Holiday rentals with a pool in Hilton Head Island

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, 122 reviews

Wide Ocean View! KING BED Beach Bar Pickleball GYM

✨Top 5% Airbnb Home✨ BIG OCEAN VIEWS FROM LIVING ROOM & BALCONY! Oceanfront Building Steps to Beach Boardwalk, Pool & Tiki Bar! FREE Pickleball, Tennis, Gym & More HGTV Featured Decorator 100% NEW Luxury renovation KING BED + 75" & 65" Smart TVs Expanded Bedroom Luxe Marble Kitchen & Bath Quiet Top Floor Well-designed 540 sq. ft. Elevator Beach Chairs + More RESORT: Oceanfront Pool & Bar & Grille Restaurants Sports Bar 4 Beach Boardwalks Bike Rental Gated 24/7 Security FREE Island Trolley Stop

A tranquil beach scene is captured, featuring soft sand leading toward shimmering ocean waves. A wooden fence guides the pathway, with grasses gently framing the foreground. The sky is illuminated with warm hues of orange and pink as the sun rises above the horizon.

4.97 out of 5 average rating, 302 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!

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.

4.98 out of 5 average rating, 139 reviews

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

This large, tastefully decorated 1BR / 2BA condo, located in Shipyard, has everything you need to kick back with family or friends. Enjoy a morning coffee or evening cocktail on the large wrap around deck. Spacious and comfortable master bedroom with king bed, walk-in closet, en-suite bath, and seating area. Fully equipped kitchen with an adjacent seating area for six. Queen sleeper sofa in the living room and second full bath with shower. In unit washer/dryer. Clean fee includes 1 car pass.

Flat 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, 162 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.

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, 117 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 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, 353 reviews

Oceanfront Luxury! KING BED 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, 221 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)

4.98 out of 5 average rating, 102 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

Governor’s Quarters Pet Friendly, Fenced in Yard

Welcome to Governor's Quarters- your Luxury Hilton Head Getaway Stay Lowcountry in this stately-designed home. Newly remodeled & fully equipped for your golfer’s retreat or family/friends' coastal vacation. 5 mins from the SeaPines Beach Club and HarbourTown Golf Links and the heated community pool! Located in famous, Sea Pines Resort. Enter the gates of resort living offering trolley rides to local restaurants, premium golf courses, HarbourTown Lighthouse, & most importantly- the beach!

Townhouse in Hilton Head Island

A wooden boardwalk leads to a sandy beach, where beach umbrellas dot the shoreline. Soft waves lap at the shore beneath a clear blue sky with fluffy clouds, creating a serene coastal scene.

4.98 out of 5 average rating, 160 reviews

Beach Resort! Luxury Golf & Lagoon View Pickleball

Gated Beach & Golf Resort! ✨Top 5% Airbnb Guest Favorite✨ Beach, Golf, Pool, Spa, Restaurants & Bars FREE Pickleball & Tennis - across street HGTV Decorator designed Panoramic Golf & Lagoon Views Double Porch Lush Scenery - Tons of Wildlife! Coastal Décor Sunny 1st Floor End Unit KING BED + 2 QUEENS 3 XL SmartTVs FAST WIFI & CABLE Chef's Kitchen Washer/Dryer BBQ Beach Cart, Chairs, Boogie Boards, Ice Chest Walk/Bike to Beach Walk to Golf Club & Pub Close to Coligny Summer Beach Shuttle

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, 215 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**

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, 120 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.

4.95 out of 5 average rating, 135 reviews

KING BED!Ocean View, Free Bikes Poolside 3rd Floor

Pack your flip-flops and get ready for fun—this sunny poolside villa on Hilton Head Island is your ticket to the ultimate coastal escape! Just steps from the beach and the refreshing Atlantic breeze, this vibrant retreat serves up the perfect mix of relaxation, adventure, and ocean views. Start your day with coffee on the balcony, soak up the sun by the pool, then hop on one of our free bikes to cruise the island like a local! The perfect getaway starts right here!

Popular amenities for Hilton Head Island rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 7 reviews

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.

Home in Palmetto Dunes

Palmetto Dunes Escape with Pool | Dock | Firepit

5 out of 5 average rating, 35 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

5 out of 5 average rating, 20 reviews

17 Firethorn - HGTV "Wow-Worthy", Pool, Fire Pit

A dining area features a reclaimed wood table surrounded by cross-back chairs. A shelving unit holds decorative items and books. Natural light brightens the stylish living room in the background, where plush seating and tasteful decor can be seen.

5 out of 5 average rating, 36 reviews

Steps to the Beach - Perfect All-Season Getaway

4.85 out of 5 average rating, 113 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 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.

4.97 out of 5 average rating, 110 reviews

Private pool/spa : pool heat available : Kg master

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, 394 reviews

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

5 out of 5 average rating, 29 reviews

The spacious backyard features a large heated sports pool surrounded by a well-manicured lawn. Deck chairs in vibrant colors are arranged along the poolside, while a covered deck is accessible from the house. Lush trees provide shade, enhancing the relaxing outdoor environment.

Home in Sea Pines

Sweet Carolina~Pool~Fenced Yard~FirePit

Apartment rentals with a pool

A serene beach scene features a boardwalk leading to the water, surrounded by soft sand and lush greenery. The sky is expansive, showcasing soft clouds merging with blue hues. The shoreline is visible in the distance, offering a peaceful atmosphere.

4.99 out of 5 average rating, 139 reviews

Beach condo with pool and stunning nature views

4.98 out of 5 average rating, 196 reviews

An outdoor dining area is shown, featuring a round table with six ornate metal chairs. A large red umbrella provides shade, and lush greenery and a view of the marina are visible in the background.

Apartment in Sea Pines

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

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.

4.96 out of 5 average rating, 146 reviews

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

Apartment in Palmetto Dunes

4.96 out of 5 average rating, 104 reviews

Oceanside Resort - Private Beach Access - 3 Pools

Apartment in Palmetto Dunes

The living area features a sectional sofa with blue and neutral throw pillows. A textured round coffee table sits in front, surrounded by two accent chairs. Decorative wall art, consisting of various woven circles, adds visual interest. Light from table lamps enhances the inviting space.

4.94 out of 5 average rating, 141 reviews

Oceanfront Breathtaking Views

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, 169 reviews

⭐Direct Oceanfront Villa Steps to Beach w/ Pool⭐

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, 146 reviews

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

4.94 out of 5 average rating, 143 reviews

Subtropical Stunner-King bed & bikes! Central Air!

Other holiday rentals with a pool

Superhost

A spacious living area is visible, featuring two comfortable sofas and a coffee table. Large glass doors provide a view of the serene wooded surroundings, which enhances the natural light in the room. A wall-mounted television is positioned near a mirrored wall, adding depth to the space.

Apartment in Sea Pines

4.78 out of 5 average rating, 55 reviews

SeaPines - Amazing Total Remodel, Pet Friendly

5 out of 5 average rating, 23 reviews

Peaceful Retreat at Seascape Villas

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, 98 reviews

Jim's Chic Direct Oceanfront 2BR Villa

5 out of 5 average rating, 13 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.

Flat in Sea Pines

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

5 out of 5 average rating, 5 reviews

Vacation Paradise - Private Pool, Fire Pit & BBQ

Flat in Hilton Head Island

4.88 out of 5 average rating, 26 reviews

Oceanfront Condo w/ Balcony | Sea Side Villas HHI

Superhost

5 out of 5 average rating, 3 reviews

Spacious Deck, Hot Tub, Second Row To Beach & Bra

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.