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Vacation rentals with a pool in Hilton Head

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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 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

1st flr villa few mins walk to beach pools & pball

Amazing vacation memories are waiting for you at our newly renovated 1st floor villa in Fiddlers Cove. STR Permit# 24587. It’s a 6-7 minute walk to Folly Field beach with private beach access and THE best sunrises. World class golf courses plus amazing restaurants are all close by. Enjoy our 2 pools, hot tub, racquetball, pickleball, and tennis courts and there is also a gym. Pools open March 1 - Oct 31, hot tub open year round. Hop on the scenic walking and bike paths and explore the island.

4.98 out of 5 average rating, 233 reviews
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

Hilton Head Beach & Tennis Resort Ocean View!

AMAZING OCEAN VIEW FROM THE BALCONY! Newly remodeled! Perfect for a family or a couple looking to enjoy a great oceanfront resort! Enjoy the site and sounds of the ocean right from the balcony!! This condo is on the second floor with an ocean view, only 5 units back from the ocean, this is a PRIME location! The unit is located in a quiet part of the resort, steps away from the ocean, Resort Pool, Beach Bar w/live music. FREE Tennis and Pickleball courts. The resort has 24/7 onsite security.

4.91 out of 5 average rating, 291 reviews
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

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

✔wlk to beach 500 yrds, bike, boat, tennis, golf ✔pet-ok✔5beds✔gourmet kitchen☼sundeck✔ping pong table &games✔screened outdoor area with grill&table✔Spectrum&AppleTV*Roku&WiFi✔W&D✔Busn traveler ready✔2 garages✔private yard space✔1st-floor kitchen, living room with love seat and cal king sofa✔semi-open sitting room aka bdrm with cal king sofa, adjacent small closet, powder room✔sun porch✔2nd floor 2 bdrms with a queen✔master bdrm with king bed Tempurpedic, wlk-in cl and bath with ♥♥shower, 2Z AC

4.87 out of 5 average rating, 406 reviews
Top guest favorite
Home in Hilton Head Island

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

4.95 out of 5 average rating, 109 reviews
Top guest favorite
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

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!

4.98 out of 5 average rating, 321 reviews
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

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)

4.97 out of 5 average rating, 238 reviews
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

6 BR, Sleeps 26, Beach Time

Just a short walk down Folly Field to the beach & locally managed by the Owner. This brand new beach house has 6 bedrooms and 4 full bathrooms. Linens, Bath Towel sets & Pool Towels included. An Amazing bunk room/play room with 6 full size bunk beds, high end furnishings, fully equipped kitchen, dining for the entire crew, 2 huge balconies with lovely lagoon views, large outdoor living area with television and shaded pool. We have thought of everything & we are at your service! PN: 040312

4.99 out of 5 average rating, 118 reviews
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

*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.

4.9 out of 5 average rating, 241 reviews
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

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.)

4.9 out of 5 average rating, 217 reviews
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

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

4.98 out of 5 average rating, 368 reviews
Top guest favorite
The private balcony features a dining table surrounded by chairs, offering serene lagoon views. Lush greenery frames the area, contrasting with the smooth wooden railing. Light filters through the trees, creating a peaceful outdoor setting, ideal for enjoying meals or morning coffee.
Condo in Hilton Head Island

Island Club Condo: Beach, Pool, Gym, Pickleball

Welcome to our 1-bedroom, 1.5-bathroom condo with lagoon views and an easy beach-day setup. • Private balcony and outdoor dining with water views • King bedroom plus twin beds and a fold-out couch • Resort access, beach gear, cruiser bikes, pool, sauna, courts, gym • About a 3 min walk to the beach; dining and groceries are a short drive away Relax, swim, and settle in with the comforts that make Hilton Head feel easy. Reserve your stay and enjoy the balcony, bikes, and resort perks.

4.92 out of 5 average rating, 103 reviews
Top guest favorite
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.
Condo in Hilton Head Island

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!

4.91 out of 5 average rating, 132 reviews

Popular amenities for Hilton Head rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
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

Wonderful Island's Retreat (With Private Pool)

4.92 out of 5 average rating, 276 reviews
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

Cozy beach house w/Private Heated Pool near park

4.98 out of 5 average rating, 136 reviews
Top guest favorite
Home in Hilton Head Island

Large home, beach close, pool

4.94 out of 5 average rating, 238 reviews
Superhost
Home in Palmetto Dunes

Blue Sky Villa: Beach/pets/golf/tennis/pickleball

4.84 out of 5 average rating, 148 reviews
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

Palmetto Dunes House: Private Pool, PDBeach, Golf

4.86 out of 5 average rating, 122 reviews
Top guest favorite
A private pool area is featured, showcasing a clear blue pool surrounded by paved decking. Several lounge chairs are positioned nearby, accompanied by a shaded cabana area with seating. Bright pink inflatable flamingos float in the water, enhancing the relaxing ambiance.
Home in Hilton Head Island

Resort-Style Pool, Cute House 88 Steps to Sand

4.97 out of 5 average rating, 136 reviews
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

Private pool/spa : pool heat available : Kg master

4.98 out of 5 average rating, 124 reviews
Top guest favorite
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.
Home in Sea Pines

Stately Governors Quarters-Pet Friendly, Fenced In

4.98 out of 5 average rating, 110 reviews

Condo rentals with a pool

Guest favorite
The image displays a large swimming pool surrounded by lounge chairs, with a view of the sandy beach and ocean beyond. The shoreline features umbrellas for shade, while the landscape includes greenery and distant beachgoers enjoying the sun.
Condo in Hilton Head Island

Relax and Unwind at this Ocean Front Resort

4.76 out of 5 average rating, 156 reviews
Top guest favorite
Condo in Palmetto Dunes

Oceanside Resort - Private Beach Access - 3 Pools

4.97 out of 5 average rating, 119 reviews
Guest favorite
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.
Condo in Hilton Head Island

Ocean Overlook - The Ultimate Vacation Experience

4.96 out of 5 average rating, 224 reviews
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

Oceanview Luxury! King Bed 75"TV Pickleball & Bar

4.99 out of 5 average rating, 145 reviews
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

Private comfy condo, steps away from the beach

4.96 out of 5 average rating, 123 reviews
Top guest favorite
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

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

4.96 out of 5 average rating, 159 reviews
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

My Blue Heaven, Direct Ocean Front View

4.98 out of 5 average rating, 172 reviews
Top guest favorite
Condo in Hilton Head Island

Ocean/Marsh View KING BED Beach Bar GYM Pickleball

4.97 out of 5 average rating, 359 reviews

Other vacation rentals with a pool

Top guest favorite
A spacious front porch features white rocking chairs with multicolored cushions, set against a backdrop of tall pine trees. Natural light filters through the porch railings, creating a serene atmosphere. The view overlooks a landscaped courtyard, enhancing the inviting outdoor space.
Townhouse in Hilton Head Island

Luxury Villa-Steps from the beach and pet friendly

4.95 out of 5 average rating, 114 reviews
Top guest favorite
A serene beach scene captures gentle waves lapping the shore, with soft pastel colors of the sky reflected on the water. Birds can be seen along the wet sand, creating a sense of calm and openness in the landscape.
Townhouse in Hilton Head Island

Piece of Paradise on Hilton Head Island

4.92 out of 5 average rating, 172 reviews
Top guest favorite
The kitchen and dining area is equipped with modern appliances, including a microwave and coffee maker. A wooden table with six chairs is set for dining, while white cabinetry and light countertops create a spacious atmosphere. A sliding door provides access to the outdoor area.
Condo in Hilton Head Island

1st Floor, 8 Min Walk Beach, King Bed, In Unit W/D

4.98 out of 5 average rating, 133 reviews
Top guest favorite
Condo in Hilton Head Island

Beach Skybox-panoramic view, hear, feel the ocean.

4.97 out of 5 average rating, 124 reviews
Top guest favorite
A modern kitchen features smooth white cabinetry and granite countertops, complemented by stainless steel appliances. A double basin sink is situated near the window, with a microwave and oven built into the cabinetry. Soft, recessed lighting illuminates the workspace.
Condo in Hilton Head Island

Heron's Haven on Port Royal Sound, 2BR/2BA

4.95 out of 5 average rating, 242 reviews
Guest favorite
Condo in Hilton Head Island

BEACH PATH At Hilton Head Beach and Tennis Resort

4.93 out of 5 average rating, 125 reviews
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

The Lookout - A Modern Beach Retreat (Oceanfront)

5.0 out of 5 average rating, 114 reviews
Top guest favorite
A serene view of a sunset over the ocean is framed by a railing, with silhouettes of trees in the foreground. The horizon displays vibrant orange and yellow hues against a deepening blue sky, providing a tranquil backdrop to the surrounding landscape.
Villa in Hilton Head Island

Direct Ocean Front S. Forest Beach

4.93 out of 5 average rating, 396 reviews

Destinations to explore