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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 €35 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 1,000 rentals that welcome pets

  • Rentals with dedicated workspaces

    3,280 properties have a dedicated workspace

  • Wifi availability

    6,120 of Hilton Head Island holiday rentals include wifi 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, 109 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

Top guest favourite
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.
Home in Hilton Head Island
4.87 out of 5 average rating, 405 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

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.
Flat 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
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.
Apartment in Hilton Head Island
5.0 out of 5 average rating, 113 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 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.
Apartment in Hilton Head Island
4.98 out of 5 average rating, 365 reviews

Ocean Front Resort Villa

Freshly decorated in coastal cottage decor, this 540 sq ft one bedroom villa sleeps up to 6 and is located within the activity-filled Hilton Head Beach and Tennis Resort. The villa was recently remodeled with all new kitchen, bathroom and fixtures and is just 50 steps to gorgeous beach. The views from the living room include ocean, oceanfront pool , beach bar and grill, and pond with fountain. The villa is full of amenities including beach towels, beach chairs, beach umbrella and much more.

Top guest favourite
A cozy living room features a modern fireplace and a large flat-screen TV mounted on the wall. Light enters through expansive sliding glass doors, leading to a deck. Comfortable seating is arranged around a circular coffee table, with decorative pillows adding subtle touches.
Townhouse in Sea Pines
4.91 out of 5 average rating, 195 reviews

Ocean Gate 13 Walk to beach villa with pickleball

This villa is perfect for the family beach vacation! We have little ones ourselves, so we've got all the gear needed to make this a comfortable and relaxing stay. We LOVE this villa because of its screened in porch, FREE TENNIS, and proximity to the beach. The screened in porch allows you to enjoy breakfast and happy hour free from mosquitoes and close enough to hear the waves! The beaches are far less crowded than other areas of the island, and it's very close to Sea Pines and Coligny Plaza.

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, 123 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 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.
Home in Hilton Head Island
4.99 out of 5 average rating, 117 reviews

6 BR, Sleeps 26, Beach Time

Just a short walk down Folly Field to the beach & locally managed by the Owner. This brand new beach house has 6 bedrooms and 4 full bathrooms. Linens, Bath Towel sets & Pool Towels included. An Amazing bunk room/play room with 6 full size bunk beds, high end furnishings, fully equipped kitchen, dining for the entire crew, 2 huge balconies with lovely lagoon views, large outdoor living area with television and shaded pool. We have thought of everything & we are at your service! PN: 040312

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.
Apartment in Hilton Head Island
4.91 out of 5 average rating, 132 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!

Top guest favourite
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
4.9 out of 5 average rating, 104 reviews

Spacious dog-friendly villa, walk to the beach

Welcome to 640 Queens Grant, 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.

Guest favourite
A light-filled living area features a cozy seating arrangement with a white sofa and a coffee table. The kitchen can be seen in the background, highlighting modern cabinetry and a casual dining setup. Natural textures are present through the woven rug and wood accents.
Apartment in Hilton Head Island
4.83 out of 5 average rating, 193 reviews

Close to BEACH bar&grill! Sleeps 6, 2 bed 2 bath!

5 minute walk to closest beach(with beach bar). 19 minute walk to Coligny beach! COME STAY at this charming beach-walk community! The pool is at the bottom of the stairs, 3/4 of a mile to Coligny circle with grocery store, shops, and restaurants. “COPPERTONE DAYS” features: 4 twin beds(memory foam), a master bedroom/master bath, laundry room, and a stocked kitchen+ highchair and a crib! We can usually accommodate early arrivals! Short term rental permit#: 029154

Guest favourite
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.
Home in Hilton Head Island
4.92 out of 5 average rating, 276 reviews

Wonderful Island's Retreat (With Private Pool)

Wonderful Island’s Retreat is found in the heart of Hilton Head Island. It is beautifully decorated with upscale decor. The decoration is personally chosen to fit the ambiance of a beach house. The beach is approximately 5 minutes away in car distance, 10 minutes in bike distance, and 15 to 20 minutes walking distance. In addition to that, you have nearby bike trails, shopping centers, and restaurants. This location is exceptional for anyone looking to visit HHI!

Popular amenities for Hilton Head Island rentals with a pool

When is the best time to visit Hilton Head Island?

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