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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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Guest favorite
A spacious bedroom features a comfortable bed dressed in a patterned coverlet, accompanied by crisp white towels. Soft lighting is provided by bedside lamps. Decorative accents include a branch art piece on the wall and a small shelf displaying coastal-themed items. Natural light filters through a window with sheer curtains.
Condo in Hilton Head Island
4.95 out of 5 average rating, 222 reviews

$59/nt -Nov 24-26 ~ CLEAN ~ KING Bed ~ Sleeps 7

Fully Furnished, Renovated Non-Smoking Villa sleeps 7 - King bed in Master, 2 Single beds in Guest Room, Leather Queen Sofa Bed & Rollaway Bed. Built-in Bar, Fully-equipped Kitchen w/ small appliances. Beach Chairs, toys, games, cards. Flat Screen HDTV w/ hundreds of channels, DVD, Free Wi-Fi. Overhead Lighting & Ceiling fans in bdrms, extra blankets & pillows. Restaurants, Tennis, 2 Pools. Sip cold drinks on the wide sandy beach & watch Amazing Sunrises & Sunsets. Relax, You're in Paradise

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, 319 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!

Superhost
A private heated saltwater pool is shown, featuring a shallow entry. Surrounding seating includes a table and chairs, positioned on a colorful rug. Lush greenery frames the space, creating a serene environment, while a grill is visible in the background.
Home in Hilton Head Island
4.89 out of 5 average rating, 107 reviews

Sleep 20, Walk to Beach, Free Heated Pool, Elev

Enjoy a Carefree Casual Getaway experience in this Beautifully appointed Hilton Head Island home away from home! Mid Island where you can walk/bike and take the trolly to the best beaches, restaurants and shopping on the island. Sleeps 20 - Spacious Beach House has 6 Comfortable bedrooms w/ TV's. Master bedroom has a romantic electric fireplace! FREE Heated Saltwater Pool with propane grill and dining/ comfortable seating. Fully stocked kitchen. Linens/towels/soap and shampoo all provided!

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, 325 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, 280 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
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, 109 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

Guest favorite
The living area features a light-colored sofa and a glass coffee table, with a view of the resort through sliding glass doors. Soft-hued walls complement the decor, while mirrored panels reflect natural light, enhancing the spacious feel. A dining table with seating for four is visible in the background.
Condo in Hilton Head Island
4.94 out of 5 average rating, 125 reviews

Desirable Oceanfront Resort*End Unit*Bikes/Chairs

Charming villa with everything you need for the perfect beach getaway- just steps from the sand! Elevated 1st floor, END UNIT offers lots of natural light and ramp for easy access. Situated in desirable C building, closest to beach, pool and Jamaica Joe'z restaurant/ tiki bar. 2 FREE bikes, chairs & beach towels! HHBT Resort provides gated security and countless amenities, including the island's largest oceanfront pool, multiple restaurants/ bars, tennis courts, playgrounds & fitness center.

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
4.98 out of 5 average rating, 101 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, 277 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, 115 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
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, 191 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, 168 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

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
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, 141 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Guest favorite
The living room displays a light, airy ambiance with large sliding glass doors leading to a private balcony. A plush couch is complemented by decorative pillows, and a patterned ottoman adds texture. Natural light filters through the windows, enhancing the inviting atmosphere.
Home in Hilton Head Island
4.84 out of 5 average rating, 56 reviews

~Couples Paradise~Villa W/Pool~Beachfront Resort

Top 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

Top guest favorite
A two-story house features a light-colored exterior with a metal roof and a front balcony. The driveway provides access to two garages, with landscaped greenery and grass surrounding the property, enhancing the overall curb appeal.
Home in Hilton Head Island
4.86 out of 5 average rating, 376 reviews

W2Bch*4TVs*1GIG I*PetsWC *WiFi*4King ßds*grill*gms

Top guest favorite
Home in Hilton Head Island
4.95 out of 5 average rating, 167 reviews

Enjoy time with Family and Friends

Top guest favorite
The front exterior of the house features a welcoming porch with a central decorative door and flanking windows. Flowering plants are suspended from the eaves, while well-maintained shrubs frame the entrance. A clear pathway leads to the door, inviting guests into the home.
Home in Bluffton
4.96 out of 5 average rating, 124 reviews

Encanto of the Lowcountry in Old Town Bluffton

Condo rentals with a pool

Top guest favorite
A spacious pool area is visible, bordered by sun loungers and palm trees. The ocean can be seen in the background, with glistening sunlight reflecting off the water. A clear blue sky enhances the inviting atmosphere of the outdoor space.
Condo in Hilton Head Island
4.91 out of 5 average rating, 213 reviews

Breathtaking OCEAN VIEW/Top Floor/Pool & Coligny

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, 195 reviews

OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6

Top 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, 211 reviews

Easy Breezy at Hilton Head Beach & Tennis

Guest favorite
A serene beach scene features gentle waves lapping at the shore under a soft pastel sky. The moon hovers above the horizon, casting a warm glow over the water. A distant figure is seen walking along the wet sand, contributing to the tranquil atmosphere.
Condo in Hilton Head Island
4.9 out of 5 average rating, 223 reviews

Oceanside Beach Retreat

Top guest favorite
A serene landscape is presented, featuring a tranquil pond surrounded by lush greenery and palm trees. The view extends toward the beach, with well-maintained walkways leading through the gardens. A clear sky with scattered clouds adds to the peaceful ambiance.
Condo in Hilton Head Island
4.92 out of 5 average rating, 142 reviews

Exclusive Oceanfront Decorator Decor Spacious Bdrm

Guest favorite
A modern kitchen is equipped with stainless steel appliances, including a refrigerator and microwave. Light-colored cabinets with decorative art pieces are visible above the sink. A dining area is adjacent, featuring a round table set with chairs, inviting relaxed meals and gatherings.
Condo in Hilton Head Island
4.84 out of 5 average rating, 176 reviews

Updated Beach Villa Resort

Top guest favorite
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.
Condo in Hilton Head Island
4.96 out of 5 average rating, 109 reviews

Beautiful Newly Renovated 2 Bedroom/2 Bath Condo

Top guest favorite
The modern kitchen features a spacious island with a marble countertop and three wooden stools. White cabinetry and a stylish backsplash enhance the functional design. High-quality appliances, including a stainless steel refrigerator and microwave, are integrated into the layout, providing a welcoming cooking space.
Condo in Hilton Head Island
5 out of 5 average rating, 104 reviews

“Sea Clarity” Custom Remodel, Pool, Steps to Beach

Other vacation rentals with a pool

Top guest favorite
Condo in Hilton Head Island
5 out of 5 average rating, 21 reviews

Oceanfront! KING BED 75" TV Pickleball BAR Tennis!

Top guest favorite
A sunlit living area showcases a stylish coffee table topped with a candle and books. A wooden chair and a potted plant invite relaxation, while sheer curtains filter natural light. The ocean view is framed by an open balcony door, enhancing the vibrant ambiance of the space.
Condo in Hilton Head Island
4.98 out of 5 average rating, 53 reviews

Romantic Ocean & Fountain Views- King Bed-Tiki Bar

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, 8 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
A serene pool area is surrounded by lush greenery, with a paved walkway leading to the water. Several lounge chairs are positioned near the pool, which is framed by a low fence. Mature trees provide ample shade, enhancing the tranquil atmosphere.
Condo in Hilton Head Island
4.85 out of 5 average rating, 176 reviews

1 Bedroom Condo, 5 Minute Walk to the Beach

Superhost
The image showcases a heated pool surrounded by palm trees and lounge chairs. Umbrellas provide shade over some seating areas. A white fence encloses the pool area, with lush greenery and ocean views in the background, creating a tranquil outdoor environment.
Villa in Hilton Head Island
4.91 out of 5 average rating, 101 reviews

💎Direct Oceanfront Villa - Heated Pool Ocean View

Guest favorite
A scenic view of a natural shoreline is captured, showcasing a sandy beach bordered by calm water and grassy areas. Soft blue skies with scattered clouds create a peaceful atmosphere, while a distant couple can be seen walking along the shore.
Apartment in Hilton Head Island
4.86 out of 5 average rating, 50 reviews

2BR, 2 Min to Beach, Pool, Tennis, King Bed

Guest favorite
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.
Apartment in Hilton Head Island
4.95 out of 5 average rating, 64 reviews

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

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