Vacation rentals with a pool in Hilton Head Island

Find and book unique homes with a pool on Airbnb

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.

%{current} / %{total}1 / 1
Guest favorite
A scenic view is presented from the balcony, showcasing a coastal landscape with sprawling greenery and a sandy beach in the distance. The sky is clear with soft clouds, enhancing the tranquil atmosphere of the surroundings.
Condo in Hilton Head Island
4.92 out of 5 average rating, 196 reviews

OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6

Enjoy 4th Floor Ocean Views. Remodeled w/Upscale Finishes & Furniture. King Master Bdrm, 2 Dressers, Nightstands, TV, AC unit. Bath w/Body Spray Rain Shower, Comfort Hgt Toilet, Vanity w/Granite Counter/Storage. Hall BunkBeds w/Over Sized Drawers, USB Storage Alcoves, Oscillating Fan. Kitchen Pullout Drawer Cabinets, SS Apps, Double Oven, Granite Counters. Dining w/Table for 3/4 & 2 at Kitchen Bar. LR Queen SleeperSofa, Flat Screen TV, DVR, Chair, Ottoman, AC unit. Balcony Comfy Seating for 4.

Top guest favorite
A bright dining area offers a view of the ocean through open doors leading to a private beachfront balcony. Coastal décor is present on the round table, complemented by neutral tones and natural light streaming in from the outdoors.
Condo in Hilton Head Island
4.97 out of 5 average rating, 328 reviews

Luxury Oceanfront! KING BED 65"TV Pickleball & BAR

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR!! Beachfront Balcony ✨Top 1% of Airbnb✨ Beachfront Pool, Bar & Grille FREE Pickleball, Tennis, Gym, Vollyball & More HGTV Decorator Renovation KING BED + Two 65" SmartTVs Spa Bath w/Walk-in Shower Expanded Bedroom w/Blackout Sleeping Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESSORT Bike Rentals on Site 4 Beach Boardwalks 3 Restaurants Sports Bar Gated 24/7 Security Seasonal IslandTrolley Stop Bradley Beach

Top guest favorite
A wooden boardwalk leads to a sandy beach, where beach umbrellas dot the shoreline. Soft waves lap at the shore beneath a clear blue sky with fluffy clouds, creating a serene coastal scene.
Townhouse in Hilton Head Island
4.97 out of 5 average rating, 150 reviews

Beach Resort 2b Luxury Golf Lagoon View Pickleball

Gated Beach & Golf Resort! ✨ Top 10% Airbnb Guest Favorite ✨ Beach, Golf, Pool, Spa, Restaurants & Bars FREE Pickleball & Tennis – across the street HGTV Decorator designed Panoramic Golf & Lagoon Views! Big Porch Huge Old Oak trees! Coastal Décor Sunny 1st Floor End Unit KING BED + 2 QUEENS 3 XL SmartTVs FREE: FAST WIFI & CABLE Marble Kitchen Washer/Dryer Beach Cart, Chairs, Boogie Boards, Ice Chest BBQ Walk & Bike Path to Beach! Walk to Golf Club & Pub Close to Coligny Summer Beach Shuttle

Top guest favorite
The kitchen and dining area is equipped with modern appliances, including a microwave and coffee maker. A wooden table with six chairs is set for dining, while white cabinetry and light countertops create a spacious atmosphere. A sliding door provides access to the outdoor area.
Condo in Hilton Head Island
4.97 out of 5 average rating, 102 reviews

1st Floor, 8 Min Walk Beach, King Bed, In Unit W/D

Welcome to "Tygers on the Beach" at Fiddler's Cove. This 1st floor fully equipped villa is 300 yards to the private beach access. The pristine beach is one of the least crowded on the island, making it ideal for families. Lounge in the heated pools, relax in the hot tub or play tennis/pickleball on site. Enjoy golf course views from the patio, king-size master bed and easy access to the bike trails, restaurants, and shops that make Hilton Head Island the perfect place to relax & unwind.

Top guest favorite
A three-story building is depicted with multiple balconies overlooking a paved driveway. Lush palm trees line the area, providing a tropical feel. The sky is partly cloudy, suggesting a bright atmosphere. Parking spaces are visible, adding convenience for guests.
Condo in Hilton Head Island
4.98 out of 5 average rating, 269 reviews

Coastal King Beach Flat Convenient to Everything!

Set in a serene location right on the beach, this complex is a peaceful gated retreat. It's a short walk to Coligny Plaza, a vibrant area offering a variety of dining, shopping, and entertainment options. The complex features a pool and sundeck, perfect for relaxation. With high-speed internet, WIFI, smart TVs, Roku, and cable, you're always connected. Enjoy the comforts of home with a fully stocked kitchen, a plush King bed, ideal for remote work, and modern updates & included amenities.

Top guest favorite
A spacious deck features a circular fire pit surrounded by four wooden adirondack chairs with cushions. A striped pouf adds comfort to the area. Scenic sunset views over the beachfront landscape create a serene backdrop.
Chalet in Sea Pines
4.98 out of 5 average rating, 102 reviews

180º Ocean Views, Treehouse "Siren's Lookout"

Waterfront and sunset views abound in this unique "treehouse", with 360 degree views. On Deer Island, just steps from the Harbour Town Lighthouse, known for its' large-boat marina, restaurants, shops and Golf Club, host of the RBC Heritage Classic, PGA Tour Event. Enjoy all the amenities of Sea Pines, including the South Beach Marina, Sea Pines Beach and Salty Dog Cafe, only 3 miles away, serviced by trollies & bike paths. Enjoy the sunset seated around the firepit. Gas grill with a view

Top guest favorite
A view from the balcony captures the serene ocean and beach during sunset. Vibrant colors reflect across the water, while lush greenery and trees frame the picturesque scene. The elegance of natural beauty is enhanced by a lantern hanging nearby.
Condo in Hilton Head Island
4.95 out of 5 average rating, 281 reviews

Cozy Oceanfront-Romantic Retreat-Mesmerizing Views

Villa is located on The Spa On Port Royal Sound complex on Hilton Head Island. Enjoy unobstructed sound & ocean views from your balcony. Natural beach access & observation pier. Beautiful landscaped grounds. 2 outdoor pools-opened Apr.-Oct. Indoor pool, hot tub, dry sauna & gym. Grills and picnic areas on premises, one near the villa, recently installed hammocks near the ocean pool. Tennis and basketball courts on site. Come enjoy the beautiful sandy beach with beautiful sunrises!a

Top guest favorite
A vibrant sunrise is captured over the Atlantic Ocean, illuminating the horizon with warm hues of orange and yellow. The sun's rays radiate across the calm water, casting reflections on the sandy beach below.
Condo in Hilton Head Island
4.96 out of 5 average rating, 201 reviews

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**

Top guest favorite
A sunlit living space features a navy blue sofa and an elegant dining table surrounded by four chairs. Large sliding glass doors provide access to the oceanfront balcony, where views of the beach and coastal landscape can be seen in the distance.
Condo in Hilton Head Island
4.97 out of 5 average rating, 198 reviews

Luxury Oceanfront! KING BED 75"TV Pickleball & BAR

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨Airbnb top 1% Home ✨ 100% New Luxury Renovation Oceanfront Balcony HGTV Featured Decorator KING BED + 75" & 65" SmartTV s Expanded Bedroom MARBLE BATHROOM Coastal Décor TOP FLOOR+Elevator Beach Chairs, Boogie Boards, Ice Chest & More RESORT Beachfront Pool Beachfront Bar & Grille Sports Bar FREE Tennis, Gym, Pickleball, Basketball, Volleyball 2nd Pool Bike Rental Gated w/24 Hour Security Free Trolley Stop Bradley Beach

Guest favorite
Condo in Hilton Head Island
4.77 out of 5 average rating, 210 reviews

BEACHFRONT KING BED VILLA, PVT BALCONY, SELF CKIN

Freshly decorated in coastal decor, this beachfront condo sleeps up to 4 and is located right by Coligny, Hilton Head's chicest neighborhood. Freshly furnished unit includes a spacious king bed and queen sofa sleeper, both fitted with luxurious memory foam mattresses. Just a three minute walk to sandy beaches, and you can catch a glimpse of gentle tides from your own private balcony! The villa is full of amenities including beach chairs, beach umbrella, games and much more.

Top guest favorite
A bright and inviting living space features a gray sofa with decorative pillows and a white coffee table on a patterned rug. The modern kitchen showcases white cabinetry and a dining area with stools. Fresh flowers are arranged in a vase on the table.
Condo in Hilton Head Island
4.99 out of 5 average rating, 406 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.

Guest favorite
The living area is furnished with a spacious sectional sofa, accented by decorative pillows and a cozy throw. A large television is mounted on the wall, and floor-to-ceiling windows provide an ocean view, allowing natural light to fill the room.
Condo in Palmetto Dunes
4.95 out of 5 average rating, 110 reviews

Ocean Views at Villamare, Steps to the Beach!

Read our reviews! We strive to provide an unforgettable Hilton Head experience in our renovated villa with ocean views, comfortable lounging, plush beds, well-appointed kitchen and 500+Mbps WiFi! Our bright, open living space features floor-to-ceiling windows overlooking the pool, beach and the Atlantic Ocean! The living room sectional expands into a massive lounger for all! Have a big group? We also offer the immediately next-door unit, identical to this one!

Popular amenities for Hilton Head Island rentals with a pool

When is the best time to visit Hilton Head Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$30,743 GYDG$31,370 GYDG$37,017 GYDG$41,827 GYDG$41,827 GYDG$47,891 GYDG$49,146 GYDG$42,245 GYDG$36,807 GYDG$32,834 GYDG$31,370 GYDG$31,370 GYD
Avg. temp10°C12°C16°C19°C23°C27°C28°C28°C25°C20°C15°C12°C

Quick stats about vacation rentals with a pool in Hilton Head Island

  • Total vacation rentals

    Explore 5,700 vacation rentals in Hilton Head Island

  • Nightly prices starting at

    Hilton Head Island vacation rentals start at G$2,091 GYD per night before taxes and fees

  • Verified guest reviews

    Over 138,410 verified reviews to help you choose

  • Family-friendly vacation rentals

    4,640 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 880 rentals that welcome pets

  • Rentals with dedicated workspaces

    3,000 properties have a dedicated workspace

  • Wi-Fi availability

    5,560 of Hilton Head Island vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Hilton Head Island rentals

  • 4.7 Average rating

    Hilton Head Island stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore