Holiday rentals with a pool in Hilton Head Island

A panoramic view from the balcony showcases the sparkling ocean and expansive blue sky. Below, palm trees dot the landscape, while the beach is glimpsed in the distance. A pool area is visible, framed by well-maintained greenery, with parking spaces filled with vehicles.

4.98 out of 5 average rating, 205 reviews

Ocean View KING BED 75"TV Beach Bar Pickleball GYM

✨Airbnb Top Guest Favorite✨ Oceanfront Building Ocean & Pool View from Balcony Steps to Beach Bar & Pool FREE Gym, Pickleball Tennis Volleyball & More! 100% NEW HGTV Designer Renovation KING BED 75" & 65" SmartTVs Beach Chairs, Boogie Boards, Ice Chest & More Marble Kitchen/Spa Bath Top Floor WiFi 557 Mbps Elevator RESORT: No Resort Fees Huge Oceanfront Pool Tiki Beach Bar & Grille- Feb-Nov Sports Bar Bike Rental Gym & Tennis Gated 24/7 Security Free Island Trolley (Apr-Sept) 4 Beach Boardwalks

ValueFamilyAccess

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, 107 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!

LocationValueSleep quality

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, 139 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

LocationFamilyGetting around

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.

FamilyValueAccess

A spacious pool area is visible, bordered by sun loungers and palm trees. The ocean can be seen in the background, with glistening sunlight reflecting off the water. A clear blue sky enhances the inviting atmosphere of the outdoor space.

4.91 out of 5 average rating, 236 reviews

Breathtaking OCEAN VIEW |Pool & Coligny| TOP FLOOR

☀️Time to BOOK YOUR HILTON HEAD ESCAPE. Wake up to sweeping oceanfront views from this top-floor Breakers villa, where sunrise steals the show. Sip coffee and watch dolphins from your private balcony, then walk just steps to the beach, pool, restaurants, and shopping at Coligny Plaza—no car required. Perfect for a romantic getaway or small family vacation, with exclusive deals on bikes & dolphin tours. This bright condo offers unbeatable location, privacy, and a stress-free island stay. 🐬🚲

ValueLocationBeach

4.91 out of 5 average rating, 220 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.

LocationValuePets

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!

LocationFamilyCleanliness

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**

ValueLocationQuiet

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, 303 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

FamilyValueWalkability

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.

ValueFamilyPool

5 out of 5 average rating, 125 reviews

Condo in Sea Pines

5 Star Location-Harbourtown-Walkable Area

Escape to our luxury villa in Hilton Head's exclusive Harbour Town in the gated Sea Pines Resort! A short walk from Harbour Town Marina, which offers enertainment, dining, shopping, water sports, cruises, golf, tennis, and a pier. You will have access to The Sea Pines Beach Club, a short trolly, bike or car ride away. This private 3rd-floor impeccilbly appointed 'coastal chic' retreat does not share any walls and offers serene lagoon views from a private balcony.

FamilyLocationNearby

4.99 out of 5 average rating, 149 reviews

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

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

Please see our almost 1000 5-star reviews at our other properties. This spacious completely remodeled, top floor villa is within a 5-10 minute walk to the beach and everything else, including a seasonal pool, several restaurants, general store, wine bar, tennis, golf, kayaks/canoes, bikes, fishing and so much more. Each master/en-suite has two Queen beds and every amenity you could imagine. Bathrooms are spacious with closed off toilet/showers.

ValueFamilyAir conditioning

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

FamilyLocationCleanliness

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

ValueLocationPool

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

FamilyValueCleanliness

4.96 out of 5 average rating, 134 reviews

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

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

FamilyValuePool

5 out of 5 average rating, 6 reviews

An expansive pool deck is illuminated with soft lighting, showcasing a private pool and built-in spa. A lounge area with multiple chairs is present, and a covered seating area is visible in the background. The setting sun casts warm hues over the space.

Home in Palmetto Dunes

Upscale Retreat w Pool & Spa | Palmetto Dunes

FamilyLocationDecor

Superhost

Home in Sea Pines

5 out of 5 average rating, 4 reviews

Sea Pines · Walk to Beach · Lagoon Deck · 3BR

LocationFamilyView

4.86 out of 5 average rating, 120 reviews

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

FamilyLocationComfort

5 out of 5 average rating, 10 reviews

Home in Shipyard

Coastal Fairways

LocationFamilyPool

Condo rentals with a pool

A spacious living area is equipped with two grey sofas adorned with striped cushions, positioned around a wooden coffee table with a glass top. Subtle artwork hangs on the wall, complementing the light decor, while natural light illuminates the room from nearby areas.

4.82 out of 5 average rating, 184 reviews

After Dune Delight | Spacious Condo, Full Kitchen

LocationValueSolo travel

4.85 out of 5 average rating, 279 reviews

A gated pool area is showcased, featuring a clear swimming pool surrounded by lounge chairs and a shaded deck. Lush palm trees and well-maintained landscaping are visible in the background. A table is positioned by the poolside, contributing to a relaxed atmosphere.

Condo in Sea Pines

South end newly renovated first floor 2 bd condo

LocationValueWi-Fi

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

LocationValueDecor

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

ValueLocationComfort

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, 363 reviews

Oceanfront Luxe KING BED 65TV Beach Bar Pickleball

LocationValueNearby

4.98 out of 5 average rating, 116 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!

ValueLocationParking

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, 234 reviews

Oceanfront Luxury! KING BED Beach Bar & Pickleball

LocationFamilyGetting around

A cozy living area features a green sofa adorned with patterned cushions, accompanied by two stylish armchairs. A wooden coffee table sits at the center, with decorative elements including a bowl. Artistic nature-themed prints are displayed on the walls, and natural light fills the space through sliding glass doors.

4.89 out of 5 average rating, 150 reviews

Sunny Treetop Getaway w/ tennis and pickleball

LocationFamilyAir conditioning

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

ValueLocationView

Home in Hilton Head Island

The living area features an open layout with a cozy sofa and patterned armchairs surrounding a wooden coffee table. Natural light streams through large sliding glass doors that provide a view of the pool and outdoor seating area. Neutral tones and decorative accents create a welcoming environment.

4.9 out of 5 average rating, 61 reviews

Modern Serenity - Steps to Beach and Coligny Plaza

ValueLocationWalkability

5 out of 5 average rating, 37 reviews

Peaceful Retreat at Seascape Villas

FamilyLocationLaundry

Apartment in Hilton Head Island

5 out of 5 average rating, 10 reviews

Near Beach Condo w/ Pool · Hot Tub · Pickleball

LocationFamilyBiking

4.92 out of 5 average rating, 39 reviews

A private pool area is surrounded by lush greenery and tall trees, providing privacy and a natural setting. The pool features a built-in spa and is bordered by a spacious stone patio. Four lounge chairs are positioned nearby for relaxation.

Home in Shipyard

Private Pool | Golf | Exq. Coffee | Seascape

ValueLocationComfort

4.96 out of 5 average rating, 84 reviews

The living room features a spacious sectional sofa with decorative throw pillows, complemented by a blue accent chair. Floor-to-ceiling windows provide ample natural light and views of the surrounding landscape. Neutral-toned decor and artwork depicting fish enhance the coastal ambiance.

Condo in Palmetto Dunes

Ocean Views at Villamare 1405, Steps to the Beach!

LocationFamilyCleanliness

4.99 out of 5 average rating, 90 reviews

A scenic view of the waterway at sunset, featuring gentle reflections of a pastel sky. Lush marshland and distant trees line the banks, enhancing the natural beauty of the surrounding landscape.

Condo in Shelter Cove

Pet friendly condo with amazing Broad Creek views

FamilyLocationCleanliness