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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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Guest favorite
A scenic view is presented from the balcony, showcasing a coastal landscape with sprawling greenery and a sandy beach in the distance. The sky is clear with soft clouds, enhancing the tranquil atmosphere of the surroundings.
Condo in Hilton Head Island
4.92 out of 5 average rating, 196 reviews

OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6

Enjoy 4th Floor Ocean Views. Remodeled w/Upscale Finishes & Furniture. King Master Bdrm, 2 Dressers, Nightstands, TV, AC unit. Bath w/Body Spray Rain Shower, Comfort Hgt Toilet, Vanity w/Granite Counter/Storage. Hall BunkBeds w/Over Sized Drawers, USB Storage Alcoves, Oscillating Fan. Kitchen Pullout Drawer Cabinets, SS Apps, Double Oven, Granite Counters. Dining w/Table for 3/4 & 2 at Kitchen Bar. LR Queen SleeperSofa, Flat Screen TV, DVR, Chair, Ottoman, AC unit. Balcony Comfy Seating for 4.

Top guest favorite
A decorative bicycle wall art piece in soft mint green is displayed alongside a playful turtle motif. The bicycle features a white woven basket and artistic details, adding a coastal charm to the interior.
Condo in Hilton Head Island
4.94 out of 5 average rating, 236 reviews

BIKE ‘n BED Hilton Head- Perfect Couple's Getaway

Come relax and enjoy Hilton Head on South Forest Beach, the most popular section of the island. Ride our free bikes for a quick trip to Coligny Plaza where the quaint local shops and restaurants are. The beach is a quick 2 or less minute walk and the pool is just down the hall. Our condo is small, but perfect for a couple's getaway or a memorable trip with the kids. We have everything you need to help make yourselves at home with full size kitchen appliances and washer/dryer room just next door.

Guest favorite
A modern kitchen area is showcased with navy blue cabinets and stainless steel appliances. A large island with seating for four is highlighted, and natural light filters in through the window. A cozy living room area is adjacent, featuring a stylish brown leather sofa.
Condo in Hilton Head Island
4.86 out of 5 average rating, 133 reviews

Oceanfront Villa on Hilton Head Island!

This one bedroom, one bath oceanfront Villa is a third floor end unit that sleeps 5. There’s an adjustable queen bed, a set of bunk beds (Intended for children) and a twin sleeper sofa. It is a three minute walk to the sandy shores of Hilton Head Island. The gated resort has these amenities: two pools (one of which is the largest beach front pool on the island), 10 tennis courts, pickle ball courts, fitness center, bike rental, playground, and three restaurants. Reserve your vacation today! Thi

Top guest favorite
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 Hilton Head Island
4.98 out of 5 average rating, 131 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.

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
4.97 out of 5 average rating, 293 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!

Guest favorite
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 Hilton Head Island
4.91 out of 5 average rating, 209 reviews

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.

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, 160 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.

Top guest favorite
A three-story building is depicted with multiple balconies overlooking a paved driveway. Lush palm trees line the area, providing a tropical feel. The sky is partly cloudy, suggesting a bright atmosphere. Parking spaces are visible, adding convenience for guests.
Condo in Hilton Head Island
4.98 out of 5 average rating, 277 reviews

Coastal King Beach Flat Convenient to Everything!

Set in a serene location right on the beach, this complex is a peaceful gated retreat. It's a short walk to Coligny Plaza, a vibrant area offering a variety of dining, shopping, and entertainment options. The complex features a pool and sundeck, perfect for relaxation. With high-speed internet, WIFI, smart TVs, Roku, and cable, you're always connected. Enjoy the comforts of home with a fully stocked kitchen, a plush King bed, ideal for remote work, and modern updates & included amenities.

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, 187 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, 286 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

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
4.97 out of 5 average rating, 206 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
A stunning sunrise illuminates the ocean, casting a warm golden glow across the water's surface. Rays of sunlight stretch outward, reflecting off the gentle waves. The shoreline is visible, framed by soft grasses, enhancing the tranquil morning scene.
Condo in Hilton Head Island
4.99 out of 5 average rating, 177 reviews

Ocean Overlook II - The Penthouse Experience

LUXURIOUS, PENTHOUSE, 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! 4TH FLOOR (TOP FLOOR)! PRIVATE BALCONY! MILLION DOLLAR OCEAN VIEWS! SPA SHOWER! 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**

Popular amenities for Hilton Head Island rentals with a pool

When is the best time to visit Hilton Head Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$30,746 GYDG$31,374 GYDG$37,021 GYDG$41,832 GYDG$41,832 GYDG$47,897 GYDG$49,152 GYDG$42,250 GYDG$36,812 GYDG$35,348 GYDG$35,348 GYDG$34,511 GYD
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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 G$4,183 GYD 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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