Palm trees

Things To Do in Orlando

Indulge, Relax, Play and more...

Whether you're looking to soak up the Orlando sun or for thrills at Orlando theme parks, we offer a variety of fun things for you and your entire family!

Check out our Events Calendar for daily updates. View our Summer Fun Guide

girls in the pool

Resort Activities*

Takes some time to hang at the Villas for non-stop fun. Whether you tee off on our premier golf course or cool off poolside, we have plenty for you to do.

  • 45 holes of Jack Nicklaus Signature-designed golf
  • Grand Cypress Academy of Golf featuring three regulation practice holes (Par 3,4 & 5)
  • Fitness Center 
  • Swimming Pool, pool bar, sauna and hot tub within walking distance of your room
  • Complimentary bicycle fleet and trails
  • Nature trails
  • Fishing poles & tackle
  • In-Room Spa Services

Even more fun just a shuttle ride away...

  • Grand Cypress Racquet Club
  • Marilyn Monroe Spa
  • Pitch 'n' Putt Golf
  • Rock Wall
  • Lake Windsong water sports
  • Game Room
  • Additional dining options

View Our Events Calendar        View Our Summer Fun Guide

Activities are subject to change without notice

Summer at Villas of Grand Cypress

Summer At The Villas

View Our Summer Fun Guide

We are committed to making your Summer at Villas of Grand Cypress an unforgettable experience. Enjoy a guided fishing tour, sing your heart out during Karaoke night, dive-in or drive-in at movie night, live like a local at the Farmers Market, and so much more. Learn more about the Summer activities we have planned for you.

Explore Summer At The Villas

Plenty of Family Fun

GUIDED FISHING TOUR | Ready to see what we have in our lakes? Join us for a 2 hours guided fishing tour. Our local fishing expert will take up to 6 people per tour to explore our beautiful and bountiful lakes amongst the greens and he’ll teach you all about what you’re reeling in.  $50 PER PERSON  


DIP. SIP. GRILL. | Sip and savor with us all day at Oasis Pool & Bar. Keep cool this Summer with a refreshing frozen tropical cocktail, beer, or drink of your choice. Pair with a delicious meal or snack or an ice cream. Food and drinks available at the bar daily. Ask us about Poolside Grillin’.  


KARAOKE THURSDAYS | Karaoke at the Villas is back! Pick out your song, loosen your vocals and get ready to belt out the hits every Thursday night! Either entertain the crowd solo or assemble the perfect boy or girl crew to become a star!  


DRIVE OR DIVE-IN MOVIE NIGHT – KIDS CHOICE | Take a dip in the pool while watching a movie with us, or enjoy it while sitting in a golf cart. Kids vote on the movie presentation. — DUSK ON SATURDAYS, JUNE 16–AUGUST 18 — For exact time, please dial x1926 from your hotel room or text 407.890.0238.


#LiveLikeALocal | Experience Orlando through local activites recommended by residents. 

  1. #LiveLikeALocal

Kidz Korner

Everyday is a packed with fun for the little ones

FUN’N STUFF POOLSIDE | We have plenty of poolside fun for the entire family this Summer. While Mom and Dad are enjoying cocktails, the kids will enjoy our fun activities. Starting at 2 pm every day, we’ll have arts & crafts, board games, table tennis, outdoor billiards, bingo and so much more. A pool table and Foosball is available for everyone to enjoy. 


SLIP N' SLIDE POOLSIDE | Summer is just not summer without an oversized waterslide. This is a fun bonus at our resort-style pool. While parents enjoy a cocktail at Oasis Pool & Bar, kids can stay cool on our waterslide. 


PASSPORT TO ADVENTURE | This complimentary passport encourages kids to experience all the fun activities at the Villas of Grand Cypress by earning stickers during their stay. It's a great way for kids to become better acquainted with the hotel during their stay. 


BICYCLE SCAVENGER HUNT | This adventure is apart of Passport to Adeventure. Accompanied by adults, children have to hunt throughout the resort while riding our complimentery bicycle to complete this activity. 

Labor Day Weekend

Enjoy family-fun festivities this Labor Day Weekend. Vibe to the sounds from a DJ and Steel Drum artist, enjoy dive-in or drive-in poolside movie night, savor our Backyard-Style BBQ and more. 

Book Online & Save 20%

Labor Day Weekend

Family-Fun Festivities (Activities May Vary Each Day)

  • Enjoy the sounds from a DJ and Steel Drum artist
  • Dive-In or drive-in poolside movie night 
  • Savor our Backyard-Style BBQ 
  • Stay cool on our slip ‘n slide poolside waterslide
  • Included in your resort fee, enjoy a game of complimentary Footgolf on our award-winning Jack Nicklaus Signature-designed golf course. Our 45 holes course is the #2 Best Florida Course on Golf Advisor.
  • Also included in the fee is access to our complimentary bicycle fleet for rides around the resort
  • Enjoy access to water sports at Lake Windsong, a rock climb wall, tennis court and much more

Events & Activities are subject to change without notice.

Labor Day Weekend

September 1-3, 2018

Book Online & Save 20%


Hold on to Summer just a bit longer into Fall with endless fun and activities. Join us Sunday nights when Football Fever starts in September, followed by our Oktoberfest celebration, a cooking demonstration hosted by our new chef and so much more.

Explore Fall At The Villas

Click here to view our calendar for more information on events and activities

OktoberFest September 22 - October 7

Enjoy our festive take on a German celebration with a special menu featuring German beer & food offerings at The Clubhouse Restaurant and Sports Bar.  

Family Fridays (October-December)

Savor family style dining during select Friday nights this Fall. Enjoy delectable Italian dishes for 4-6 people while overlooking the breathtaking view of the golf course. 

Fall Football Fever

Our Clubhouse Restaurant & Sports Bar is the perfect venue to catch all the action this Football Season with a range of food & drink offers for fans.

Thanksgiving Meals & Holiday Cocktails

Join us as we celebrate Thanksgiving with your traditional favorites, as well as our Chef inspired specialties. 

11am - 3pm    Thanksgiving brunch buffet at Nine 18 Restaurant

4pm - close    Special Thanksgiving menu

Events & Activities are subject to change without notice.

Enjoy An Endless Summer This Fall

The Fun Does Not End With Summer

Cool Drinks Poolside

Enjoy drink specials at our Oasis Pool & Bar.

Water Play

A short shuttle ride to 1,000 feet of white sandy beach at the 21-acre Lake Windsong with beach volleyball, tether ball, watersports with paddleboats, kayaks, hydro bikes, canoes, aqua cycles and sailboats.

Complimentary Bike Rides Around the Resort

Fall is the perfect time to grab one, two, or more bikes for you and the family! Ride from your villa to the pool, Clubhouse or simply around our beautiful and serene resort. 

Events & Activities are subject to change without notice.

Downtown Orlando at night

Discover Orlando

We can help you experience Orlando like a local.

Transportation is provided from the resort to many local activites, including a neighborhood Farmers Market and scenic nature trail. Learn how you can #LiveLikeALocal and ask our Concierge for help in creating an itinerary. 



Our Experience. Your Visit. 

Quirky, under-the-radar, unique city highlights recommended by locals. Try one (or all) of these activities. Perfect for every member of the family. 

We provide transportation to the following locations.

Winter Garden Farmers Market

Local Street Fair Saturdays 10am-2pm

Enjoy live music, food & drinks while you shop and explore locally grown produce, baked goods, fresh flowers and homemade items.

Tibet-Butler Preserve

Free Scenic Nature Center

Boardwalks & hiking trails around a 440-acre facility along Lake Tibet-Butler. Engage with nature and get an opportunity to indulge in this perfect haven.

Disney Springs

Outdoor Shopping, Dining & Entertainment Complex 

Discover an eclectic mix of unique shops, one-of-a-kind restaurants and lively entertainment for a day or night of absolute fun. 

Crossroads at Lake Buena Shopping Center

25 Shops & Restaurants

This plaza provides 25  shops and your favorite restaurants just across from the Disney World Buena Vista entrance. 

We'll Get You There

Need A Ride? Just hop aboard.

Transportation to most locations are complimentary. Dial X1926 for more information.

We provide transportation to the following local locations.


Disney Springs (Daily)

Depart resort: 4:10pm, 6:10pm, 8:10pm

Return pick ups: 6:30pm, 8:30pm, 10:00pm  

Winter Garden Farmers Market (Saturdays Only)

Depart resort: 10am

Return pick up: 2pm  

Tibet-Butler Preserve (Daily)

By reservation between 10am-2pm  

Crossroads at Lake Buena Vista Shopping Center (Daily)

Depart resort: 5pm, 7pm

Return pick up: 7:15pm, 9:00pm 

By reservation      

The Adventurist

When simply “seeing” a destination just won’t do.

FEATURE ADVENTURE: Scotland in Florida

It’s the closest thing you’re going to get to playing the famed Old Course at St. Andrews in Scotland – without having to leave American soil. Designed by Jack Nicklaus, the New Course at Villas of Grand Cypress was built to model the Scottish links masterpiece. While the entire course isn’t an exact copy of St. Andrews, it certainly has the feel with double greens, stone bridges and walls, gorse mounds, burns, and pot bunkers as deep as 12 feet. Holes number 1 and 18, however, are replicas – hole 18 is a dogleg right that replicates the legendary Road Hole, while hole 1 includes a drive across a stone bridge. 

Discovery Cove

SeaVenture Tour | Discovery Cove


After shimmying into wet suits and easing into a man-made coral reef consisting of 1.2 million gallons of saltwater, a dive helmet is lowered over you, feeding oxygen as you wander along the bottom of the reef floor. During the 20-minute experience, you’ll come eye-to-eye with sharks, pet velvety rays, and cut through schools of fish like Moses parting the Red Sea.

Airboat Cruise | Boggy Creek Airboat Rides


Four unique airboat adventures soar up to 45 miles per hour atop the swamp water around Lake Tohopekaliga in Kissimmee, then slow to sashay through canals and marshlands to take in views of exotic birds, turtles, and the Florida alligator wallowing in their natural environment. Daily 30-minute, 45-minute, and one-hour tours are available.


Orlando Watersports Complex

Wakeboarding | Orlando Watersports Complex


Whether you're learning to get up for the first time or trying to master advanced tricks, a one- to four-hour lesson at Orlando Watersports Complex is guaranteed to take your ability to the next level. Regardless of your skill, a wide range of different cables allows even the most seasoned riders a challenge.

Like a Local

Quirky, under-the-radar highlights only a local could recommend. 

Disney Springs

Disney Springs is an outdoor shopping, dining, and entertainment complex at the Walt Disney World Resort in Bay Lake, Florida, near Orlando. The complex offers a great mix of unique shops, one-of-a-kind restaurants, lively entertainment, and activities for the entire family, while couples enjoy quality-time and business travelers relish time away from work. 

Scenic Boat Tour

Winter Park, famous for being one of the most scenic small towns in America, is home to Scenic Boat Tour, a leisurely one-hour boat ride through the Winter Park Chain of Lakes. During the tour on the 18-passenger pontoon boat, you will enjoy spectacular local scenery, including views of extravagant waterfront mansions and Florida wildlife. 

Paddleboat at Lake Eola

Escape from Orlando’s busiest attractions with a fun paddleboat ride on Lake Eola. Better yet, head out on a Sunday to pair it with stroll through Lake Eola’s renowned Farmer’s Market, featuring much more than your average farmer’s market, including seasonal fresh produce, unique drinks, home-cooked barbeque, and much more.

Winter Garden Farmers’ Market

Voted the number one farmers’ market in the nation by the American Farmland Trust, this downtown gem occupying a massive four blocks every Saturday from 10 a.m. to 2 p.m. is known for its variety of vendors. We’re talking everything from Indian chutneys at Nisha’s Flavors of India, smoked fish dips from Captain Jo’s, herbs and spices from Cacao n’ Spices, and the best pickles you’ve ever had from Mr. and Mrs. Pickles. With transportation to and from the market provided by the Villas of Grand Cypress ($10 per person), there’s no excuse not to visit.

Tibet-Butler Nature Preserve 

Located on the shore of Lake Butler, this 440-acre wildlife haven within earshot of Disney World is a bit of real Florida wilderness among the dense urban sprawl. A dream for nature lovers, photographers, and hikers, a trail system loops through a variety of habitats, including pine forests, swamps, and a cypress-lined shoreline, offering peeks at local flora and fauna like barred owls, ospreys, lizards, tortoises, and more. Complimentary transportation is offered by the resort with reservations.  

The Weekender

How to spend 36 hours in Orlando, with Villas of Grand Cypress as your base camp. 


5 p.m. | Bike & Dine around Villas of Grand Cypress
Get your bearings of this 1,500-acre golf resort by borrowing a bike from the pool and taking it for a spin around the grounds (there are designated bike trails). Finish with dinner at The Club. Cap off the night relaxing by the pool that is central to the villas.  


10 a.m. | In-Room Breakfast
Villas of Grand Cypress takes room service to a whole new level. Instead of simply ordering from the on-site restaurants and having your meals delivered, the resort also offers the option of sending a chef to cook right in front of you, in the comfort of your room's fully equipped kitchen. Choose from an array of breakfast options, including fresh waffles, lemon brioche French toast, omelets, and more.

12:30 p.m. | Check out the Winter Garden Farmers Market
Browse the nation's premier farmers’ market, located in downtown Winter Garden and offering everything from local crafts to baked goods to artisan food items. Of course, it wouldn’t be a farmers’ market without produce, of which you’ll find scores of golden beets, rainbow carrots, massive mangoes, and sweet bell peppers under the city pavilion.

2 p.m. | Lunch at The Whole Enchilada 
Located within easy walking distance of the farmers’ market on Plant Street, this Tex-Mex restaurant offers a rooftop patio and bar for open-air eats. The menu features nachos, salads, tacos, burritos, and, as the name implies, enchilada platters, plus a variety of margaritas.

7 p.m. | A Show in the Church Street District
Head to Orlando’s historic downtown, home to the city’s top entertainment venues, fine dining, and nightlife, for a 7:30 show at Mad Cow Theatre. Photos from more than 100 productions – a mix of classics, contemporary plays, and musicals – from 15 seasons grace a colorful wall in the lobby. While a small theater, that just means you’re that much closer to the stage.

9:30 p.m. | Late Dinner at Kres Chophouse
The kitchen of this steakhouse, located across the street from Mad Cow, doesn’t close until 12 a.m., so if you haven’t had dinner or just want a quick drink after the show, this is the place. Housed in a historic 1930s building, the steak house bills itself as“modern while still honoring the classics,” with prime beef aged in-house, hand cut to order, and ultra-fresh Florida fish delivered daily. 


10 a.m. | Lounge Out at the Villa Pool
The beauty of the Villas at Grand Cypress is that you’re right on the edge of Disney World, yet you couldn’t feel further away. Relish the serenity at this pool, reminiscent of a natural lagoon that weaves through tropical vegetation and rocks. Drinks are brought to your lounge chair under the shade of palm trees.

1 p.m. | Stroll the Tibet-Butler Nature Preserve 
The 2.6-mile Tibet-Butler Nature Trail at this 440-acre wildlife haven loops through a variety of habitats, including pine forests, swamps, and a cypress-lined shoreline, offering peeks at local flora and fauna like barred owls, ospreys, lizards, tortoises, and more. Complimentary transportation is offered by the resort with reservations.  


Flavor of…

The best food artisans, farms, and local markets.

Courtesy of Crooked Can Brewing Company

Crooked Can Brewing Company

It’s not easy to find good craft beer at $4 to $5 a pop, but Winter Garden’s new microbrewery has done it with 16 taps serving beers only brewed in-house, ranging from stouts to IPAs to amber ales. The best part? Crooked Can is located inside the Plant Street Market, a cluster of artisan shops, so you can actually walk around and peruse the other stores with a beer in hand. 

Courtesy of Erin McKenna's Bakery NYC

Erin McKenna's Bakery NYC

Indulgent edibles are around every corner in Disney. However, this bakery, which opened in 2015 in the Disney Springs shopping district on the edge of the park parameters, filled a hole in the dessert roster: It only serves vegan and gluten-free items, including some of the best cookies, cupcakes, focaccia, and cinnamon rolls that even non-gluten-free patrons have said they’ve ever had. Have a craving? The resort offers free transportation to the district. 

Courtesy of Quantum Leap Winery

Quantum Leap Winery

Central Florida’s first urban winery has a two-fold mission: to make good wine from grapes from around the world, but to do so in an environmentally friendly way. All raw, unrefined wines are imported not in bottles but large plastic vessels to their Ivanhoe Village location, where – after aging, blending, and finishing – they’re packaged in kegs, pouches, or boxes – all low-carbon-footprint vessels. 


Based in a historic building in downtown Winter Garden, Scoops is the old-fashioned ice cream shop of your childhood dreams with classic wooden counters and stools and checker-topped tables for a game of chess. Flavors range from key lime to cappuccino to salted caramel and include sorbets, sundaes, and milkshakes, but what the spot is really known for is its generous portions; one scoop is technically the size of three at only $2.50 to boot.


If looking to take advantage of your room’s fully equipped kitchen, this is your market to stock up at (the resort even offers complimentary shuttle service to and from). Located in the Crossroads shopping center, the hometown grocery rolls a full-service pharmacy, bakery, deli, seafood supplier, and general market shopping experience all into one. Check out their sushi – it's made fresh throughout the day by the on-site sushi chef.