Become a host

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.

1 of 1 pages1 / 1
Top guest favorite
Condo in Hilton Head Island
4.97 out of 5 average rating, 353 reviews

Ocean/Marsh View KING BED Beach Bar GYM Pickleball

✨Top Guest Favorite Home✨ Beachfront Building! Steps to Beach, Pool, Tiki Bar & Grille! Quiet Top Floor: Marsh & Ocean Views KING BED + 2 XL SmartTVs FREE Pickleball, Tennis, Gym + More HGTV Decorator FAST WiFi (574 mbps) Couples Retreat Beach Chairs, Boogie Boards, Ice Chest+More 🏝️RESORT🏝️ 4 Private Beach Boardwalks Huge Oceanfront Pool Beachfront Tiki Bar & Grille Sports Bar & Grille 2nd Pool Bike Rentals in Resort Gated 24 HR Security HUGE shady Playground FREE Island Trolly (April-Sept)

Top guest favorite
Home in Hilton Head Island
4.95 out of 5 average rating, 108 reviews

Steps to Beach, Pool, 5BR, Great Location

Make this brand new (2023) custom built home, Sur La Mer at Burkes Beach, your vacation destination! This 5 bedroom home is a guaranteed picture perfect destination for your family or group of up to 14 people and features a heated private pool* and a short walk to the beach. Sur Le Mer is located just steps from beach access and right next to Chaplin Community Park (basketball, playground, tennis, baseball diamond and open field). It's also short drive to local restaurants, bars, grocery store

Top guest favorite
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.
Condo in Hilton Head Island
4.98 out of 5 average rating, 230 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 favorite
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.
Condo in Hilton Head Island
4.99 out of 5 average rating, 140 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 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, 360 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
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.
Condo 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 favorite
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.
Condo 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 to Beach Boardwalk! 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

Top guest favorite
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 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, 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 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, 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 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
4.9 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 favorite
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.
Condo 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.)

Popular amenities for Hilton Head rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
The private heated pool area features a calming blue water surface surrounded by a stone patio. Five lounge chairs are positioned for relaxation, and a grill is located nearby, with lush greenery providing a natural backdrop and a view of the golf course beyond.
Home in Palmetto Dunes
4.86 out of 5 average rating, 121 reviews

Palmetto Dunes House: Private Pool, PDBeach, Golf

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
4.87 out of 5 average rating, 403 reviews

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

Guest favorite
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
4.96 out of 5 average rating, 135 reviews

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

Top guest favorite
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
4.98 out of 5 average rating, 134 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 Sea Pines
4.96 out of 5 average rating, 166 reviews

Peaceful Harbour Town Treehouse with Marsh Views

Superhost
A single-story home is highlighted by a charming front porch and a well-maintained landscaped entrance. The American flag is displayed prominently above the entryway, while cobblestone pathways guide visitors to the entrance amid surrounding greenery.
Home in Hilton Head Island
4.92 out of 5 average rating, 273 reviews

Wonderful Island's Retreat (With Private 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 Palmetto Dunes
4.86 out of 5 average rating, 154 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

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, 122 reviews

Private pool/spa : pool heat available : Kg master

Condo rentals with a pool

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

The Lookout - A Modern Beach Retreat (Oceanfront)

Top guest favorite
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
4.98 out of 5 average rating, 149 reviews

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

Top guest favorite
A scenic view captures the expansive marsh and ocean in the distance. A long wooden boardwalk meanders through the greenery, leading to the beach. Light green grass and shrubs can be seen in the foreground, enhancing the natural landscape.
Condo in Palmetto Dunes
4.94 out of 5 average rating, 289 reviews

Ocean View | Top Floor | Walk to Beach | Pools!

Top guest favorite
A large, inviting pool area is surrounded by palm trees and lounge chairs. The pool's curvy shape is highlighted by soft lighting, creating a relaxing atmosphere. Adjacent to the pool, a spacious building features expansive windows, enhancing the connection to the outdoor space.
Condo in Hilton Head Island
4.96 out of 5 average rating, 145 reviews

Beachside Hilton Head Villa Fully Renovated

Top guest favorite
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, 120 reviews

Private comfy condo, steps away from the beach

Top guest favorite
Condo in Sea Pines
5.0 out of 5 average rating, 126 reviews

5 Star Location-Harbourtown-Walkable Area

Guest favorite
A view from the balcony showcases lush greenery and a tranquil pond, with a gentle fountain visible. In the distance, the ocean glimmers under a blue sky. A palm tree stands prominently in the foreground, enhancing the coastal scenery.
Condo in Hilton Head Island
4.91 out of 5 average rating, 288 reviews

Hilton Head Beach & Tennis Resort Ocean View!

Top guest favorite
A spacious living area features a large sectional sofa with throw pillows and a cozy blanket. Natural light enters through large windows, illuminating the room. A coffee table sits in the center, complemented by a small side table, while soft lighting is provided by floor and table lamps.
Condo in Palmetto Dunes
4.99 out of 5 average rating, 151 reviews

Walk to Ocean | Pool | Large Bedrooms | Sea’Esta

Other vacation rentals with a pool

Top guest favorite
The kitchen features modern appliances, including a stainless steel refrigerator and a sleek oven. White cabinetry with glass accents showcases dishware. A marble countertop provides ample workspace, and recessed lighting brightens the room, enhancing its inviting ambiance.
Apartment in Hilton Head Island
4.97 out of 5 average rating, 167 reviews

Fully Renovated 2 Bedroom Villa - Walk to Beach

Top guest favorite
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

Top guest favorite
Apartment in Hilton Head Island
5.0 out of 5 average rating, 7 reviews

Luxury 2026 Renovation+Oceanfront Views!

Top guest favorite
Apartment in Sea Pines
5.0 out of 5 average rating, 30 reviews

Harbour Town Marina Studio | Walk to Lighthouse

Top guest favorite
A dining table is set for four, featuring blue and white dishware and glassware. A comfortable living area showcases a sectional couch, two accent chairs, and a large TV mounted on the wall. Natural light filters in through glass doors, leading to an outdoor space.
Townhouse in Hilton Head Island
5.0 out of 5 average rating, 21 reviews

Folly Fun! Permit # 076134

Top guest favorite
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
4.91 out of 5 average rating, 78 reviews

Dream Paradise Oceanfront Beach/Pool Steps Away

Top guest favorite
Apartment in Hilton Head Island
5.0 out of 5 average rating, 11 reviews

Near Beach Condo w/ Pool · Hot Tub · Pickleball

Top 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
4.9 out of 5 average rating, 81 reviews

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

Destinations to explore