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Vacation rentals with a pool in Hilton Head Island

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Hilton Head Island

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
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.
Condo in Hilton Head Island
4.91 out of 5 average rating, 220 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. Watch dolphins & sip morning coffee on 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. 🐬🚲

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
4.97 out of 5 average rating, 335 reviews

Oceanfront Luxury! KING BED 65"TV Pickleball & BAR

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! Beachfront Balcony ✨Top 1% Airbnb Home✨ Beachfront Pool, Bar & Grille FREE Pickleball, Tennis, Gym, Volleyball & More HGTV Designer Renovation KING BED + Two 65" SmartTVs Spa Bath w/Walk-in Shower Expanded Bedroom w/Blackout Sleeping Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESORT Bike Rentals on Site 4 Beach Boardwalks 3 Restaurants Sports Bar Gated 24/7 Security Seasonal Island Trolley Stop Bradley Beach

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, 337 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 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.
Condo in Hilton Head Island
4.97 out of 5 average rating, 291 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!

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, 159 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.

Guest favorite
Large windows frame stunning ocean views, allowing natural light to flood the room. A flat-screen TV is positioned on a glass stand opposite the windows, with a white shelving unit displaying decorative items. The space features maple hardwood flooring and a sliding glass door leading to an outdoor area.
Apartment in Hilton Head Island
4.83 out of 5 average rating, 186 reviews

Jim's Stunning Direct Ocean Front 2BR Villa

This 2nd floor villa has breathtaking, unobstructed ocean views from the living room and master bedroom. Walk to Coligny! Two bedroom suites (new mattresses and ceiling fans), with separate renovated baths. Beautiful maple hardwood & tile floors throughout. Fully appointed kitchen boasts granite countertops, maple cabinets, and stainless steel appliances. New Washer/Dryer. Jim Says "I personally stay in each of my units to ensure they are maintained to my highest level of expectations."

Top guest favorite
A view from the balcony captures the serene ocean and beach during sunset. Vibrant colors reflect across the water, while lush greenery and trees frame the picturesque scene. The elegance of natural beauty is enhanced by a lantern hanging nearby.
Condo in Hilton Head Island
4.94 out of 5 average rating, 285 reviews

Cozy Oceanfront-Romantic Retreat-Mesmerizing Views

Villa is located on The Spa On Port Royal Sound complex on Hilton Head Island. Enjoy unobstructed sound & ocean views from your balcony. Natural beach access & observation pier. Beautiful landscaped grounds. 2 outdoor pools-opened Apr.-Oct. Indoor pool, hot tub, dry sauna & gym. Grills and picnic areas on premises, one near the villa, recently installed hammocks near the ocean pool. Tennis and basketball courts on site. Come enjoy the beautiful sandy beach with beautiful sunrises!a

Guest favorite
A serene bedroom space features a spacious bed with a light patterned coverlet. A mirror and a closet are visible, while a smart TV is positioned atop a white cabinet. Soft natural light enters the room through a nearby door leading to an adjacent area.
Condo in Hilton Head Island
4.91 out of 5 average rating, 223 reviews

Ocean front condo with amazing ocean view!

Ocean front condo with amazing view of the ocean and beach from balcony. You are just steps to the beach. In addition, you will be within walking distance to Coligny Plaza with many great restaurants and shops. Guests get to enjoy the onsite pool, sun deck, and grilling area. Luggage carts are located by the pool and elevator to easily transport all your luggage to the condo. Fast upgraded wifi for streaming and work needs. No pets allowed. Preapproval required for service animals.

Guest favorite
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.
Villa in Hilton Head Island
4.96 out of 5 average rating, 107 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.

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
4.98 out of 5 average rating, 205 reviews

Oceanfront Luxury! KING BED 75"TV Pickleball & BAR

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨Airbnb top 1% Home ✨ Oceanfront Balcony 100% New Luxury Renovation HGTV Featured Decorator KING BED + 75" & 65" SmartTV s Expanded Bedroom MARBLE BATHROOM Coastal Décor TOP FLOOR w/Elevator Beach Chairs, Boogie Boards, Ice Chest & More RESORT Beachfront Pool Beachfront Bar & Grille Sports Bar FREE Tennis, Gym, Pickleball, Basketball, Volleyball 2nd Pool Bike Rental Gated w/24 Hour Security Free Trolley Stop Bradley Beach

Top guest favorite
Condo in Sea Pines
5 out of 5 average rating, 107 reviews

5 Star Location-Pool, Walk to Dining/Shops/Marina

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.

Top guest favorite
A private deck features a comfortable sectional sofa with neutral cushions, inviting relaxation. A coffee table is positioned in the center, while a gas grill is seen nearby. Sunlight filters through palm trees, illuminating the serene lagoon view beyond the railing.
Condo in Palmetto Dunes
4.96 out of 5 average rating, 136 reviews

Sunset Serenity - Luxury on The Lagoon!

LUXURIOUS, SPACIOUS, ONE-OF-A-KIND RESORT HOME! CLOSE TO THE BEACH! CORNER VILLA! POOL ACCESS! LARGEST LAGOON VIEW IN THE RESORT! PRIVATE DECK! ENJOY MILLION DOLLAR SUNSETS! WATCH THE WILDLIFE PLAY! FIVE FOOT CUSTOM COFFEE BAR! KING BED IN MASTER! QUEEN & TWIN IN GUEST BEDROOM! XBOX! NETFLIX! THIS IS LUXURY LIVING WITH RESORT AMENITIES CLOSE BY! SAVE THOUSANDS OF DOLLARS COMPARED TO OTHER RESORT LUXURY HOTEL PROPERTIES!

Popular amenities for Hilton Head Island rentals with a pool

When is the best time to visit Hilton Head Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ540ﺩ.ﺇ551ﺩ.ﺇ650ﺩ.ﺇ735ﺩ.ﺇ735ﺩ.ﺇ841ﺩ.ﺇ863ﺩ.ﺇ742ﺩ.ﺇ646ﺩ.ﺇ621ﺩ.ﺇ621ﺩ.ﺇ606
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Quick stats about vacation rentals with a pool in Hilton Head Island

  • Total vacation rentals

    Explore 5,760 vacation rentals in Hilton Head Island

  • Nightly prices starting at

    Hilton Head Island vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 136,170 verified reviews to help you choose

  • Family-friendly vacation rentals

    4,740 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 910 rentals that welcome pets

  • Rentals with dedicated workspaces

    3,350 properties have a dedicated workspace

  • Wi-Fi availability

    5,730 of Hilton Head Island vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Hilton Head Island rentals

  • 4.7 Average rating

    Hilton Head Island stays receive an average rating of 4.7 out of 5 from guests

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