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Vacation 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 favorite
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.
Condo in Hilton Head Island
4.96 out of 5 average rating, 316 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!

Top guest favorite
A modern kitchen and living area feature stainless steel appliances, including a microwave and refrigerator. A spacious dining table is set for four, while a light-colored sofa offers comfortable seating. Soft blue accents complement the coastal decor, creating a relaxed atmosphere.
Condo in Hilton Head Island
4.98 out of 5 average rating, 319 reviews

Ocean Front Resort Villa

Freshly decorated in coastal cottage decor, this 540 sq ft one bedroom villa sleeps up to 6 and is located within the activity-filled Hilton Head Beach and Tennis Resort. The villa was recently remodeled with all new kitchen, bathroom and fixtures and is just 50 steps to gorgeous beach. The views from the living room include ocean, oceanfront pool , beach bar and grill, and pond with fountain. The villa is full of amenities including beach towels, beach chairs, beach umbrella and much more.

Top guest favorite
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.
Condo in Hilton Head Island
4.97 out of 5 average rating, 278 reviews

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!

Superhost
An aerial view captures the villa and surrounding area, highlighting the proximity to the beach. The ocean is visible in the background, while the spacious grounds feature multiple buildings and a parking area. Nearby greenery enhances the coastal atmosphere.
Condo in Hilton Head Island
4.88 out of 5 average rating, 144 reviews

Ocean View 1-bdrm. Steps to the Beach and Pool.

Enjoy the Ocean views from the balcony of this stylish 1-bedroom condo. Comfortable furnishing throughout. Perfect for a couple or small family. The condo sleeps 4 with a queen bed in the private bedroom, and a sleeper sofa. The kitchen is fully stocked with everything you need to prepare a meal. Enjoy dining outside as you enjoy the ocean view from the 2nd. floor balcony. The bathroom with tub/shower can be accessed from the bedroom or hallway. Beach chairs, umbrella, and cooler are provided.

Guest favorite
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.
Condo 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 favorite
A panoramic view from the balcony showcases the sparkling ocean and expansive blue sky. Below, palm trees dot the landscape, while the beach is glimpsed in the distance. A pool area is visible, framed by well-maintained greenery, with parking spaces filled with vehicles.
Condo in Hilton Head Island
4.98 out of 5 average rating, 163 reviews

Luxury OceanView KING BED 65"TV Bar Pickleball GYM

✨ Airbnb Top 5% Guest Favorite ✨ Oceanfront Building! BIG Ocean Views Steps to Beach & Poo! 100% NEW HGTV Designer Renovation! KING BED Expanded Bedroom Two 65" SmartTVs Coastal Decor Beach Chairs, Boogie Boards, Ice Chest & More Marble Kitchen & Spa Bath Quiet Top Floor Elevator RESORT: Huge Oceanfront Pool Beachfront Bar & Grille (Misc. Hours) Sports Bar FREE Gym, Pickleball, Tennis Basketball, Volleyball & More Bike Rental Gated 24 Hour Security Free Seasonal Trolley 4 Beach Boardwalks

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, 275 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 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.
Condo in Hilton Head Island
4.96 out of 5 average rating, 114 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 favorite
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, 360 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 favorite
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, 102 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 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, 188 reviews

Oceanfront Luxury! KING BED 75"TV Pickleball | BAR

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨Airbnb top 5% 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

Top guest favorite
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.
Condo in Hilton Head Island
4.99 out of 5 average rating, 165 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**

Popular amenities for Hilton Head rentals with a pool

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Guest favorite
A screened pool area showcases a serene blue swimming pool, framed by large glass doors offering views of the surrounding greenery. Relaxing lounge chairs are positioned nearby, and natural light floods the space, enhancing the inviting atmosphere.
Home in Hilton Head Island
4.93 out of 5 average rating, 15 reviews

27 Kingston: Spacious Shipyard Home, Private Scree

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, 140 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Guest favorite
An inviting living space features a sectional sofa, a wooden coffee table, and a dining area with several chairs. Natural light illuminates the room through multiple windows, highlighting the coastal-inspired decor and airy layout. A chandelier complements the open, relaxed atmosphere.
Home in Hilton Head Island
4.94 out of 5 average rating, 121 reviews

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

Top guest favorite
A private pool area is framed by lush greenery and palm trees, featuring a turquoise swimming pool with a pink float. Two sun loungers are positioned beside the pool, with a shaded cabana offering seating and a dining area.
Home in Hilton Head Island
4.98 out of 5 average rating, 121 reviews

Resort-Style Pool, Cute House 88 Steps to Sand

Top guest favorite
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, 103 reviews

Private pool/spa : pool heat available : Kg master

Guest favorite
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
4.98 out of 5 average rating, 120 reviews

Cozy beach house w/Private Heated Pool near park

Superhost
A covered patio area features a heated swimming pool with clear water. A dining table with several chairs sits nearby, complemented by comfortable seating. The backdrop includes a tranquil body of water and charming buildings, creating a serene outdoor ambiance.
Home in Hilton Head Island
4.83 out of 5 average rating, 160 reviews

Luxe Family Gem-FREE Heated Pool~Walk to Beach~BBQ

Guest favorite
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

Condo rentals with a pool

Guest favorite
An aerial view captures a large pool shaped like a star, surrounded by lounge chairs. The pool area is complemented by umbrellas and seating, with a sandy beach and the ocean visible in the background under clear blue skies.
Condo in Hilton Head Island
4.89 out of 5 average rating, 210 reviews

Easy Breezy at Hilton Head Beach & Tennis

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, 100 reviews

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

Guest favorite
A wooden swing is suspended under a pergola in a grassy area. The surrounding landscape features lush greenery and palm trees, with a bright blue sky and scattered clouds above, creating a tranquil outdoor setting.
Condo in Hilton Head Island
4.9 out of 5 average rating, 191 reviews

A+ Condo! 2 Min to Beach~ Ocean View~2 Bikes! #109

Guest favorite
A comfortable living area features a blue sofa with yellow accent pillows, complemented by a patterned armchair. A textured area rug covers the floor, and a coffee table with a tray is centrally positioned. Natural light filters through sheer curtains, creating a warm ambiance.
Condo in Hilton Head Island
4.9 out of 5 average rating, 164 reviews

Coastal Comfort! Condo in beachfront resort.

Guest favorite
A modern kitchen is illustrated with granite countertops and sleek cabinetry. Stainless steel appliances, including a microwave and oven, are visible. A large island with seating for three complements the space, which transitions into a cozy dining area beyond, illuminated by overhead lighting.
Condo in Hilton Head Island
4.94 out of 5 average rating, 195 reviews

Coastal Chic & Tranquil Beach on Hilton Head!

Guest favorite
A stretch of sandy beach is depicted under a bright sky, featuring three blue umbrellas positioned over wooden lounge chairs. Gentle ocean waves are seen rolling onto the shore, and the sun reflects off the water, creating a serene coastal atmosphere.
Condo in Hilton Head Island
4.97 out of 5 average rating, 209 reviews

Ocean Front Beach & Tennis Resort 2 BR 2 BA Villa

Guest favorite
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.
Condo in Hilton Head Island
4.95 out of 5 average rating, 136 reviews

Gorgeous OCEAN View, Resort Amenities & Beach!

Guest favorite
A spacious bedroom features a large bed adorned with a colorful floral quilt and accented by several plush pillows. A bedside lamp provides soft lighting, while a window offers a view of the outside greenery, contributing to a calm atmosphere.
Condo in Hilton Head Island
4.92 out of 5 average rating, 170 reviews

By the Beautiful Sea, 30 Day Discounts available

Other vacation rentals with a pool

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 Hilton Head Island
4.99 out of 5 average rating, 98 reviews

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

Top guest favorite
The image displays a serene waterfront view featuring a marina filled with various boats. Lush greenery lines the foreground, adding a natural touch. The sky is clear with soft clouds, and the calm water reflects the surrounding scenery, enhancing the tranquil atmosphere.
Apartment in Hilton Head Island
5 out of 5 average rating, 15 reviews

Harbourside Haven

Guest favorite
Apartment in Hilton Head Island
5 out of 5 average rating, 9 reviews

Beachfront Escape w Balcony+Pool

Top guest favorite
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, 19 reviews

Luxury Waterfront Tree House | Harbour Town | Pool

Top guest favorite
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, 19 reviews

Modern Beach Escape | Private Pool~Steps to Beach

Superhost
A view of the resort's building complex is presented, featuring multiple balconies and terracotta roofs. The outdoor pool is visible, surrounded by greenery and lounge chairs. A tranquil waterway lies in the background, with natural landscapes of grass and trees framing the scene.
Condo in Hilton Head Island
5 out of 5 average rating, 7 reviews

Marriott Sunset Pointe - 2BD

Guest favorite
A bright living area features a comfortable sofa and a small round table positioned near large sliding glass doors that reveal ocean views. Light curtains frame the windows, allowing natural light to enhance the space. A cozy rug is placed on the floor.
Condo in Hilton Head Island
5 out of 5 average rating, 74 reviews

THE SANDPIPER’s NEST Luxury direct Oceanfront

Guest favorite
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, 40 reviews

54 Folly Field Rd - Amazing Beach Home with Pool

Destinations to explore