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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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Guest favourite
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.
Home in Palmetto Dunes
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

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 out of 5 average rating, 108 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!

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

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.

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, 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.

Top Guest favourite
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.
Condo in Hilton Head Island
4.97 out of 5 average rating, 235 reviews

Oceanfront Luxury! KING BED Beach Bar & Pickleball

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨See the Ocean Sunrise & Hear the Waves! ✨ Oceanfront Balcony FREE Tennis, Gym, Pickleball, Basketball, Volleyball HGTV Decorator Renovation KING BED + 75" & 65" SmartTV s Expanded Bedroom MARBLE BATHROOM Coastal Décor TOP FLOOR w/Elevator Beach Chairs, Boogie Boards, Ice Chest & More RESORT No Resort Fees! Beachfront Pool w/Bar & Grille Sports Bar 2nd Pool Bike Rental in Resort Gated 24/7 Security Free Island Trolley Stop (April-Sept)

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.

Top Guest favourite
A modern kitchen features smooth white cabinetry and granite countertops, complemented by stainless steel appliances. A double basin sink is situated near the window, with a microwave and oven built into the cabinetry. Soft, recessed lighting illuminates the workspace.
Condo in Hilton Head Island
4.95 out of 5 average rating, 241 reviews

Heron's Haven on Port Royal Sound, 2BR/2BA

Do you love nature? Walking on the beach? Birding? Photography? Tennis? Golf? Shopping? Wonderful restaurants? This is our beautiful Villa that is located in Port Royal Sound directly on the most unique and natural beach on the island. On both sides are public parklands and nature preserves to walk and view the wildlife. A perfect location to enjoy all that Hilton Head has to offer, yet it is quiet, serene and away from all the crowds. It's why we love it, and we're sure you will too.

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, 223 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**

Top Guest favourite
A neatly arranged bedroom features a spacious bed with a light-colored knitted blanket. Natural light filters through a nearby window, illuminating the room. Decorative wall art, displaying leaf motifs, complements the neutral color palette, while a circular mirror adds depth and brightness.
Condo in Hilton Head Island
4.89 out of 5 average rating, 304 reviews

Anchor at the Beach ⛱ Eat & Shop at Coligny plaza!

Oceanfront building with a side view of the ocean from the balcony. Park your car and walk to everything. This beautiful 2 bed/2 bath beach condo is perfect for your family vacation or romantic getaway. No streets to cross to get to the beach! Location, location, location. Gated entry, private, and just a 5-minute walk to all the amenities of Coligny Plaza (70 Shops & Restaurants). I also provide beach chairs, umbrella, and beach cart for your convenience during your stay! #072058

Top Guest favourite
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.
Villa in Hilton Head Island
4.97 out of 5 average rating, 133 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.

Top Guest favourite
Condo in Sea Pines
5 out of 5 average rating, 126 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.

Popular amenities for Hilton Head Island rentals with a pool

When is the best time to visit Hilton Head Island?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$278 NZD$279 NZD$330 NZD$364 NZD$362 NZD$425 NZD$398 NZD$342 NZD$298 NZD$286 NZD$286 NZD$279 NZD
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