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 65 properties available
29 Singleton Beach, Hilton Head Island is a modern home ideal for large groups, families with kids, or couples seeking a retreat! Its open-concept floor plan includes a sleek gourmet kitchen flowing into the dining room, perfect for meal preparation and socializing. After a day of adventures, unwind in the master suite with its oversized ensuite ba
Hot HOT 35
29 Singleton Beach Place
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 4.8 (153)
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)
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
Hot HOT 17
411 Oceanwalk
Forest Beach
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
16 Singleton Shores Manor, Hilton Head Island.Enjoy marsh and ocean views from every level of this home. Step into the open and bright living area, complete with a wet bar, pool table, and access to your private pool deck. Upstairs, an updated kitchen, second living area, and spacious dining room await, perfect for family gatherings. Retreat to the
Hot HOT 24
16 Singleton Shores Manor
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 14 guests
Rating 4.9 (71)
**FREE POOL & SPA HEAT FOR MARCH-MAY**47 Off Shore Dr is an incredible opportunity for a relaxing getaway! This 3-bedroom, 2.5-bath home is located in Palmetto Dunes and offers a perfect blend of privacy and convenience. Being nestled in a quiet area yet still close to Shelter Cove Towne Center & Harbour for various activities such as dinin
FREE Pool Heat FREE Pool Heat
FREE Pool Heat
September & October/ April & May
47 Off Shore Dr
Palmetto Dunes Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths / 1 half bath
Guests 8 guests
Rating 4.7 (54)
Welcome to 1 Barrier Beach Cove — your perfect Hilton Head getaway. Just a short stroll from the beach, this beautifully designed 6-bedroom, 6.5-bath coastal retreat was made for gathering, celebrating, and truly unwinding together.Start your mornings with coffee on the balcony as the coastal breeze rolls in, spend sun-soaked afternoons by th
Hot HOT 19
1 Barrier Beach Cove
Burkes Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths / 1 half bath
Guests 18 guests
Rating 5 (35)
4 Collier Beach Road, Hilton Head Island, is an oceanfront house with 6 bedrooms and 6.5 bathrooms, comfortably accommodating up to 18 guests. Its spacious layout is perfect for large groups, with two living areas for added convenience. The open concept kitchen offers top-of-the-line Wolf and Sub-Zero appliances. Enjoy the private pool and unbeatab
Hot HOT 17
4 Collier Beach Road
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths / 2 half baths
Guests 18 guests
Rating 4.9 (78)
2 Collier Beach, Hilton Head Island. Experience luxury living at its finest in this magnificent oceanfront 5-bedroom, 5.5-bathroom home boasting an oceanfront pool and one of the only pet friendly homes on Singleton Beach. Each bedroom comes with its own private bath, ensuring maximum comfort and convenience for all guests. The beautiful kitchen is
Hot HOT 30
2 Collier Beach Road
Singleton Beach Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths / 1 half bath
Guests 14 guests
Rating 4.8 (94)
10 Collier Beach, Hilton Head Island is an escape to paradise in this stunning 6-bedroom, 7-bathroom oceanfront home, offering breathtaking ocean views and the ultimate in privacy. Relax by the private pool, enjoy direct access to the beach, and indulge in the luxury of a chef's kitchen. Entertain friends and family in the game room, or let tee
Hot HOT 19
10 Collier Beach Road
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 7 baths / 1 half bath
Guests 16 guests
Rating 4.9 (79)
This remarkable oceanfront estate showcases 7 bedrooms and 7.5 bathrooms, exuding unmatched beauty and luxury. 3 Singleton Beach Place is positioned in the perfect location, granting effortless access to nearby local restaurants, and shopping centers. The focal point of this home is its splendid open kitchen, boasting a double oven and an expansive
Hot HOT 19
3 Singleton Beach Place
Singleton Beach
Bedrooms 7 bedrooms
Bathrooms 7 baths / 1 half bath
Guests 26 guests
Rating 5 (30)
Welcome to 12 Sea Front Lane, an exquisite oceanfront estate located in the prestigious Burkes Beach neighborhood of Hilton Head Island, SC. This expansive property boasts 7 bedrooms and 7 bathrooms, comfortably accommodating up to 22 guests. Each room is designed to offer a serene and sophisticated ambiance, perfect for relaxation and rejuvenation
Hot HOT 29
12 Sea Front Lane
Burkes Beach Pet Friendly
Bedrooms 7 bedrooms
Bathrooms 8 baths
Guests 22 guests
Rating 4.8 (8)
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 20
15 Collier Beach Road
Singleton Beach Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 6 baths / 1 half bath
Guests 26 guests
Rating 4.9 (49)

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