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, 165 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.

26 Oct – 2 Nov

$175 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.)

18–25 Mar

$162 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.98 out of 5 average rating, 222 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

$234 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.98 out of 5 average rating, 131 reviews

"Beach Time" - a cozy HHI Condo, steps from beach

No price increase 2023 & 24! Low fees! New Solbello sail sunshade. HHI Beach & Tennis is a beachfront resort with many vacation amenities. Our condo is a first floor condo in Building B, close to the pool and beach activities but far away enough from noise of pool and restaurant. Our condo is 2-3 minutes from the beach. We provide a clean, safe, comfortable and affordable space for our guests. Our condo is cleaned, sanitized and ozonized. We have an air system, air purifier and dehumidifier.

14–21 Nov

$164 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.89 out of 5 average rating, 151 reviews

Beachfront property with ocean/sunrise view!

Ocean sunrises from your private balcony! Steps to the beach! Newly renovated 1 Bed/1 Bath villa in a gated ocean community. New flooring throughout with new central air/heat. Nicely appointed, fully equipped and immaculate. Perfect for up to 4 guests. Boardwalk to beach. Outdoor pool/showers. 2 beach cruiser bicycles included. Easy walk to Coligny Plaza for many restaurants, shops, grocery, etc. Great golf courses, tennis, biking/hiking trails, boating/fishing, parks in area.

15–22 Dec

$209 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.97 out of 5 average rating, 120 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 Jan – 2 Feb

$324 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.

22–29 Mar

$150 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.

23–30 Dec

$162 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.99 out of 5 average rating, 312 reviews

Ocean Front Resort Condo

Enjoy Coastal Cottage Living in a lovely 540 sq ft one bedroom vacation villa within the activity-filled gated resort of Hilton Head Beach and Tennis. Completely remodeled from with all new fixtures, furnishings, housewares and accessories, this charming beach villa has just opened its doors for guests in March 2019. Amenities include coffee, popcorn, breakfast treats and bottled water to consume; and beach towels, chairs, umbrellas and other items to borrow while here.

13–20 Jan

$192 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

$224 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.92 out of 5 average rating, 101 reviews

Secluded 1st Floor Beach Getaway

Newly Remodeled - 2 Bedroom/2 Bath First Floor Villa in a Gated Community - less than a five minute walk through our complex to a private, natural beach! Everything you need to enjoy a relaxing, peaceful getaway and all that Hilton Head Island is famous for. Located in a beautiful, quiet community that offers 2 outdoor pools and one indoor pool that can be enjoyed year round. Come discover why this island has been voted the #1 best island in the United States!

31 Oct – 7 Nov

$187 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.99 out of 5 average rating, 145 reviews

Reno’d 1st floor walk to beach, pools pickleball

Welcome to our lovely renovated 1st floor unit in Fiddler's Cove. Perfect for a tennis, golf, biking or beach holiday! A 6-7 min walk to Folly Field beach via private beach access. Use our beach gear. Great secure wifi. Surrounded by world class golf courses. Enjoy 5 star amenities including 2 pools, hot tub, racquetball, pickle ball courts and gym. Pools are open from march 1st-October 31st and hot tub remains open year round.

11–18 Nov

$201 SGD per night