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Holiday rentals with a pool in Hilton Head

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Top-rated rentals with a pool in Hilton Head

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

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Condo 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.)

14–21 Nov

$239 NZD per night

Guest favourite

Condo in Hilton Head Island

4.98 out of 5 average rating, 224 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

$348 NZD per night

Guest favourite

Condo 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.

12–19 Jan

$234 NZD per night

Guest favourite

Condo in Hilton Head Island

4.97 out of 5 average rating, 224 reviews

Oceanfront Designer! KING BED 65"TV Bar Tennis GYM

PANORAMIC OCEANFRONT VIEWS THE MOMENT YOU OPEN THE DOOR! HGTV Featured Decorator! 100% Luxury Renovation KING BED (2) 65" SmartTVs Coastal Décor Expanded Bedroom Full Kitchen Oceanfront Balcony Beach Chairs, Umbrella, Boogie Boards , Ice Chest, Pool Noodles! Spa Bath RESORT: No Resort Fees Huge Oceanfront Pool Beachfront Bar & Grille Sports Bar FREE Tennis, Gym, Pickleball, Basketball, Volleyball & More Bike Rental 2cd Pool Gate w/24 Hour Security Trolley Stop Bradley Beach 4 Beach Boardwalks

2–9 Aug

$991 NZD per night

Condo in Hilton Head Island

4.81 out of 5 average rating, 112 reviews

HILTON HEAD RESORT CONDO - NEWLY RENOVATED

NEWLY RENOVATED condo near the beach! Ready for a relaxing time away? This newly renovated condo is tucked away in the lovely Hilton Head Resort - a gated community w/ 24 hr security, perfect for families who want to create lasting memories at the beach! The resort has everything you need - indoor/outdoor pools, sauna, spa, fitness room, tennis/pickle ball courts, and a private boardwalk to the beautiful beach. Within just a few miles are grocery stores, restaurants, shopping centers, and more!

16–23 Dec

$261 NZD per night

Guest favourite

Condo 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.

16–23 Oct

$274 NZD per night

Guest favourite

Condo 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**

28 Feb – 7 Mar

$481 NZD per night

Guest favourite

Guest suite in Hilton Head Island

4.94 out of 5 average rating, 276 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.

9–16 Apr

$209 NZD per night

Guest favourite

Condo 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.

8–15 Apr

$354 NZD per night

Guest favourite

Condo 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

$325 NZD per night

Guest favourite

Condo in Hilton Head Island

4.92 out of 5 average rating, 102 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!

16–23 Jan

$261 NZD per night

Guest favourite

Condo in Hilton Head Island

4.99 out of 5 average rating, 147 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.

26 Mar – 2 Apr

$321 NZD per night

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Popular amenities for Hilton Head rentals with a pool

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House rentals with a pool

Guest favourite

Home in Hilton Head Island

4.97 out of 5 average rating, 107 reviews

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

24–31 Jan

$968 NZD per night

Guest favourite

Home in Hilton Head Island

4.94 out of 5 average rating, 129 reviews

Spa/Fully Screened Heated Pool/Elevator/Fenced-79

24 Feb – 3 Mar

$1,386 NZD per night

Guest favourite

Home in Hilton Head Island

4.85 out of 5 average rating, 101 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

13–20 Jan

$833 NZD per night

Home in Hilton Head Island

4.84 out of 5 average rating, 126 reviews

FREE Heated Pool, Walk to Beach, Elevator, Theater

23–30 Sep

$1,851 NZD per night

Guest favourite

Home in Hilton Head Island

4.96 out of 5 average rating, 122 reviews

Peaceful Harbour Town Treehouse with Marsh Views

23–30 Sep

$575 NZD per night

Guest favourite

Home in Hilton Head Island

4.85 out of 5 average rating, 204 reviews

Coastal Town Gallery House - live like a local!

8–15 Jan

$803 NZD per night

Guest favourite

Home in Hilton Head Island

4.86 out of 5 average rating, 345 reviews

W2Beach*4TVsRokuAppleTV*Pets *WiFi*3King ßds*grill

13–20 Nov

$767 NZD per night

Guest favourite

Home in Hilton Head Island

5.0 out of 5 average rating, 53 reviews

180º Ocean Views, Treehouse "Siren's Lookout"

10–17 Jan

$856 NZD per night

Condo rentals with a pool

Guest favourite

Condo in Hilton Head Island

4.98 out of 5 average rating, 181 reviews

Lost Tiki Lounge TOP Floor Oceanfront 322 Breakers

31 Dec – 7 Jan

$440 NZD per night

Guest favourite

Condo in Hilton Head Island

4.85 out of 5 average rating, 190 reviews

Shore Fun-Beautiful, Many upgrades! w/Bikes&Chairs

18–25 Jan

$288 NZD per night

Condo in Hilton Head Island

4.87 out of 5 average rating, 133 reviews

Cozy upgraded Villa ! 10 min walk to the Beach

1–8 Nov

$213 NZD per night

Guest favourite

Condo in South Beach

4.85 out of 5 average rating, 234 reviews

Charming Sea Pines Villa with View on Hilton Head

21–28 Apr

$287 NZD per night

Guest favourite

Condo in Tybee Island

4.93 out of 5 average rating, 523 reviews

Adorable Beachfront Condo

1–8 Dec

$242 NZD per night

Guest favourite

Condo in Hilton Head Island

4.91 out of 5 average rating, 281 reviews

Turtle Tracks, Hilton Head Island, SC

25 Jan – 1 Feb

$267 NZD per night

Guest favourite

Condo in Hilton Head Island

4.93 out of 5 average rating, 108 reviews

Spacious Two Bedroom Villa in Hilton Head Resort!

10–17 Nov

$266 NZD per night

Guest favourite

Condo in Hilton Head Island

4.91 out of 5 average rating, 183 reviews

Anchor at the Beach ⛱ Eat & Shop at Coligny plaza!

14–21 Dec

$335 NZD per night

Destinations to explore