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Holiday rentals with a pool in Hilton Head Island

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Hilton Head Island

  • Total holiday rentals

    Explore 6,120 holiday rentals in Hilton Head Island

  • Nightly prices starting at

    Hilton Head Island holiday rentals start at $68 NZD per night before taxes and fees

  • Verified guest reviews

    Over 138,130 verified reviews to help you choose

  • Family-friendly holiday rentals

    5,010 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 1,000 rentals that welcome pets

  • Rentals with dedicated workspaces

    3,280 properties have a dedicated workspace

  • Wi-Fi availability

    6,120 of Hilton Head Island holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Hilton Head Island rentals

  • 4.8 Average rating

    Hilton Head Island stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in Hilton Head Island

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Hilton Head Island
4.95 out of 5 average rating, 107 reviews

Steps to Beach, Pool, 5BR, Great Location

Make this brand new (2023) custom built home, Sur La Mer at Burkes Beach, your vacation destination! This 5 bedroom home is a guaranteed picture perfect destination for your family or group of up to 14 people and features a heated private pool* and a short walk to the beach. Sur Le Mer is located just steps from beach access and right next to Chaplin Community Park (basketball, playground, tennis, baseball diamond and open field). It's also short drive to local restaurants, bars, grocery store

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Top Guest favourite
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.
Apartment in Hilton Head Island
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.

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Top Guest favourite
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.
Condo in Hilton Head Island
5.0 out of 5 average rating, 107 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!

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Top Guest favourite
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.
Condo in Hilton Head Island
4.99 out of 5 average rating, 140 reviews

Big Ocean View KING BED 75"TV Beach Bar Pickleball

✨Top Airbnb Guest Favorite Home✨ Big Ocean Views - Living Room & Balcony Oceanfront Building Steps to Beach Boardwalk, Pool & Tiki Bar FREE Pickleball, Tennis, Gym & More KING BED + 75" & 65" Smart TVs Expanded Bedroom HGTV Featured Decorator 100% NEW Luxury renovation Marble Kitchen & Bath Quiet Top Floor Well-designed 540 sq. ft. Elevator Beach Chairs + More RESORT: Oceanfront Pool & Bar & Grille 3 Restaurants Sports Bar 4 Beach Boardwalks Bike Rental Gated 24/7 Security FREE Island Trolley

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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
5.0 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.

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Top Guest favourite
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.
Condo in Hilton Head Island
4.98 out of 5 average rating, 364 reviews

Oceanfront Luxe KING BED 65TV Beach Bar Pickleball

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 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 & More RESORT Beach Bar/Sports Bar 3 Restaurants Bike Rentals on Site 4 Beach Boardwalks Gated 24/7 Security Seasonal Island Trolley Stop

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Guest favourite
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
4.91 out of 5 average rating, 221 reviews

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.

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Top Guest favourite
A spacious oceanfront pool area is surrounded by lush green landscaping, featuring lounge chairs and a shallow entry. A winding path leads toward the beach, with the ocean visible in the background, flanked by tall trees creating a serene atmosphere.
Villa in Hilton Head Island
4.94 out of 5 average rating, 143 reviews

Modern Oceanfront Villa With Views and Heated Pool

Welcome to Villa Lucia, our oceanfront retreat on S. Forest Beach. Enjoy the ocean views from the balcony and convenient year-round heated pool just outside your door. The villa has been fully renovated with modern amenities and has personal touches throughout. Our location is unbeatable on S. Forest Beach between Coligny Beach and Sea Pines - Away from the crowds, but close enough (.5 mi) to bike or walk to all that’s offered. After a long day enjoy a drink with lush foliage and sea views.

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Top Guest favourite
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
4.96 out of 5 average rating, 168 reviews

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!

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Guest favourite
A vibrant sunrise is captured over the Atlantic Ocean, illuminating the horizon with warm hues of orange and yellow. The sun's rays radiate across the calm water, casting reflections on the sandy beach below.
Condo in Hilton Head Island
4.96 out of 5 average rating, 222 reviews

Ocean Overlook - The Ultimate Vacation Experience

LUXURIOUS, 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! 3RD FLOOR! CORNER UNIT! PRIVATE BALCONY! OCEAN VIEWS FROM EVERY ROOM! WATCH EVERY SUNRISE & SUNSET! 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**

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Top Guest favourite
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.
Condo in Hilton Head Island
4.91 out of 5 average rating, 128 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!

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Top Guest favourite
Condo in Sea Pines
5.0 out of 5 average rating, 125 reviews

5 Star Location-Harbourtown-Walkable Area

Escape to our luxury villa in Hilton Head's exclusive Harbour Town in the gated Sea Pines Resort! A short walk from Harbour Town Marina, which offers enertainment, dining, shopping, water sports, cruises, golf, tennis, and a pier. You will have access to The Sea Pines Beach Club, a short trolly, bike or car ride away. This private 3rd-floor impeccilbly appointed 'coastal chic' retreat does not share any walls and offers serene lagoon views from a private balcony.

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Popular amenities for Hilton Head Island rentals with a pool

When is the best time to visit Hilton Head Island?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$280 NZD$282 NZD$333 NZD$367 NZD$366 NZD$429 NZD$401 NZD$345 NZD$301 NZD$289 NZD$289 NZD$282 NZD
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