Holiday rentals with a pool in Hilton Head Island

4.91 out of 5 average rating, 193 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.

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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.

5 out of 5 average rating, 108 reviews

The Lookout - A Modern Beach Retreat (Oceanfront)

Welcome to The Lookout! The moment you step into this villa you will be greeted by an open floor plan, a fully stocked kitchen, & every amenity that you'll need for your stay. Take a seat on one of the high top adirondack chairs & enjoy your favorite beverage while overlooking the most popular beaches on the island. Truly - every square inch of this unit has been meticulously utilized to give you an unforgettable vacation. We look forward to hosting you at Seaside Villa's premier luxury villa!

LocationFamilyQuiet

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.

4.99 out of 5 average rating, 140 reviews

Big Ocean View KING BED 75"TV Beach Bar Pickleball

✨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

ValueFamilySleep quality

Apartment in Hilton Head Island

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.

4.97 out of 5 average rating, 167 reviews

Fully Renovated 2 Bedroom Villa - Walk to Beach

Make yourself at home in this comfortable 2 story, ground floor Condo. Easy walk to the beach. Open concept living, dining and fully equipped kitchen and 1/2 bath on main floor. Chose either the comfy King or Queen bedroom with walk-in shower or bathtub of your choice. Private courtyard with Grill and outside seating. All this, in a setting of azaleas, palms and 20 steps to pool with stores and restaurants just 2 blocks away. Please note there is only 1 parking space available for your stay.

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Home in Hilton Head Island

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, 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.

LocationValueBeach

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.

4.98 out of 5 average rating, 364 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 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 & More RESORT Beach Bar/Sports Bar 3 Restaurants Bike Rentals on Site 4 Beach Boardwalks Gated 24/7 Security Seasonal Island Trolley Stop

FamilyValueWalkability

4.91 out of 5 average rating, 221 reviews

A spacious living area is presented with large windows offering views of the surrounding greenery. Two armchairs and a sectional sofa provide comfortable seating, while a circular coffee table sits on a patterned rug. Soft lighting is provided by floor lamps, enhancing the inviting atmosphere.

Townhouse in Shipyard

Stylish Tennis-Golf- Beach Retreat-Renovated!

Welcome to my home! The condo is located in a lush gated community with tennis, golf, and beach, south end of the island, close to all the tourist attractions. Things you can do without getting in your car: stroll on the beach, have a meal at the Sonesta resort, suntan at the community pool, play golf or tennis, ride bicycles. Pet's MUST be included in reservation dropdown at booking. Approval for 2nd dog prior to booking with additional fee charged. Pets are not allowed on the furniture.

LocationFamilyGetting around

4.96 out of 5 average rating, 168 reviews

Aerial view captures the lush greenery surrounding the property, with tree canopies creating a natural border. A highlighted path directs toward the beach, while the serene lagoon is visible nearby, surrounded by the abundant foliage and manicured landscape.

Townhouse in Shipyard

Beachfront Resort 2B Golf Beach Pickleball Tennis

✨Top 5% Guest Favorite✨ Gated Beachfront Resort Golf, Tennis, Pickleball, Pool, Restaurants & Bars Gorgeous Sunny Villa Panoramic Lagoon & Golf Views! Beautiful & Lush Scenery Huge Old Oaks dripping in Spanish Moss! Walk/Bike to Beach Abundant Wildlife! Walk to Shipyard Golf Club & Pub! Modern Coastal Sunny 1st Floor KING BED Master 3 XL SmartTVs WIFI 287 mps Fully Stocked Kitchen Walk-in Shower Washer/Dryer Beach Chairs, Boogie Boards & More! BBQ Bike & Walk Paths Close to Coligny!

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Home in Hilton Head Island

5 out of 5 average rating, 99 reviews

Walk to Beach-Amazing New Home-Hot Tub-Heated Pool

Maximum 16 guests. Welcome to Sea Mist Manor-A quick walk to one of islands best beaches.. Our family has created an amazing ocean getaway. Featuring upscale furnishings & decor from local shops. Creature comforts include-high end hot tub-infra red sauna-arcade-fun kids room-golf themed room.. We welcome you with open arms to Sea Mist Manor-A Seaside Extravaganza! As seasoned hosts, achieving 8+yrs of Airbnb Super Host status, rest assured you're in good hands. Town Permit #053482

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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, 222 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**

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A neatly arranged bedroom features a spacious bed with a light-colored knitted blanket. Natural light filters through a nearby window, illuminating the room. Decorative wall art, displaying leaf motifs, complements the neutral color palette, while a circular mirror adds depth and brightness.

4.89 out of 5 average rating, 304 reviews

Anchor at the Beach ⛱ Eat & Shop at Coligny plaza!

Oceanfront building with a side view of the ocean from the balcony. Park your car and walk to everything. This beautiful 2 bed/2 bath beach condo is perfect for your family vacation or romantic getaway. No streets to cross to get to the beach! Location, location, location. Gated entry, private, and just a 5-minute walk to all the amenities of Coligny Plaza (70 Shops & Restaurants). I also provide beach chairs, umbrella, and beach cart for your convenience during your stay! #072058

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Villa in Hilton Head Island

The outdoor space features a year-round heated pool surrounded by lush greenery, with a clear view of the ocean. Umbrellas offer shade over picnic tables, while tall trees enhance the serene atmosphere of the beachside setting.

4.97 out of 5 average rating, 132 reviews

Oceanfront Scandi Oasis Amazing View & Heated Pool

Villa Aalto is a new Scandinavian style oceanfront oasis created for ease and relaxation throughout your beach vacation. The streamlined interior offers high-end finishes and luxurious hotel-like amenities, with a fully functional kitchen and serene living area overlooking the ocean. The year-round heated pool and private path to the beach make for stress-free days, but the close proximity to Coligny allows you to bike to restaurants, playgrounds and shops within minutes as well.

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Popular amenities for Hilton Head Island rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 108 reviews

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

FamilyLocationAir conditioning

Home in Hilton Head Island

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, 115 reviews

6 BR, Sleeps 26, Beach Time

LocationFamilyLayout

A spacious backyard features a free heated pool with a paved surrounding. A cozy fire pit made of stone is accompanied by four comfortable chairs, perfect for gatherings. Lush greenery and palm trees provide a natural setting, while the home offers large windows overlooking the area.

5 out of 5 average rating, 9 reviews

Palmetto Dunes Escape with Pool | Dock | Firepit

LocationFamilyOutdoor spaces

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.

4.86 out of 5 average rating, 153 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

FamilyLocationLong stay

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.

4.96 out of 5 average rating, 135 reviews

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

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Superhost

Home in Sea Pines

5 out of 5 average rating, 3 reviews

Family Memories Are Made Better at Deer Run

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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.

4.86 out of 5 average rating, 120 reviews

Palmetto Dunes House: Private Pool, PDBeach, Golf

LocationValueCleanliness

5 out of 5 average rating, 11 reviews

Home in Shipyard

Coastal Fairways

LocationFamilyWalkability

Condo rentals with a pool

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.

4.9 out of 5 average rating, 238 reviews

*New* Easy Breezy at Hilton Head Beach & Tennis

FamilyLocationLong stay

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, 170 reviews

Turtle View Villa

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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.

4.98 out of 5 average rating, 360 reviews

Ocean Front Resort Villa

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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.

4.98 out of 5 average rating, 168 reviews

My Blue Heaven, Direct Ocean Front View

LocationFamilyBathroom

4.98 out of 5 average rating, 149 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

ValueLocationBiking

4.98 out of 5 average rating, 117 reviews

A lounge area features a comfortable sofa adorned with decorative cushions. A round coffee table sits in front of it, surrounded by a soft area rug. A large wall-mounted television is complemented by a striking maritime mural, while natural light filters through blue drapes.

Condo in Shipyard

Hilton Head Island VILLA: STEPS 2 Beach & Coligny!

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4.94 out of 5 average rating, 156 reviews

A scenic view of the ocean is displayed from a top-floor balcony. The tranquil water reflects the clear blue sky, while marshland and vegetation frame the landscape. A boardwalk is visible, leading toward the beach, enhancing access to the natural surroundings.

Condo in Palmetto Dunes

Gorgeous OCEAN Views! Resort Amenities & Beach!

ValueFamilyCondition

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, 176 reviews

⭐Direct Oceanfront Villa Steps to Beach w/ Pool⭐

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Other holiday rentals with a pool

5 out of 5 average rating, 28 reviews

Apartment in Sea Pines

Harbour Town Marina Studio | Walk to Lighthouse

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4.93 out of 5 average rating, 42 reviews

A private residence is set among tall trees, featuring a spacious patio area with a circular pool at its center. A barbecue grill and poolside loungers are visible, surrounded by natural landscaping, creating a serene outdoor retreat.

Home in Sea Pines

Starfish Beach House with Pool and Bikes

ValueFamilyWi-Fi

5 out of 5 average rating, 10 reviews

Palmetto Dunes Villa – Golf, Pools & Bike to Beach

LocationFamilyCondition

5 out of 5 average rating, 37 reviews

Peaceful Retreat at Seascape Villas

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Apartment in Hilton Head Island

5 out of 5 average rating, 10 reviews

Near Beach Condo w/ Pool · Hot Tub · Pickleball

LocationFamilyWalkability

4.95 out of 5 average rating, 129 reviews

The bungalow is nestled among lush greenery and tall trees, surrounded by a natural environment. Palm leaves frame the structure, and a small deck is visible at the front, inviting warmth and privacy in this woodland setting.

Bungalow in Sea Pines

Closest to Beach Path, Screened Porch, 1 dog ok

LocationValueAmenities

5 out of 5 average rating, 20 reviews

A spacious living area is furnished with a blue sectional sofa and a coffee table. Soft lighting is provided by two lamps on either side of the sofa. A large patio door opens to an outdoor seating area, allowing natural light to fill the room.

Apartment in Sea Pines

Renovated 1BR HHI – Walk to Beach & Salty Dog Café

LocationFamilyKitchen

A modern home is surrounded by lush greenery, featuring large glass windows that invite natural light. A spacious outdoor area includes multiple lounge chairs and umbrellas, along with a large dining table. A pool area is visible, enhancing the outdoor living experience.