting quick warm-ups or end-of-day resets that keep balance consistent.
With free Wi-Fi, hot breakfast, fitness access, and guest laundry, travelers keep connection, energy, and upkeep aligned through changing plans.
OYO Budget Inn Bartow
Upon leaving OYO Budget Inn Bartow, Cypresswood Golf & Country Club is a simple commute to avoid traffic, simplifying your visit.
Travelers using the OYO app can expect a tech-friendly arrival, with digital booking confirmation simplifying the check-in process. The functional design of the rooms provides a simple, uncluttered space for travelers to relax and organize their belongings with ease. The front desk serves as a central hub for guest services, with staff available at all times to ensure a smooth and hassle-free experience.
Every stay is enhanced by free Wi-Fi, a television, a private bathroom, and the constant availability of front desk staff for assistance.
OYO Superior Budget Inn Bartow
For guests in the Winter Haven region, OYO Superior Budget Inn Bartow is a sensible base, a location that makes for a hassle-free start to the day.
The minimalist design of an OYO lobby reinforces the brand's commitment to providing essential comforts and affordability for travelers. All guest rooms offer a comfortable bed and quality pillows, reflecting the brand's core focus on delivering a good night's sleep. Lobby spaces are designed for efficiency and cleanliness, providing a straightforward, no-frills common area that prioritizes value.
By ensuring every room has AC, a TV, and fresh linens, along with 24/7 reception, the hotel provides a standardized quality experience.
Holiday Inn Express Bartow by IHG
The hotel's sensible regional placement ensures Cypresswood Golf & Country Club is a simple commute, underscoring its suitability as a hub.
Holiday Inn Express coffee and tea service signals care and consistency, giving travelers refreshing touches immediately upon entry. Guest rooms are arranged with branded bath amenities, showers, and towels, refreshing travelers and sustaining daily routines. Meeting rooms with flexible layouts, breakout tables, and AV equipment allow professional groups to collaborate effectively on site.
Pet-friendly rooms, reliable Wi-Fi, and hot breakfast pair with self-parking and laundry, simplifying family and extended-stay needs.
Stay Inn and Suites
Cypresswood Golf & Country Club is a simple commute from Stay Inn and Suites, a setup that ensures the pre-event journey is always a calm one.
Stay Inn and Suites typically offers easy check-in, on-site parking, and a modest lobby space focused on practicality and efficiency. Accommodations often feature compact seating areas, work surfaces, and Wi-Fi, providing convenience for both rest and daily routines. Facilities often provide vending access, compact breakfast areas, and laundry spaces that maintain clarity and reliability for guests.
A stay often provides Wi-Fi, guest laundry, compact breakfast corners, and parking, supporting reliable routines in budget hospitality.
Omni Orlando Resort at ChampionsGate
This convenient location permits Omni Orlando Resort at ChampionsGate to serve as a calm starting point before the easy regional drive to Cypresswood Golf & Country Club.
At family-forward resorts, Omni highlights Omni Kids Crew at arrival, setting expectations for kid amenities that ease the first evening. Every suite organizes HDMI-friendly TVs, bedside outlets, and fast Wi-Fi, keeping presentations and media handy for trip purposes. Rooftop pools at select properties join cabanas, skyline views, and bar service, turning downtime into relaxed recovery above the city.
Between EV charging at select garages, valet, Wi-Fi, and meeting suites, mobility, connection, and coordination stay tightly integrated.
Alhambra Villas
Because Alhambra Villas is a practical base, guests can appreciate a moment of fresh air before their drive to Cypresswood Golf & Country Club.
At Alhambra Villas, arrivals may highlight personalized greetings, unique décor, and complimentary lobby tea or coffee service. Accommodations often provide eclectic décor, curated minibars, and unique design details that emphasize boutique hospitality. Facilities often highlight co-working areas, artisanal coffee shops, and cozy lounges that reflect boutique creativity and comfort.
Guests may enjoy Wi-Fi, yoga mats, laundry facilities, and self-serve markets, maintaining practical balance during boutique stays.
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Cypresswood Golf & Country Club Local Area Guide
Welcome to Cypresswood Golf & Country Club, a premier destination for golf enthusiasts and event attendees in Winter Haven, Florida. This guide is designed for players, families, and groups looking to plan their visit, understand the local surroundings, and make the most of their time here. Discover essential information about navigating the course, nearby amenities, dining options, and local attractions to ensure a smooth and enjoyable experience at Cypresswood.
Area contextNeighborhood Overview – Cypresswood Golf & Country Club (Winter Haven, FL)
Cypresswood Golf & Country Club is situated in Winter Haven, Florida, a city known for its chain of over 50 lakes and its role in the state's citrus industry, located about midway between Tampa and Orlando. Access to the club is primarily via Clubhouse Road, which connects to the main thoroughfares like Cypress Gardens Boulevard (State Road 540) and further afield to U.S. Highway 17 and State Road 542. These routes provide relatively straightforward access to larger cities and their respective airports. For those driving, parking is ample and typically located directly at the clubhouse and surrounding the course. Public transportation options are limited in this area, making a personal vehicle or rideshare service the most practical ways to reach Cypresswood. Plan to arrive at least 20-30 minutes before your tee time or event to allow ample time for check-in, finding parking, and navigating to the correct starting point, especially during peak golf seasons or organized tournaments.
Lodging contextWhere to Stay Near Cypresswood Golf & Country Club
The immediate vicinity of Cypresswood Golf & Country Club offers a mix of residential areas and other recreational facilities, but the core hotel accommodations are generally found a short drive away in the main Winter Haven area or along the corridors connecting to Lakeland and Haines City. Many visitors opt to stay closer to the city's downtown or the main commercial arteries where hotel clusters are more concentrated. Demand for lodging can spike around significant golf tournaments or community events hosted at the club, making early booking a strategic advantage. When searching for accommodations, utilizing map filters to view hotels within a 5-10 mile radius will yield the most convenient options. Consider hotels that offer amenities catering to golfers, such as extended check-out times or proximity to dining and shopping, to enhance your stay near Cypresswood.
View nearby hotels Quick Plan EssentialsQuick-Plan Overview
- Orlando International Airport (MCO) is about 50 miles away, a 1-hour drive.
- Arrive 30 minutes early for check-in and to familiarize yourself with the clubhouse area.
- Explore Lake Wales downtown for local shops and casual dining options nearby.
- Visit the Bok Tower Gardens for a serene, indoor-outdoor experience if weather is unpredictable.
- The clubhouse patio or a nearby lakeside restaurant are excellent spots to regroup after play.
Game Day Flow
Check-In & Warm-Up
As you approach Cypresswood, locate the main clubhouse for your initial check-in, whether for a tee time or an event. Allow ample time to handle registration, confirm your starting hole, and pick up any necessary scorecards or event materials. The practice facilities, including the driving range and putting green, are accessible from the clubhouse area; familiarize yourself with their locations to get in a proper warm-up. This pre-round window is crucial for settling in, gathering your gear, and mentally preparing for the course or your event activities. Ensure you know the exact time your round or event is scheduled to begin to avoid any last-minute rushes.
Mid-Day Regroup
During your time at Cypresswood, the clubhouse offers a central hub for players and guests. If you have a break between rounds or need a place to gather before an afternoon event, the clubhouse facilities are available. Consider utilizing the lounge areas or the outdoor patio for a relaxed regrouping session. For those playing a full 18 holes, the turn between the front and back nine often presents an opportunity for a quick snack or beverage, though dedicated lunch services are typically best utilized before or after your primary activity. Stay hydrated throughout your game, especially during Florida’s warmer months, by utilizing water coolers on the course or visiting the clubhouse.
Wrap-Up & Departure
Upon completing your round or event, return to the clubhouse to settle any outstanding balances, review scores, or enjoy post-game refreshments. Many golfers opt to have a casual meal or drinks at the Cypresswood Grille to discuss their performance and unwind. If you have a longer drive ahead, this is also a good time to gather your belongings and prepare for departure. Be mindful of traffic patterns, particularly if there are other large groups departing simultaneously, and allow extra time for exiting the club grounds. A final check of the clubhouse facilities ensures you haven't left any personal items behind before heading out.
Things to Do Near Cypresswood Golf & Country Club
Walkable
Cypresswood Golf & Country Club
This premier golf club features an 18-hole championship course designed to challenge golfers of all skill levels. Beyond the fairways and greens, the club offers practice facilities, a pro shop, and a welcoming clubhouse with dining options. It serves as a central point for both daily play and larger tournaments and events, providing a scenic and well-maintained environment for a full day of golfing activities. The course layout itself offers a natural setting, winding through mature trees and strategically placed water hazards, promising a memorable golfing experience.
1099 Clubhouse Rd · On siteCypresswood Grille
Located within the Cypresswood Golf & Country Club, the Grille offers a convenient dining experience for golfers and visitors. Serving breakfast, lunch, and sometimes dinner, it provides a relaxed atmosphere to enjoy a meal before or after a round, or while attending an event. The menu typically features classic American fare, with options ranging from light snacks and sandwiches to more substantial entrees. Enjoying a meal here allows you to soak in the golf course views and the camaraderie of fellow enthusiasts, making it an integral part of the club experience.
1099 Clubhouse Rd · On site5–15 Minutes Away
Lake Evamarie Park
A local neighborhood park offering a peaceful escape with its scenic lake views. Lake Evamarie Park features walking paths, picnic areas, and open green spaces, making it a pleasant spot for a leisurely stroll or a family outing. It's an ideal location for a short break from golf, offering a glimpse into the natural beauty of the Winter Haven area. Visitors can enjoy the tranquility of the water and the surrounding Florida landscape, providing a relaxed setting for recreation or simply to enjoy the outdoors.
1500 Lake Evamarie Rd · 1.5 miWinter Haven Public Library
A community hub offering a quiet environment for reading, research, or accessing public computers. The library provides a good indoor option for a short visit, especially if seeking a break from outdoor activities or needing a moment of calm. It's a place where visitors can find local information, relax with a book, or utilize free Wi-Fi. While not a typical tourist attraction, it serves as a functional and accessible community resource for those looking for a quiet indoor space.
300 Ave A NW · 3.3 miBeyond the Event: Venture slightly further into Winter Haven to explore its abundant chain of lakes, offering opportunities for watersports or scenic drives. The city also hosts various community events throughout the year, from local festivals to farmers' markets, that can add a unique flavor to your visit. For a longer excursion, the theme parks of Orlando and the vibrant culture of Tampa are accessible within an hour's drive, providing a wealth of entertainment options beyond the immediate vicinity of Cypresswood.
Dining & nightlifeFood & Drink Near Cypresswood Golf & Country Club
Inside & Adjacent
Cypresswood Grille
This on-site restaurant at Cypresswood Golf & Country Club provides a convenient and relaxed dining option for golfers and visitors. Open for breakfast, lunch, and often early dinner, the Grille serves a menu of American classics designed to satisfy post-game appetites or provide a casual meal between activities. With views of the golf course, it’s an ideal spot for a laid-back lunch or a refreshing drink. Expect a comfortable atmosphere that complements the golf club setting, perfect for unwinding after a round.
1099 Clubhouse Rd · On siteClubhouse Bistro (Potential/Seasonal)
While not always a permanent fixture, some golf clubs have seasonal or secondary bistro services available at their clubhouses. This option, if active, would offer lighter fare or grab-and-go items suitable for a quick bite between holes or before a tournament. It’s worth checking with the club directly upon arrival to see if any additional casual dining outlets are operating. These spots often focus on speed and convenience, serving sandwiches, salads, and snacks.
Approx. 1 mile · VariesNearby Gathering Spots
Salty's Tropical Bar & Grill
A popular local spot offering a casual atmosphere with a focus on seafood and American pub fare. Salty's is known for its relaxed vibe, making it a good place for groups to gather after a day on the course. They often feature a diverse menu that includes burgers, sandwiches, fresh catches, and appetizers, alongside a selection of beverages. It’s a go-to for many in the Winter Haven area looking for a friendly, unpretentious dining experience with consistent quality.
3310 Cypress Gardens Blvd · 2.1 mi99th Flavors
This restaurant offers a diverse culinary experience, often highlighting international flavors with American influences, catering to a range of palates. It provides a comfortable setting for groups looking for a sit-down meal with varied menu options, from savory entrees to lighter bites. 99th Flavors is known for its welcoming service and a menu that aims to please many, making it a reliable choice for team dinners or family outings looking for a bit more variety.
5647 Cypress Gardens Blvd · 2.7 miLocal & Elevated Picks
Champs Sports Bar & Grill
Champs offers a lively sports bar atmosphere coupled with a solid menu of American favorites, including wings, burgers, and sandwiches. It's a great spot for watching games or gathering with friends in a boisterous setting. The plentiful seating and extensive drink menu make it suitable for larger groups looking for a casual and entertaining dining experience. Expect a casual environment with friendly service and a menu designed for crowd-pleasing.
2427 Havendale Blvd NW · 4.5 miThaimee
A well-regarded establishment offering authentic Thai cuisine in a pleasant dining environment. Thaimee provides an excellent option for those seeking flavorful curries, noodle dishes, and other traditional Thai specialties. The restaurant is known for its carefully prepared dishes and often offers a more refined dining experience compared to casual sports bars or grills. It's a good choice for groups looking for a flavorful and slightly more upscale meal in the heart of Winter Haven.
125 E Central Ave, Winter Haven · 3.9 miLocal Tips & Year-Round Info
- Florida’s afternoon thunderstorms are common in summer; always check the forecast before teeing off.
- Hydration is key; carry water bottles as course water stations may be spaced out.
- Book tee times well in advance, especially for weekends or during peak winter season.
- Local traffic can be unpredictable around major event dates or during holiday periods.
- Embrace the slower pace of life in Winter Haven; factor in extra travel time for relaxed drives.
Weather & Seasons at Cypresswood Golf & Country Club
- Winter: Winter offers mild and comfortable days, typically ranging from the high 60s to low 70s Fahrenheit, with cooler evenings. This season is ideal for golf, with sunny skies being common. Visitors should pack layers, including a light jacket for mornings and evenings, but daytime play usually requires just golf attire. Rain is infrequent but possible; check forecasts before heading out.
- Spring & early summer: As spring progresses into early summer, temperatures begin to climb, with daytime highs commonly reaching the low to mid-80s Fahrenheit. Humidity starts to increase, and the possibility of daily afternoon thunderstorms becomes more frequent. Lightweight, breathable clothing is recommended for comfort on the course. Be prepared for quick, heavy rain showers that usually pass quickly.
- Mid-summer: Mid-summer in Winter Haven is characterized by high heat and humidity, with daytime temperatures frequently in the high 80s to low 90s Fahrenheit, often feeling hotter due to the humidity. Morning tee times are strongly advised to avoid the most intense heat and potential storms. Lightweight, moisture-wicking fabrics are essential. Always have rain gear handy for sudden downpours.
- Fall season: Fall brings a welcome respite from the summer heat, with temperatures gradually cooling to pleasant levels, averaging in the 70s Fahrenheit. Humidity decreases, making for very comfortable playing conditions. The skies are often clear, and the transition offers a great period for outdoor activities without the intensity of summer. Light layers are still a good idea for cooler mornings and evenings.
- Rain & snow: Snow is virtually non-existent in this region of Florida. Rainfall is most common during the summer months as afternoon thunderstorms, which can cause temporary course closures or delays. Spring and fall see less frequent but still possible rain showers. Winter is the driest season. Always have a waterproof jacket or poncho available, especially from May through September, and be aware of lightning protocols on the course.
Venue Facts & Trip Essentials
Venue facts
- Primary team: N/A (Golf Club)
- Neighborhood: Lake Chain Area
- Nearest airport: Orlando International (MCO)
- Parking: Clubhouse lot, ample space
- Walkable district: Limited to course & clubhouse
Trip essentials
- Groceries & supplies: Publix (nearby on Cypress Gardens Blvd)
- Pharmacy: CVS/Walgreens (multiple locations within 4 miles)
- Urgent care: Winter Haven Urgent Care (approx. 4 miles)
- Downtime: Lakeside parks, Winter Haven shopping centers
- Pro tip: Factor in Florida’s heat and humidity; hydrate and play early or late.

