
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 $51 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 900 rentals that welcome pets

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

Wifi availability
5,240 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.

A "WOW" factor-Palmetto Dunes Retreat in Turnberry
Come for a relaxing time in Palmetto Dunes Resort at Turnberry Village- centrally located on Hilton Head overlooking the 9th & 10th hole of the Robert Trent golf course. This villa has it all- updated villa, deck with golf course view, secluded location, and fully equipped with modern decor, appliances, and linens to make your stay a memorable and enjoyable vacation with 3 miles of sun-kissed beaches, world-class golf, restaurants, shopping and 11 miles of lagoons to enjoy. {STR Permit#073278}

Wide Ocean View! KING BED Beach Bar Pickleball GYM
✨Top 5% Airbnb Home✨ BIG OCEAN VIEWS FROM LIVING ROOM & BALCONY! Oceanfront Building Steps to Beach Boardwalk, Pool & Tiki Bar! FREE Pickleball, Tennis, Gym & More HGTV Featured Decorator 100% NEW Luxury renovation KING BED + 75" & 65" Smart TVs Expanded Bedroom Luxe Marble Kitchen & Bath Quiet Top Floor Well-designed 540 sq. ft. Elevator Beach Chairs + More RESORT: Oceanfront Pool & Bar & Grille Restaurants Sports Bar 4 Beach Boardwalks Bike Rental Gated 24/7 Security FREE Island Trolley Stop

KING BED Luxury! 65"TV + Beach Bar FREE Pickleball
✨Airbnb Top Guest Favorite✨ Oceanfront Building BIG Ocean View from Balcony Steps to Beach Bar & Pool FREE Gym, Pickleball Tennis Volleyball & More! 100% NEW HGTV Designer Renovation! KING BED 75" & 65" SmartTVs Beach Chairs, Boogie Boards, Ice Chest & More Marble Kitchen/Spa Bath Top Floor WiFi 557 Mbps Elevator RESORT: No Resort Fees Huge Oceanfront Pool Tiki Beach Bar & Grille- Feb-Nov Sports Bar Bike Rental Gym & Tennis Gated 24/7 Security Free Island Trolley (Apr-Sept) 4 Beach Boardwalks

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 KING BED 65"TV Beach Bar Pickleball GYM
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

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

Beach Resort! Luxury Golf & Lagoon View Pickleball
Gated Beach & Golf Resort! ✨Top 5% Airbnb Guest Favorite✨ Beach, Golf, Pool, Spa, Restaurants & Bars FREE Pickleball & Tennis - across street HGTV Decorator designed Panoramic Golf & Lagoon Views 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 Overlook - The Ultimate Vacation Experience
LUXURIOUS, 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! 3RD FLOOR! CORNER UNIT! PRIVATE BALCONY! OCEAN VIEWS FROM EVERY ROOM! WATCH EVERY SUNRISE & SUNSET! 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**

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!

Oceanfront Scandi Oasis Amazing View & Heated Pool
Villa Aalto is a new Scandinavian style oceanfront oasis created for ease and relaxation throughout your beach vacation. The streamlined interior offers high-end finishes and luxurious hotel-like amenities, with a fully functional kitchen and serene living area overlooking the ocean. The year-round heated pool and private path to the beach make for stress-free days, but the close proximity to Coligny allows you to bike to restaurants, playgrounds and shops within minutes as well.

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.”

KING BED!Ocean View, Free Bikes Poolside 3rd Floor
Pack your flip-flops and get ready for fun—this sunny poolside villa on Hilton Head Island is your ticket to the ultimate coastal escape! Just steps from the beach and the refreshing Atlantic breeze, this vibrant retreat serves up the perfect mix of relaxation, adventure, and ocean views. Start your day with coffee on the balcony, soak up the sun by the pool, then hop on one of our free bikes to cruise the island like a local! The perfect getaway starts right here!
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

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

Steps to Beach, Pool, 5BR, Great Location

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

Palmetto Dunes House: Private Pool, PDBeach, Golf

Private pool/spa : pool heat available : Kg master

Peaceful Harbour Town Treehouse with Marsh Views
Apartment rentals with a pool

Big OceanView Beach Bar FREE Pickleball Tennis Gym

My Blue Heaven, Direct Ocean Front View

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

Ocean Views at Villamare, Right on the Beach!

Oceanside Resort - Private Beach Access - 3 Pools

Few mins walk to beach 1st flr pools hot tub pball

Stunning Ocean & Coastal Views | Resort Perks!

1 Minute walk to the beach *Amazing ocean view*
Other holiday rentals with a pool

#4203 Renovated/1BR/2BA/Direct Ocean Views/Sofa Bd

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

SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest

Oceanfront Luxury! KING BED Beach Bar + Pickleball

Palmetto Dunes/Pet Friendly/Beach Walk/Pool/Golf

Chic Coligny walkable beach villa w/Pool

Oceanfront Condo w/ Balcony | Sea Side Villas HHI

New Listing! Penthouse Oceanfront Sea Cloisters Co
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 | $211 SGD | $212 SGD | $250 SGD | $257 SGD | $257 SGD | $294 SGD | $302 SGD | $259 SGD | $226 SGD | $217 SGD | $217 SGD | $212 SGD |
| 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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- Coligny Beach Park
- Savannah Historic District
- Forsyth Park
- Harbour Town Golf Links
- Hunting Island State Park Beach
- Tybee Beach Pier and Pavilion
- North Beach, Tybee Island
- Bonaventure Cemetery
- Harbour Town Lighthouse
- Edisto Beach State Park
- Wormsloe Historic Site
- Hunting Island State Park
- Shelter Cove Towne Centre
- Oatland Island Wildlife Center
- Skidaway Island State Park
- Cathedral of Saint John the Baptist
- Jepson Center for the Arts
- Kiawah Beachwalker Park
- Fort Pulaski National Monument
- 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
- Tours Hilton Head Island
- Nature and outdoors Hilton Head Island
- Sightseeing Hilton Head Island
- Food and drink Hilton Head Island
- Art and culture Hilton Head Island
- Things to do Beaufort County
- Tours Beaufort County
- Sightseeing Beaufort County
- Nature and outdoors Beaufort County
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