Vacation rentals with a pool in Hilton Head Island

A private balcony overlooks a pool surrounded by lounge chairs and lush greenery. The ocean is visible in the distance, framed by tall trees under a clear blue sky. The space includes a small round table with two chairs.

4.9 out of 5 average rating, 173 reviews

⭐Direct Oceanfront Villa Steps to Beach w/ Pool⭐

Welcome to Ocean Pearl Villa. Sit back, relax and listen to the crashing of the waves, while relaxing on your private balcony of our two bedroom, two bath beautiful oceanfront condo. Ocean Pearl is located in Beachwood Place, a 24 unit gated private complex, on Hilton Heads finest South Forest Beach & only 3 minute walk to Coligny Plaza, the heart of Hilton Head's restaurants, Shopping & family activities. You will enjoy the wonderful accommodations and spectacular views at 2H Beachwood Place.

A candle is displayed on a table, surrounded by seashells, with a sunset view of the ocean in the background. The warm colors of the sky reflect off the water, while a cup is placed nearby, adding to the serene atmosphere of the balcony.

4.99 out of 5 average rating, 125 reviews

Ocean View KING BED 75"TV Beach Bar Pickleball GYM

✨Top 5% Airbnb Home✨ BIG OCEAN VIEWS FROM LIVING ROOM & BALCONY! Oceanfront Building Steps to Beach Boardwalk, Pool & Tiki Bar! FREE Pickleball, Tennis, Gym & More HGTV Featured Decorator 100% NEW Luxury renovation KING BED + 75" & 65" Smart TVs Expanded Bedroom Luxe Marble Kitchen & Bath Quiet Top Floor Well-designed 540 sq. ft. Elevator Beach Chairs + More RESORT: Oceanfront Pool & Bar & Grille Restaurants Sports Bar 4 Beach Boardwalks Bike Rental Gated 24/7 Security FREE Island Trolley Stop

A tranquil beach scene is captured, featuring soft sand leading toward shimmering ocean waves. A wooden fence guides the pathway, with grasses gently framing the foreground. The sky is illuminated with warm hues of orange and pink as the sun rises above the horizon.

4.97 out of 5 average rating, 305 reviews

Ocean View! Remodeled! Steps to beach/Pool/Bar

FULLY REMODELED OCEAN VIEW VILLA Located in Hilton Head Beach & Tennis Resort, this beautiful 540 Square foot Villa is perfect for a small family or couple looking for a relaxing and fun getaway. The second floor balcony offers a view of both the ocean and pool, as well as, offering the soothing sounds of the ocean waves Located within a gated community and with access to the beach just steps away. The resort also features 2 private pools, 3 restaurants, bike rentals, a private gym & more!

A bright dining area offers a view of the ocean through open doors leading to a private beachfront balcony. Coastal décor is present on the round table, complemented by neutral tones and natural light streaming in from the outdoors.

4.97 out of 5 average rating, 354 reviews

Oceanfront KING BED 65"TV Beach Bar Pickleball GYM

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! Beachfront Balcony Watch Sunrise/Hear Waves 1 min to Beach Boardwalk! Beachfront Pool, Tiki Bar & Grille FREE Pickleball, Tennis & Gym HGTV Designer Renovation Two 65" SmartTVs KING BED Expanded Bedroom Blackout Sleeping Marble Spa Bath Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESORT Bike Rentals on Site 4 Beach Boardwalks 3 Restaurants Beach Bar/Sports Bar Gated 24/7 Security Seasonal Island Trolley Stop

4.98 out of 5 average rating, 104 reviews

The open-concept living space features handmade Saltillo tiles and a vaulted ceiling. A comfortable couch and a fireplace are visible along with a large dining table. A staircase leads to the upper level, enhancing the spacious layout. Sliding glass doors provide access to the outdoor area.

Home in Sea Pines

Governor’s Quarters Pet Friendly, Fenced in Yard

Welcome to Governor's Quarters- your Luxury Hilton Head Getaway Stay Lowcountry in this stately-designed home. Newly remodeled & fully equipped for your golfer’s retreat or family/friends' coastal vacation. 5 mins from the SeaPines Beach Club and HarbourTown Golf Links and the heated community pool! Located in famous, Sea Pines Resort. Enter the gates of resort living offering trolley rides to local restaurants, premium golf courses, HarbourTown Lighthouse, & most importantly- the beach!

A clear view of the ocean is visible from the balcony, showcasing a sandy beach lined with colorful umbrellas. Gentle waves roll onto the shore, and distant figures can be seen enjoying the beach. Lush greenery frames the foreground, enhancing the coastal scene.

4.9 out of 5 average rating, 122 reviews

Oceanfront, 3rd floor, King Bed

Direct oceanfront! Perfect for a couples get away, week vacation or anything in between. Take a walk across the street to Coligny Square where there are more than 60+ shops and restaurants. Ride your bike on more than 100 miles of trails. Onsite parking, pool and free wifi. Just bring your bathing suit and a towel! We provide the rest for you to have a relaxing vacation; beach chairs, umbrella, cooler, all kitchen spices, a Coffee Bar, shampoo, conditions, body wash and tide pods!

Large windows frame stunning ocean views, allowing natural light to flood the room. A flat-screen TV is positioned on a glass stand opposite the windows, with a white shelving unit displaying decorative items. The space features maple hardwood flooring and a sliding glass door leading to an outdoor area.

4.83 out of 5 average rating, 192 reviews

Jim's Stunning Direct Ocean Front 2BR Villa

This 2nd floor villa has breathtaking, unobstructed ocean views from the living room and master bedroom. Walk to Coligny! Two bedroom suites (new mattresses and ceiling fans), with separate baths. Beautiful maple hardwood & tile floors throughout. Fully appointed kitchen boasts granite countertops, maple cabinets, and stainless steel appliances. New Washer/Dryer. Jim Says "I personally stay in each of my units to ensure they are maintained to my highest level of expectations."

A living area features a leather recliner sofa and a cozy woven coffee table. A light-colored accent chair and a lamp are positioned nearby. A television is mounted on a decorative cabinet, and three framed art pieces are displayed on the wall above.

4.97 out of 5 average rating, 150 reviews

1st Floor, 1 BR Condo - Steps to Beach and Pool!

Renovated 1st floor, 1 BR getaway located across the street from the beach! Private deck overlooks community pool just steps from back door. Great location - plenty of restaurants, bars, shopping and grocery stores nearby. New appliances, smart TVs in living area and bedroom (cable in living room). Bedroom has a queen-size bed and brand new leather recliner sofa in the living room. Rental includes 2 beach chairs, cart and umbrella. Absolutely no pets and no smoking allowed.

A stunning sunrise illuminates the ocean, casting a warm golden glow across the water's surface. Rays of sunlight stretch outward, reflecting off the gentle waves. The shoreline is visible, framed by soft grasses, enhancing the tranquil morning scene.

4.99 out of 5 average rating, 193 reviews

Ocean Overlook II - The Penthouse Experience

LUXURIOUS, PENTHOUSE, DIRECT OCEANFRONT HOME! UNOBSTRUCTED OCEAN VIEWS! SO CLOSE YOU CAN HEAR THE WAVES CRASH WITH THE WINDOWS CLOSED! DIRECT BEACH ACCESS! POOL ACCESS! ALL BRAND NEW! 4TH FLOOR (TOP FLOOR)! PRIVATE BALCONY! MILLION DOLLAR OCEAN VIEWS! SPA SHOWER! KING BED! CAN SLEEP 4! THIS IS LUXURY LIVING WITH NO RESORT AMENITY CHARGES! SAVE THOUSANDS OF DOLLARS COMPARED TO OTHER NAMED RESORTS LUXURY HOTEL PROPERTIES! **UPGRADED INTERNET & HD TV PACKAGE + FREE AMENITIES**

4.95 out of 5 average rating, 138 reviews

KING BED!Ocean View, Free Bikes Poolside 3rd Floor

Pack your flip-flops and get ready for fun—this sunny poolside villa on Hilton Head Island is your ticket to the ultimate coastal escape! Just steps from the beach and the refreshing Atlantic breeze, this vibrant retreat serves up the perfect mix of relaxation, adventure, and ocean views. Start your day with coffee on the balcony, soak up the sun by the pool, then hop on one of our free bikes to cruise the island like a local! The perfect getaway starts right here!

4.94 out of 5 average rating, 121 reviews

The living area is furnished with a spacious sectional sofa, accented by decorative pillows and a cozy throw. A large television is mounted on the wall, and floor-to-ceiling windows provide an ocean view, allowing natural light to fill the room.

Condo in Palmetto Dunes

Ocean Views at Villamare, Right on the Beach!

Read our reviews! We strive to provide an unforgettable Hilton Head experience in our updated villa with ocean views, comfortable lounging, plush beds, well-appointed kitchen and 500+Mbps WiFi! Our bright, open living space features floor-to-ceiling windows overlooking the pool, beach and the Atlantic Ocean! The living room sectional expands into a massive lounger for all! Have a big group? We also offer the immediately next-door unit, identical to this one!

A sunset view is captured from the balcony, showcasing the golden sun descending over the ocean horizon. Silhouettes of palm trees and a grassy area are visible, creating a serene coastal atmosphere. The sky displays soft hues of orange, pink, and gray.

4.96 out of 5 average rating, 389 reviews

1 Minute walk to the beach *Amazing ocean view*

Enjoy Amazing ocean and beach views from your balcony. This is the 3rd unit from the ocean on the 3rd floor and honestly the view beats the direct oceanfront views because of the panoramic effect. Sea Side Villas is minutes away from the very popular Coligny Beach Park area where you can enjoy the many restaurants and shops. Also very close to the new Lowcountry Celebration Park where they have festivals and events. Town of HHI STR-Permit #049652

Popular amenities for Hilton Head Island rentals with a pool

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, 112 reviews

6 BR, Sleeps 26, Beach Time

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, 117 reviews

98 Sandcastle Ct

4.95 out of 5 average rating, 102 reviews

Steps to Beach, Pool, 5BR, Great Location

A dining area features a reclaimed wood table surrounded by cross-back chairs. A shelving unit holds decorative items and books. Natural light brightens the stylish living room in the background, where plush seating and tasteful decor can be seen.

5 out of 5 average rating, 38 reviews

Steps to the Beach - Perfect All-Season Getaway

4.85 out of 5 average rating, 115 reviews

An outdoor area features a heated private pool surrounded by a spacious patio and lounge chairs. The home, with updated siding, has a shaded seating area and a barbecue grill. Lush greenery and colorful flowers enhance the tranquil ambiance.

Home in Palmetto Dunes

Palmetto Dunes House: Private Pool, PDBeach, Golf

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, 129 reviews

Cozy beach house w/Private Heated Pool near park

4.97 out of 5 average rating, 158 reviews

A modern treehouse-like structure is elevated on stilts and surrounded by trees, providing marsh views. A wide wooden deck with railings leads to the entryway, where large glass doors invite natural light into the space.

Home in Sea Pines

Peaceful Harbour Town Treehouse with Marsh Views

Superhost

5 out of 5 average rating, 4 reviews

1 Min Walk to Beach | Private Pool Retreat

Condo rentals with a pool

A spacious pool area is visible, bordered by sun loungers and palm trees. The ocean can be seen in the background, with glistening sunlight reflecting off the water. A clear blue sky enhances the inviting atmosphere of the outdoor space.

4.91 out of 5 average rating, 229 reviews

Breathtaking OCEAN VIEW |Pool & Coligny| TOP FLOOR

A serene beach scene at sunset displays soft hues of orange and pink reflecting on the water. Two figures stroll along the shoreline, leaving footprints in the sand. Gentle waves lap against the beach, creating a peaceful coastal atmosphere.

4.9 out of 5 average rating, 186 reviews

Cozy in Coligny

A comfortable living area features a blue sofa with yellow accent pillows, complemented by a patterned armchair. A textured area rug covers the floor, and a coffee table with a tray is centrally positioned. Natural light filters through sheer curtains, creating a warm ambiance.

4.89 out of 5 average rating, 179 reviews

Coastal Comfort! Condo in beachfront resort.

A living area features a blue sofa adorned with decorative pillows, a wooden coffee table, and a large television mounted on a black stand. A ceiling fan with wooden blades provides airflow. Light yellow walls and framed artwork contribute to a bright and inviting ambiance.

4.8 out of 5 average rating, 273 reviews

Beautiful Beach Condo in Paradise

Superhost

4.8 out of 5 average rating, 179 reviews

Beach Front Villa Oak Tree Lined Views to Water

A serene beach scene features gentle waves lapping at the shore under a soft pastel sky. The moon hovers above the horizon, casting a warm glow over the water. A distant figure is seen walking along the wet sand, contributing to the tranquil atmosphere.

4.9 out of 5 average rating, 239 reviews

Oceanside Beach Retreat

4.9 out of 5 average rating, 268 reviews

A calm bedroom features a spacious bed with a pink patterned quilt, complemented by a decorative beach-themed sign above. Two white closet doors are visible along one wall, while a bedside table holds a lamp. Coastal decor accents enhance the serene atmosphere.

Condo in Palmetto Dunes

HHI. Easy Direct Beach Access. 3 pools- 1 indoor.

A serene pool area is surrounded by lush greenery, with a paved walkway leading to the water. Several lounge chairs are positioned near the pool, which is framed by a low fence. Mature trees provide ample shade, enhancing the tranquil atmosphere.

4.85 out of 5 average rating, 193 reviews

1 Bedroom Condo, 5 Minute Walk to the Beach

Other vacation rentals with a pool

4.96 out of 5 average rating, 25 reviews

Stunning Ocean View | King Bed | Beach/Pool Resort

4.98 out of 5 average rating, 41 reviews

#402 Renovated 1BR/1BA /New Sofa Bed /B/Balcony

Villa in Hilton Head Island

A serene view of a sunset over the ocean is framed by a railing, with silhouettes of trees in the foreground. The horizon displays vibrant orange and yellow hues against a deepening blue sky, providing a tranquil backdrop to the surrounding landscape.

4.92 out of 5 average rating, 386 reviews

Direct Ocean Front S. Forest Beach

4.98 out of 5 average rating, 96 reviews

A bright living area is filled with soft furnishings in soothing tones. Two comfortable couches are positioned around a central coffee table, while light streams in through sliding glass doors that open to a private patio. Decorative beach-themed artwork adds a touch of coastal charm.

Villa in Sea Pines

HHI South Forest beach/WLK TO BEACH, dining, pool

The living area features comfortable gray seating arranged around a coffee table, with a colorful area rug underfoot. A mounted television is visible on the wall, providing entertainment options, while natural light filters in through the curtains.

4.97 out of 5 average rating, 29 reviews

Beachside Bliss: Walk to Beach / Coligny Plaza

5 out of 5 average rating, 16 reviews

A spacious living area is furnished with a blue sectional sofa and a coffee table. Soft lighting is provided by two lamps on either side of the sofa. A large patio door opens to an outdoor seating area, allowing natural light to fill the room.

Apartment in Sea Pines

Renovated 1BR HHI – Walk to Beach & Salty Dog Café

The living area is furnished with a comfortable sofa and armchairs, complemented by decorative pillows. A light wood coffee table is situated in the center, while a dining space with white chairs and a wooden table is visible in the background. Soft lighting enhances the relaxed atmosphere.

5 out of 5 average rating, 74 reviews

Seas the Day! 2BR/2BA/Walk to Beach/Dogs welcome!