
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 5,250 holiday rentals in Hilton Head Island

Nightly prices starting at
Hilton Head Island holiday rentals start at $70 NZD per night before taxes and fees

Verified guest reviews
Over 128,680 verified reviews to help you choose

Family-friendly holiday rentals
4,310 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 900 rentals that welcome pets

Rentals with dedicated workspaces
2,770 properties have a dedicated workspace

Wi-Fi availability
5,240 of Hilton Head Island holiday 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.

Oceanfront Luxe KING BED 75TV Beach Bar Pickleball
PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨ Ocean Sunrise / Hear the Waves ✨ Oceanfront Balcony FREE Tennis, Gym, Pickleball HGTV Decorator Renovation KING BED + 75" & 65" SmartTV s Expanded Bedroom MARBLE BATHROOM WiFi 515 Mbps Coastal Décor TOP FLOOR w/Elevator Couples Escape! Beach Chairs, Boogie Boards, Ice Chest & More! RESORT No Resort Fees Beachfront Pool w/Tiki Bar & Grille Sports Bar 2nd Pool Bike Rental in Resort Gated 24/7 Security Free Island Trolley Stop (April-Sept)

Beachfront Resort 2b Golf Lagoon Pickleball Tennis
✨Top Airbnb Guest Favorite Home✨ Gated Beachfront Golf Resort! Beach, Golf, Pool, Spa, Restaurants & Bars FREE Pickleball & Tennis - across street HGTV Decorator designed Panoramic Golf & Lagoon Views XL Double Porch Lush Scenery - Tons of Wildlife! Coastal Décor Sunny 1st Floor End Unit KING BED + 2 QUEENS 3 XL SmartTVs FAST WIFI & CABLE Chef's Kitchen Washer/Dryer BBQ Beach Cart, Chairs, Boogie Boards, Ice Chest Walk/Bike to Beach Walk to Golf Club & Pub Close to Coligny Summer Beach Shuttle

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!

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!

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.

Oceanfront Luxe KING BED 65TV Beach Bar Pickleball
PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! Beachfront Balcony Watch Sunrise/Hear Waves 1 min to Beach Boardwalk! Beachfront Pool, Tiki Bar & Grille FREE Pickleball, Tennis & Gym HGTV Designer Renovation Two 65" SmartTVs KING BED Expanded Bedroom Blackout Sleeping Marble Spa Bath Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESORT Bike Rentals on Site 4 Beach Boardwalks 3 Restaurants Beach Bar/Sports Bar Gated 24/7 Security Seasonal Island Trolley Stop

Beachfront Resort 2B Golf Beach Pickleball Tennis
✨Top 10% Guest Favorite✨ Gated Beachfront Resort Golf, Tennis, Pickleball, Pool, Restaurants & Bars Gorgeous Sunny Villa Panoramic Lagoon & Golf Views! Beautiful & Lush Scenery Huge Old Oaks dripping in Spanish Moss! Walk/Bike to Beach Abundant Wildlife! Walk to Shipyard Golf Club & Pub! Modern Coastal Sunny 1st Floor KING BED Master 3 XL SmartTVs WIFI 287 mps Fully Stocked Kitchen Walk-in Shower Washer/Dryer Beach Chairs, Boogie Boards & More! BBQ Bike & Walk Paths Close to Coligny!

Hilton Head Villa With Golf View, Stroll to beach
Proudly selected by HGTV as one of nine “Wow Worthy Vacation Homes and Design on HHI”, alongside the 2020 HGTV Dream Home. This upscale home offers seamless in/outdoor living and a generous granite kitchen. During your stay, enjoy the comforts of home - from the plush sectional sofa and Smart TV's, to the hotel-like King bed and en suite bathroom in the master suite. Enjoy the indoor/ outdoor living of your own private villa in the exclusive Greens community of Shipyard Plantation.

1st Floor, 1 BR Condo - Steps to Beach and Pool!
Renovated 1st floor, 1 BR getaway located across the street from the beach! Private deck overlooks community pool just steps from back door. Great location - plenty of restaurants, bars, shopping and grocery stores nearby. New appliances, smart TVs in living area and bedroom (cable in living room). Bedroom has a queen-size bed and brand new leather recliner sofa in the living room. Rental includes 2 beach chairs, cart and umbrella. Absolutely no pets and no smoking allowed.

Island Club 4502-Beautiful Ocean View
Our two bedroom ocean view villa will comfortably sleep 5-7. Our unit has an oversized balcony. The master suite includes a king size bed and master bath. The guest room includes two full size beds with its own bath. The Island Club maintains gas grills from a picnic area. The Island Club has nine free tennis courts, a large heated pool with a children's pool, a tanning pool, fitness center, hot tub, basketball, and bike rentals. Check out our condo's reviews at VRBO 513502.

Ocean Overlook II - The Penthouse Experience
LUXURIOUS, PENTHOUSE, DIRECT OCEANFRONT HOME! UNOBSTRUCTED OCEAN VIEWS! SO CLOSE YOU CAN HEAR THE WAVES CRASH WITH THE WINDOWS CLOSED! DIRECT BEACH ACCESS! POOL ACCESS! ALL BRAND NEW! 4TH FLOOR (TOP FLOOR)! PRIVATE BALCONY! MILLION DOLLAR OCEAN VIEWS! SPA SHOWER! KING BED! CAN SLEEP 4! THIS IS LUXURY LIVING WITH NO RESORT AMENITY CHARGES! SAVE THOUSANDS OF DOLLARS COMPARED TO OTHER NAMED RESORTS LUXURY HOTEL PROPERTIES! **UPGRADED INTERNET & HD TV PACKAGE + FREE AMENITIES**

Jim's Chic Direct Oceanfront 2BR Villa
Lovely 4th floor villa with a breathtaking, unobstructed ocean view from the living room and master bedroom. Two bedroom suites, each with separate baths. Fully appointed kitchen - granite countertops, updated cabinets, and stainless steel appliances. Walk to all of the amazing shops & restaurants of Coligny Plaza and the brand-new Celebration Park. Jim Says: “I personally stay in each of my units to ensure they are maintained to my highest level of expectations.”
Popular amenities for Hilton Head Island rentals with a pool
House rentals with a pool

6 BR, Sleeps 26, Beach Time

Governor’s Quarters Pet Friendly, Fenced in Yard

Wren's Nest - 4BR SeaPines Retreat+Backyard Oasis

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

Palmetto Dunes House: Private Pool, PDBeach, Golf

Private Pool | Golf | Exq. Coffee | Seascape

Peaceful Harbour Town Treehouse with Marsh Views

Perfect spot for a great getaway
Condo rentals with a pool

Breathtaking OCEAN VIEW |Pool & Coligny| TOP FLOOR

After Dune Delight | Spacious Condo, Full Kitchen

KING BED 1BR Oceanview Top Floor Villa

Ocean Views at Villamare, Steps to the Beach!

HHB&T 3 min walk to the sand

Coastal Comfort! Condo in beachfront resort.

Avail July 4th! King Bed/pools/3 blocks to beach

Ocean Front Beach & Tennis Resort 2 BR 2 BA Villa
Other holiday rentals with a pool

Upscale Retreat w Pool & Spa | Palmetto Dunes

SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest

Stunning Ocean View | King Bed | Beach/Pool Resort

Sea la Vie @Fiddler's Cove - Fitness Room

1st floor, oceanfront, 65" TV, pickleball, 2 pools

SeaPinesVilla - Harbor Town, Free Bikes, Pets OK

Pet friendly condo with amazing Broad Creek views

Walk to the Beach! Coastal Villa w Large Balcony!
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 | $289 NZD | $291 NZD | $344 NZD | $352 NZD | $352 NZD | $404 NZD | $414 NZD | $356 NZD | $310 NZD | $298 NZD | $298 NZD | $291 NZD |
| 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
- Rentals with pools South Carolina
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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
- Harbour Town Lighthouse
- Bonaventure Cemetery
- Edisto Beach State Park
- Wormsloe Historic Site
- Skidaway Island State Park
- Oatland Island Wildlife Center
- Jepson Center for the Arts
- Hunting Island State Park
- Shelter Cove Towne Centre
- Kiawah Beachwalker Park
- Fort Pulaski National Monument
- Cathedral of Saint John the Baptist
- Savannah College of Art and Design
- Seabrook Island Beach
- Owens-Thomas House
- Tybee Island Marine Science Center
- Tybee Island Light Station
- Things to do Hilton Head Island
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- Nature and outdoors Hilton Head Island
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