Vacation rentals with a pool in Hilton Head Island

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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

Condo 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

Nov 10 – 17

$145 per night

Superhost

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.)

Jan 11 – 18

$98 per night

Guest favorite

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!

Nov 20 – 27

$141 per night

Guest favorite

Condo 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.

Dec 28 – Jan 4

$119 per night

Guest favorite

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.

Dec 17 – 24

$105 per night

Guest favorite

Condo 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.

Nov 19 – 26

$127 per night

Guest favorite

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**

Jan 26 – Feb 2

$199 per night

Guest favorite

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.

Aug 19 – 26

$118 per night

Guest favorite

Condo in Hilton Head Island

4.92 out of 5 average rating, 101 reviews

Cozy in Coligny

Welcome to the Cozy in Coligny condo! Located at The Breakers, a highly desirable beachfront property, you are only steps away from the pool and beach. You will be in the heart of award-winning Coligny Beach – park your car and leave it! You can spend the day playing in the sun and sand then walk across the street to Coligny Plaza – home to the beloved Piggly Wiggly grocery store and 60+ shops, restaurants, entertainment, tour information, beach equipment, and bike rentals.

Feb 3 – 10

$146 per night

Guest favorite

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.

Mar 23 – 30

$149 per night

Guest favorite

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!

Nov 8 – 15

$148 per night

Guest favorite

Condo in Hilton Head Island

4.88 out of 5 average rating, 182 reviews

Cozy Hilton Head Island Condo

A cozy condo, approximately a five minute walk to the beach! Conveniently situated near shopping, and dining at Coligny Plaza. Accommodates 5 people with two parking spaces. Fully equipped unit with two bedrooms. Two TVs, wireless internet, fully equipped kitchen. Guest have access to pool, picnic area w/ grills and tables near a lagoon. Feel free to reach out with any questions and how we can make your time at the beach the best that it can be!

Jan 4 – 11

$104 per night