Holiday 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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Top guest favourite

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.

Apartment in Hilton Head Island

4.96 out of 5 average rating, 138 reviews

Cozy Villa 6 Minute Walk From the Beach & Golf

Recently updated villa only a 6 min. walk to the beach with private & public beach access and a 7 min. drive to Port Royal Plantation GC. Villa has 1 queen and 2 twin beds, full size sleeper sofa, 55" tv in the living room and tvs in both bedrooms. Many family amenities, Washer/Dryer in the unit, and a deck overlooking the Port Royal golf course. Fiddler's Cove is a gated community with 10 Har-Tru tennis courts, 2 indoor racquet ball courts, 2 pools, hot tub, work out facility and Tot lots.

Top guest favourite

A renovated kitchen features modern stainless steel appliances including a microwave, oven, and dishwasher. White cabinetry and granite countertops create a clean aesthetic. Ample storage is provided by drawers and cabinets, while laminate flooring adds a warm touch to the space.

Apartment in Hilton Head Island

4.98 out of 5 average rating, 231 reviews

Reno’d 1st flr walk to beach pools hot tub & more

Our newly renovated 1st floor villa in Fiddler's Cove. STR Permit# 24587. It’s a 6-7 minute walk to Folly Field beach with private beach access. THE best sunrises are a few minutes walk from our door. Close to world class golf courses and restaurants. Onsite amenities include 2 pools, a hot tub, racquetball, pickleball, tennis and gym. Pools open March 1 - Oct 31, hot tub open year round. If you love the ocean, golf biking, pickleball and tennis, it’s the perfect place for your next vacation.

Top guest favourite

A candle is displayed on a table, surrounded by seashells, with a sunset view of the ocean in the background. The warm colors of the sky reflect off the water, while a cup is placed nearby, adding to the serene atmosphere of the balcony.

Apartment in Hilton Head Island

4.99 out of 5 average rating, 141 reviews

Oceanview Luxury! King Bed 75"TV Pickleball & Bar

✨Top Airbnb Guest Favorite Home✨ Big Ocean Views - Living Room & Balcony Oceanfront Building Steps to Beach Boardwalk, Pool & Tiki Bar FREE Pickleball, Tennis, Gym & More KING BED + 75" & 65" Smart TVs Expanded Bedroom HGTV Featured Decorator 100% NEW Luxury renovation Marble Kitchen & Bath Quiet Top Floor Well-designed 540 sq. ft. Elevator Beach Chairs + More RESORT: Oceanfront Pool & Bar & Grille 3 Restaurants Sports Bar 4 Beach Boardwalks Bike Rental Gated 24/7 Security FREE Island Trolley

Top guest favourite

A serene waterfront scene features two boats navigating through calm waters, with gentle ripples created in their wake. Lush greenery lines the horizon, while a clear sky reflects the soft colors of the evening light. The tranquility of the setting showcases the natural beauty of the harbor.

Apartment in Shelter Cove

4.98 out of 5 average rating, 108 reviews

Stunning Views in a Perfect Location!

Escape to Shelter Cove Harbour and enjoy Palmetto Dunes beach access! Dolphin Cove is a contemporary 1 bedroom villa in Captain's Quarters, with stunning views of Shelter Cove Harbour and Broadcreek! In addition to it's third floor premium location, this open living design has been completely remodeled with upscale furnishings and custom cabinetry. Located in a private gated community, Dolphin Cove is next door to Shelter Cove's quaint shops, local restaurants and numerous marina activities.

Top guest favourite

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

5.0 out of 5 average rating, 122 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.

Top guest favourite

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.

Apartment in Hilton Head Island

4.97 out of 5 average rating, 235 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)

Top guest favourite

A calm beach scene is captured at dusk, featuring gentle waves lapping at the shore. The horizon showcases a soft gradient of colors, transitioning from deep blue to warm peach and pink tones. The tranquil sea reflects the fading light of dusk.

Villa in Palmetto Dunes

4.9 out of 5 average rating, 101 reviews

Spacious dog-friendly villa, walk to the beach

Welcome to your perfect family getaway on Hilton Head Island! This vibrant 3BR, 2.5BA luxurious villa is professionally decorated, accented with inviting, colorful coastal decor throughout. The villa offers a fully-remodeled kitchen, a spacious and comfortable living area with plenty of ways to relax and unwind. Outside, there is a large, private patio with a gas grill, an outdoor dining set and fast access to five community swimming pools and the beach. Snowbirds and long-term guests welcome

Top guest favourite

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.

Apartment in Hilton Head Island

4.98 out of 5 average rating, 169 reviews

My Blue Heaven, Direct Ocean Front View

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.

Top guest favourite

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.

Apartment in Hilton Head Island

4.96 out of 5 average rating, 120 reviews

Private comfy condo, steps away from the beach

Light and spacious beach-side condo centrally located within a gated community. Walk to the beach via one of several private beach accesses or to the community’s pools, grills, courts, gym, and play areas within minutes. Located in a quiet and relaxed area away from the bustle of the island’s southern end makes this perfect for families and retirees alike. Golf courses, stores and entertainment are only a short drive from the property. No-contact check-in using your personal numeric code.

Top guest favourite

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.

Apartment in Hilton Head Island

4.9 out of 5 average rating, 238 reviews

*New* Easy Breezy at Hilton Head Beach & Tennis

Newly renovated in March 2026 and completely redesigned from floor to ceilings, enjoy our wide ocean view from our 3rd floor Ocean Villa. Wake up to sunrise over the Atlantic, grab coffee on your private balcony, and walk to the beach in under two minutes. Spend the afternoon at Hilton Head’s largest oceanfront pool before ending the day with dinner and live music just steps from your condo. Beach chairs, wagon, pickleball, tennis, free parking, & close to the building's only elevator.

Top guest favourite

A pair of flip-flops and a set of brown sandals are placed on the soft, sandy beach. Sparse green grass and plants are visible in the background, complementing the tranquil beach setting.

Apartment in Hilton Head Island

4.9 out of 5 average rating, 216 reviews

Hilton Head Hidden Gem

Comfy 3rd floor walk up retreat. Calm decor. Screened balcony. Equipped kitchen. WIFI, beach chairs/umbrella, gym, pickleballl, basketball & tennis courts, charcoal grills/picnic tables; pools. Steps from your door: explore a sandy beach, watch fish jump & dolphins swim; observe nature on a private pier. See the sunrise on the water. Grocery/restaurants w/in 1-5 miles. Make a meal or a reservation! Short drive to all island locales. Great island bike paths. (No pets or smoking.)

Top guest favourite

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.

Apartment in Hilton Head Island

4.98 out of 5 average rating, 364 reviews

Oceanfront Luxe KING BED 65TV Beach Bar Pickleball

Panoramic 180° Oceanfront views the Moment You Open the Door! Beachfront Balcony Watch Sunrise/Hear the Waves 1 min walk to Beach! Beachfront Pool, Tiki Bar/Grill KING BED FREE Pickleball, Tennis, Gym HGTV Designer Renovation Two 65" SmartTVs Expanded Bedroom Blackout Sleeping Marble Spa Bath Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest RESORT Beach Bar/Sports Bar 3 Restaurants Bike Rentals on Site 4 Beach Boardwalks Gated 24/7 Security Seasonal Island Trolley Stop