Pickleball Court Membership

Looking for an exciting new way to play on your Hilton Head vacation? Your stay with Vacation Homes of Hilton Head (VHHH) includes a complimentary membership with Dill Dinkers HHI, the island's premier indoor pickleball club, featuring 8 regulation sized Pro Cushion™️pickleball courts with individual fencing in a climate-controlled environment. Benefits of membership for Guest (and Homeowners) include: 5-day advanced booking window, 1/2 Price Court Fees, 1/2 Price or greater value, Open Play/Events Fees, 10–20% off Leagues, Clinics & Classes, 10% off at the Pro Shop, FREE Ball Machine rental (after court fees) 

Hilton Head’s Hottest Pickleball Spot Located on Mathews Drive just minutes from the beach and many Hilton Head vacation rentals, Dill Dinkers Hilton Head is more than a place to play, it’s a vibrant pickleball community with top-notch indoor courts, professional instruction, and a welcoming atmosphere.

Learn More About Dill Dinkers Pickleball Courts

Enjoy a complimentary membership

During your vacation on Hilton Head you can now enjoy the fastest-growing sport in the U.S. today! Hilton Head is embracing the Pickleball trend and we're offering all of our guests a complimnetary membership at Dill Dinkers of Hilton Head! Whether you’re looking to stay active, try to explore off  the beach, or meet fellow vacationers, Dill Dinkers is the place to do it. Great for Groups, Indoor Comfort in Summer Heat, Fun for All Ages and best of all it's easy to learn & play! Search our rentals below and book your Hilton Head getaway today!


Dill Dinkers Pickleball Club is at 93 Mathews Drive, Unit 150, Hilton Head Island, SC. They’re open every day from 7 AM to 9 PM, so you can hit the courts morning, afternoon, or evening. It’s all indoors and climate-controlled, so the weather’s never an issue. Just show up ready to play and have fun!


Properties Available 64 properties available
Welcome to 15 Collier Beach Road. This three-level home offers ocean, marsh, and tidal creek views. The main level features a gourmet kitchen with a large island, a family room with an 82-inch smart TV, and a dining room, all with water views. The second level has three en suite bedrooms, including a master suite with a king bed, sitting area, pull
Hot HOT 38
15 Collier Beach Road
Singleton Beach Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 6 baths / 1 half bath
Guests 26 guests
Rating 4.9 (49)
18 Sand Dollar, Hilton Head Island. Your search for the perfect vacation rental ends here! With 7 bedrooms, 7 bathrooms, and an open-concept floor plan, this property is sure to impress. The oversized chef’s kitchen is perfect for cooking up delicious meals for the whole group. Upstairs, enjoy family fun with the pool table, ping pong, and fo
Hot HOT 35
18 Sand Dollar Road
Folly Field Beach
Bedrooms 7 bedrooms
Bathrooms 7 baths
Guests 20 guests
Rating 4.9 (192)
4 Brigantine, Hilton Head Island is your perfect family vacation at this second-row home! With 6 bedrooms, each with a full bath, and ocean views from the second-floor living area, this home offers comfort and relaxation. Enjoy convenience with an elevator, oversized pool, and beach access just across the street. The large pool area boasts a table
Hot HOT 36
4 Brigantine
Palmetto Dunes
Bedrooms 6 bedrooms
Bathrooms 6 baths / 2 half baths
Guests 18 guests
Rating 4.9 (34)
Welcome to 8 Sea Front Lane, a luxurious oceanfront retreat located in the stunning Burkes Beach area of Hilton Head Island. This magnificent 10-bedroom, 11-bathroom property is designed to accommodate up to 22 guests, making it the perfect destination for family reunions, group getaways, or special celebrations.The property features a private boar
Hot HOT 39
8 Sea Front Lane
Burkes Beach
Bedrooms 10 bedrooms
Bathrooms 10 baths / 2 half baths
Guests 22 guests
Rating 4.7 (4)
Discover coastal luxury at 25 Bradley Circle, a brand-new vacation rental home ready for summer 2025! This stunning property features 6 spacious bedrooms and 7.5 bathrooms, offering ample room for large families or groups. With two elegant living areas, a rooftop deck perfect for sunset views, and a ground-floor pool complemented by a heated* spa,
New & Roof Top Deck! New & Roof Top Deck!
New & Roof Top Deck!
This property was built in 2025 and not only offers luxury finished and a close proximity to the beach, but 25 Bradley Circle also has a unique ROOF TOP & OCEAN VIEW deck- perfect for morning coffees and afternoon cocktails!
25 Bradley Circle
Burkes Beach
Bedrooms 6 bedrooms
Bathrooms 7 baths / 1 half bath
Guests 16 guests
Rating 5 (3)
This condo has been taken back to the studs for a TOTAL renovation including: raised & smoothed ceilings, new flooring, new paint, all new bathrooms and kitchen, and lastly a new furniture package. This beautiful 3 bedroom condo is located in the heart of Palmetto Dunes Resort. Stop by the general store for lunch or have ice cream in the hot su
Hot HOT 23
205 Barrington Arms
Palmetto Dunes
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (104)
14 Collier Beach, Hilton Head Island is a stunning oceanfront estate that offers a state-of-the-art chef's kitchen, an open-concept living and dining area leading to an oceanfront pool, deck, and grill. The home features a luxurious master suite with breathtaking views of the Atlantic Ocean, a marble bathroom, and a free-form tub. With a privat
Hot HOT 26
14 Collier Beach Road
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rating 4.9 (120)
**WINTER/ SPRING 2026 UPDATES INCLUDE: adding 2 new bathrooms so that each bedroom will have its own ensuite! New pictures & floor plans coming April 2026!**9 Singleton Beach, Hilton Head Island. This oceanfront gem is a 10/10 with awe-inspiring views! Ideal for multiple families, this stunning seven-bedroom, seven-and-a-half-bathroom home span
Hot HOT 28
9 Singleton Beach Place
Singleton Beach
Bedrooms 7 bedrooms
Bathrooms 7 baths / 1 half bath
Guests 20 guests
Rating 4.8 (26)
**NEW LIVING ROOM FURNITURE and UPDATED PAINTING!**412 Shorewood Villas is a 3-bedroom/3-bathroom oceanfront villa  and an absolute gem for vacationing couples and families alike. The panoramic views afforded by the wide floor-to-ceiling windows are simply breathtaking, offering a constant reminder of the beauty of the ocean and the inviting c
Hot HOT 30
412 Shorewood Villas
Forest Beach
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (87)
Enjoy the beautiful beach in the southeast on Hilton Head island at our newly remodeled beach condo! Oceanwalk Oasis sleeps 6 and boasts an outdoor pool AND  and an indoor pool and hot tub! With two king bedrooms plus extra-long bunk beds, your family will enjoy plenty of space to kick back after a great day at the beach. Located just across t
411 Oceanwalk
Forest Beach
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
**New to the rental market! This newly renovated Palmetto Dunes property offers 5 bedrooms, an eat in kitchen, outdoor seating, an oversized indoor pool (perfect for year round use in rain or shine) and a dock on the the famous 11 mile lagoon!** (note: duffy boat is not for guest use)FREE activities included with our signature Southern Hospitality
Never before rental! Never before rental!
Never before rental!
new to the rental market! Be one of the first guests to enjoy this amazing Palmetto Dunes beach house!
85 Port Tack
Palmetto Dunes
Bedrooms 5 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 11 guests
6 Terra Bella Trace, Hilton Head Island is nestled between the salt marsh and the Atlantic Ocean, 6 Terra Bella Trace is a beach lover's paradise. This outstanding property features 6 bedrooms and 8 bathrooms. The chef's kitchen boasts top-of-the-line Wolf and Sub-Zero appliances and an oversized island with wrap-around seating. The open-co
Hot HOT 70
6 Terra Bella Trace
Burkes Beach
Bedrooms 6 bedrooms
Bathrooms 8 baths
Guests 20 guests
Rating 4.9 (130)

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