Vacation rentals with a pool in Hilton Head Island

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.

4.97 out of 5 average rating, 324 reviews

Oceanfront Luxury! KING BED 65"TV Pickleball & BAR

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR!! Beachfront Balcony ✨Top 5% 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

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.

4.96 out of 5 average rating, 324 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.

4.97 out of 5 average rating, 282 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!

4.95 out of 5 average rating, 125 reviews

A spacious living area is accentuated by vaulted ceilings and large windows, allowing natural light to fill the room. Comfortable sofas are arranged around a central coffee table, with decorative cushions adding color. A lamp and a decorative vase create a welcoming ambiance in this inviting space.

Home in Palmetto Dunes

Lovely 3BR in Palmetto Dunes w/ new pool & spa

Lovely 3 BR home on #2 tee of the Fazio golf course in Palmetto Dunes Resort. Near tennis/pickleball center, general store, & restaurants. Newer pool and spa. Quartz countertops. Two King BRs, 3rd BR with 2 Queens. Flat screen TVs, cable, ROKU in all BRs. Doorbell cam at front door porch with recording capability for host/guest safety. Beach access @ Omni resort and the Dunes House a 5-10 min ride by bike or 15 min walk. Beach towels/umbrellas/chairs not provided. Pool/spa heat for extra fee.

4.98 out of 5 average rating, 102 reviews

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

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

4.95 out of 5 average rating, 134 reviews

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.

Condo in Palmetto Dunes

Oceanfront Breathtaking Views

Gorgeous Ocean front views await your perfect vacation at this beautifully decorated beach condo in Palmetto Dunes. Five star rated condo features lush landscaping, palm trees, and tropical flowers will entice your senses. Amenities nearby, swimming pools, barbecue grill, hot tub, white sandy beaches, bike cruisers, kayak, pickle ball, golf, fishing and tennis await you. Your condo features a spacious 1 bedroom, 2 bathrooms , kitchen, dining, living room, and balcony for your comfort .

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.

4.95 out of 5 average rating, 280 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

Guest suite in Shelter Cove

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.

4.93 out of 5 average rating, 362 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.

A clear view of the ocean is visible from the balcony, showcasing a sandy beach lined with colorful umbrellas. Gentle waves roll onto the shore, and distant figures can be seen enjoying the beach. Lush greenery frames the foreground, enhancing the coastal scene.

4.89 out of 5 average rating, 105 reviews

Oceanfront, 3rd floor, King Bed

Direct oceanfront! Perfect for a couples get away, week vacation or anything in between. Take a walk across the street to Coligny Square where there are more than 60+ shops and restaurants. Ride your bike on more than 100 miles of trails. Onsite parking, pool and free wifi. Just bring your bathing suit and a towel! We provide the rest for you to have a relaxing vacation; beach chairs, umbrella, cooler, all kitchen spices, a Coffee Bar, shampoo, conditions, body wash and tide pods!

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.

4.97 out of 5 average rating, 196 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

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.

4.99 out of 5 average rating, 171 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**

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.

4.99 out of 5 average rating, 405 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 Island rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The open-concept living space features handmade Saltillo tiles and a vaulted ceiling. A comfortable couch and a fireplace are visible along with a large dining table. A staircase leads to the upper level, enhancing the spacious layout. Sliding glass doors provide access to the outdoor area.

4.98 out of 5 average rating, 94 reviews

Governor’s Quarters: Stately Sea Pines Stay on HHI

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.

5 out of 5 average rating, 95 reviews

98 Sandcastle Ct

Luxe

A light-filled living room features high ceilings and large windows that offer views of the outdoors. A neutral-colored area rug covers the floor beneath a white coffee table. Soft sofas are adorned with decorative pillows, and a simple fireplace is positioned on one wall.

5 out of 5 average rating, 5 reviews

21 Shell Ring

4.85 out of 5 average rating, 142 reviews

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 Palmetto Dunes

Palmetto Dunes Home on 1st Tee Fazio Golf Course

The exterior of the home is showcased at dusk, featuring a spacious heated pool illuminated in blue. Surrounding the pool are multiple lounge chairs, providing a serene outdoor space for relaxation. The multi-level structure is elegantly designed, with expansive balconies above and a well-lit entrance.

4.96 out of 5 average rating, 97 reviews

5 Bedroom-Beach Access-Pool-Sleeps 14!

5 out of 5 average rating, 12 reviews

A multi-level home is captured by clear blue skies, showcasing a private pool surrounded by lush greenery. Lounge chairs are arranged neatly by the poolside, offering ample space for relaxation. A patio area is visible, complete with an umbrella for shade.

Home in Palmetto Dunes

Gorgeous Home With Pool & Golf Views Hilton Head

A scenic outdoor dining area features two high white chairs and a small table, offering a view of the marsh and water beyond. The surrounding greenery includes palm and pine trees, creating a tranquil atmosphere.

4.88 out of 5 average rating, 162 reviews

Water Views Treehouse walkable to Harbour Town

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.

4.98 out of 5 average rating, 103 reviews

Private pool/spa : pool heat available : Kg master

Condo rentals with a pool

4.98 out of 5 average rating, 178 reviews

An outdoor dining area is shown, featuring a round table with six ornate metal chairs. A large red umbrella provides shade, and lush greenery and a view of the marina are visible in the background.

Condo in Sea Pines

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

4.94 out of 5 average rating, 102 reviews

Gorgeous Ocean View 65"TV Pickleball BAR GYM!

A decorative bicycle wall art piece in soft mint green is displayed alongside a playful turtle motif. The bicycle features a white woven basket and artistic details, adding a coastal charm to the interior.

4.95 out of 5 average rating, 227 reviews

BIKE ‘n BED Hilton Head- Perfect Couple's Getaway

The open-plan living and dining area is bathed in natural light, featuring a stylish dining table set for six. A comfortable blue sofa invites relaxation, while a patterned area rug adds warmth. The room is complemented by decorative elements, including a lantern and dried floral arrangements.

4.88 out of 5 average rating, 147 reviews

Turtle View Villa

A living area is characterized by a comfortable seating arrangement, featuring a light-colored sofa and a patterned armchair. A wooden coffee table is placed centrally, and a television is mounted above a decorative fireplace. Large windows provide views of the outdoor deck and surrounding greenery.

4.98 out of 5 average rating, 128 reviews

1BR/2BA condo w/private beach access in Shipyard

4.94 out of 5 average rating, 109 reviews

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

Ocean Views at Villamare, Right on the Beach!

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.

4.96 out of 5 average rating, 115 reviews

Beach Front Resort - Ocean View King Bed

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.

4.92 out of 5 average rating, 144 reviews

Exclusive Oceanfront Decorator Decor Spacious Bdrm

Other vacation rentals with a pool

5 out of 5 average rating, 24 reviews

Oceanfront Luxury! KING BED 75"TV Pickleball & BAR

A dining area features a reclaimed wood table surrounded by cross-back chairs. A shelving unit holds decorative items and books. Natural light brightens the stylish living room in the background, where plush seating and tasteful decor can be seen.

5 out of 5 average rating, 24 reviews

Steps to the Beach - Perfect All-Season Getaway

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 Shelter Cove

5 out of 5 average rating, 8 reviews

Marriott Sunset Pointe - 2BD

5 out of 5 average rating, 31 reviews

Brand New Sea Pines Remodel - Minutes To Beach

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.

5 out of 5 average rating, 42 reviews

54 Folly Field Rd - Amazing Beach Home with Pool

Superhost

An expansive view captures the community pool surrounded by lush greenery and palm trees. Beyond the pool, the glimmering ocean and a clear blue sky filled with soft clouds are visible, enhancing the serene coastal atmosphere.

Villa in Palmetto Dunes

5 out of 5 average rating, 4 reviews

407 Barrington Arms: Beachfront Villa. 2 Bedrooms.

A comfortable living area is highlighted by a sectional sofa adorned with decorative pillows. A wooden coffee table sits in front, featuring accessories and board games. The open layout leads to a dining area with a wooden table, complementing the warm, inviting decor.

4.9 out of 5 average rating, 21 reviews

Newly Renovated Condo HiltonHead