Holiday rentals with a pool in Hilton Head Island

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Top-rated rentals with a pool in Hilton Head Island

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Guest favourite

Apartment in Hilton Head Island

4.93 out of 5 average rating, 166 reviews

Hilton Head BIKE 'n BED - 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.

28 Dec – 4 Jan

$159 SGD per night

Superhost

Apartment in Hilton Head Island

4.83 out of 5 average rating, 101 reviews

Salt Sand and Serenity! The great escape to HHI

Enjoy your time with family, friends & loved ones on the Number 1 Island in the Continental U.S! Hilton Head Resort has an abundance of amenities for you to spend your memorable moments. Our resort offers PICKLE Ball Courts, Two Outdoor Pools, Heated Pool. Hot-tub, Tennis Courts and PRIVATE BEACH ACCESS! There is also a tiki bar & grill on the beach where you can soak up the sunshine while sipping on a tropical cocktail. We welcome you to make yourself at home in our piece of paradise. Namaste!

8–15 May

$172 SGD per night

Superhost

Apartment in Hilton Head Island

4.88 out of 5 average rating, 160 reviews

Hilton Head Hidden Gem

Comfy 3rd floor walk up retreat. Peaceful decor. Screened balcony. Furnished kitchen. Free use of WIFI, beach chairs/umbrella, gym, basketball & tennis courts, charcoal grills/picnic tables; pools. Steps from your door: explore our sandy beach, watch fish jump & dolphins swim; observe nature on a private pier. See the sunrise on the water. Grocery/restaurants w/in 1-5 miles. Make a meal or a reservation! Short drive to all island locales. Great island bike paths. (No pets or smoking.)

19–26 Oct

$153 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.98 out of 5 average rating, 223 reviews

Ocean View Luxe! KING BED 65"TV Bar Pickleball GYM

Beachfront Building! Quiet Views of Coastal Marsh, Ocean & Trees - Not Parking Lot HGTV Featured Decorator Coastal Decor KING BED Expanded Bedroom 2 SmartTVs Private Balcony Beach Chairs, Umbrella, Boogie Boards, Ice Chest, Pool Noodles Full Kitchen Top Floor Elevator RESORT: No Resort Fees Huge Oceanfront Pool 2nd Pool Beachfront Bar & Grille Sports Bar FREE Tennis, Gym, Pickleball, Basketball, Volleyball & More Bike Rentals Gated/24 Hour Security Trolley Stop 4 Beach Boardwalks Bradley Beach

10–17 Nov

$227 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.98 out of 5 average rating, 239 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.

11–18 Nov

$206 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.88 out of 5 average rating, 195 reviews

Our Villa by the Sea

Enjoy our villa by the sea with a short board walk to one of the longest beaches in the US. Complementary beach accessories waiting for you. Relax on the balcony with the fresh ocean breeze and a peak of the ocean. Located on Hilton Head Beach & Tennis Resort, enjoy all of the amenities as our guest ... bar & grill on the beach, pool with ocean view, tennis courts, bike rentals, restaurant, and fitness center. Or just venture out and discover Hilton Head Island's beautiful attractions.

18–25 Jan

$163 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.86 out of 5 average rating, 234 reviews

Shore To Please! Elegant couples retreat w/bikes

Stylish beach retreat: Enjoy ocean views and comfortable, Scandinavian design from this newly renovated villa located steps from the beach and within walking distance to many shops, restaurants & entertainment. This well-appointed villa features a beautiful, stocked kitchen, new flooring, walk-in shower and separate bedroom with a desk perfect for getting a little work done. Enjoy ocean-view dining on the balcony or at the kitchen island. There are beach chairs and 2 bikes for your use.

20–27 Nov

$200 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.97 out of 5 average rating, 121 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**

26 Dec – 2 Jan

$314 SGD per night

Guest favourite

Guest suite in Hilton Head Island

4.94 out of 5 average rating, 275 reviews

LOCATION! Harbour, Dining, Shops, Beach-1.4 mile

Location .. Location .. Location !!! Private guest suite with independent entrance from outside, total privacy, and complete amenities, queen bed and full bath (no kitchen). Just step outside - great water-front restaurants with live music, weekly fireworks during summer, bars, shops, outdoor pool and BBQ. Supermarkets and more restaurants in 10 minutes walking. Free shuttle from April till September, beach only 1.4 miles. Great golfing, biking, tennis, fishing and water sports.

8–15 Feb

$146 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.89 out of 5 average rating, 167 reviews

Hilton Head Island - Beach Retreat !!

Newly painted 3rd fl. 2 BR/2 Bath walk-up (2.5 short flights of stairs) unit, new kitchen floor & carpet. Sleeps 6. A total of 5 beds includes 1 king, 1 twin bed, twin over full/bunk beds & a sofa bed. Fully equip. kitchen w/new appliances. Unit has an open fl. plan w/view of lagoon & fountain. 5 min walk across the parking lot to the beach. Coconutz Sports Bar & Jamaica Joez Beach Bar on site. Gym & Laundry room on premises. Resort Parking Pass Fee is $35.00 per vehicle.

3–10 Nov

$157 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.95 out of 5 average rating, 228 reviews

Ocean View! Steps to beach! Remodeled HHBT Condo

Newly remodeled - just last year! Adorable beach front condo located in Hilton Head Beach and Tennis Resort. Watch and listen to the ocean waves right from your 2nd floor balcony! The condo is in a gated area within the resort where guests will have access to a private beach, 2 pools, resort restaurants, tennis, pickleball, beach volleyball, playgrounds, cookout areas, bike rentals, and a newly renovated gym. It's all here! 😊The 2024 getaway your been waiting for! 😎

8–15 Nov

$218 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.98 out of 5 average rating, 181 reviews

Lost Tiki Lounge TOP Floor Oceanfront 322 Breakers

Step into oceanfront comfort. This beautiful condo has all the comforts of home and is located in the heart of the south end of the island steps away to restaurants, shopping and the pristine Coligny beach. It’s the perfect place for a romantic beach getaway for 2. Upon entry you will see an incredible view of the ocean in this light and bright TOP floor Breakers condo.The condo is cleaned/managed by the local owner to ensure 100% satisfaction by my guests.

14–21 Dec

$297 SGD per night