House holiday rentals in Hilton Head Island

5 out of 5 average rating, 26 reviews

Modern Beach Escape | Private Pool~Steps to Beach

Welcome to your private slice of Hilton Head paradise—completely rebuilt and just steps from the sand. This 4BR, 3.5BA showstopper sits on a corner lot, 30ft from a private beach path. Enjoy the tropical pool area, fire pit, outdoor shower, and a massive balcony overlooking this beachside oasis. Inside: two stylish living areas, Smart TVs in every room, & luxe finishes throughout. Sleeps 11 & dog friendly. Minutes from top-tier golf, dining, & endless island adventures—book your dream stay now!

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.

4.87 out of 5 average rating, 386 reviews

W2Bch*4TVs*1GIG I*PetsWC *WiFi*4King beds*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

4.99 out of 5 average rating, 140 reviews

“Sea La Vie” 3BR, Sea Pines, Walk to Dining, Shops

Privately-owned 2000 SF one-level home sits on a wooded corner lot conveniently located inside the entrance of Sea Pines Resort. This 3 BR, 2BA home was extensively renovated in August 2020, with inviting French-inspired coastal decor for a relaxing cozy feel. "Sea La Vie" chalet is within walking distance to grocery stores, shops, and restaurants. A short drive or bike ride takes you to the private Beach Club, housing oceanfront dining and bar, upscale facilities, and wide beaches. Bienvenue!

A newly constructed beach house is shown from the front, featuring a light blue exterior and a welcoming porch. Palm trees frame the scene, complemented by manicured landscaping. A driveway leads to a two-car garage beneath the home, creating a spacious entryway.

4.99 out of 5 average rating, 69 reviews

Beach House, Elevator, Sleeps 12

Stroll just a few steps from Fish Haul Beach to discover our haven of relaxation.This newly built beach house boasts 3 bedrooms and 2.5 baths complete with complimentary linens and bath towel sets.Enjoy a fully equipped kitchen, ample dining space,and 2 expansive balconies to soak in the coastal ambiance.Enhance your beach stay with included amenities such as boogie boards,backpack beach chairs and wagons.We've anticipated every need and are dedicated to ensuring your stay exceeds expectations!

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.

5 out of 5 average rating, 108 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.

4.91 out of 5 average rating, 124 reviews

An inviting living space features a sectional sofa, a wooden coffee table, and a dining area with several chairs. Natural light illuminates the room through multiple windows, highlighting the coastal-inspired decor and airy layout. A chandelier complements the open, relaxed atmosphere.

Home in Palmetto Dunes

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

Offered by owner /manager. Master bath w/ walk in shower, spacious bright open concept LR, DR, kitchen, w/ private cozy courtyard. Designer inspired coastal chic for the beachy atmosphere. Sit and relax in the courtyard, lounge in the sun while having an afternoon drink and BBQ. Watch golfers at the driving range or Trent golf course just a short walk from the villa. Go for a swim in 1 of 5 community pools. Under 10 minute walk to Palmetto Dunes beach or call seasonal dune buggy for a ride.

Home in Hilton Head Plantation

A hot tub is situated in the foreground, surrounded by greenery and string lights hanging from the trees. The house showcases a covered patio area with minimal outdoor seating, blending into the natural landscape of the property.

4.86 out of 5 average rating, 170 reviews

Sycamore at the Sound — live like a local!

This beautiful home is nestled on a cul-de-sac street in Hilton Head Plantation and offers a private back yard sanctuary in which to truly enjoy low country life. The home features a sun room with ample seating, a pool table and game table, as well as an additional living area with sectional sofa. Each bedroom has its own television and attached bathroom. The kitchen is fully equipped, and the dining area offers seating for eight. Additional amenities include Wi-Fi, gas grill, and hot tub.

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.

4.98 out of 5 average rating, 123 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.

5 out of 5 average rating, 78 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.

A pristine pool area is surrounded by lush greenery, featuring a spacious pool and a relaxing spa. Poolside seating includes turquoise chairs and an umbrella. A dining table with outdoor chairs is situated nearby, all on a textured stone patio.

4.98 out of 5 average rating, 107 reviews

Private pool/spa : pool heat available : Kg master

Private pool and 4 person spa! Enjoy breakfast by the pool with the birds chirping and end your day relaxing in the spa under the stars! ‣1800 ft² , One level ‣Parking for 4 cars ‣Fully equipped kitchen ‣Washer/Dryer ‣2 Living/Seating areas ‣Dining table for 8/Island seats 4 ‣Bunk room with 2 triple bunkbeds ‣King master w/ desk space ‣Smart TVs ‣Pool Heating available for extra fee ➼Folly Field Beach: 0.5 mi/5 min bike/12 min walk

4.99 out of 5 average rating, 82 reviews

A charming circular home is nestled among tall trees, featuring a spacious deck with white lounge chairs. The wooden steps lead up to the entrance, showcasing large windows that allow ample natural light. The surrounding greenery enhances the sense of privacy and seclusion.

Home in Harbour Town

Harbour Town Treehouse | Deer Island | Pool

Please see our almost 1000 5-star reviews at our other properties. Enjoy unbelievable tranquility high in the Sea Pines tucked away on Deer Island next to Harbour Town. Walk to the shops, restaurants, entertainment, and the Yacht Basin in just minutes. Feed the deer from your hand while you connect with nature. The Sea Loft is just one house away from the Turtle Trail that winds along the marshlands.

A charming beach cottage is framed by mature trees and lush landscaping. A pathway of gravel leads to the entrance, featuring a well-maintained lawn. An American flag is displayed prominently, enhancing the welcoming atmosphere of the exterior.

4.98 out of 5 average rating, 54 reviews

80 Steps to Private Beach Access • Walk to Coligny

Welcome to Curlew Cottage! Nestled only 80 steps from a private beach access (marker 61B) and 2 blocks north of Coligny Plaza. Sleeps up to 4 adults + 2 kids, 2 BR/1 BA, large screened porch, private outdoor hot shower, firepit, fully equipped kitchen, smart TVs, NFL Sunday Ticket. One dog allowed on a case-by-case. I am a local owner and available to help you plan your stay.

Popular amenities for house rentals in Hilton Head Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A well-lit bedroom features two spacious beds, each adorned with vibrant blue and green bedding. A decorative wall basket adds a natural touch, while a window with patterned curtains allows for natural light. A small chair and side table enhance the room's functionality.

4.99 out of 5 average rating, 104 reviews

6 BR, Sleeps 26, Beach Time

A private residence is set among tall trees, featuring a spacious patio area with a circular pool at its center. A barbecue grill and poolside loungers are visible, surrounded by natural landscaping, creating a serene outdoor retreat.

5 out of 5 average rating, 32 reviews

Starfish Beach House with Pool and Bikes

4.85 out of 5 average rating, 148 reviews

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

Palmetto Dunes Home on 1st Tee Fazio Golf Course

4.93 out of 5 average rating, 30 reviews

The villa's exterior is framed by lush greenery, featuring palm trees and manicured shrubs. A gravel pathway leads to the entrance, enhancing the peaceful, natural setting. The light-colored siding and slatted shutters contribute to the inviting curb appeal.

Home in Palmetto Dunes

Charming Beach Villa at Palmetto Dunes!

A light-filled living area showcases a spacious sectional sofa accented with patterned cushions. A wooden coffee table sits in front, complemented by a contemporary chair. Large windows surround the room, offering views of the surrounding greenery, while a flat-screen TV is mounted on a white entertainment unit.

4.83 out of 5 average rating, 40 reviews

The Ocean Lily of Sea Pines

The exterior of the house presents a modern coastal design, featuring a spacious deck with multiple seating areas, a large umbrella, and a grassy surrounding. Large glass doors invite natural light into the interior while a BBQ grill is visible on the deck.

5 out of 5 average rating, 34 reviews

New Sea Pines Remodel Close To Beach

5 out of 5 average rating, 79 reviews

4BR with Private Pool, Pets Welcome, Steps to Sand

A comfortable living area is highlighted by a sectional sofa adorned with decorative pillows. A wooden coffee table sits in front, featuring accessories and board games. The open layout leads to a dining area with a wooden table, complementing the warm, inviting decor.

4.91 out of 5 average rating, 22 reviews

Newly Renovated Condo HiltonHead

Weekly house rentals

The exterior of the two-story villa showcases a modern design with a light-colored façade and multiple windows. A welcoming entrance is framed by manicured shrubs and greenery, creating an inviting approach. A short pathway leads to the main door, highlighting the tranquil surroundings.

4.96 out of 5 average rating, 27 reviews

Ocean Gate Hideaway! 7 min walk to the beach

The front entrance features a vibrant blue door adorned with a decorative wreath. Flanking the door are two tall, narrow windows with decorative glass accents. A light fixture is mounted to the left of the door, complementing the inviting entryway.

5 out of 5 average rating, 6 reviews

42 Firethorn Lane · Beautifully Decorated Three Be

A serene lagoon scene is presented, featuring calm water bordered by leafy trees. Palm trees stand prominently in the foreground, while charming homes line the water's edge under a clear blue sky, providing a tranquil backdrop.

4.92 out of 5 average rating, 76 reviews

Updated! Sea Pines Lagoon View Oasis

The outdoor area features a private pool with a cozy seating arrangement nearby. A fire pit with glowing embers is central to the setting, surrounded by large loungers and a dining table. A large umbrella shades the outdoor seating, while a whimsical inflatable swan floats in the water.

5 out of 5 average rating, 33 reviews

Marsh Views | Pool, HotTub, Game Room&Pet Friendly

A spacious outdoor pool area features lounge chairs arranged around a large swimming pool, with several guests enjoying the water. Two hot tubs are visible nearby, surrounded by palm trees and blue umbrellas. The ocean can be seen beyond the pool, creating a serene backdrop.

4.96 out of 5 average rating, 24 reviews

Oceanfront condo with elevator and gated entrance!

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.

4.98 out of 5 average rating, 58 reviews

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

4.95 out of 5 average rating, 44 reviews

Luxury Beach House w/ Heated Pool & Outdoor Grill

A blue exterior of a house is framed by tall palm trees and lush greenery. A wooden deck with seating is visible, offering a welcoming outdoor space. The surrounding landscape features well-maintained shrubs, contributing to a calm and natural ambiance.

5 out of 5 average rating, 68 reviews

A WAVE FROM IT ALL! Rest, Relax, Recharge!

Private house rentals

Superhost

An inviting outdoor area features a swimming pool surrounded by lounge chairs, with a spacious al fresco dining table positioned nearby. The home’s exterior showcases large windows and multiple entrances, with the surrounding greenery providing a serene ambiance as dusk settles.

4.8 out of 5 average rating, 40 reviews

Wisteria by AvantStay | Entertainer's Home

The exterior of the home features a grand two-story structure with a large covered porch and multiple entry points. Lush landscaping with palm trees enhances the inviting curb appeal. A paved driveway provides access to the garage, surrounded by neatly trimmed bushes and grass.

5 out of 5 average rating, 35 reviews

5 Sandy Beach Trail- Beach House w/ Private Pool

A private deck is shown featuring a hot tub and two turquoise lounge chairs. Surrounding greenery adds a natural backdrop, while soft outdoor lighting enhances the space. Large windows from the house allow for views of the deck and the serene outdoor setting.

4.95 out of 5 average rating, 42 reviews

22 Lagoon View | Hot Tub | Sea Pines Retreat

Superhost

Home in Harbour Town

5 out of 5 average rating, 4 reviews

Waterfront Treehouse Oasis steps from Harbourtown

4.88 out of 5 average rating, 48 reviews

An outdoor space features a newly installed pool surrounded by lounge chairs and a dining area. A putting green, marked with golf holes, lies nearby. The home is set against a backdrop of tall trees, creating a serene environment.

Home in Shipyard

Heels in the Sand- Private Pool & Putting Green

5 out of 5 average rating, 14 reviews

Short walk to the Beach!

A serene pool area is surrounded by lush greenery, featuring a spacious swimming pool with lounge chairs nearby. Colorful umbrellas provide shade, and a stone patio extends around the pool, inviting relaxation and outdoor enjoyment.

4.93 out of 5 average rating, 54 reviews

Sea Pines - S. Beach Charmer - Private Pool/Spa

The spacious living area features high ceilings and a fan above. A soft gray sofa is positioned beside a coffee table with decorative items. The wall is adorned with a large flat-screen TV, and a fireplace adds a focal point. Large windows allow natural light to fill the space.