
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.

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!
4.98 out of 5 average rating, 121 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
4.95 out of 5 average rating, 109 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
4.87 out of 5 average rating, 406 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!
5.0 out of 5 average rating, 114 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.
4.97 out of 5 average rating, 167 reviews
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!
4.98 out of 5 average rating, 320 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.
5.0 out of 5 average rating, 123 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
4.99 out of 5 average rating, 117 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
4.89 out of 5 average rating, 310 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.
4.9 out of 5 average rating, 104 reviews
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.
4.99 out of 5 average rating, 453 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!
4.92 out of 5 average rating, 276 reviewsPopular amenities for Hilton Head Island rentals with a pool
House rentals with a pool

Stately Governors Quarters-Pet Friendly, Fenced In
4.98 out of 5 average rating, 110 reviews
Palmetto Dunes House: Private Pool, PDBeach, Golf
4.86 out of 5 average rating, 121 reviews
Large home, beach close, pool
4.94 out of 5 average rating, 238 reviews
Palmetto Dunes Home on 1st Tee Fazio Golf Course
4.85 out of 5 average rating, 156 reviews
Cozy beach house w/Private Heated Pool near park
4.98 out of 5 average rating, 135 reviews
Lovely 3BR in Palmetto Dunes w/ new pool & spa
4.96 out of 5 average rating, 136 reviews
4BR | Pool, Spa & Walk to Beach | 32 Baynard Cove
4.96 out of 5 average rating, 25 reviews
SeaPines - Private Beach Path, Private Pool, Bikes
4.88 out of 5 average rating, 73 reviewsApartment rentals with a pool

Oceanfront, 3rd floor, King Bed
4.91 out of 5 average rating, 132 reviews
Exclusive Oceanfront Decorator Decor Spacious Bdrm
4.89 out of 5 average rating, 162 reviews
1BR/2BA condo w/private beach access in Shipyard
4.98 out of 5 average rating, 151 reviews
Oceanfront Luxe KING BED 65TV Beach Bar Pickleball
4.98 out of 5 average rating, 368 reviews
1st flr villa few mins walk to beach pools & pball
4.98 out of 5 average rating, 232 reviews
Oceanside Resort - Private Beach Access - 3 Pools
4.97 out of 5 average rating, 119 reviews
Gorgeous OCEAN Views! Resort Amenities & Beach!
4.94 out of 5 average rating, 160 reviews
Spacious Villa in Hilton Head Resort! STR#024945
4.94 out of 5 average rating, 147 reviewsOther holiday rentals with a pool

Walk to the Beach, One Level Villa, COMFY beds
4.91 out of 5 average rating, 141 reviews
Ocean Gate 13 Walk to beach villa with pickleball
4.91 out of 5 average rating, 195 reviews
5BR: 400 steps to beach Private Pool+Hot Tub+Sauna
4.95 out of 5 average rating, 55 reviews
Family Retreat | 1 Min to Beach | Pool Spa Theater
5.0 out of 5 average rating, 15 reviews
Private Pool | Golf | Exq. Coffee | Seascape
4.93 out of 5 average rating, 44 reviews
Walk2Beach~Pool~Putting Green~Fenced Yard~EV
4.99 out of 5 average rating, 70 reviews
Canopy House | Walk to Harbour Town | Marshfront
5.0 out of 5 average rating, 4 reviews
Sea Pines Villa•Steps to Beach•Coffee Bar•King Bed
4.94 out of 5 average rating, 83 reviewsWhen 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 | €186 | €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 |
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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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