Holiday rentals with a pool in Hilton Head Island

Apartment in Hilton Head Island

The kitchen features modern appliances, including a stainless steel refrigerator and a sleek oven. White cabinetry with glass accents showcases dishware. A marble countertop provides ample workspace, and recessed lighting brightens the room, enhancing its inviting ambiance.

4.97 out of 5 average rating, 167 reviews

Fully Renovated 2 Bedroom Villa - Walk to Beach

Make yourself at home in this comfortable 2 story, ground floor Condo. Easy walk to the beach. Open concept living, dining and fully equipped kitchen and 1/2 bath on main floor. Chose either the comfy King or Queen bedroom with walk-in shower or bathtub of your choice. Private courtyard with Grill and outside seating. All this, in a setting of azaleas, palms and 20 steps to pool with stores and restaurants just 2 blocks away. Please note there is only 1 parking space available for your stay.

4.98 out of 5 average rating, 149 reviews

A living area is characterized by a comfortable seating arrangement, featuring a light-colored sofa and a patterned armchair. A wooden coffee table is placed centrally, and a television is mounted above a decorative fireplace. Large windows provide views of the outdoor deck and surrounding greenery.

Condo in Shipyard

1BR/2BA condo w/private beach access in Shipyard

This large, tastefully decorated 1BR / 2BA condo, located in Shipyard, has everything you need to kick back with family or friends. Enjoy a morning coffee or evening cocktail on the large wrap around deck. Spacious and comfortable master bedroom with king bed, walk-in closet, en-suite bath, and seating area. Fully equipped kitchen with an adjacent seating area for six. Queen sleeper sofa in the living room and second full bath with shower. In unit washer/dryer. Clean fee includes 1 car pass.

A spacious living area is accentuated by vaulted ceilings and large windows, allowing natural light to fill the room. Comfortable sofas are arranged around a central coffee table, with decorative cushions adding color. A lamp and a decorative vase create a welcoming ambiance in this inviting space.

4.96 out of 5 average rating, 135 reviews

Lovely 3BR in Palmetto Dunes w/ new pool & spa

Lovely 3 BR home on #2 tee of the Fazio golf course in Palmetto Dunes Resort. Near tennis/pickleball center, general store, & restaurants. Newer pool and spa. Quartz countertops. Two King BRs, 3rd BR with 2 Queens. Flat screen TVs, cable, ROKU in all BRs. Doorbell cam at front door porch with recording capability for host/guest safety. Beach access @ Omni resort and Dunes House is 5-10 min by bike or 15 min walk. Beach towels/umbrella/chairs not provided. Pool/spa heat unavailable after 6/1/26

A welcoming living area is presented, featuring a comfortable sofa and a round dining table with two chairs. A wall-mounted television is visible. Natural light floods in through sliding glass doors, offering a view of palm trees and outdoor seating.

5.0 out of 5 average rating, 110 reviews

The Lookout - A Modern Beach Retreat (Oceanfront)

Welcome to The Lookout! The moment you step into this villa you will be greeted by an open floor plan, a fully stocked kitchen, & every amenity that you'll need for your stay. Take a seat on one of the high top adirondack chairs & enjoy your favorite beverage while overlooking the most popular beaches on the island. Truly - every square inch of this unit has been meticulously utilized to give you an unforgettable vacation. We look forward to hosting you at Seaside Villa's premier luxury villa!

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.

5.0 out of 5 average rating, 122 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.

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.

4.98 out of 5 average rating, 364 reviews

Oceanfront Luxe KING BED 65TV Beach Bar Pickleball

Panoramic 180° Oceanfront views the Moment You Open the Door! Beachfront Balcony Watch Sunrise/Hear the Waves 1 min to Beach Boardwalk! Beachfront Pool, Tiki Bar/Grill KING BED FREE Pickleball, Tennis, Gym HGTV Designer Renovation Two 65" SmartTVs Expanded Bedroom Blackout Sleeping Marble Spa Bath Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest RESORT Beach Bar/Sports Bar 3 Restaurants Bike Rentals on Site 4 Beach Boardwalks Gated 24/7 Security Seasonal Island Trolley Stop

4.9 out of 5 average rating, 101 reviews

A calm beach scene is captured at dusk, featuring gentle waves lapping at the shore. The horizon showcases a soft gradient of colors, transitioning from deep blue to warm peach and pink tones. The tranquil sea reflects the fading light of dusk.

Villa in Palmetto Dunes

Spacious dog-friendly villa, walk to the beach

Welcome to your perfect family getaway on Hilton Head Island! This vibrant 3BR, 2.5BA luxurious villa is professionally decorated, accented with inviting, colorful coastal decor throughout. The villa offers a fully-remodeled kitchen, a spacious and comfortable living area with plenty of ways to relax and unwind. Outside, there is a large, private patio with a gas grill, an outdoor dining set and fast access to five community swimming pools and the beach. Snowbirds and long-term guests welcome

4.91 out of 5 average rating, 221 reviews

A spacious living area is presented with large windows offering views of the surrounding greenery. Two armchairs and a sectional sofa provide comfortable seating, while a circular coffee table sits on a patterned rug. Soft lighting is provided by floor lamps, enhancing the inviting atmosphere.

Townhouse in Shipyard

Stylish Tennis-Golf- Beach Retreat-Renovated!

Welcome to my home! The condo is located in a lush gated community with tennis, golf, and beach, south end of the island, close to all the tourist attractions. Things you can do without getting in your car: stroll on the beach, have a meal at the Sonesta resort, suntan at the community pool, play golf or tennis, ride bicycles. Pet's MUST be included in reservation dropdown at booking. Approval for 2nd dog prior to booking with additional fee charged. Pets are not allowed on the furniture.

A light-filled living area features a white sofa complemented by a blue accent chair. A decorative table with a tray of flowers and a plush area rug enhances the space. Large glass doors open to a balcony, offering expansive views of the ocean.

4.98 out of 5 average rating, 169 reviews

My Blue Heaven, Direct Ocean Front View

Welcome to our ocean front rental, a haven for couples seeking a romantic and stylish getaway. With its breathtaking ocean view, five-star reviews, and recent remodel in 2023, this rental promises an unforgettable experience. Our guests have praised the attention to detail, the stunning view, and the overall ambiance of the space. Rest assured that your stay will be nothing short of extraordinary. Step out onto the balcony and take in the fresh sea breeze as you relax in the swinging chair.

An aerial view captures a large pool shaped like a star, surrounded by lounge chairs. The pool area is complemented by umbrellas and seating, with a sandy beach and the ocean visible in the background under clear blue skies.

4.9 out of 5 average rating, 238 reviews

*New* Easy Breezy at Hilton Head Beach & Tennis

Newly renovated in March 2026 and completely redesigned from floor to ceilings, enjoy our wide ocean view from our 3rd floor Ocean Villa. Wake up to sunrise over the Atlantic, grab coffee on your private balcony, and walk to the beach in under two minutes. Spend the afternoon at Hilton Head’s largest oceanfront pool before ending the day with dinner and live music just steps from your condo. Beach chairs, wagon, pickleball, tennis, free parking, & close to the building's only elevator.

4.96 out of 5 average rating, 168 reviews

Aerial view captures the lush greenery surrounding the property, with tree canopies creating a natural border. A highlighted path directs toward the beach, while the serene lagoon is visible nearby, surrounded by the abundant foliage and manicured landscape.

Townhouse in Shipyard

Beachfront Resort 2B Golf Beach Pickleball Tennis

✨Top 5% Guest Favorite✨ Gated Beachfront Resort Golf, Tennis, Pickleball, Pool, Restaurants & Bars Gorgeous Sunny Villa Panoramic Lagoon & Golf Views! Beautiful & Lush Scenery Huge Old Oaks dripping in Spanish Moss! Walk/Bike to Beach Abundant Wildlife! Walk to Shipyard Golf Club & Pub! Modern Coastal Sunny 1st Floor KING BED Master 3 XL SmartTVs WIFI 287 mps Fully Stocked Kitchen Walk-in Shower Washer/Dryer Beach Chairs, Boogie Boards & More! BBQ Bike & Walk Paths Close to Coligny!

Villa in Hilton Head Island

The outdoor space features a year-round heated pool surrounded by lush greenery, with a clear view of the ocean. Umbrellas offer shade over picnic tables, while tall trees enhance the serene atmosphere of the beachside setting.

4.97 out of 5 average rating, 134 reviews

Oceanfront Scandi Oasis Amazing View & Heated Pool

Villa Aalto is a new Scandinavian style oceanfront oasis created for ease and relaxation throughout your beach vacation. The streamlined interior offers high-end finishes and luxurious hotel-like amenities, with a fully functional kitchen and serene living area overlooking the ocean. The year-round heated pool and private path to the beach make for stress-free days, but the close proximity to Coligny allows you to bike to restaurants, playgrounds and shops within minutes as well.

Popular amenities for Hilton Head Island rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.86 out of 5 average rating, 154 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

The private heated pool area features a calming blue water surface surrounded by a stone patio. Five lounge chairs are positioned for relaxation, and a grill is located nearby, with lush greenery providing a natural backdrop and a view of the golf course beyond.

4.86 out of 5 average rating, 121 reviews

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, 134 reviews

Cozy beach house w/Private Heated Pool near park

4.98 out of 5 average rating, 108 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

Stately Governors Quarters-Pet Friendly, Fenced In

Superhost

A single-story home is highlighted by a charming front porch and a well-maintained landscaped entrance. The American flag is displayed prominently above the entryway, while cobblestone pathways guide visitors to the entrance amid surrounding greenery.

4.92 out of 5 average rating, 273 reviews

Wonderful Island's Retreat (With Private 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, 115 reviews

6 BR, Sleeps 26, Beach Time

Superhost

Home in Sea Pines

5.0 out of 5 average rating, 4 reviews

Family Memories Are Made Better at Deer Run

5.0 out of 5 average rating, 12 reviews

Home in Shipyard

Coastal Fairways

Condo rentals with a pool

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, 141 reviews

Oceanview Luxury! King Bed 75"TV Pickleball & Bar

A sunlit living space features a navy blue sofa and an elegant dining table surrounded by four chairs. Large sliding glass doors provide access to the oceanfront balcony, where views of the beach and coastal landscape can be seen in the distance.

4.97 out of 5 average rating, 235 reviews

Oceanfront Luxury! KING BED Beach Bar & Pickleball

A modern kitchen and living area feature stainless steel appliances, including a microwave and refrigerator. A spacious dining table is set for four, while a light-colored sofa offers comfortable seating. Soft blue accents complement the coastal decor, creating a relaxed atmosphere.

4.98 out of 5 average rating, 361 reviews

Ocean Front Resort Villa

A cozy living area features a green sofa adorned with patterned cushions, accompanied by two stylish armchairs. A wooden coffee table sits at the center, with decorative elements including a bowl. Artistic nature-themed prints are displayed on the walls, and natural light fills the space through sliding glass doors.

4.89 out of 5 average rating, 152 reviews

Sunny Treetop Getaway w/ tennis and pickleball

A bright living area features a comfortable sofa and additional seating, including a wicker chair. A coffee table sits on a decorative rug, while large sliding glass doors allow natural light and views of the outdoors. Simple decor adds a relaxed beach ambiance.

4.92 out of 5 average rating, 198 reviews

Stay by the Beach ⛱ Eat & Shop at Coligny plaza!

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, 399 reviews

1 Minute walk to the beach *Amazing ocean view*

4.93 out of 5 average rating, 136 reviews

A welcoming living room features a combination of comfortable seating, including a brown sofa and two patterned chairs. Artistic prints of coastal scenes adorn the walls. A coffee table sits centrally on a decorative rug, while a fireplace adds a charming focal point.

Condo in Palmetto Dunes

Newly Renovated Condo!

4.98 out of 5 average rating, 259 reviews

TOP Floor Oceanfront | Remodeled | Coligny Beach

Other holiday rentals with a pool

Townhouse in Palmetto Dunes

4.96 out of 5 average rating, 103 reviews

Steps to Pool + Private Beach | Baby Gear!

5.0 out of 5 average rating, 30 reviews

Apartment in Sea Pines

Harbour Town Marina Studio | Walk to Lighthouse

5.0 out of 5 average rating, 20 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

5.0 out of 5 average rating, 39 reviews

Peaceful Retreat at Seascape Villas

Superhost

A sweeping view of the beach is captured from a balcony, showcasing a sandy shore lined with umbrellas and beach chairs. Lush green vegetation leads to the water, where gentle waves meet the coastline under a clear blue sky.

Condo in Palmetto Dunes

4.77 out of 5 average rating, 96 reviews

Palmetto Dunes - Captains Walk, Penthouse View

4.93 out of 5 average rating, 46 reviews

Luxury Oceanfront| Sunrise Views|Beachfront Resort

A modern home is surrounded by lush greenery, featuring large glass windows that invite natural light. A spacious outdoor area includes multiple lounge chairs and umbrellas, along with a large dining table. A pool area is visible, enhancing the outdoor living experience.

4.91 out of 5 average rating, 22 reviews

Luxury Palmetto Dunes Retreat with Private Pool