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

4.93 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.

Mar 11 – 18

G$34,634 GYD 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 22 – 29

G$24,222 GYD per night

Guest favorite

Condo 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

Nov 10 – 17

G$35,092 GYD per night

Guest favorite

Condo 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**

Nov 16 – 23

G$48,507 GYD 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.

Dec 29 – Jan 5

G$22,507 GYD 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.

Jan 13 – 20

G$28,777 GYD 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

G$33,341 GYD per night

Guest favorite

Condo 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!

Dec 3 – 10

G$26,737 GYD per night

Guest favorite

Condo 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.

Jan 7 – 14

G$45,834 GYD 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!

Nov 3 – 10

G$25,165 GYD per night

Guest favorite

Condo in Hilton Head Island

4.96 out of 5 average rating, 113 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!

Oct 27 – Nov 3

G$20,604 GYD per night

Guest favorite

Condo in Hilton Head Island

4.95 out of 5 average rating, 201 reviews

Cozy Renovated Unit Great Location

Completely renovated, new everything! Easy access to beach, public restrooms and open bar / food / fire pits at beach access (see photo). High speed internet, 3 TV’s w/ YouTube TV included (70 channels, Golf, Tennis, ESPN family of channels, SportsSouth, Disney family of channels), local Cable through Spectrum included. The perfect location near Coligny Plaza, Sea Pines, the beach, miles of bike trails!

Nov 13 – 20

G$26,652 GYD per night