
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 $51 SGD 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.

Hilton Head Island VILLA: STEPS 2 Beach & Coligny!
Welcome to The Hilton Head Islander! A cozy retreat meticulously maintained for up to 6 guests. Situated in North Forest Beach, it's near Hilton Head's treasures beaches, bars, shops, and eateries. Enjoy a 6-min walk to the beach and the beautiful Celebration Park and 2-min walk to Coligny Plaza! Essentials like toiletries, Kcups, beach gear, & more are provided. While cozy with one bathroom, your comfort is guaranteed. Relax by the onsite pool and enjoy the spectacular beaches. Enjoy your stay!
FamilyValueBathroom

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
FamilyLocationCheck-in

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
LocationFamilyView

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.
ValueLocationIndoor spaces

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!
FamilyValueParking

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.
LocationFamilyGrill

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.
FamilyLocationAir conditioning

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
LocationValueBeach

Stately Governors Quarters-Pet Friendly, Fenced In
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!
LocationFamilyBiking

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
LocationFamilyLaundry

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!
ValueFamilyLayout

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.
LocationValueIndoor spaces
Popular amenities for Hilton Head Island rentals with a pool
House rentals with a pool

Walk to Beach-Amazing New Home-Hot Tub-Heated Pool
ValueLocationAmenities

Palmetto Dunes House: Private Pool, PDBeach, Golf
LocationValueCleanliness

Wonderful Island's Retreat (With Private Pool)
LocationValueAccess

Cozy beach house w/Private Heated Pool near park
ValueLocationKitchen

Large home, beach close, pool
LocationFamilyBack garden

Palmetto Dunes Home on 1st Tee Fazio Golf Course
ValueLocationComfort

Resort-Style Pool, Cute House 88 Steps to Sand
ValueLocationWalkability

Lovely 3BR in Palmetto Dunes w/ new pool & spa
ValueLocationBack garden
Apartment rentals with a pool

Oceanview Luxury! King Bed 75"TV Pickleball & Bar
LocationFamilyWalkability

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

Hilton Head Beach & Tennis Resort Ocean View!
ValueFamilyView

The Lookout - A Modern Beach Retreat (Oceanfront)
FamilyValueAccess

Ocean View KING BED 75"TV Beach Bar Pickleball GYM
ValueLocationCheck-in

Exclusive Oceanfront Decorator Decor Spacious Bdrm
ValueFamilyHiking

3BR Condo w Pool, Tennis & Turtle Views
FamilyValueBathroom

Breathtaking OCEAN VIEW |Pool & Coligny| TOP FLOOR
LocationValueCleanliness
Other holiday rentals with a pool

Beachfront Resort 2B Golf Beach Pool Pickleball
ValueFamilyCheckout

Direct Ocean Front S. Forest Beach
LocationValueCleanliness

Coastal Fairways
FamilyLocationCheckout

Luxury 2026 Renovation+Oceanfront Views!
LocationFamilyCondition

Palmetto Dunes Beach House
LocationFamilyCleanliness

Private Pool ~ Cabana ~ 5 Deer Run Lane
FamilyLocationCondition

SeaPines - Private Beach Path, Private Pool, Bikes
LocationFamilyBiking

Family Memories Are Made Better at Deer Run
FamilyConditionCleanliness
When is the best time to visit Hilton Head Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $208 SGD | $209 SGD | $247 SGD | $272 SGD | $271 SGD | $318 SGD | $298 SGD | $256 SGD | $223 SGD | $214 SGD | $214 SGD | $209 SGD |
| Avg. temp | 10°C | 12°C | 16°C | 19°C | 23°C | 27°C | 28°C | 28°C | 25°C | 20°C | 15°C | 12°C |
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- Rentals with pools Beaufort County
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- Savannah Historic District
- Coligny Beach Park
- Forsyth Park
- Harbour Town Golf Links
- Hunting Island State Park Beach
- North Beach, Tybee Island
- Tybee Beach Pier and Pavilion
- Edisto Beach State Park
- Bonaventure Cemetery
- Hunting Island State Park
- Shelter Cove Towne Centre
- Wormsloe Historic Site
- Kiawah Beachwalker Park
- Oatland Island Wildlife Center
- Skidaway Island State Park
- Savannah College of Art and Design
- Owens-Thomas House
- Fort Pulaski National Monument
- Cathedral of Saint John the Baptist
- Tybee Island Marine Science Center
- Tybee Island Light Station
- Henry C Chambers Waterfront Park
- Seabrook Island Beach
- Sheldon Church Ruins
- Things to do Hilton Head Island
- Wildlife Hilton Head Island
- Cultural tours Hilton Head Island
- Things to do Beaufort County
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- Art workshops South Carolina
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