
Vacation rentals with a pool in Hilton Head Island
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Hilton Head Island

Total vacation rentals
Explore 6,120 vacation rentals in Hilton Head Island

Nightly prices starting at
Hilton Head Island vacation rentals start at G$8,364 GYD per night before taxes and fees

Verified guest reviews
Over 138,130 verified reviews to help you choose

Family-friendly vacation rentals
5,010 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
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 vacation 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.

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!
FamilyValueAccess

W2Bch*4TVs*1GIG I*PetsWC *WiFi*4King ßds*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
FamilyValueParks

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
LocationFamilySleep quality

Exclusive Oceanfront Decorator Decor Spacious Bdrm
Beautiful 2 Bedroom Oceanfront Condo just steps from the Beach renovated in 2022 with many upgrades such as: *Freshly painted with all new flooring throughout *New 55 inch Samsung Smart QLED TV in living room *New 43 inch Samsung Smart QLED TV in both bedrooms *New Samsung French Door Refrigerator *New Keurig *New Tommy Bahama bedding and pillows *New ceiling fans with LED lights *Updated bathrooms *LED lights throughout *New closet fixtures *New doorknobs & hinges *Non Smoking Unit *No Pets
FamilyLocationComfort

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!
ValueLocationParking

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.
LocationValueAmenities

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!
ValueLocationLayout

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.
FamilyLocationAccess

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
FamilyLocationLayout

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
FamilyLocationTV

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!
LocationValueWalkability

Ocean Front Resort Condo
Enjoy Coastal Cottage Living in a lovely 540 sq ft one bedroom vacation villa within the activity-filled gated resort of Hilton Head Beach and Tennis. Completely remodeled from with all new fixtures, furnishings, housewares and accessories, this charming beach villa has just opened its doors for guests in March 2019. Amenities include coffee, popcorn, breakfast treats and bottled water to consume; and beach towels, chairs, umbrellas and other items to borrow while here.
FamilyLocationAmenities
Popular amenities for Hilton Head Island rentals with a pool
House rentals with a pool

Stately Governors Quarters-Pet Friendly, Fenced In
FamilyLocationBathroom

Wonderful Island's Retreat (With Private Pool)
FamilyValueCheck-in

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

Palmetto Dunes House: Private Pool, PDBeach, Golf
ValueLocationHospitality

Cozy beach house w/Private Heated Pool near park
ValueLocationNearby

Blue Sky Villa: Beach/pets/golf/tennis/pickleball
ValueLocationWifi

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

SeaPines - Private Beach Path, Private Pool, Bikes
FamilyLocationCondition
Condo rentals with a pool

Oceanfront Luxury! KING BED Beach Bar & Pickleball
FamilyLocationCheckout

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

1st flr villa few mins walk to beach pools & pball
FamilyLocationBathroom

Oceanfront Luxe KING BED 65TV Beach Bar Pickleball
LocationValueDecor

Spacious Villa in Hilton Head Resort! STR#024945
ValueFamilyCleanliness

My Blue Heaven, Direct Ocean Front View
FamilyValueBiking

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

TOP Floor Oceanfront | Remodeled | Coligny Beach
LocationValueGetting around
Other vacation rentals with a pool

Spacious dog-friendly villa, walk to the beach
LocationFamilyIndoor spaces

Closest to Beach Path, Screened Porch, 1 dog ok
FamilyValueComfort

Ocean Gate 13 Walk to beach villa with pickleball
ValueFamilyLayout

HHI South Forest beach/WLK TO BEACH, dining, pool
FamilyLocationPets

Walk to the Beach, One Level Villa, COMFY beds
ValueLocationCleanliness

Harbour Town Marina Studio | Walk to Lighthouse
FamilyValueBeach

Canopy House | Walk to Harbour Town | Marshfront
LocationFamilyComfort

Renovated 1BR HHI – Walk to Beach & Salty Dog Café
FamilyLocationNearby
When is the best time to visit Hilton Head Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$34,291 GYD | G$34,500 GYD | G$40,773 GYD | G$44,955 GYD | G$44,746 GYD | G$52,482 GYD | G$49,137 GYD | G$42,237 GYD | G$36,800 GYD | G$35,337 GYD | G$35,337 GYD | G$34,500 GYD |
| 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
- Hunting Island State Park Beach
- Harbour Town Golf Links
- 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
- Fort Pulaski National Monument
- Owens-Thomas House
- Cathedral of Saint John the Baptist
- Tybee Island Marine Science Center
- Tybee Island Light Station
- Seabrook Island Beach
- Henry C Chambers Waterfront Park
- 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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- Wildlife Beaufort County
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- Cooking South Carolina
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- Art workshops South Carolina
- Water sports South Carolina
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