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Holiday rentals with a pool in Hilton Head

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Top-rated rentals with a pool in Hilton Head

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite
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, 147 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 favourite
A wooden boardwalk leads through grassy dunes towards the beach. The path extends toward the calm ocean, under a gray sky. Soft sand is visible at the boardwalk's end, inviting guests to access the beachfront.
Apartment in Hilton Head Island
4.96 out of 5 average rating, 315 reviews

Ocean View! Steps to beach! Remodeled HHBT Condo!

Newly remodeled just last year! Adorable beach front condo located in HH Beach & Tennis Resort. Watch & listen to the ocean waves right from your 2nd floor balcony! The condo is in a gated area within where guests will have access to a private beach, 2 pools, resort restaurants, tennis, pickleball, beach volleyball, playgrounds, cookout areas, bike rental, and a gym. We also provide beach chairs, coolers, boogie boards and coffee! It's all here! The getaway you've been waiting for and deserve!

Guest favourite
Apartment in Hilton Head Island
4.96 out of 5 average rating, 308 reviews

Ocean & Marsh View KING BED 65"TV Bar Pickleball!

✨ Airbnb Guest Favorite ✨ 2-3 min walk to Beach Beachfront Building Quiet Views of Coastal Marsh, Ocean & Trees - Not Parking Lot! KING BED + Big SmartTVs HGTV Decorator Designed Coastal Decor Private Top Floor Balcony Beach Chairs + Ice Chest Provided Couples Retreat! Well designed 540 square foot condo RESORT: 4 Beach Boardwalks! Huge Oceanfront Pool Beachfront Bar & Grille Sports Bar 2nd Pool FREE Tennis, Gym, Pickleball, Basketball, Volleyball & More Bike Rentals Gated w/24 Hour Security!!

Guest favourite
A spacious kitchen featuring sleek white cabinetry and a large marble island with seating for four. Modern appliances, including a stainless steel refrigerator and oven, are visible, along with a stylish black backsplash that complements the overall design.
Apartment in Hilton Head Island
4.9 out of 5 average rating, 105 reviews

Luxe Hilton Head Beach Villa w/ Pool Views

Escape to our beautiful beach getaway where you are just a short walking distance to a beautiful natural beach. Our completely restored condo is designed with the perfect blend of luxury and relaxation to enjoy your time in Hilton Head. Our spacious and open floor plan creates a bright and an inviting atmosphere that is perfect for lounging with loved ones and friends. Our bedrooms will give you a perfect night of rest and relaxation while each bathroom provides the perfect spa like experience

Top guest favourite
A light-filled living area features a white sofa complemented by a blue accent chair. A decorative table with a tray of flowers and a plush area rug enhances the space. Large glass doors open to a balcony, offering expansive views of the ocean.
Apartment in Hilton Head Island
4.98 out of 5 average rating, 158 reviews

My Blue Heaven, Direct Ocean Front View

Welcome to our ocean front rental, a haven for couples seeking a romantic and stylish getaway. With its breathtaking ocean view, five-star reviews, and recent remodel in 2023, this rental promises an unforgettable experience. Our guests have praised the attention to detail, the stunning view, and the overall ambiance of the space. Rest assured that your stay will be nothing short of extraordinary. Step out onto the balcony and take in the fresh sea breeze as you relax in the swinging chair.

Guest favourite
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.
Apartment in Hilton Head Island
4.95 out of 5 average rating, 274 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 favourite
A bright kitchen and dining area is featured, showcasing light wooden cabinetry, stainless steel appliances, and a dining table with four chairs. A large flat-screen TV is mounted on the wall, and tasteful decor adds a cozy touch to the space. Natural light fills the room.
Apartment in Hilton Head Island
4.96 out of 5 average rating, 112 reviews

Beach Front Resort - Ocean View King Bed

OCEAN VIEW-Amazing View-Beachfront 3 MINUTE WALK to the ocean Beachfront condo- Hilton Head Island Beach and Tennis Resort. - Hilton Head is the # 1 rated island by Conde Nast. A tropical landscape- miles of beaches, bike trails, restaurants, boating, fishing, and golf galore. Sleeps 4- 1 KING BED w/bunks in the same room Bunks are NOT twin-size; they are kid-size. Beachfront RESORT, private beach, three restaurants, beachfront pool, Tennis/Pickleball, fitness center & bike rental.

Top guest favourite
An aerial view captures a cluster of modern buildings with red roofs, surrounded by lush greenery. Sailboats are docked in the marina, with a scenic waterfront area in the background. A glimpse of residential areas and palm trees adds to the inviting atmosphere.
Guest suite in Hilton Head Island
4.93 out of 5 average rating, 359 reviews

LOCATION! Harbour, Dining, Shops, Beach-1.4 mile

Location .. Location .. Location !!! Private guest suite (256 sq ft) with independent entrance from outside, total privacy, and complete amenities, queen bed and full bath (no kitchen). Just step outside - great water-front restaurants with live music, bars, shops and weekly fireworks during summer. Supermarkets and more restaurants in 10 minutes walking. Free shuttle to attractions in 2 miles radius from April till September, beach 1.4 miles away, biking, fishing and water sports.

Guest favourite
The outdoor space features a year-round heated pool surrounded by lush greenery, with a clear view of the ocean. Umbrellas offer shade over picnic tables, while tall trees enhance the serene atmosphere of the beachside setting.
Villa in Hilton Head Island
4.96 out of 5 average rating, 101 reviews

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.

Top guest favourite
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.
Apartment in Hilton Head Island
4.97 out of 5 average rating, 183 reviews

Oceanfront Luxury! KING BED 75"TV Pickleball | BAR

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! 100% New Luxury Renovation Oceanfront Balcony HGTV Featured Decorator KING BED + 75" & 65" SmartTV s ✨Airbnb top 10% Home ✨ 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

Top guest favourite
A stunning sunrise illuminates the ocean, casting a warm golden glow across the water's surface. Rays of sunlight stretch outward, reflecting off the gentle waves. The shoreline is visible, framed by soft grasses, enhancing the tranquil morning scene.
Apartment in Hilton Head Island
4.99 out of 5 average rating, 163 reviews

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**

Top guest favourite
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.
Apartment in Hilton Head Island
4.99 out of 5 average rating, 399 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.

Popular amenities for Hilton Head rentals with a pool

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Guest favourite
The image captures a private heated pool beneath a covered patio. Comfortable lounge chairs surround the pool, and an outdoor dining area features a large table with chairs. A shaded umbrella stands above the table, while greenery and a grill are visible, enhancing the outdoor setting.
Home in Hilton Head Island
5 out of 5 average rating, 89 reviews

98 Sandcastle Ct

Superhost
An outdoor deck features a shapely pool surrounded by lounging chairs. Lush greenery and palm trees are visible in the background, offering a view of the golf course. A purple umbrella stands next to the pool, providing shade.
Home in Hilton Head Island
4.84 out of 5 average rating, 139 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Top guest favourite
A pristine pool area is surrounded by lush greenery, featuring a spacious pool and a relaxing spa. Poolside seating includes turquoise chairs and an umbrella. A dining table with outdoor chairs is situated nearby, all on a textured stone patio.
Home in Hilton Head Island
4.98 out of 5 average rating, 102 reviews

Private pool/spa : pool heat available : Kg master

Top guest favourite
A modern two-story home is nestled among lush trees, featuring a large outdoor pool surrounded by a paved deck. A spacious covered balcony offers seating, providing a view of the inviting pool area and landscaped grounds, perfect for relaxing or entertaining.
Home in Hilton Head Island
5 out of 5 average rating, 18 reviews

Modern Beach Escape | Private Pool~Steps to Beach

Guest favourite
A shaded balcony is furnished with two woven chairs and a small table, complemented by a decorative area rug. Lush greenery is visible beyond the railing, providing a natural backdrop, while large windows allow for ample light to fill the space.
Home in Hilton Head Island
4.97 out of 5 average rating, 119 reviews

Cozy beach house w/Private Heated Pool near park

Top guest favourite
A modern treehouse-like structure is elevated on stilts and surrounded by trees, providing marsh views. A wide wooden deck with railings leads to the entryway, where large glass doors invite natural light into the space.
Home in Hilton Head Island
4.97 out of 5 average rating, 151 reviews

Peaceful Harbour Town Treehouse with Marsh Views

Guest favourite
Aerial view of a private backyard featuring a kidney-shaped pool surrounded by a natural stone patio. Comfortable lounge chairs are positioned by the pool, and a covered area with overhead beams houses an outdoor kitchen. A fenced perimeter ensures privacy.
Home in Hilton Head Island
5 out of 5 average rating, 37 reviews

54 Folly Field Rd - Amazing Beach Home with Pool

Guest favourite
A modern home is surrounded by lush greenery, featuring large glass windows that invite natural light. A spacious outdoor area includes multiple lounge chairs and umbrellas, along with a large dining table. A pool area is visible, enhancing the outdoor living experience.
Home in Hilton Head Island
5 out of 5 average rating, 10 reviews

Island Paradise Getaway

Apartment rentals with a pool

Guest favourite
A serene bedroom space features a spacious bed with a light patterned coverlet. A mirror and a closet are visible, while a smart TV is positioned atop a white cabinet. Soft natural light enters the room through a nearby door leading to an adjacent area.
Apartment in Hilton Head Island
4.93 out of 5 average rating, 214 reviews

Ocean front condo with amazing ocean view!

Guest favourite
The living area showcases comfortable seating arrangements with two plush sofas and an accent chair. A light area rug features a subtle pattern. Large glass doors invite natural light and connect the space to an outdoor balcony. Art adorns the walls.
Apartment in Hilton Head Island
4.96 out of 5 average rating, 109 reviews

Private comfy condo, steps away from the beach

Top guest favourite
The image captures a sandy beach at sunset, with gentle waves lapping at the shore. Tall grass frames the scene, and the sun casts a warm glow over the water. Silhouettes of individuals can be seen in the distance, enjoying the serene ambiance.
Apartment in Hilton Head Island
4.97 out of 5 average rating, 277 reviews

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

Guest favourite
A calm bedroom features a spacious bed with a pink patterned quilt, complemented by a decorative beach-themed sign above. Two white closet doors are visible along one wall, while a bedside table holds a lamp. Coastal decor accents enhance the serene atmosphere.
Apartment in Hilton Head Island
4.89 out of 5 average rating, 244 reviews

HHI. 3 Pools- 1 Indoor. Tennis. Easy Beach Access.

Guest favourite
The living area features a sectional sofa with blue and neutral throw pillows. A textured round coffee table sits in front, surrounded by two accent chairs. Decorative wall art, consisting of various woven circles, adds visual interest. Light from table lamps enhances the inviting space.
Apartment in Hilton Head Island
4.95 out of 5 average rating, 134 reviews

Oceanfront Breathtaking Views

Guest favourite
A comfortable living area is featured, furnished with a sectional sofa and accent chair. Natural light pours in from the sliding glass door, which leads to a private balcony. A mounted television and a decorative mirror enhance the space, creating a cozy setting.
Apartment in Hilton Head Island
4.95 out of 5 average rating, 199 reviews

Hilton Head Beach & Tennis Getaway!

Guest favourite
A scenic view of the ocean is displayed from a top-floor balcony. The tranquil water reflects the clear blue sky, while marshland and vegetation frame the landscape. A boardwalk is visible, leading toward the beach, enhancing access to the natural surroundings.
Apartment in Hilton Head Island
4.95 out of 5 average rating, 135 reviews

Gorgeous OCEAN View, Resort Amenities & Beach!

Superhost
Apartment in Hilton Head Island
4.85 out of 5 average rating, 146 reviews

Pool + Beach Views | Sauna | Indoor Pool

Other holiday rentals with a pool

Guest favourite
The living area is furnished with a light-colored sofa and two armchairs, offering a comfortable seating arrangement. A coffee table is centered on the floor. Natural light enters through a nearby window, enhancing the soft tones of the walls, complemented by decorative elements.
Apartment in Hilton Head Island
4.81 out of 5 average rating, 194 reviews

1st Floor Condo, Just Steps away from the Beach!

Top guest favourite
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 Hilton Head Island
4.99 out of 5 average rating, 96 reviews

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

Top guest favourite
Apartment in Hilton Head Island
5 out of 5 average rating, 16 reviews

Luxury Oceanfront KING BED 75"TV Pickleball Tennis

Guest favourite
Flat in Hilton Head Island
5 out of 5 average rating, 8 reviews

Beachfront Escape w Balcony+Pool

Top guest favourite
A serene view of calm waters features a distant sailboat gliding gracefully across the horizon. Lush greenery and tall grasses frame the scene, with a palm tree located in the foreground, offering a glimpse of the natural coastal landscape.
Treehouse in Hilton Head Island
5 out of 5 average rating, 17 reviews

Luxury Waterfront Tree House | Harbour Town | Pool

Guest favourite
A cozy living area is presented with a navy blue sofa featuring decorative striped pillows and a whimsical crab-shaped pillow. Flanking the sofa are two beige lamps on side tables, while a round coffee table sits beneath an artistic wall piece depicting marine life.
Apartment in Hilton Head Island
4.88 out of 5 average rating, 49 reviews

Dream Paradise Oceanfront Beach/Pool Steps Away

Guest favourite
The backyard features a newly built pool surrounded by loungers on artificial turf. A large green space hosts a putting green with four holes. The exterior of the home displays a two-story structure, with a staircase leading to a second-level porch.
Flat in Hilton Head Island
4.95 out of 5 average rating, 64 reviews

Coastal Oasis - 200 yards to Beach! (Lower Unit)

Guest favourite
A clear view of the indoor pool area is highlighted, featuring a large swimming pool surrounded by lounge chairs. Hot tubs are visible nearby, with the indoor track and additional amenities surrounding the space. Natural light filters through the upper levels of the building.
Apartment in Hilton Head Island
4.96 out of 5 average rating, 109 reviews

Beautiful Newly Renovated 2 Bedroom/2 Bath Condo

Destinations to explore