
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.

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

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

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.

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!

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.

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.

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.

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

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!

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.

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

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
House rentals with a pool

Stately Governors Quarters-Pet Friendly, Fenced In

Palmetto Dunes House: Private Pool, PDBeach, Golf

Large home, beach close, pool

Resort-Style Pool, Cute House 88 Steps to Sand

Cozy beach house w/Private Heated Pool near park

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

Palmetto Dunes Home on 1st Tee Fazio Golf Course

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

Ocean View! Remodeled! Steps to beach/Pool/Bar

Oceanfront Luxe KING BED 65TV Beach Bar Pickleball

Oceanfront Luxury! KING BED Beach Bar & Pickleball

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

Spacious Villa in Hilton Head Resort! STR#024945

Beach Front Villa Oak Tree Lined Views to Water

Exclusive Oceanfront Decorator Decor Spacious Bdrm

*New* Easy Breezy at Hilton Head Beach & Tennis
Other holiday rentals with a pool

Walk to the Beach, One Level Villa, COMFY beds

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

Jim's Stunning Direct Ocean Front 2BR Villa

Oceanfront Scandi Oasis Amazing View & Heated Pool

Beautiful Oceanfront Condo at Island Club

Incredible Hilton Head condo - private beach!

Beach Haven | Quiet Corner | Easy Beach Access

Coastal Fairways
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 | €143 | €144 | €170 | €187 | €187 | €219 | €205 | €176 | €153 | €147 | €147 | €144 |
| 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 |
Destinations to explore
- Four Corners Holiday rentals
- Atlanta Holiday rentals
- Orlando Holiday rentals
- Myrtle Beach Holiday rentals
- Charlotte Holiday rentals
- Gatlinburg Holiday rentals
- Savannah Holiday rentals
- Pigeon Forge Holiday rentals
- Jacksonville Holiday rentals
- Charleston Holiday rentals
- North Myrtle Beach Holiday rentals
- Kissimmee Holiday rentals
- Rentals with beach access Hilton Head Island
- Apartment rentals Hilton Head Island
- Mansion rentals Hilton Head Island
- Hotel rooms Hilton Head Island
- Beach house rentals Hilton Head Island
- Villa rentals Hilton Head Island
- Rentals with a kayak Hilton Head Island
- Serviced apartment rentals Hilton Head Island
- Rentals with a sauna Hilton Head Island
- Rentals with breakfast Hilton Head Island
- Rentals with lake access Hilton Head Island
- Beach apartment rentals Hilton Head Island
- Townhouse rentals Hilton Head Island
- Family-friendly rentals Hilton Head Island
- Waterfront rentals Hilton Head Island
- Rentals with a hot tub Hilton Head Island
- House rentals Hilton Head Island
- Flat rentals Hilton Head Island
- Pet-friendly rentals Hilton Head Island
- Rentals with an accessible-height bed Hilton Head Island
- Rentals with an accessible-height toilet Hilton Head Island
- Luxury rentals Hilton Head Island
- Resort rentals Hilton Head Island
- Beachfront rentals Hilton Head Island
- Rentals with pools Beaufort County
- Rentals with pools South Carolina
- Rentals with pools United States
- 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
- Cultural tours Beaufort County
- Wildlife Beaufort County
- Things to do South Carolina
- Wildlife South Carolina
- Cooking South Carolina
- Food tours South Carolina
- Cultural tours South Carolina
- Outdoors South Carolina
- Landmarks South Carolina
- Tastings South Carolina
- Art workshops South Carolina
- Water sports South Carolina
- Things to do United States
- Shopping and fashion United States
- Dining United States
- Museums United States
- Cultural tours United States
- Architecture United States
- Workouts United States
- Flying United States
- Art workshops United States
- Wellness United States
- Food tours United States
- Wildlife United States
- Landmarks United States
- Water sports United States
- Performances United States
- Tastings United States
- Galleries United States
- Cooking United States
- Beauty United States
- Outdoors United States







