Mansion holiday rentals in Hilton Head Island

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Top-rated mansion rentals in Hilton Head Island

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Top guest favourite

The image features a coastal-style home surrounded by lush palm trees and manicured landscaping. A welcoming sign indicates the entrance to the private community. A paved pathway leads up to the house, providing a serene view of the property in a tranquil setting.

Home in Hilton Head Island

4.98 out of 5 average rating, 56 reviews

40 Crabline: Walk to Beach w/ Pool & Beach Shuttle

+ 4 Bedrooms (2 Kings, 4 Queens, 1 Twin, 1 Mini Crib, 2 Pack ‘n Plays + 4 Full En-suite Bathrooms + 10 minute walk/4 minute bike ride to beach + Free private golf cart shuttle to and from beach 9-5pm (Memorial- Labor Day) + Free Wifi + Cable/Smart-Apple TV in every bedroom + Two Accessible Balconies + Updated High End Finishes + Private/ Fully Fenced in Covered Pool + Pool Heating is available for an extra minimum charge of $200 for first 3 nights, then $50/night each additional night booked

Top guest favourite

A spacious screened porch equipped with a dining table and chairs offers a relaxing area for gatherings. Two ceiling fans provide comfort, and a fireplace adds a cozy touch. A large window showcases the private backyard, enhancing the connection to the outdoors.

Home in Hilton Head Island

4.84 out of 5 average rating, 242 reviews

Private Beach Access-Pet Friendly-Hot Tub!

Welcome to The Beach House-A Family Fun Home! Immerse yourself in the ambiance of your 4-bdrm oasis, featuring a separate Bunk House for added privacy. Luxuriate in your hot tub under the stars in the HUGE backyard with Fire Pit and Covered Grill pole barn. Challenge your friends and family to ping pong or unwind in the screen porch with fireplace and dining area. With a Gorilla Cart at your disposal, hauling beach gear is a breeze. Get ready for endless fun and memories at your beach getaway!

Top guest favourite

A two-story house features a light-colored exterior with a metal roof and a front balcony. The driveway provides access to two garages, with landscaped greenery and grass surrounding the property, enhancing the overall curb appeal.

Home in Hilton Head Island

4.86 out of 5 average rating, 376 reviews

W2Bch*4TVs*1GIG I*PetsWC *WiFi*4King ßds*grill*gms

✔wlk to beach 500 yrds, bike, boat, tennis, golf ✔pet-ok✔5beds✔gourmet kitchen☼sundeck✔ping pong table &games✔screened outdoor area with grill&table✔Spectrum&AppleTV*Roku&WiFi✔W&D✔Busn traveler ready✔2 garages✔private yard space✔1st-floor kitchen, living room with love seat and cal king sofa✔semi-open sitting room aka bdrm with cal king sofa, adjacent small closet, powder room✔sun porch✔2nd floor 2 bdrms with a queen✔master bdrm with king bed Tempurpedic, wlk-in cl and bath with ♥♥shower, 2Z AC

Superhost

A private heated saltwater pool is shown, featuring a shallow entry. Surrounding seating includes a table and chairs, positioned on a colorful rug. Lush greenery frames the space, creating a serene environment, while a grill is visible in the background.

Home in Hilton Head Island

4.89 out of 5 average rating, 107 reviews

Sleep 20, Walk to Beach, Free Heated Pool, Elev

Enjoy a Carefree Casual Getaway experience in this Beautifully appointed Hilton Head Island home away from home! Mid Island where you can walk/bike and take the trolly to the best beaches, restaurants and shopping on the island. Sleeps 20 - Spacious Beach House has 6 Comfortable bedrooms w/ TV's. Master bedroom has a romantic electric fireplace! FREE Heated Saltwater Pool with propane grill and dining/ comfortable seating. Fully stocked kitchen. Linens/towels/soap and shampoo all provided!

Top guest favourite

The image captures a private heated pool beneath a covered patio. Comfortable lounge chairs surround the pool, and an outdoor dining area features a large table with chairs. A shaded umbrella stands above the table, while greenery and a grill are visible, enhancing the outdoor setting.

Home in Hilton Head Island

5 out of 5 average rating, 93 reviews

98 Sandcastle Ct

98 Sandcastle Ct Brand New 6 Bedroom Home near Beach with Pool, Elevator/ (Sleeps Up To 22 Guests ) 20 in beds & 2 in Queen Sofa Sleeper. Over 3200 sq feet, 6 Bedrooms, Heated Pool, Elevator & about .3 miles from the beach = Tons of Fun!!! * 6 Bedrooms * 4 Full Baths * Walking Distance to Ocean. * Heated Private Pool. (Free pool Heat :) * Elevator Available: Free use Adults Only. * Free Parking: 4-6 reg cars/mini vans.. LRG SUV's or LRG Vans = 4 parking spots. Note: 2 = garage 4 =driveway.

Guest favourite

An outdoor deck features a shapely pool surrounded by lounging chairs. Lush greenery and palm trees are visible in the background, offering a view of the golf course. A purple umbrella stands next to the pool, providing shade.

Home in Palmetto Dunes

4.84 out of 5 average rating, 141 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Beautiful home located in Palmetto Dunes Resort. Deck with pool overlooking the first tee of Fazio Golf course with fantastic views of the sunset. Carolina room makes a great 5th bedroom. Private Cul-De-Sac street. Short walk to the beach, general store and tennis center. Enjoy all the amenities of the resort including its beaches, three golf courses, fishing, kayaking, tennis, pickleball, bike trails, restaurants and Dunes Buggy shuttle. Perfect for family beach trips or golf getaways.

Top guest favourite

The exterior of the home is showcased at dusk, featuring a spacious heated pool illuminated in blue. Surrounding the pool are multiple lounge chairs, providing a serene outdoor space for relaxation. The multi-level structure is elegantly designed, with expansive balconies above and a well-lit entrance.

Home in Hilton Head Island

4.96 out of 5 average rating, 96 reviews

5 Bedroom-Beach Access-Pool-Sleeps 14!

Make our brand new custom built home, Sur La Mer at Burkes Beach, your vacation destination! This stunning 3,200 square foot home was completed in 2023. Our 5 bedroom home is a guaranteed picture perfect destination for your family or group of up to 14 people. Our home features a heated private pool and a short walk to the beach. We are centrally located across the street from beach access, a short drive to local restaurants, bars, grocery store and Hilton Head Airport (HHH).

Guest favourite

A shaded balcony is furnished with two woven chairs and a small table, complemented by a decorative area rug. Lush greenery is visible beyond the railing, providing a natural backdrop, while large windows allow for ample light to fill the space.

Home in Hilton Head Island

4.98 out of 5 average rating, 120 reviews

Cozy beach house w/Private Heated Pool near park

Short walk to Singleton beach or Burkes beach. This oversized 4 bedroom 4 ensuite is the perfect retreat close to everything the Island has to offer. The home features a screened in pool with TV and adjacent ping pong table. The open concept living space is perfect for entertaining with access to a large porch and grill. The property is steps away from Chaplin Park that hosts Tennis, Playground, Soccer, Baseball, Basketball, Trails and Fields for the kids to play. Sleeps 12.

Superhost

An expansive pool deck is illuminated with soft lighting, showcasing a private pool and built-in spa. A lounge area with multiple chairs is present, and a covered seating area is visible in the background. The setting sun casts warm hues over the space.

Home in Palmetto Dunes

5 out of 5 average rating, 3 reviews

47 Haul Away Estate @ Palmetto Dunes | Pool & Spa

Experience refined elegance at 47 Haul Away by Host & Home, a luxurious Palmetto Dunes estate with captivating golf course views. Unwind on the expansive pool deck with a private spa, outdoor bar, and grill, perfect for entertaining. Inside, enjoy a chef’s kitchen, a private office, and multiple sophisticated living spaces. Conveniently located near Hilton Head’s pristine beaches, world-class golf, and premier dining, this property offers the ultimate in Lowcountry luxury.

Top guest favourite

Home in Sea Pines

5 out of 5 average rating, 70 reviews

Sea Pines house ~ Golf Sim / Putting Green / Games

Centrally located in HHI just within the gates of Sea Pines, with golf simulator, outdoor putting green, 2 game rooms, and a backyard area with games, outdoor dining, fire table & lounging areas, this home is a one-of-a-kind experience. Sleeping up to 10 guests (2 king beds and 4 double beds), this luxurious space will offer unparalleled comfort, amenities, and the perfect location for you to use as your central base to enjoy the best of Hilton Head Island.

Guest favourite

Home in Sea Pines

5 out of 5 average rating, 16 reviews

LARGE Private Pool & Spa ~ Designer Decorated

Escape to Island Time, a 4BR/3BA retreat in Sea Pines, just 0.5 miles to the beach & 0.7 miles to the Beach Club. This spacious home features a private heated pool & spa, golf course views, a screened-in porch, and multiple indoor & outdoor living areas. Enjoy the grill (cleaned before arrival, propane included) and a Solo Stove fire pit (guest provides firewood). Experience the perfect blend of relaxation and Lowcountry charm—book your stay today!

Top guest favourite

A two-story house features a light blue exterior with white trim and black shutters, showcasing a spacious driveway. A six-person black golf cart is parked in front, contrasting against the landscaped area with tropical plants and a nearby streetlamp.

Home in Hilton Head Island

4.93 out of 5 average rating, 216 reviews

Great family gathering spot, golf cart included

Home sleeps up to 22 guests (17 Beds) depending on sleeping arrangements and is in a Gated Community, Short walk to the Beach . Home has 5 Bedrooms plus bonus room with Bunk Beds, 4 Baths.. Open concept.. There is a deck of the living room with table and chairs also to enjoy. The heated screened pool and BBQ are for your enjoyment. Rear yard is fenced. 6 person golf cart available with restrictions. Dill Dinkers indoor pickleball close by.