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Holiday 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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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.)

18–25 Jan

$240 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

- 885 sq ft condo on the 2nd floor (top floor) - Private balcony with electrical barbecue - Tucked into an area rich with foliage, palmetto trees and nature - Community pool only steps away - 10 minutes walk to the beach - Fully stocked and equipped kitchen - Washer & dryer in the villa - Baby crib and toys available - Onsite parking for 2 cars - Extremely safe community - Check out our 3D virtual tour: scan the QR code on the last picture with your cell phone to be redirected to the 3D tour.

24–31 Oct

$206 NZD per night

Guest favourite

Condo in Hilton Head Island

4.97 out of 5 average rating, 199 reviews

HHBT Resort-OceanView-Remodeled-Steps to beach!

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!

6–13 Dec

$294 NZD per night

Guest favourite

Condo in Hilton Head Island

4.96 out of 5 average rating, 106 reviews

Beautiful Couples Retreat !

Welcome to Serenity by the Shore. Escape to this top floor unit which is steps away to the beautiful ocean. Our condo features a heavenly pillowtop mattress in the master bedroom, private ocean view balcony and fully equipped kitchen for all your cooking needs. The condo is perfectly located within the Hilton Head Beach and Tennis Resort, the island's largest ocean front pool, tennis courts, Pool Bar & Grill. This luxury condo is great for a solo getaway, family vacation or romantic escape!

11–18 Feb

$311 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**

17–24 Nov

$482 NZD per night

Guest favourite

Guest suite in Hilton Head Island

4.94 out of 5 average rating, 277 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.

26 Mar – 2 Apr

$209 NZD per night

Guest favourite

Condo in Hilton Head Island

4.89 out of 5 average rating, 168 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.

26 Jan – 2 Feb

$253 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.

28 Nov – 5 Dec

$310 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

$324 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.

21–28 Nov

$292 NZD per night

Guest favourite

Condo in Hilton Head Island

4.96 out of 5 average rating, 116 reviews

Beach&Tennis, Stylish, Modern, Folly Field Beach!

Hilton Head Beach & Tennis, 1-bedroom, fully remodeled! New queen mattress, stainless appliances, Queen Sleeper Sofa. 5 units from the ocean, partial ocean view. Enjoy a glass of wine, and listen to the ocean on the private patio. Free Wi-Fi! Don't stay in a tiny hotel room with no kitchen. Hotels are cold and sterile, our home is warm and welcoming! 100 feet to our beautiful beach and oceanfront pool! 12 Pickleball courts!

2–9 Nov

$207 NZD per night

Guest favourite

Condo in Hilton Head Island

4.98 out of 5 average rating, 118 reviews

Salty Tides ~ 2 BR/2 Bath ~ Short Walk to Beach!

Nestled in the Folly Field Beach community, Fiddler's Cove Beach & Racquet Club is only 300 yards to the beach. Our 2 bedroom / 2 bathroom condo is located in the 2nd villa on the 3rd floor (no elevator). The master bedroom has a King bed and the guest room has 2 Twin beds. The villa is conveniently located for easy access to the beaches, pool, tennis, pickleball and clubhouse.

19–26 Dec

$229 NZD per night

Holiday rentals for every style

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Popular amenities for Hilton Head Island rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

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

21–28 Feb

$988 NZD per night

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

30 Jan – 6 Feb

$1,286 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

30 Aug – 6 Sep

$576 NZD per night

Guest favourite

Home in Hilton Head Island

4.85 out of 5 average rating, 205 reviews

Coastal Town Gallery House - live like a local!

14–21 Sep

$796 NZD per night

Home in Hilton Head Island

4.92 out of 5 average rating, 106 reviews

Luxe & Fun Family Gem ~ Walk to Beach ~ Pool ~ BBQ

6–13 Mar

$1,053 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

5–12 Jan

$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"

30 Oct – 6 Nov

$856 NZD per night

Condo rentals with a pool

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

2–9 Aug

$991 NZD per night

Guest favourite

Condo in Hilton Head Island

4.95 out of 5 average rating, 202 reviews

Cozy Renovated Unit Great Location

4–11 Jan

$255 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!

7–14 Feb

$238 NZD per night

Guest favourite

Condo in Hilton Head Island

4.94 out of 5 average rating, 424 reviews

(5) Location! Walk to Coligny Beach Shops Dining!

31 Jan – 7 Feb

$329 NZD per night

Guest favourite

Condo in Hilton Head Island

4.9 out of 5 average rating, 127 reviews

Coastal Comfort! Condo in beachfront resort.

21–28 Feb

$319 NZD per night

Condo in Hilton Head Island

4.84 out of 5 average rating, 107 reviews

AWESOME Retreat! King bed! Ocean View! 2 Bikes 218

24–31 Oct

$346 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

18–25 Sep

$341 NZD per night

Guest favourite

Condo in Hilton Head Island

4.98 out of 5 average rating, 181 reviews

Lost Tiki Lounge TOP Floor Oceanfront 322 Breakers

6–13 Oct

$541 NZD per night

Quick stats about holiday rentals with a pool in Hilton Head Island

Total rentals
4.8K properties
Rentals with dedicated workspaces
2.4K properties have a dedicated workspace
Pet-friendly rentals
670 properties allow pets
Family-friendly rentals
3.9K properties are a good fit for families
Total number of reviews
102K reviews
Nightly prices starting at
$17 NZD before taxes and fees

Destinations to explore