
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 €34 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!

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 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!

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

Beachfront Resort 2B Golf Beach Pool Pickleball
✨Gated Beachfront Golf Resort✨ Beach Access via 2 Private Boardwalks Golf, Tennis, Pickleball, Pool Gorgeous Modern Coastal Villa Panoramic Golf & Lagoon Views! Walk or Bike to Beach Enjoy Sonesta Restaurants & Bars Walk to Golf Club & Pub! Beautiful Lush & Wooded location! Enjoy watching Wildlife! Sunny 1st Floor KING BED Master 3 XL SmartTVs WIFI 287 mps Fully Stocked Kitchen 2 Renovated Bathrooms Washer/Dryer Beach Chairs, Boogie Boards & More! BBQ Bike & Walk Paths Close to Coligny!

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

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.

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.
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

Wonderful Island's Retreat (With Private Pool)

Cozy beach house w/Private Heated Pool near park

Palmetto Dunes Home on 1st Tee Fazio Golf Course

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

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

Luxury Pool Home in Sea Pines | Sleeps 15
Apartment rentals with a pool

Oceanfront Luxury! KING BED Beach Bar & Pickleball

*New* Easy Breezy at Hilton Head Beach & Tennis

Across from the beach and Coligny Plaza!

Exclusive Oceanfront Decorator Decor Spacious Bdrm

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

Reno’d 1st flr walk to beach pools hot tub & pball

TOP Floor Oceanfront | Remodeled | Coligny Beach

Oceanfront Luxe KING BED 65TV Beach Bar Pickleball
Other holiday rentals with a pool

Jim's Stunning Direct Ocean Front 2BR Villa

Family Retreat | 1 Min to Beach | Pool Spa Theater

Luxury home/tiki bar/pool/private beach boardwalk

Family Memories Are Made Better at Deer Run

Modern Home ~ Golf Course Views ~ .8 Mile to Beach

Private Pool | Golf | Exq. Coffee | Seascape

Luxury Palmetto Dunes Retreat with Private Pool

Marsh Views | Pool, HotTub, Game Room&Pet Friendly
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 | €141 | €142 | €168 | €185 | €184 | €216 | €202 | €174 | €151 | €145 | €145 | €142 |
| 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
- 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
- Kiawah Beachwalker Park
- Wormsloe Historic Site
- Oatland Island Wildlife Center
- Skidaway Island State Park
- Savannah College of Art and Design
- Fort Pulaski National Monument
- Cathedral of Saint John the Baptist
- Owens-Thomas House
- 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
- Water sports Hilton Head Island
- Wildlife Hilton Head Island
- Cultural tours Hilton Head Island
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