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Vacation rentals with a pool in Hilton Head

Find and book unique homes with a pool on Airbnb

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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A private heated saltwater pool reflects the surrounding palm trees and greenery. Comfortable outdoor seating is situated nearby, alongside a propane grill for casual dining and entertaining. The space is framed by a covered patio, offering a serene and inviting atmosphere.

Home in Hilton Head Island

4.8 out of 5 average rating, 196 reviews

6BR Hilton Head Beach House W/Pool, Fire Pit, Elev

Experience The Hilton House, a 6BR, 4BA beach house on Hilton Head Island, just 6 min from pristine beaches. Sleeps up to 25 guests and is perfect for large groups or family getaways. Enjoy a heated saltwater pool, propane fire pit, movie theater room, all floor elevator, commercial arcade, fast Wi-Fi & fully stocked kitchen .Pets welcome with a fee. Located near top attractions, restaurants, and golf courses. Ideal for reunions, retreats, and beach vacations. Book now for an unforgettable stay!

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, 312 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!

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, 275 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!

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

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, 102 reviews

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

Completely remodeled in 2022 with stylish functional design, top-notch appliances, and beautiful quartzite, our 2 BR 2 BA villa is ready for your arrival. Located at the north-end of Hilton Head Island in a beachfront gated community, our 3rd-floor villa offers you a relaxing place to unwind with all the comforts of home. Enjoy amenities including tennis courts, indoor & outdoor pools, hot tub, dry sauna, and exercise room. For quiet unspoiled beaches surrounded by nature, come to Sea Clarity.

Top guest favorite

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.

Condo in Hilton Head Island

4.98 out of 5 average rating, 156 reviews

My Blue Heaven, 28 Days available in February

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.

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

4.94 out of 5 average rating, 272 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, 109 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.

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, 180 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 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, 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 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, 397 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.

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Popular amenities for Hilton Head rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

A well-lit bedroom features two spacious beds, each adorned with vibrant blue and green bedding. A decorative wall basket adds a natural touch, while a window with patterned curtains allows for natural light. A small chair and side table enhance the room's functionality.

Home in Hilton Head Island

4.99 out of 5 average rating, 92 reviews

6 BR, Sleeps 26, Beach Time

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, 88 reviews

98 Sandcastle Ct

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, 138 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

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

Home in Hilton Head Island

4.95 out of 5 average rating, 166 reviews

Enjoy time with Family and Friends

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 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

Top guest favorite

Home in Hilton Head Island

5 out of 5 average rating, 74 reviews

Hilton Head 4BR Retreat w/Salt-Pool + Beach Access

Condo rentals with a pool

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, 209 reviews

Easy Breezy at Hilton Head Beach & Tennis

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.

Condo in Hilton Head Island

4.96 out of 5 average rating, 108 reviews

Private comfy condo, steps away from the beach

A modern kitchen features white cabinetry and stainless steel appliances. A light blue tiled backsplash provides a lively contrast. A round dining table set for four is positioned next to a window that allows natural light to fill the space.

Condo in Hilton Head Island

4.96 out of 5 average rating, 136 reviews

Heron Hideaway: lovely updated near-beach 2bd/2ba

Top guest favorite

Two individuals are silhouetted against a vibrant sunset on the beach, with deep orange and purple hues reflecting on the water. The shoreline glistens, capturing the light while gentle waves lap at the sand. A fishing pole is anchored in the foreground.

Condo in Hilton Head Island

4.97 out of 5 average rating, 153 reviews

Salty Tides ~ 2 BR/2 Bath ~ Short Walk to Beach!

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!

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, 268 reviews

Coastal King Beach Flat Convenient to Everything!

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.

Condo in Hilton Head Island

4.95 out of 5 average rating, 197 reviews

Hilton Head Beach & Tennis Getaway!

A cozy living area features a spacious gray sofa with decorative pillows. Soft lighting from two side lamps illuminates the room. Large sliding glass doors open to a deck, providing a view of the surrounding trees. Wall art depicting a turtle adds a touch of character.

Condo in Hilton Head Island

4.96 out of 5 average rating, 122 reviews

Cozy Villa 6 Minute Walk From the Beach & Golf

Other vacation rentals with a pool

Top guest favorite

A spacious living area features comfortable seating arrangements, including a cozy sectional sofa and armchairs. Large glass doors provide access to the balcony, with views of the outdoors. The room is bright, complemented by a flat-screen TV and decorative shelving.

Apartment in Hilton Head Island

5 out of 5 average rating, 37 reviews

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

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, 95 reviews

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

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, 16 reviews

Luxury Waterfront Tree House | Harbour Town | Pool

Top guest favorite

A bright kitchen area features modern appliances, including a stainless-steel refrigerator and a spacious island with seating. Soft lighting illuminates the open space, which flows seamlessly into a dining area with a window offering natural light.

Villa in Hilton Head Island

5 out of 5 average rating, 62 reviews

Beach & Birdie Kid Friendly Close to Beach & Golf

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, 146 reviews

Beach Resort 2b Luxury Golf/Lagoon View Pickleball

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, 139 reviews

Exclusive Oceanfront Decorator Decor Spacious Bdrm

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.

Condo in Hilton Head Island

4.88 out of 5 average rating, 49 reviews

Dream Paradise Long Term Rates Work Oceanfront

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, 36 reviews

54 Folly Field Rd - Amazing Beach Home with Pool

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