Vacation rentals with a pool in Hilton Head Island

4.95 out of 5 average rating, 129 reviews

Big OceanView Beach Bar FREE Pickleball Tennis Gym

✨ Top Airbnb Guest Favorite ✨ Oceanfront Building Big Ocean View from Living Room & Balcony! Steps to Beach, Pool & Tiki Bar/Grille FREE: Pickleball, Tennis, Gym, Volleyball Queen Bed | Queen Sofa | 2 Bunks Updated by HGTV Decorator Top Floor w/Elevator 65" SmartTV Fast WiFi 652 mbps Beach Chairs, Boogie Boards & More Couples/Small Families RESORT: Oceanfront Pool & Bar/Grille 4 Beach Boardwalks Sports Bar w/Pool Table Bike Rentals Big Shady Playground 2nd pool 3 BBQ Areas Gated 24/7 Security

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, 305 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!

4.92 out of 5 average rating, 190 reviews

A cozy living room features a modern fireplace and a large flat-screen TV mounted on the wall. Light enters through expansive sliding glass doors, leading to a deck. Comfortable seating is arranged around a circular coffee table, with decorative pillows adding subtle touches.

Townhouse in Sea Pines

Ocean Gate 13 Walk to beach villa with pickleball

This villa is perfect for the family beach vacation! We have little ones ourselves, so we've got all the gear needed to make this a comfortable and relaxing stay. We LOVE this villa because of its screened in porch, FREE TENNIS, and proximity to the beach. The screened in porch allows you to enjoy breakfast and happy hour free from mosquitoes and close enough to hear the waves! The beaches are far less crowded than other areas of the island, and it's very close to Sea Pines and Coligny Plaza.

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, 118 reviews

98 Sandcastle Ct

98 Sandcastle Ct Brand New 6 Bedroom Home near Beach with Pool, Elevator/ (Sleeps Up To 22 Guests ) 20 in beds & 2 in Queen Sofa Sleeper. Over 3200 sq feet, 6 Bedrooms, Heated Pool, Elevator & about .3 miles from the beach = Tons of Fun!!! * 6 Bedrooms * 4 Full Baths * Walking Distance to Ocean. * Heated Private Pool. (Free pool Heat :) * Elevator Available: Free use Adults Only. * Free Parking: 4-6 reg cars/mini vans.. LRG SUV's or LRG Vans = 4 parking spots. Note: 2 = garage 4 =driveway.

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.

4.91 out of 5 average rating, 231 reviews

Breathtaking OCEAN VIEW |Pool & Coligny| TOP FLOOR

☀️Time to BOOK YOUR HILTON HEAD ESCAPE. Wake up to sweeping oceanfront views from this top-floor Breakers villa, where sunrise steals the show. Sip coffee and watch dolphins from your private balcony, then walk just steps to the beach, pool, restaurants, and shopping at Coligny Plaza—no car required. Perfect for a romantic getaway or small family vacation, with exclusive deals on bikes & dolphin tours. This bright condo offers unbeatable location, privacy, and a stress-free island stay. 🐬🚲

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, 356 reviews

Oceanfront Luxe KING BED 65TV Beach Bar Pickleball

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! Beachfront Balcony Watch Sunrise/Hear Waves 1 min to Beach Boardwalk! Beachfront Pool, Tiki Bar & Grille FREE Pickleball, Tennis & Gym HGTV Designer Renovation Two 65" SmartTVs KING BED Expanded Bedroom Blackout Sleeping Marble Spa Bath Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESORT Bike Rentals on Site 4 Beach Boardwalks 3 Restaurants Beach Bar/Sports Bar Gated 24/7 Security Seasonal Island Trolley Stop

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, 227 reviews

Oceanfront Luxury! KING BED Beach Bar & Pickleball

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨See the Ocean Sunrise & Hear the Waves! ✨ Oceanfront Balcony FREE Tennis, Gym, Pickleball, Basketball, Volleyball HGTV Decorator Renovation KING BED + 75" & 65" SmartTV s Expanded Bedroom MARBLE BATHROOM Coastal Décor TOP FLOOR w/Elevator Beach Chairs, Boogie Boards, Ice Chest & More RESORT No Resort Fees! Beachfront Pool w/Bar & Grille Sports Bar 2nd Pool Bike Rental in Resort Gated 24/7 Security Free Island Trolley Stop (April-Sept)

A vibrant sunrise is captured over the Atlantic Ocean, illuminating the horizon with warm hues of orange and yellow. The sun's rays radiate across the calm water, casting reflections on the sandy beach below.

4.96 out of 5 average rating, 217 reviews

Ocean Overlook - The Ultimate Vacation Experience

LUXURIOUS, 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! 3RD FLOOR! CORNER UNIT! PRIVATE BALCONY! OCEAN VIEWS FROM EVERY ROOM! WATCH EVERY SUNRISE & SUNSET! 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, 439 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.

A balcony offers a table and two chairs, providing a space for relaxation and enjoyment of ocean views. The horizon features a clear blue sky and the serene expanse of water. Lush greenery and trees frame the scenery, enhancing the tranquil atmosphere.

4.86 out of 5 average rating, 100 reviews

Jim's Chic Direct Oceanfront 2BR Villa

Lovely 4th floor villa with a breathtaking, unobstructed ocean view from the living room and master bedroom. Two bedroom suites, each with separate baths. Fully appointed kitchen - granite countertops, updated cabinets, and stainless steel appliances. Walk to all of the amazing shops & restaurants of Coligny Plaza and the brand-new Celebration Park. Jim Says: “I personally stay in each of my units to ensure they are maintained to my highest level of expectations.”

Superhost

A cozy living area is showcased, featuring a light beige sofa with blue accent pillows and a coffee table displaying colorful magazines. A kitchenette is visible to the left, with white cabinetry and essential appliances. Artwork hangs on the wall, adding a subtle touch to the serene space.

4.88 out of 5 average rating, 166 reviews

Hip Nautic | Pickleball, Indoor Pool & Jacuzzi

Stay at Hip Nautic, a cozy 1BR retreat just a short walk to the beach and Coligny’s shops, dining, and live music. This simple, comfortable condo includes a kitchenette (fridge, stove, oven), queen bedroom, full bath, and a relaxed living area for unwinding after a day out. Enjoy indoor and outdoor pools, jacuzzi, pickleball/tennis courts, and easy parking. Ideal for couples and beach lovers wanting a convenient base near everything Hilton Head offers.

4.92 out of 5 average rating, 106 reviews

Beauty at the Beach! Oceanview King bed free bikes

Wake up to breathtaking ocean views in this beautifully renovated villa, perfect for a romantic getaway. Located in Seaside, a gated oceanfront complex, you're just steps from the beach and a short stroll to restaurants, shops, and live entertainment. Unwind in a luxurious King bed, relax in the stylish living area with a new Queen sleeper, and enjoy a spa-like walk-in shower. Beach chairs and bikes included for the ultimate island retreat! 🌊❤️☀️

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, 105 reviews

Governor’s Quarters Pet Friendly, Fenced in Yard

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.

4.99 out of 5 average rating, 113 reviews

6 BR, Sleeps 26, Beach Time

A charming circular home is nestled among tall trees, featuring a spacious deck with white lounge chairs. The wooden steps lead up to the entrance, showcasing large windows that allow ample natural light. The surrounding greenery enhances the sense of privacy and seclusion.

4.98 out of 5 average rating, 94 reviews

Harbour Town Tree House | Private Office | HT Pool

4.89 out of 5 average rating, 18 reviews

Private Pool ~ Cabana ~ 5 Deer Run Lane

The outdoor area features a private pool surrounded by palm trees, with a spacious deck. Comfortable loungers and umbrellas are arranged nearby. Two inflatable swan floats rest on the water's surface, adding a playful touch to the serene setting.

4.94 out of 5 average rating, 52 reviews

5BR Private Pool+Hot Tub+Sauna, 400 Steps to Beach

4.85 out of 5 average rating, 117 reviews

An outdoor area features a heated private pool surrounded by a spacious patio and lounge chairs. The home, with updated siding, has a shaded seating area and a barbecue grill. Lush greenery and colorful flowers enhance the tranquil ambiance.

Home in Palmetto Dunes

Palmetto Dunes House: Private Pool, PDBeach, Golf

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.

4.87 out of 5 average rating, 396 reviews

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

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.

4.97 out of 5 average rating, 159 reviews

Peaceful Harbour Town Treehouse with Marsh Views

Condo rentals with a pool

5 out of 5 average rating, 120 reviews

Condo in Sea Pines

5 Star Location-Harbourtown-Walkable Area

4.98 out of 5 average rating, 144 reviews

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.

Condo in Shipyard

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

4.89 out of 5 average rating, 175 reviews

Avail July 4th! King Bed/pools/3 blocks to beach

A comfortable bedroom features a spacious bed adorned with white and blue striped bedding. Two bedside lamps provide gentle lighting beside the bed, while a large mirror reflects the room’s arrangement. Windows allow natural light to illuminate the space, highlighting the soft gray carpeting.

4.91 out of 5 average rating, 187 reviews

Beach condo in gated resort w/ tons of amenities!

A sunset view is captured from the balcony, showcasing the golden sun descending over the ocean horizon. Silhouettes of palm trees and a grassy area are visible, creating a serene coastal atmosphere. The sky displays soft hues of orange, pink, and gray.

4.96 out of 5 average rating, 390 reviews

1 Minute walk to the beach *Amazing ocean view*

A private balcony overlooks a pool surrounded by lounge chairs and lush greenery. The ocean is visible in the distance, framed by tall trees under a clear blue sky. The space includes a small round table with two chairs.

4.9 out of 5 average rating, 173 reviews

⭐Direct Oceanfront Villa Steps to Beach w/ Pool⭐

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.

4.97 out of 5 average rating, 198 reviews

Ocean View KING BED 65"TV Beach Bar Pickleball GYM

A living area features a leather recliner sofa and a cozy woven coffee table. A light-colored accent chair and a lamp are positioned nearby. A television is mounted on a decorative cabinet, and three framed art pieces are displayed on the wall above.

4.97 out of 5 average rating, 151 reviews

1st Floor, 1 BR Condo - Steps to Beach and Pool!

Other vacation rentals with a pool

Apartment in Hilton Head Island

5 out of 5 average rating, 8 reviews

SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest

4.96 out of 5 average rating, 57 reviews

Oceanfront Luxe KING BED 75TV Beach Bar Pickleball

Apartment in Hilton Head Island

4.96 out of 5 average rating, 26 reviews

Stunning Ocean View | King Bed | Beach/Pool Resort

Apartment in Hilton Head Island

The living area features comfortable gray seating arranged around a coffee table, with a colorful area rug underfoot. A mounted television is visible on the wall, providing entertainment options, while natural light filters in through the curtains.

4.97 out of 5 average rating, 32 reviews

Beachside Bliss: Walk to Beach / Coligny Plaza

4.99 out of 5 average rating, 82 reviews

A scenic view of the waterway at sunset, featuring gentle reflections of a pastel sky. Lush marshland and distant trees line the banks, enhancing the natural beauty of the surrounding landscape.

Condo in Shelter Cove

Pet friendly condo with amazing Broad Creek views

A light-filled living area features a large sectional sofa and an ottoman on a patterned rug. Floor-to-ceiling glass doors open to a private balcony overlooking lush greenery. A pair of stylish lamps and decorative wall mirrors enhance the space's inviting ambiance.

4.97 out of 5 average rating, 33 reviews

MyStay at 307 Forest Beach Villas - Prime Coligny!

Superhost

Villa in Hilton Head Island

4.67 out of 5 average rating, 6 reviews

Beach Bliss Villa with Scenic Ocean Views

A welcoming living area is presented, featuring a comfortable sofa and a round dining table with two chairs. A wall-mounted television is visible. Natural light floods in through sliding glass doors, offering a view of palm trees and outdoor seating.